Best Vacation Rentals in Oak Bluffs

This oceanfront bed and breakfast in Martha’s Vineyard is just a 5 minute walk from the ferry and features free Wi-Fi and full daily breakfast. The Niantic Park Tennis Courts are a 10 minute walk away. Each room at Isabelle’s Beach House has a flat-screen cable TV and refrigerator. They are decorated in bright colors and beach themed decor. Select rooms have a balcony or sitting area. Admire the ocean views of the large front terrace at Isabelle’s Beach House B&B. Relax in the communal living area or read a complimentary newspaper by the fireplace. The Flying Horses Carousel, a national historic landmark, is a 7 minute walk from the bed and breakfast. Shops and dining in Oak Bluffs center are within a 10 minute walk of the property.

- "We will be back! What a great place to spend your vacation" - "Excellent location by the iconic and historic Inkwell Beach.The staff goes beyond to meet your needs" - "A beautiful traditional property in a fabulous beach location. Very relaxed with everything you need for a leisurely bre" - "The location on the beach, the porch allowing al fresco dining, friendliness of Coleen were perfect." - "Super cozy super sweet" - "Quaint with some missed goals."

Sandy fun near Cottage Museum and Oak Bluffs Ferry Terminal
Along with a snack bar/deli, this smoke-free hotel has coffee/tea in a common area and a meeting room. WiFi in public areas is free. Other amenities include self parking, concierge services, and a 24-hour front desk.
Summercamp offers 95 accommodations with bathrobes and hair dryers. Beds feature premium bedding. Televisions come with digital channels and Netflix.

Bathrooms include showers. Guests can surf the web using the complimentary wireless Internet access (speed: 50+ Mbps). Housekeeping is offered daily and hypo-allergenic bedding can be requested.

- "Fun last minute stop" - "We had an awesome stay! Everything was so clean and the staff was so kind. My only complaint is the walls are a bit thin, so we could hear our neighbors talking. Besides that, it was great, the atmosphere is very comfortable and fun. We absolutely adored the game room. Will definitely be coming back! " - "The front desk completely accommodated our desire to be in the main building vs the annex. They provided us with a king room with a view on the 3rd floor despite not being fully opened on the upper floors. Everyone was super hospitable & friendly. We will definitely return for another stay. "

Located in Oak Bluffs and with Oak Bluffs Town Beach reachable within a 6-minute walk, The Oak Bluffs Inn has concierge services, allergy-free rooms, a garden, free WiFi and a shared lounge. Featuring a terrace, this 4-star inn has air-conditioned rooms with a private bathroom. Guests can enjoy city views. At the inn, rooms contain a closet. Certain rooms are equipped with a kitchenette with a fridge and a microwave. An à la carte, continental or vegetarian breakfast is available at the property. Edgartown Lighthouse is 6.2 miles from The Oak Bluffs Inn. Martha's Vineyard Airport is 5 miles from the property, and the property offers a paid airport shuttle service.

- "The host is the best - Erik is attentive to details and very responsive." - "The oak bluffs inn exceeded all of our expectations and we will definitely be back!" - "A perfect setting for our maiden voyage to Martha’s Vineyard!" - "Fantastic stay." - "Highly recommended!!" - "It was relaxing and fun." - "Distinctive inn, welcoming host, great location." - "Cozy and comfortable with care given to make your stay a memorable one!"

Hotel with free breakfast, steps from Inkwell Beach
Coffee/tea in a common area, a business center, and a 24-hour front desk are available at this smoke-free hotel. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include tour/ticket assistance and a garden.
Pequot Hotel offers 32 air-conditioned accommodations with hair dryers and irons/ironing boards. Guests can surf the web using the complimentary wireless Internet access. Bathrooms include showers and complimentary toiletries. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "Charming, convenient, and comfortable. Staff is very friendly and accommodating. Breakfast has variety and is tasty. We would stay here again." - "Location is perfect - a quick stroll to the main street and the beach in Oak Bluffs. Beautiful property surrounded in flowers and friendly staff. We enjoyed the daily breakfast and freshly baked cookies! One downside was there was no mini fridge in the room, but they did have an ice machine. "

Yellow Brick Road House offers accommodations in Oak Bluffs, 7.5 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 10-minute walk from Eastville Beach. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with free toiletries. A flat-screen TV with streaming services and DVD player, as well as an iPod docking station and a CD player are provided. There's also a seating area and a fireplace. Martha's Vineyard Airport is 5 miles away.

- "It is a beautiful and peaceful place to stay!" - "Great house, great service when needed, close to everything. Would definitely stay there again or recommend to friends" - "Beautiful house, comfortable, perfect place to land after a hectic day and perfect place to relax if you just need to st" - "I would stay here again" - "Very cute house. Great value for the money. Needs some minor work." - "The home & location was nice! However, the cleaning team did not do a good job cleaning the bedding & bathroom b"

Hotel in Oak Bluffs, steps from Circuit Avenue
Along with self parking, this smoke-free hotel has coffee/tea in a common area and a garden.
MV Surfside Hotel offers 37 air-conditioned accommodations, which are accessible via exterior corridors and feature irons/ironing boards and complimentary toiletries. Accommodations are furnished with desks and desk chairs. Beds feature down comforters. Televisions come with cable channels. Housekeeping is offered daily and hair dryers can be requested. Cribs/infant beds (complimentary) are also available.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "Great staff Everyone from check in to the cleaning staff, all very friendly and helpful " - "My friend and I enjoyed our stay very much and we plan to make it a tradition! It was exceptionally Clean, efficient and at a wonderful location! The Garden was absolutely the best place to catch the morning sun, relax and enjoy the ocean breezes and read a book! Thank you!!" - "Great stay! Clean room, perfect location. " - "We stayed here until our house in Katama was ready. Our two day stay was perfect. It was a great suite, with a large room and living room. Very nice!"

Canary Cottage offers accommodations in Oak Bluffs, a 13-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse. This vacation home offers accommodations with a terrace. The vacation home also offers facilities for disabled guests. The vacation home features 5 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are featured in the vacation home. For added privacy, the accommodation features a private entrance. Martha's Vineyard Airport is 5 miles away.

- "If you are looking for luxury, with many modern amenities, this is not it. However, it is clean, quiet, convenient and" - "It was an ok stay for one week."

Hotel in Oak Bluffs
Concierge services and free WiFi in public areas are available at this smoke-free hotel.
Housekeeping is available on request.
Morgan Hotel offers 14 air-conditioned accommodations with designer toiletries and hair dryers. Each accommodation is individually decorated. Beds feature premium bedding. 43-inch flat-screen televisions come with cable channels.

Bathrooms include showers with rainfall showerheads. Guests can surf the web using the complimentary wired and wireless Internet access. Housekeeping is provided on request.

- "It was nice" - "Love the location in Oak bluff. Rates are reasonable. I would like to see a 2nd chair in the room for relaxation, watching tv, " - "Parking could be a challenge during a busier time, but is was fine for our stay. Attentive staff, clean, overall positive experience!" - "The OpenKey is great idea but the app should do a better job with icons to provide visibility to all doors that might need to be accessed. "

Marthas Vineyard Apt about 1 Mile to Inkwell Beach! offers accommodations in Oak Bluffs, 7.3 miles from Edgartown Lighthouse. Free Wifi is available throughout the property and Eastville Beach is a 17-minute walk away. The air-conditioned apartment consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a shower and a hair dryer. Towels and bed linen are provided in the apartment. The property has an outdoor dining area. Martha's Vineyard Airport is 6.2 miles away.

- "Great location and peaceful" - "Excellent location for a family vacation on Martha’s Vineyard" - "Perfect for a family trip" - "Very clean and well stocked unit." - "Nice place to stay on Martha’s Vineyard" - "Nice place, a bit musty. Great location."

Hotel in Oak Bluffs
This smoke-free hotel features free WiFi in public areas.
Housekeeping is available on request.
The Attleboro House offers 10 air-conditioned accommodations with blackout drapes/curtains. Guests can surf the web using the complimentary wireless Internet access. Bathrooms include shower/tub combinations. Housekeeping is offered on request and irons/ironing boards can be requested.

- "Beautiful Gingerbread House, Lovingly managed, it’s quite simple accommodation but it’s clean and in a great location. We will return! Cool drinks available in the entrance, kind staff, relaxed and easy going feel. Perfect place to chill out. The view over the sea is great too. Lovely front terrace. Thank you for being so welcoming! We stayed in July 2023. " - "Property location was ideal, accommodations were spotless and staff was welcoming and responsive."

Fresh Pond Chateau Renovated Bright and Cozy Home offers accommodations in Oak Bluffs, 5.1 miles from Edgartown Lighthouse. This vacation home offers air-conditioned accommodations with a balcony and free Wifi. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. A TV is featured. The accommodation is non-smoking. Guests can also relax in the garden. Martha's Vineyard Airport is 3.1 miles away.

- "Great Spot at the Vinyard" - "Great Place. I would stay here again. Property Management reachable at all times."

Resort with free parking, near Inkwell Beach
This smoke-free resort features outdoor tennis courts, a seasonal outdoor pool, and laundry facilities. Free WiFi in public areas, free self parking, and a free beach shuttle are also provided. Additionally, a 24-hour front desk, a garden, and charcoal grills are onsite.
Housekeeping is available on request.
The Island Inn on Martha's Vineyard offers 51 accommodations with air conditioning. Cable television is provided.

Bathrooms include bathtubs or showers. This Oak Bluffs resort provides complimentary wireless Internet access, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices). Housekeeping is provided on request.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "The staff is absolutely wonderful. Beautiful Property. Well worth the money!" - "Love how quiet it was and it was a great convenient spot with a walkable distance to beaches and also bus stops in case needed. The Inn was beautiful, well kept and clean and staff was friendly. Fair pricing, gorgeous views. Definitely recommend " - "We love the island inn, it was very cozy, private, and had a great restaurant within walking distance, Nomans! Really enjoyed their drinks and our first lobster roll"

Breezy Oak Bluffs Condo - Steps to Inkwell Beach! is located in Oak Bluffs, just a few steps from Oak Bluffs Town Beach and 5.9 miles from Edgartown Lighthouse. This beachfront property offers access to a balcony and free Wifi. The apartment features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with free toiletries. The property offers sea views. Martha's Vineyard Airport is 5.6 miles from the property.

- "Great relaxation & rest time!" - "Overall, I enjoyed the location and accommodations and would stay again." - "Awesome" - "Comfortable and modern living across from Ink Well Beach in Oak Bluffs Martha’s Vineyard. Close to everything… with mil"

Located in Oak Bluffs, enjoy what this 2-bedroom apartment has to offer. With a washing machine, WiFi, AC, iron, hair dryer, and heating, this wonderful and enjoyable property provides all the comforts you need. The bathroom is equipped with everything you'll need for a comfortable stay. Kickback, relax, and enjoy everything Oak Bluffs and our apartment has to offer.

- "I stayed there with my 18 yo son. The house is brand new and doesn't look like anyone has ever stayed there. The owner's are wonderful and you can't beat the location. It's 10 min to Vineyard Haven. 10 min to Oaks Bluffs and 10 min from Edgartown. This house feel like staying in a high end hotel and the interior if beautiful. I can't recommend this house enough." - "This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"

Oak Bluffs Beauty is located in Oak Bluffs, just a 14-minute walk from Eastville Beach and 7.2 miles from Edgartown Lighthouse. The vacation home has access to a restaurant. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a walk-in shower and a hair dryer. Towels and bed linen are offered 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 Oak Bluffs, like cycling. The vacation home has a picnic area where you can spend the day outdoors. Martha's Vineyard Airport is 5 miles from the property.

- "Good location and nice house but terrible customer service"

15 minute walk to Oak Bluffs town and beach. 2 queen beds. 5 minute walk to the bus. 5 minute walk to library. 1 bedroom upstairs apartment with 750 square feet of living space. It’s above a garage (garage not accessible). 2 outside parking spaces available. Upstairs deck with grill and 4 chairs. 1 queen bed in bedroom. 1 queen pullout sofa bed in open LR/kitchen. Outside yard available to enjoy next to the shed. Our neighbor has a rooster across the street.

- "Perfect place for us to stay as we visited our son who is playing collegiate summer league for MV. Great apartment! Very accommodating. Quiet spot. Super clean and comfortable. Easy walk into Oak Bluffs and to the beach. Definitely enjoyed our stay!"

Set Sail offers accommodations in Oak Bluffs, 6.7 miles from Edgartown Lighthouse. The vacation home has access to a restaurant. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. Guests at Set Sail will be able to enjoy activities in and around Oak Bluffs, like cycling. A children's playground is also available for guests at the accommodation. Martha's Vineyard Airport is 3.7 miles from the property.

- "Wonderful, Great Location, Spacious Home!"

The Rootskeller

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Nestled at the end of a tranquil cul de sac, this charming cabin-style home in Oak Bluffs, MA, offers a warm and inviting ambiance that welcomes you from the moment you arrive. With its updated exterior and cozy interior, this property serves as the perfect home base for those eager to explore the beauty of Martha's Vineyard. The open layout and quaint decor create an inviting atmosphere, ideal for unwinding after a day filled with adventure. The fenced in yard is the perfect place to relax and watch the children playing. Enjoy movie nights on the flatscreen TV or simply relax with loved ones in this delightful retreat.

Conveniently located just a mile from the Oak Bluffs Ferry and the picturesque village green, you'll find yourself in close proximity to the island's vibrant entertainment and dining options. The famous gingerbread homes of Oak Bluffs are also nearby, adding a touch of charm to your stay. For beach lovers, Inkwell Beach is just a short drive away, perfect for soaking up the sun and enjoying the ocean breeze. If you're a golf enthusiast, the immaculate greens of Farm Neck Golf Club await just a quick drive from your doorstep.

This home is not only a serene escape but also a gateway to the island's many attractions. Film buffs will appreciate the proximity to the iconic Jaws Bridge, located just five miles away. Whether you're interested in whale watching, kayaking, or simply exploring the local shops and restaurants, Oak Bluffs has something for everyone. After a day of exploration, return to your cozy haven, where you can enjoy the comforts of home, including a fully equipped kitchen and outdoor dining area.

With amenities such as central AC, a washer/dryer, and a spacious deck, this Oak Bluffs home is designed for your comfort and convenience. Experience the best of Martha's Vineyard while enjoying the rustic charm of this delightful property. Book your stay today and create unforgettable memories in this beautiful island getaway!

Things to Know

Parking notes: There is free parking available for 4 vehicles.

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.

Gingerbread Dream is located in Oak Bluffs, just a 13-minute walk from Oak Bluffs Town Beach and 6.9 miles from Edgartown Lighthouse. Guests can benefit from a terrace and a children's playground. There's a restaurant. The vacation home consists of 3 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. A TV with streaming services and DVD player, as well as a CD player are offered. The property has an outdoor dining area. Guests at the vacation home will be able to enjoy activities in and around Oak Bluffs, like cycling. The vacation home has a picnic area where you can spend the day outdoors. Martha's Vineyard Airport is 5 miles from the property.

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

This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard.

Literally just step outside your door for breakfast or ice cream, a great selection of restaurants in all price ranges, or pick up groceries and wine across the street. Have breakfast or dinner on your porch or deck. Stroll to the ocean beach in three minutes. One of the nation's most historic brass ring carousels is just down the street. The famous gingerbread cottages are in your backyard. Frequent concerts and other cultural events are hosted at the historic open air Tabernacle and other local venues. There is no better place on the island to fly a kite than at Ocean Park just down the street where they also have band concerts in the newly restored gazebo.

Two modern, clean, bright, units are available in this historic building right in the heart of the town of Oak Bluffs. Two apartments have a water view. Enjoy your own private deck or front porch with some of the best views in town.

Beach, park, restaurants, shopping, movie theaters, game room, historic carousel, bicycle rentals, charming gingerbread cottages, open air concerts, are all at your doorstep. The island ferries from the mainland dock just down the street. The Island shuttle buses to other Island towns operate frequently and are within a four minute walk. Superb in-town location. Ideal for friends, couples, and families with children or teenagers.

A CAR IS NOT NECESSARY FOR VISITING THIS PROPERTY.

Nearby Attractions:
Lifeguard Beach, Biking, Fitness Center, Fishing, Shopping, Restaurants, Cinemas, Game Room, Historic Carousel, Parks, Sightseeing, Mini golf, Game Arcade, Swimming, Boating, Jet skis, Sailing, Bi-plane tours, Churches, Historic Tabernacle Concerts.

- "Everything about this place was AMAZING!! Within walking distance to everything, very clean, quiet, and Larry couldn't have been a better host! We will definitely be staying again!" - "Stayed in 2nd floor unit #1–loved the huge deck above Circuit Ave. for relaxation and people watching. Lots of space, like a whole apartment! Awesome location. Bring earplugs for late night partiers at Sharky’s right below. Would definitely rent again, even with the nighttime noise. It was that comfortable! Easy walk to beach, too!"