Charming Vacation Rentals in Chilmark, MA

Chilmark Guest House offers accommodations in Chilmark, 15 miles from Edgartown Lighthouse. The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests. The vacation home features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Guests at Chilmark Guest House will be able to enjoy activities in and around Chilmark, like cycling. A children's playground is also available for guests at the accommodation. Martha's Vineyard Airport is 8.7 miles from the property.

- "Highly recommended, would gladly come again!" - "This property is clean, comfortable, private and relaxing." - "We really enjoyed the house and it was very clean, quiet, and relaxing."

The house is a large family house in the Abels Hill community of Chilmark. The community shares use of a private south shore beach with beautiful Chilmark Pond for kayaking or canoeing, a tennis court, and access to miles of hiking trails.

The house has 6 bedrooms, and sleeps 13. 3 King sized beds, 1 Queen. 2 Doubles. One of the double bedrooms also has a twin. A large vaulted ceiling living/dining room looks out a glass wall over the 5 acre meadow with stone wall and organic vegetable garden that you can harvest from for your dinner or green smoothie! An exterior seating area on a deck w grill extends the living room and overlooks the meadow.

2 full bathrooms plus a powder room and outdoor shower with stained glass window!

A TV room and a music room, with electric piano, saxophone, bass, drum kit and drum machine are extra spaces for rainy days.

Its easy to walk to the beach and the pond from the house, which is across south road, just down the hill. To get to the beach you either use the Abel’s hill small boat which seats 4, our kayak (which seats 2), or wade across the shallow pond. Hiking trails for woodland running or hiking from Abels Hill take you to acres of magical preserved forests.

The house is simple, colorful and joyful.

- "We loved the house and property and the host could not be more gracious. Coming back a third time." - "Wish we had booked this place for a longer stay! The house is beautiful and the location can't be beat. Thanks for a lovely stay!" - "We needed a place to accommodate a few needs:1) enough beds/bedrooms for 9 adults (2 families 5+4) and bathrooms too. [With sheets, bath towels and extra toiletries if needed.] 2) close proximity to wedding venue. [Within 5 miles] 3) cooking/kitchen amenities. This home fulfilled them all and then some extras! Great livingroom/dining area, with sliding door leading to deck/patio, separate TV room, ping pong table, board games, bluetooth speakers, art supplies-drawing paper, pencils, pastels, paint. 4) access to walking paths and beach access. Highly recommend stayong here and would definitely stay here again! Thank you for a Fabulous place(home away from home) to get together with famy from long distances (Texas, Maryland, North Carolina, New York and Connecticut!) Precious (priceless) memories made!!!!!😍💖"

13 miles from Edgartown Lighthouse in Chilmark, Bijha's View offers accommodations with access to spa facilities. The vacation home has access to a restaurant. The vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Guests at the vacation home will be able to enjoy activities in and around Chilmark, like cycling. The vacation home has a picnic area where you can spend the day outdoors. Martha's Vineyard Airport is 6.8 miles away.

Restaurant • Laundry • Guest Services • Balcony/Terrace • Barbecue/Outdoor Cooking • Wellness Facilities • Security/Safety • Child Friendly • Fireplace/Heating • Spa • Sports/Activities

One of Chilmark's most stately and classic Captains House, THE BLUE BARQUE has been thoughtfully and fashionably edited and updated with every modern comfort in modern farmhouse style.The house is in a central location on South Road, behind stone walls and amidst large acreage. One can enjoy a brief walk or ride to a private beach on Chilmark's South shore. There is also easy access to Chilmark's famous Lucy Vincent Beach and Squibnocket Beach, with the purchase of a car or walk-on pass at the Chilmark Town Hall. Menemsha Fishing Village and Beach is just around the corner ,with interesting shops, fish markets and eateries.
There are four comfortable bedrooms, plus a queen sofa bed on the sunporch, updated with antiques, paintings ,a bright color palette ,and comfortable furnishings. A thoughtful renovation and reimagining includes, a gourmet cook's kitchen ,screened porch and sunny living room, two large living rooms in total, outdoor deck and patio, central AC and every amenity. There are large, comfortable spaces indoors and out for relaxation and fun. The location is conveniently situated between two nearby villages. West Tisbury, is the location of the Farmer's Market ,Antique and Artisan Fairs ,and Alley's Store and Farm Stand. Nearby ,are the Library and Community Center and popular 7A Foods Shop. Further down South Road ,is Middleton Village with an Apothecary, Beauty Salon, offices, the popular State Road Restaurant, West Tisbury Post Office and Cronig's Up Island Market.
A short distance away, in the other direction, is Chilmark Center, Lucy Vincent Beach and Chilmark Community Center, Chilmark Store, local farm stands and eateries, and a charming New England seaside village, called Menemsha, with fresh fish markets, shops, restaurants, food stands and a legendary sunset. A gate key provides access to private Hancock Beach on the South shore, and is only a few moments from the house, 8/10 mile down a sandy lane. It is definitely the icing on the cake!.The Blue Barque is a wonderful destination house for family and friends, and a stunning , relaxing and fun place to enjoy your vacation.

- "Wonderful stay with grandparents and cousins, plenty of space and well equipped for family meals! Short drive to the best beach, and just down the road from the Grey Barn for fresh bread every morning. Thank you Lucinda and for being such great hosts!" - "we had an uncle, 2 grandparents, plus a family unit of 4 (kids 10 & 11) and the house had spots for everyone to hide if needed and to connect and have FUN! plenty of room for family meals, an EPIC outdoor shower (my favorite), the beds were super comfy, just about everything you need to enjoy the beach, PLUS a GORGEOUS BEACH!!!!! the location felt convenient to everything! lucinda was a DREAM! so responsive and so detailed in her responses which made everything so much easier - and the flowers she greeted us with were gorgeous!! we brought a badminton net and it worked perfectly in the yard - everyone got involved! we put together puzzles. we flew kites on the beach and they were awesome! we even made it for a sunrise on the beach - it felt like it was our own private beach! ohh and the art throughout the house was amazing! THANK YOU!!!!! highly recommend this home!"

The Eliot Noyes offers accommodations in Chilmark, 14 miles from Edgartown Lighthouse. Guests are welcome to go for a swim in the private pool. Outdoor seating is also available at the vacation home. The Eliot Noyes features 4 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with free toiletries. A flat-screen TV with satellite channels is offered. The property offers sea views. Martha's Vineyard Airport is 7.5 miles from the property.

View • Laundry • Barbecue/Outdoor Cooking • Pool • Child Friendly • Balcony/Terrace • Guest Services • Security/Safety

Petite Guest house is private with its own driveway, yard, and easy walk to Menemsha Pond. Amazing location; walk to Menemsha harbor, beach, Galley restaurant & ice cream, fish markets. Views of Pond, Vineyard sound, Aquinnah. 2 bedrooms, galley kitchen, living room wrapped in sliding glass doors out to deck. Beach pass to Lucy Vincent & Squibnocket avail. Well behaved dogs welcome, streaming TV, Wifi, A/C, heat, laundry + level-2 EV charger. Outdoor furniture included upholstered couch with small table, lounge chairs with giant umbrella. Enjoy Weber gas BBQ. Close to Chilmark Store, Chilmark Community Center. Nestled in nature with a small lily pond onsite & ideal for disconnecting. .4 miles (7 mins) walk to Pond boat launch - great for paddle boarding or fishing. Close to Menemsha Inn & Beach Plum Inn. Great dirt roads for running or walking. Loads of hiking trails nearby. Enjoy incredible light + sunsets from the deck.

Recently renovated with reclaimed barn door, translucent panels, new kitchen +bath. Simple Menemsha living with amenities. This cozy home is ideal for a single person, couple, or 3 close friends. A previous guest have compared it to a small houseboat as it's cozy inside. Enjoy outdoor shower, professionally manicured grounds, and bubbling brook next to house to add to chill ambiance. Kitchen has all the modern amenities, microwave, dishwasher and is fully stocked.

NOTE - Our Main house just across a gentle stream via bridge is double the size of this home and may be rented together (if both available). Search VRBO # 2604149.

2026 bookings open October 2025. Reach out if interested.

- "We had a great vacation! Communication with Christian was clear, fast and he was always available. Place was clean, updated, very well equipped and accurately described in the listing. Abundant natural light! Great location, a little removed from the hustle and bustle which we loved. Very pet friendly. Beach umbrella and chairs were in great condition. All of the outdoor furniture was of nice quality. Would definitely come back!" - "Menemsha is our favorite location on the island and this charming guest house was simply perfect in every regard. We enjoyed the sunsets from the deck, watching the 4 bunnies enjoy the lush grass on the sweeping lawn, long walks on backroads, and quick trips to Larsen's for fresh seafood. The house is well equipped with everything we needed, and the owners have paid attention to every detail to make our stay very comfortable and easy."

Wayside Camp offers accommodations in Chilmark, a 5-minute walk from Menemsha Beach and 16 miles from Edgartown Lighthouse. The vacation home has access to a restaurant. The vacation home features 3 bedrooms, a fully equipped kitchen with an oven and a microwave, a washing machine, and 1 bathroom with a hair dryer. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Guests at Wayside Camp will be able to enjoy activities in and around Chilmark, like cycling. The vacation home has a picnic area where you can spend the day outdoors. Martha's Vineyard Airport is 9.3 miles away.

Laundry • Pet Friendly • Restaurant • Barbecue/Outdoor Cooking • Guest Services • Security/Safety • Sports/Activities • Child Friendly • Balcony/Terrace

Mid-Century modern glass house, in Menemsha, on Marthas Vineyard. Designed by a Frank Lloyd Wright apprentice, this all glass house, embodies the integration of nature and architecture, with simple utilitarian design in serene location, minutes from Menemsha or Lucy Vincent Beach. Built in the early 1960s, and recently updated, this all glass house, features 3 bedrooms, 2 bath rooms, and a large open concept living & dining area. The house features floor to ceiling glass in every room. There is a wrap-around deck around the entire exterior, and another deck around the interior open-air courtyard area. The house has a large, new outdoor shower, with a stone sink. There are distance water views of the vineyard sound and the Elizabeth islands. The house is a short 5 min drive from the Homeport Restaurant, Menemsha Market, Chilmark Store, or Lucy Vincent Beach. Awarded Progressive Architecture's design excellence award in 1963, this historical updated mid-century modern house, offers the best of simple indoor/outdoor living, with all updated modern conveniences.

New in addition to The Glass House in 2023, is The Studio, a gorgeous space (about 16 x 16), with a wrap around deck, that is bulit over looking a stream. This Studio is accross the driveway from the main house (about 80 ft) and can be used as an additional bedroom with a queen bed or a home office space.

** The Glass House was featured in Martha's Vineyard Magazine in Spring 2018 issue. The full article is here: http://mvmagazine.com/news/2018/03/01/exurban-renewal

- 3 Bedroom, 2 Bathroom. (BR1 Queen, BR2 Queen, BR3 (2) bunk beds) - Sleeps 8 (+2 in Studio)
- The Studio, 1 Bedroom, no bath (BR4 - Queen) - Sleeps 2
- Access to Lucy Vincent Beach and Squibnocket Beaches
- Access to Menemsha Pond (via Cove Rd, deeded access)
- WiFi / Internet - Available throughout the house
- Chef's kitchen with 5 burner stove (all new appliances)
- Dishwasher, Drawer Microwave, Oven; BBQ on deck
- Coffee Maker & Kreurig
- Direct TV / Flat Panel TV
- Sonus - Audio System
- Amazing outside shower

FAQ - Privacy in a Glass House - Although the house is 100% glass, 100% privacy can be achieved as all the walls have curtains which can be closed for complete privacy. We typically recommend having the curtains open to enjoy the floor to ceiling views of the natural surroundings, and achieve the intended feeling of the living space's integration into the nature surroundings, but all rooms (bathrooms, bedrooms, etc) can be 100% private as you would need and expect.

- "We so enjoyed our week at the Glasshouse! The open-air layout was unique and gave the wonderful feeling of practically living outdoors, which was wonderful on breezy days and cool nights and harder on full-sun days and humid nights, though the house is well-supplied with fans. We felt like we were living in a treehouse, in the best way. Outdoor shower was a treat, house well-equipped with a modern, well-appointed kitchen. Nice linens, bathrobes, towels.... everything you need. (Roku TV was an added bonus, so we could watch Wimbledon with our Fubo!) Joe was a communicative and friendly host, making our stay relaxing as can be."

Hillside Oak offers accommodations in Chilmark, 15 miles from Edgartown Lighthouse. The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests. Providing a patio with garden views, this vacation home also provides guests with a satellite flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 4 bathrooms with a bath and a hair dryer. For added privacy, the accommodation features a private entrance. Guests at the vacation home will be able to enjoy activities in and around Chilmark, like cycling. Martha's Vineyard Airport is 8.7 miles away.

Fireplace/Heating • Restaurant • Laundry • Pet Friendly • Security/Safety • Barbecue/Outdoor Cooking • Accessibility • Guest Services • Balcony/Terrace • Wheelchair Accessible • Sports/Activities • Child Friendly

Location! Location! Location!
Charming, and nestled away, this must see post and beam home is situated on the edge of the Keith Farm, which provides multiple sweeping pastoral views and occasional visits by the beautiful horses who graze on the neighbor's property. We have been asked to enjoy their beauty but not to feed them.
Both the isolated beauty of this secluded one acre property and the convenience of this amazing central location, are what make it so special.
This home is beautiful yet not fussy, furnished with both elegance and comfort in mind, with well thought out amenities, including but not limited to a wonderful new kitchen completed in 2022. This fully equipped "Cooks" kitchen includes a large table that seats 8-10. The deck is appointed with teak furnishings , a large direct line gas grill and wonderful views of the beautiful Vineyard sunsets. Along with the kitchen a new full house A/C systems been installed. Our guests rave about the large outdoor shower. Inside the main house is an open concept living room with cathedral ceilings and the loft area above has a T. V. which is great for hanging out but also can be used as an extra space for house guests on the pull out futon.
4 Bedrooms (each with their own bathrooms) are furnished with plush mattresses and bedding (3 bedrooms are in the main house, the 4th is in the detached cottage) Detached cottage provides an additional bedroom and 500 sq ft of guest space.
With a screen door and AC unit, you have your choice of enjoying the cool breeze with the screen doors open or to cool off in the AC. Most past guests say this is the prime bedroom!

AND THERE'S MORE..........

2 minute drive or 10 minute walk to the famed Lucy Vincent Beach; 2 minute drive or 10 minute walk to the Center of Chilmark, the library and the Chilmark Community Center, where you can access a bus during the summer season multiple times a day, to any town on the island; Chilmark is the home to the picturesque working village of Menemsha, which is famous for fresh catch seafood and spectacular sunsets; If you enjoy walking trails, Chilmark has the most of any town on the island; A 10 minute drive out of town will bring you to the famed red clay cliffs with beach below to the town of Aquinnah, formerly known as Gayhead.

- "Location and house, especially the new kitchen addition that everyone hung out in, are just so comfortable and pleasant to spend time at." - "Was really wonderful in all aspects. Fit our family’s needs perfectly." - "So good! Best house, location, owners and four legged neighbors!" - "Located between Lucy Vincent Beach and the Chilmark Community Center, the house provided easy access to our favorite spots on the Vineyard. It's a beautiful property and the owners are easy to reach with any questions."

The air-conditioned accommodation is 15 miles from Edgartown Lighthouse. Free Wifi is available throughout the property and Menemsha Beach is a 9-minute walk away. Featuring a patio and garden views, the spacious vacation home includes 4 bedrooms, 2 living rooms, cable flat-screen TV, an equipped kitchen, and 3 bathrooms with a bath and a shower. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. Guests staying at the vacation home can relax in the garden or on-site spa and wellness center. Martha's Vineyard Airport is 8.7 miles from the property.

Spa • View • Accessibility • Guest Services • Other • Transportation/Shuttle • Oceanfront • Security/Safety • Parking • Internet • Ocean View • Fireplace/Heating

This spectacular newly renovated home in Menemsha on Martha's Vineyard, was originally designed by a Frank Lloyd Wright apprentice, and features 3 bedrooms and 2 bathrooms and a large open concept living dining area. A total renovation was completed in the spring of 2020 and the house features, a modern updated gourmet kitchen, 3 comfortable bedrooms, 2 new bathrooms, and an open concept living/dinning area with vaulted ceilings, bar area and a large dining area. There is a wrap around deck around the entire house and dramatic floor to ceiling glass in the living area. The house also features a loft area perfect for extra sleeping capacity, kids play area, work out area, or home office. There is also an amazing new outside shower, with a 16" rain fall shower head, plenty of hot water and a gorgeous modern design of wood/concrete/steel, that provides an incredible outdoor shower experience. The house is a short 5 min drive from the Menemsha Beach, Larsen's Fish Market, Homeport Restaurant, Menemsha Market, Chilmark Store, and Lucy Vincent Beach.

** The house was published in Dwell Magazine online in Sept 2020, a link to the article is here: https://www.dwell.com/article/the-shop-erin-pellegrino-makethink-759aeaad
** The house won 1st place in the 2021 Global Architecture and Design Awards, Rethinking the Future Awards 2021, for the Private Residence category. A link to the article is here: https://awards.re-thinkingthefuture.com/rtf-awards-2021-winners/the-shop-by-matter/
** The house was also published in AN Interior Magazine in Dec 2020, a link to the article is here: https://aninteriormag.com/marthas_vineyard_the_shop/

- 3 Bedroom, 2 Bathroom. (BR: 1 King, BR2: Queen, BR3: (1) bunk bed and (1) Trundle); Loft: 2 Queen, 1 Twin.
- Bedrooms (7) + Loft (5) = 12

- Access to Lucy Vincent Beach and Squibnocket Beaches (10 min away) (Beach stickers can be purchased at Chilmark Town Hall/Online). Mememsha Beach (5 min away) is open to public.

- Access to Menemsha Pond (via Cove Rd, deeded access)

- Beach Chairs, Beach Towels & Boogie Boards

- WiFi / Internet (High speed)- Available throughout the house (Plenty of bandwidth for Zoom/Teams calls)

- Chef's kitchen with 5 burner stove (all new appliances)

- Dishwasher, Microwave, Oven, Washer/Dryer.

- Coffee Maker & Keurig

- Comcast Cable/Flat Panel TV/DVD/Streaming

- Sonus - Audio System

- BBQ grill and outdoor seating

- Peloton exercise bike (new summer 2020)

- Spectacular Outside Shower (new summer 2020)

- Air Conditioning (new summer 2021)!

- ""The Shop" was the perfect location for our family to enjoy Thanksgiving weekend in Chilmark. Clean, modern well equipped home provided the perfect off season experience! Sadly, due to the time of year we couldn't enjoy the outdoor shower, but I imagine Summer is when "The Shop" really shines! Joe was a superb host, very responsive and filled with Island knowledge. It was a pleasure spending time at this home." - "Beautiful house. Comfortable. Easy check in. Just an excellent trip"

*** Please make an inquiry before booking. ***

This quintessential Up-Island 1920s summer house has panoramic water sunsets thanks to its hillside position overlooking the Vineyard Sound. (An East Coast novelty to look west over water.) The view spans the Menemsha Harbor, Menemsha Bight, Gay Head Lighthouse in Aquinnah, Elizabeth Islands, and, on clear days, all the way past Buzzards Bay to the mainland.

Day or night it doesn't get any more Vineyard than taking in the breathtaking views from the tranquil deck. The sun's final dunk into the sea is sometimes heralded—depending on the direction of the breezes—by the faint sound of applause up from Menemsha Beach picnickers who see a slightly earlier sunset from their lower vantage point a half mile away.

The house has three bedrooms—two upstairs and one downstairs—plus a queen sleeper sofa in the living room, and a small loft which overlooks the living room.

The house is full of light and air with a cathedral ceiling and many windows, plus the original, working stone and brick fireplace opens on two sides to the living room and the kitchen. There are two bathrooms, and a bathtub downstairs and an outside shower. There is a also a side deck with a shaded hammock.

Modern conveniences include wireless highspeed Internet, iTunes wireless audio, flat screen TV with DVD and DirecTV satellite, linens, washer/dryer, and dishwasher.

The house has been in our family for more than forty years, and our grandparents first stayed as renters in the early 1940s. In one family story, our grandmother reported a sighting of a possible German submarine one night to the Coast Guard station, only to be told drily by the dutyman that she had correctly decoded the (then) three-whites-a-red signal of the Gay Head Lighthouse. They named the house Menucha, as a biblical reference to rest and tranquility that plays on the village's Wampanoag name of Menemsha. As an umpire of the Sunday softball game, our grandfather was also famous for his idiosyncratic strike zone.

Hillside walking path to Vineyard Sound beach and Menemsha harbor, or take house bikes to Menemsha dock, Chilmark and Lucy Vincent ocean beach.

Keywords: house, summer camp, beach path, Menemsha, Chilmark, Upisland, Vineyard Sound, Menemsha Bight, Menemsha harbor, Menemsha jetty, Up Island, sunset views, beach pass, Lucy Vincent, Squibnocket, Gay Head Lighthouse, sunset

- "Not only was the property a slice of history, it was quiet and secluded enough that we felt like we had the area to ourselves. Perfect for a reunion trip with life-long friends. Nathaniel made us feel like we were truly guests in his home - welcoming us to enjoy the amenities as if we had known him personally. The kitchen was well-appointed, so, based on great recommendations from Nathaniel, we sourced most of our meals from local farm stands and spent time cooking and taking in the sunset from the large deck. We walked the shore to Menemsha Beach, took in the sites of the various other towns, went to the Alpaca Farm, etc. enjoying each for its different experience. There were five of us and we each, except for two twins in one room, had a private space. The garage was available for storing my bikes when it rained. When it turned cold & blustery for one evening, we made use of the fireplace and our comfort was never compromised. I can see why this is often booked so far in advance with repeat customers. We wanted for nothing all week. Thank you!"

Japanese inspired, Mid-Century Modern beach house with sweeping views of Menemsha pond, Vineyard sound, Aquinnah. Pond access via path. Stunningly bright and fully renovated in '20 with open floorplan, large deck, outdoor shower, parking. Walk to Menemsha Harbor, beach, fish markets, Galley. Large yard with lily pond, grape vines, blueberry bushes. Gas BBQ, plenty of lounge chairs & outdoor dining table. Beach sticker to Lucy Vincent & Squibnocket avail. This home is all about relaxing and enjoying nature. Central A/C, laundry, Wifi. Perfect for someone who loves the beach, ocean, nature, and a relaxed simple summer getaway. .4 miles (7 mins) walk to Pond.

2024 UPDATE: 4 brand new Anderson glass sliding doors installed this winter!

NOTE: Our smaller 2bed 1bath "Guest house" (ideal for 1-3 adult guests ) located across a stream over a small bridge + could be available to rent together if the dates align. VRBO 2604183 to search it.

Bike storage avail in Shed.

Note, repeat renter takes July & Aug. But our smaller guest house next door may be. Check out VRBO id 2604183

- "We loved our stay in Menemsha! We were within walking distance to the beach, fish markets, restaurants, shops and galleries in this small village in Chilmark. The house was comfortable and had everything we needed. It had a great deck overlooking Menemsha Pond and Vineyard Sound. The owner was very responsive and a pleasure to work with." - "We had a great stay at his property. The owner was very easy to work with, and we really enjoyed the house and yard. I would stay here again, and I have recommended it to others."

Located in Menemsha Village. This quaint cottage is located a stones throw from the Menemsha Harbor. It is the smallest and most affordable of the three houses we rent, yet offers great views.

The house has a living. room, kitchen area and bathroom on the first floor. The one sink is located in the kitchen area. The upstairs has a full size bed, skylight and windows on each side for a nice breeze. This room also has an AC unit, if needed. The stairs are narrow and somewhat steep. There is a picture provided.

Walk out your door and across the street to the harbor. Stroll the dock and end up at the beach to enjoy the sunsets...or you can stay right at home and enjoy the sunsets from the living room. Menemsha village has takeout, fish markets, shops and a wonderful family beach all in walking distance. Bus service is also available to take you to other parts of the island.

This cottage is comfortable for a couple or a single person. Also, all renters living in town have access, for a fee, to two exclusive beaches for a fee: Squibnocket and Lucy Vincent.

Cancellation Policy: A full refund will be given if we are able to re-rent a canceled week.

- "Perfect getaway." - "The time spent on this property in Chilmark last week confirmed what I love about this island. The view from the front porch toward Menemsha looks out over marshes with egrets and sea gulls, then beyond to the sea. We walked two minutes to the fish market for dinner which we cooked in the cottage. I woke up early one morning to watch the full moon descend to the horizon, then took a walk around the peer and the boats as the sun came up. The location is breathtakingly beautiful. The hosts, like the accommodations, gave us everything we needed, and nothing we didn’t. I highly recommend this cottage for those who love the quiet (October) beauty of the Vineyard."

Think resort-type elegance in a relaxed beach house vibe. 4BR, 3 bath, outdoor shower, 4-ft deep spa pool. Lots of light!

Chilmark is the laid-back end of Martha's Vineyard. The house is near Lucy Vincent Beach and Menemsha, the charming fishing village that will steal your heart.

Miles of conservation trails are steps outside the door. This part of The Vineyard is quite scenic and quiet.

Fully Air-Conditioned.

- "Wonderful stay that included children 7 and 10. House - a mid century light filled one level - was truly fully equipped ( games for kids, every cooking utensil) and artfully decorated. Pool was a great plus and the best beaches are nearby - the owner was very responsive and helpful." - "Warm and welcoming and a perfect family retreat. Comfortable and accommodating in every way. Light filled and surrounded by Chilmark’s natural beauty. Pool a huge plus. Thank you Harriet!"

Sunrises, sunsets and all-day sunlight grace this welcoming, elegant and beautifully-kept hilltop home. Its glorious wrap-around views extend over fields, meadows, ponds, far-islands and many miles of ocean -- rare indeed for the Vineyard.
Linger over breakfast in the bright, eat-in kitchen, or savor the panorama first-hand from the large dining table on the spacious, sunny deck, where lounge chairs also encourage lingering. Relax in 2 well-furnished and comfortable living rooms (one casual).

Catch frisbee on the expansive lawns, or savor the sunset from deep seating on the front porch. Seafood meals get merry around the gracious dining table, followed by drinks or cards in the tower living room. Your master bedroom is upstairs in the same lovely tower, or choose the 1st floor master with joining handicap-accessible bathroom. Each bedroom has ocean views, art, and comfortable beds.
Accessible daily: just down the hill is our intimate, private Beach #1, perfect for young and old (no surf), where you can also secure your kayak or small sailboat. Visit 2 local town beaches, or access our pristine, key-member Beach #2 for surf -- or quieter pursuits in the big adjacent pond.

A stand-out home, with an outstanding history, the house is an up-island landmark for its yellow-painted Queen Anne main house with red roof, and ball-topped tower. The grounds include a meadow-sized lawn beyond the main house, perfect for weddings and large, tented parties or celebrations. The Tower House estate property has changed hands only once since beginning as a multi-acre farm in the early 1800's. It has been our family's summer home for over 50 years (note: without central heat or AC, fans are provided in summer; space-heaters in shoulder seasons).
Our family's third generation now provides the property's responsive, active care.
Adding to this property's special character: access to two private, unspoiled Chilmark beaches. One of these is below the house (5 minutes by car), the other off South Road (15 minutes by car, key entry).

A wealth of activities nearby...: Countless memorable enjoyments are within close reach of the Tower House -- besides our lovely beaches! Sample wonderful restaurants, good casual eateries, an active community center, public library, and lively grocery store within 3 miles. Menemsha village is just across the pond, with charming shops, fishing charters, and just-caught seafood arriving off traditional trawlers as they dock. A brisk bike-ride from the house takes you to Lobsterville for 'insider' shoreline fishing, or to Aquinnah's beaches and magnificently colored cliffs. Farmer's markets, art galleries, craft and antique fairs start at West Tisbury mid-island, with exceptional shopping boutiques, good live theater, bookstores and ever-changing movies just beyond in 3 bustling towns. Nature walks and bike trails criss-cross the island, 3 golf courses offer tee-times, and history comes alive in charming byways and museums. Or simply relax at home, with ball games on the lawn, internet, good books, puzzles & games, shady nap-spots!

WEDDINGS.
September is the month of weddings at the property. During this month, weekly rentals of the Tower House run Wed. to Wed allowing for wedding event set-up/breakdown and a wonderful weekend celebration in-between! The 5-bedroom Tower House allows up to 10 people to easily stay on-site for all or part of the wedding week. This Victorian-era summer house with its ample gathering rooms and decks is without central heat or AC, so fans and space heaters are provided for weather that's extra-hot or -cold.
The expansive and level field adjoining the Tower House accommodates large dining, dancing and kitchen tents as well as additional bar stations, lounge areas, etc. The marriage ceremony most often takes place overlooking the water-and-islands view, on a side lawn with ample space for guest seating. The property's vine-trimmed stone walls, planting beds, arched garden arbor and gingerbread-trimmed porches add further areas for exceptional family and wedding party photography.
Our guest book attests to our many wedding families' joyful memories made here!

- "We had a wonderful visit! Such a great family house that wonderful memories were made at. We will definitely return!" - "We had an awesome week at the Tower House in Chilmark. The house itself housed our two families (4 adults and 6 2nd grade to baby boys) with ease. Everyone had space both inside and out. The kids ran through the grass, played in the hammock and ate dinner watching deer and boats in the distance. We enjoyed the porch, kitchen and back deck. Bob was in close contact and Charlie the caretaker was a fast and lovely resource. The gem of this property is the key to Hancock Beach. We’ll never forget our time there and will look to rent again from owners that over the spectacular bonus. Thank you for granting us such beautiful memories."

Relax at this retreat in the woods when you are not spending time on Lucy Vincent Beach or enjoying the sunset down the road in Menemsha. Surrounded by stone walls and walking paths over 20 acres of woods, this spacious three bedroom house is next to a stream (with a campfire ring) and is cut off from the world down a quarter-mile driveway. After a day on the deck or at the beach, enjoy the rustic outdoor shower.

If you are looking for a private spot, this secluded retreat with lush greenery and simple elegance will rejuvenate your spirits. A long private driveway leads to ample parking for this charming New England house.

This light filled home with wide open spaces sleeps 6. The main level includes a master bedroom with a queen size bed, a quiet room with futon couch surrounded by a library, and a bathroom with a full size tub. The open floor plan includes a spacious and sunny living room with various couches and a cozy stove for the occasional cool nights, a piano, a large dining room table, and an open kitchen with a new fridge, earthen dishware, coffeemaker, microwave, blender, toaster, and a fondue set. The entryway stores all shoes and coats out of the way. A separate laundry room with washer and dryer is well stocked with environmentally-friendly laundry detergent. In a hallway closet, a sound system harbors many vinyl records and is connected to speakers in the main room. The second floor has two bedrooms, one with a queen size bed, another room with two twin beds. There is a second bathroom with a step-in shower.

The outdoor living space is breathtaking, comprised of a deck off the kitchen, with a large table and seating for 6, a grill, enclosed hot and cold outdoor shower, and a large lawn area. Our hammock is ideal for an afternoon nap or diving into one of the many books from the house. A tire swing brings playful charm. Interesting mossy stone walls border the lawn area to the wild wooded area beyond. A few steps into the woods, a trail leads to a stream and benches around a fire ring fit for a cozy campfire and perfect for s'mores and singalongs. Trails and a small foot bridge across a bubbling stream are ideal for contemplative walks.

This property is only minutes away from Menemsha Beach with its famous sunsets, Lucy Vincent Beach, the Chilmark public library with many public programs for all ages, and a short drive to the legendary West Tisbury General store. Art galleries, town beaches and many restaurants nearby will keep everyone entertained. Short drive to Cronig’s supermarket.

We use only environmentally friendly cleaning supplies, allergen free bedding and have all hardwood floors. A small flock of guineas keep any ticks and mosquitoes away from the house!

Renters are eligible for passes to Lucy Vincent Beach. Beach towels included.

- "My family of five enjoyed our stay at this home in Chilmark. The house fit us well and was lovingly decorated and very comfortable. We enjoyed the nearby beach, Lucy Vincent, the general store and tavern, and the charming town of Menemsha. Little things i especially appreciated are - separate den for TV, extensive book selection, including a lovely children’s section, games and toys for the kids, a separate laundry/office room, ample space to store clothes and suitcases and a great outdoor shower."

Small, but cozy bedroom with smart TV, kitchenette with microwave, refrigerator, toaster oven and Keurig coffee maker.
Use of heated swimming pool. Outdoor shower.
Weber grill and table for two private sitting area.
Short walk to Peaked Hill (highest point on the Island) walking trails.
Walk-on pass to Lucy Vincent Beach.
I do not recommend staying here without a car. The property is down a long dirt road and not in walking distance to public transportation.

- "Very nice apartment, the space was clean and Ronnie the host was very nice." - "This is a great property for an individual or a couple looking to explore the island!" - "This is a great little place to stay in Chilmark for a couple. Ronni was responsive and helpful when we needed it. The pool area was nice to lounge in. We'd stay here again" - "Clean, quiet, and respectful hosts!" - "My best friend and I had such a lovely time staying at Ronni’s place in the quieter town of Chilmark! It was such a fabulous bonus to have access to her in-ground pool, outdoor shower, and a guest pass to Lucy Vincent beach (arguably the most breathtaking on the island, especially for sunrise). We preferred the location being a short 20 minute drive away from the typical tourism, and felt we really got to see the most of the island being out in the suburbs. With that being said, we definitely would say a car is a requirement; not just a recommendation. A lot of Ubers/Lyfts would cancel our rides due to location, and the shuttle bus wasn’t running on the times scheduled. We didn’t foresee coming without a car to pose such an issue in a world of ride-shares and public transportation, but if you choose to stay at Ronni’s (which you should!) you must bring a car. Would absolutely stay here again! Thanks Ronni!"

This secluded Chilmark cottage, beautifully landscaped, sits on a high point off of Meeting House Road with a sweeping view of the Atlantic ocean. The house is light-filled and airy, with comfortable living spaces, a master bedroom with queen bed, a smaller room with one full bed & one single bed. Access to private dock on Chilmark Pond over which you boat in our kayaks/canoe to Hancock Beach. Cook's kitchen and outdoor shower make this a vacation dream.

- "The house was clean and exactly as advertised. The owner did a great job with our reservation, communication and having the house ready for us." - "The views, the porch, the breezes, the kitchen, were all beautiful. We are long time visitors to the island and this property is first rate. Can't wait to return. Thank you!" - "Lovely, comfortable, scenic home in peaceful setting." - "This house was a perfect up-island getaway. We were more impressed with the location and inside of the home when we saw it in person. Nancy was excellent communicating updates, rules, etc throughout the year leading up to our vacation, checked in with us when we arrived and gave a reminder the day before we left. The house is stocked with absolutely everything you could possibly need- kitchenware, linens, beach supplies etc. The pond/ beach access is one of the most beautiful and exclusive locations on the island and we loved using the canoe to have beach days. We wished we could have stayed all summer!"

Best view of sunset on island.
Fully equipped modern house; air conditioning, large deck, barbecue, outdoor shower, linens, towels, beach chairs, kitchen with dishes, flat ware, cooking utensils, pots, pans, microwave, gas stove, etc high speed internet, cable television. Master bedroom with queen bed, second bedroom with two twin beds, sleeping loft with two twin beds, den with queen pull-out sofa bed. Very short walk down path from house to private beach (end of Menemsha Beach) and walk down beach into Menemsha Harbor in 5 minutes.

- "My wife and two sons had a great stay at this house and hope to return. It has everything you need in a vacation house, and is just a short walk to the quiet end of Menemsha Beach, which we visited daily. The open kitchen/dining/living area works well for groups, and the AC was nice to have during some of the warmer moments. All in all a fantastic trip." - "Fantastic place!" - "Gem! Came here to celebrate birthday week, and loved every bit of it. Perfect sunset, private pathway to beach, and modern interiors. Everything was great and the host was soo good with communication! Thank you for a great stay!"

Chilmark Guest House

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Tucked away in a private glen on three secluded acres, this light-filled home in Chilmark is Martha's Vineyard at its most peaceful. It's the perfect escape for beach-goers, as it sits within minutes of Menemsha (three miles), Lucy Vincent Beach (four miles), and Squibnocket Beach (five miles).
The house enjoys a beautiful, natural setting, with thickets of woods surrounding the grassy lawn. On summer mornings, ride your bikes or walk less than two miles to the tranquil expanse of Great Rock Bight Preserve. Upon your return, linger outside on the deck and sip a steaming cup of coffee in a rocking chair.

It's a joy to come home after a day at the beach, as you light the gas grill, set the outdoor table for a sunset dinner, and watch the kids release any lingering energy on the outdoor play structure. Back inside, lofty ceilings, exposed cross beams, and large panes of glass bring in an abundance of light and nature. As a result, you'll feel surrounded by the island's beauty as you cook in the kitchen, play board games at the table, and stream movies in the living room.

Both bedrooms open to the deck, one of which is a charming children's room with bunks and a selection of toys and books. A private washer/dryer and complimentary WiFi are provided for your comfort and convenience as well.

Things to Know

If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.
Parking notes: There is free parking available for 3 vehicles.

Please note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

- "Private with beach access minutes away." - "We had such a lovely time staying at this house. It was absolutely immaculate inside and appointed with everything we could need and more. The house is light and airy inside, which helped when we had a few days of rain. The location is secluded in the woods (be careful, we did find ticks on us) but a short drive away from the beaches. We will definitely be back " - "This was an amazing house to stay in. The kitchen is well equipped, the bathroom has no issues, the kids' bedroom has a few toys, our bedroom had a huge comfortable bed, and the living area offers a fantastic view. The BBQ is working well—it is brand new. The swing and slide outside were a great hit. I wish to come again. The location worked perfectly for us."

The "Grapevine" is located on a private road in Menemsha, It was completely rebuilt not to long ago. originally it was a shack purchased from the government in 1950 and dragged on a flatbed truck. Since my wife and I took ownership we rebuild the home and added a foundation, an addition, it was quite an undertaking trying to preserve the look of the neighborhood. With the help of a wonderful builder and designer/architect together we have made a fantastic home that dreams are made of. The home has 3+ generous size bedrooms all with large full private bathrooms, Fully central air conditioned , 2 of the bedrooms are located on the second floor, the Master bedroom on the second floor also has a private deck with fantastic water views, the second bedroom on the 2nd floor has water views, 1 bedroom is located on the first floor with a private large full size bathroom and private Epi wood deck and wonderful water views. As well as the Open concept living with a chef's Kitchen, living room ,dining area and fireplace area all with stunning Brazilian cherry hardwood floors plus an additional 1st floor 1/2 bathroom and laundry room. From the 1st floor exit out the Sliding doors to your very large spacious deck with propane gas grill, wonderful views to Vineyard sound and Elizabeth Islands as well as excellent stargazing at night . Or exit out to your side Epe wood Screened in porch with tons of seating ,exit out the back to your Private enclosed Epe wood Outdoor shower and smaller deck and stone walls. The Basement/lower level has an extra living room/ bedroom equipped with sofa ,chairs and a flat screen tv, second refrigerator and large open area. Take a stroll down the Private Trail, pass by a barn with animals, walk out to a meadow and to Menemsha Beach. All the amenities you could want. You will be able to get Beach Passes to the famous Lucy Vincent Beach in Chilmark or squibnocket beach. Walk/drive to Menemsha Beach and Village, boat rentals, fishing, Eating, swimming bike ferry and so much more.... Parking available for 6 cars. Sited on over 3/4 acres professionally landscaped lot with water irrigation ,stone walls manicured lawn with blossoming garden flower beds all summer long. Fun things everyone does is go to Menemsha beach or Homeport restaurant, Stroll down the docks grab fresh seafood at menemsha fish market/Larsons fish market byob and watch the sunsets or catch the bands that play during special times in the summer only moments away. Fish off of the Jettie, kid friendly area or shop in the local stores such as Menemsha Blues, Pandoras box .Bike ferry over to Lobsterville. While at the beach the Menemsha Texaco has Ice cream, drinks and of course gasoline or just a moment away is The Galley with ice cream food and a rear deck for eating and water viewing which is next to the jaws movie production it's all right there just to name a few.

- "This house was comfortable, clean, private and well equipped. We spent hours on the deck enjoying the views to the water, the breeze and the wild turkeys walking through the yard. The walk down the road and across the marsh to Menemsha at sunset was glorious. The owner was quick to respond to all questions and made check-in very easy. We look forward to returning." - "We enjoyed and appreciated greatly the beautiful and comfortable Beach Plum Lane home, including the open living and dining area, the well appointed and designed kitchen, and all amenities (AC; grill; etc.) The grounds are lovely. This is a great place for a wonderful vacation."

Well located off beloved Middle Road, property embodies all of the natural beauty of Chilmark: old stone walls, perennial plantings & mature trees. Property abuts 100 acres of Sheriff's Meadow Conservation land. Main house has three bedrooms each w ensuite baths. A separate private guest cottage w a bedroom, full bath, covered porch, kitchenette & back deck with outdoor shower. Main and guest house have air conditioning. Guest house & little summer bunkhouse meant for summer use. Main house is winterized and available for year round use. Each bedroom and the dining room has it own split air conditioning unit. Upstairs 2 bedrooms each with king beds, downstairs bedroom has 2 twin beds. The guest house also has a split AC unit, but is not winterized. The guest house will not be available for use from October through May. The sweet little bunkhouse does not have air conditioning nor it is winterized.

- "The location was perfect. The home was lovely and kitchen was very well appointed which was great for our family as we love to cook. The Guest House was a great extra space and was perfect for our son and SO. We would definitely stay here again. John" - "The property is amazingly beautiful and fully stocked with all that you need for cooking, a day at the beach, or playing games and watching TV on a rainy day. Sam was a very attentive host and exceptional to work with. We highly recommend this property and host."

Designed by a student of the famous architect Walter Gropius, our house was built in 1949. The house is open and light, with floor to ceiling windows and sliding glass doors, a fireplace with a 50's "conversation pit" for cozying up in, perfect for an evening of charades or quiet reading. The giant dining table has room for a large family to spread out, or have a group of friends over for a long summer dinner. The multiple couches and seating areas suit a grandma reading aloud to small ones while in another area teenagers chat or grownups have cocktails on the porch, looking at the serene view of the nature preserve across the pond. There is a good layout for two families with children to share the house. It is also a romantic spot for two people to enjoy a beautiful private place.

We have lots of amusements and we are TV free. We have a fantastic collection of children's books, from picture books to favorite read-alouds and young adult books. There is a croquet set and lots of rainy day games and little kid toys. We have a modest but peaceful writers cabin/shed that can be used for quiet work time (no Wi-Fi there).
Our point of land the house sits on (see map) is 9/10ths surrounded by water, Menemsha Pond on one side and Quitsa Pond on the other. Part of the 11 acres is conserved land and the view is beautiful from anywhere. Children love exploring the mowed paths and most likely will find the hidden tree house. Chockers Point has always been occupied by sailors and you can beach a sunfish easily. It is also excellent for jumping into a kayak and exploring the ponds. We provide 2 single kayaks. We also have clamming supplies, our beach is rich with steamer clams in the summer.

This house is perfect for small children, the third generation of our family is now proving that. Children can toddle or paddle about on the private beach on Menemsha Pond, 'Short Beach' (we share it with the other houses on our short road but there is always room) where we all learned to swim. Beach passes for the restricted town ocean beaches are available for purchase from the town with your lease. The free Menemsha public beach and it's great fish markets are nearby. There is a fantastic local farmer's market in nearby West Tisbury twice a week.
Chilmark has a wonderful community center summer camp program that runs every weekday morning for children up to 12, where your kids can play sports or make glorious messes. You can sign up by the week. Retrieve your children at noon and go across the street to get a pizza for lunch from the popular Chilmark store. The Chilmark library is excellent and has a lot of kid's programs.

In the fall it is a great spot for quiet adult time. The island is more peaceful and the colors are spectacular. The weather is generally wonderful then and if it is not the wood stove is exceedingly cosy.

This is not a fancy house. It is built very simply, in a style of '50's summer camp minimalism. The comfortable furniture is a little worn, but it's classic style (Eames etc) echos the house. We have only one full and one half bath and a beautiful reconstructed outdoor shower. The house has a very warm feel that we hope you love as we do.

We no longer provide Wi-Fi. Because we are located on a peninsula, the Wi-Fi was provided via a hotspot and we were not able to guarantee the quality of the Wi-Fi for multiple simultaneous users. We have decided that because it is very simple to either use a smartphone as a Wi-Fi hotspot or bring an additional Wi-Fi hotspot as part of a standard phone plane, it is much more reliable for people who need to work remotely to provide their own Wi-Fi and that way they can monitor if other guests are sharing the Wi-Fi with them. Both Verizon and ATT get good service at Chockers Point. Please reach out if you have questions about this.

We do not rent for under 1 week, NO weekends. We give discounts for long rentals.

Keywords: Summer House, Derby, Kayaks, Dogs

- "Words can’t describe this unique treasure of a home, but I’ll try: perfectly situated overlooking Menemsha Pond, private but easily accessible, and filled to the brim with charm and family history. We’ve never achieved such complete relaxation so quickly on a vacation. Hazel was so helpful before and during our stay with tips for first time visitors to Martha’s Vineyard. Hoping we can return again next summer." - "Wonderful house with beautiful views. Simply fantastic."

Charming rustic cottage located a short distance off South Rd just past Abels Hill in Chilmark. Chilmark is very rual with rolling hills and stone walls. Water views from upper deck. Access to Lucy Vincent beach a mile down South Road and Squibnocket beach by purchasing stickers at town hall.The sound of sheep during the day and the ocean waves at night is very soothing. Views of the night sky can be wonderful since there is no light pollution. A short walk up our road there are scenic and wooded Landbank trails.

- "We had a fantastic stay at Polly's house. It is a bit of paradise on MV. If you like rural charm, beautiful beaches and quiet relaxation, this is the place for you. We visited every part of the island and each time, one of the four of us would say, "I am so glad to be returning to our secluded spot in Chilmark. Polly is super chill and easy to communicate with. Total relaxation!" - "The rustic house is clean, charming, warm, and inviting. The deck view to the ocean is peaceful and lovely. The location is fantastic for exploring all up island Vineyard spots -- as hikers, swimmers, beach goers, and bikers, this was ideal for us, since we like to avoid going into the crowded towns in summer. Polly and Craig were extremely friendly, hospitable, and helpful. All in all a wonderful place!"

Menemsha cottage adjacent to Menemsha Harbor in the Town of Chilmark. Historic village cottage for four people. 100 feet to Menemsha Harbor and a two minute walk to the beach. Also, access to two exclusive town beaches (for Town Fee): Squibnocket and Lucy Vincent.

Walk out your door and across the street to the harbor. Stroll the dock and end up at the beach to enjoy the sunsets. Our village has a restaurant, fish markets, art galleries, shops and a wonderful family beach, all in walking distance. Bus service is also available to take you to other parts of the island.

Cancellation: A FULL refund will be given if we are able to re-rent the week cancelled.

Keywords: House

- "This is THE place to stay for those who love the little fishing village of Menemsha. The location cannot be beat - you can walk to everything: the beach, sunsets, Menemsha Fish Market, Larsens, Homeport, Menemsha Galley, and there are little shops to explore, as well the fantastic art at Ruel Gallery just steps from the cottage. The house has everything you need for a comfortable stay. Check in/check out was seamless, the house was clean and well stocked, and Barbara is an absolutely lovely host! We will be back to enjoy it all over again!"

The Little House was built in 1960 as a one room studio/cabin. Since then a gourmet kitchen wing has been added, as well as a detached bunkhouse. The main structure has an open floor plan with bright living and dining room area with skylight and a woodstove, and a full kitchen with center island. Through a covered causeway is a large master bedroom with a queen bed, and just off the back, past the outside shower, a detached bunkhouse with a twin bunk bed, and double bed. The property is perfect for two couples or a family with kids.

While having an authentically vineyard feel, the Little House has been updated to meet the needs of our time, with a heat pump system (including in the bunk house) for cool or sultry nights, dishwasher, wifi and television.

The large deck is great for lounging but there is also a deeded right of way to Menemsha Beach (ten minute walk) . Lucy Vincent and Squibnocket beaches are ten minute drive away. (Beach stickers are available at the Chilmark Town Hall.)

- "Peaceful location near conservation trail and a short drive to Lucy Vincent and the Chilmark Store. Clean, spacious and comfortable for our family of six adults. The owner mailed the key and information about the house ahead of our stay, which was helpful. Highly recommended!" - "We received a personal welcome, and enjoyed every aspect of our stay." - "We loved this cottage. Simple but totally authentic Vineyard. The kitchen has everything we needed, and more. Everything was comfortable and homey. A delightful place."

A wonderful two bedroom cottage nicknamed The Palace ,and it truly is one!
on a private estate with private access to the Chilmark Pond barrier beach facing the Atlantic. newly renovated, updated, modernized and reimagined. Air conditioning and two comfortable bedrooms, one with a Queen, the other with two single beds. and a large living room kitchen between. A large rear deck overlooking an expansive lawn, and all amenities, including a canoe and paddles, and an outdoor shower comfortable deck furniture. Very private yet only moments to either Chilmark center or West Tisbury center. A perfect retreat. Nicely done!

- "Newly renovated small cottage— 2 bedrooms and one bathroom (outdoor shower too). Canoe and kayaks provided. Quiet location with extensive grounds. Convenient to both Alley’s and Chilmark Store. Great deck with furniture, table, and large gas grill. Nicely decorated with everything you need. Highly recommended."

This newly renovated one bedroom guest house with open-style living is the perfect Chilmark get away for a couple with one or two young children. With cathedral ceilings, the first floor great room has a fully equipped kitchen with breakfast spot, separate dining and living areas, pull-out sofa, half-bath with full laundry, and access to a private covered porch for cookouts and gatherings as well as an outdoor shower. The second floor has a loft style bedroom with a king bed and full bath. Short drive to Menemsha harbor, Beetlebung Corner and Chilmark General Store, as well as Lucy Vincent and Squibnocket Beaches. Beach sticker for town beaches available. Main house, approximately 200 feet away, is occupied but the guest house remains private.

Fireplace/Heating • Internet • Child Friendly • Security/Safety • Kitchen • Bedding/Linens • Laundry • Wellness Facilities • Air Conditioner

Your cozy retreat in Chilmark with 1 bedroom featuring 3 comfortable twin beds upstairs in the loft. This charming house offers essential amenities like a washing machine, AC, WiFi, half bath and beautiful Outdoor Shower. Experience a wonderful stay in this enchanting property, perfect for solo travelers or couples looking for a peaceful getaway. We're happy to assist with any questions while you stay at our house. You have access to the properties 1000 feet of private South Shore Beach, truly one of the most beautiful beaches on the East Coast.

Security/Safety • Wellness Facilities • Child Friendly • Laundry • Parking • Air Conditioner • Barbecue/Outdoor Cooking • Bedding/Linens • Tv • Internet • Fireplace/Heating