Best Villa Rentals in Massachusetts

Top Villa Rentals in Massachusetts

Indulge in the comforts of home with our curated guide to the best villa rentals in Massachusetts. Each property has been selected for its unique charm and quality, catering to discerning travelers.

Villa Rentals in Massachusetts
Roslindale village condos
Apartment
127 Selwyn Street, Boston, MA, MA 02131, USA

Roslindale village condos offers accommodations in Boston, 5 miles from Boston Museum of Fine Arts and 5.3 miles from Fenway Park. There's a private entrance at the apartment for the convenience of those who stay. There's a sun terrace and guests can access free Wifi and free private parking. At the apartment complex, all units are fitted with air conditioning, a seating area, a flat-screen TV with streaming services, a kitchen, a dining area, and a private bathroom with slippers, a bath, and a hair dryer. A microwave, a toaster, and fridge are also provided, as well as a coffee machine and a kettle. At the apartment complex, each unit comes with bed linen and towels. The area is popular for golfing and hiking, and free use of bicycles is available at the apartment. Boston University is 5.9 miles from Roslindale village condos, while Back Bay is 6.1 miles away.

Guest Reviews:

- "Would absolutely recommend and host was very tentative and communication was easy and helpful." - "Excellent. 5 star" - "Very happy to have found this place" - "If this is available, book it!" - "Boston 4 night family stay" - "Great Place to Stay!!" - "Refreshing, relaxing, comfortable, and great location outside of city chaos and traffic" - "Perfect spot" - "An exceptional place at an exceptional price." - "Great"

Villa Rentals in Massachusetts
Villa with Access to Amazing Amenities!
Villa
South Lee, Massachusetts, USA

Sleeps 4 up to 6 people (Max 5 Adults)

- Large and small outdoor pool
- Two indoor pools: Open
- Hot Tub
- 2 on-site Bar
- *18-hole mini golf course
- *Sports courts
- *Barbecue grills
- *Fitness center
- *Parking
- *Wi-Fi
- *Fitness gyms
- Hiking Trail
- Game Room: arcade-style games
- On-site Café and Marketplace grab & go

2-bedroom villa in The Berkshires, Massachusetts! This unit is located in the perfect position for day trips to Albany, NY (only an hour away), Hartford, CT (an hour away), and Boston (2 hours away). We recommend visiting the Norman Rockwell museum, just an 11 minute drive away. For some fun outside, we suggest hiking the Appalachian Trail during autumn, and skiing Butternut or Jiminy Peak during the winter. This is an excellent location for those who want to explore outside or take in the local culture. During winter, hit up Butternut or Jiminy Peak for prime powder. During the summer, go hiking, rafting, or boating.

Bedding Configuration:
- 1st Bedroom with 1 Queen bed
- 2nd Bedroom with 1 Queen bed
- Sofa bed in the living area

Living Space:
- Cable TV

Kitchen:
- Microwave
- Refrigerator
- Generic coffee machine

Bathroom:
- 2 Bathrooms
- Jacuzzi tub in the master bathroom
- Hairdryer
- Complimentary toiletries

OTHER THINGS TO NOTE:
Upon arrival:
- A refundable damage deposit of $115 that will be returned provided there is no damage or additional cleaning required
- The items above denoted by an asterisk (*): that includes a variety of onsite activities and amenities, including Wi-Fi access, parking, arcade, sauna, indoor pool, fitness center, sports courts access, barbecue grills, mini golf, and movie theater access

Important Notes
- Access to all amenities depends on the current situation and government instructions
- Large and small outdoor pool: Open seasonally and weather permitting
- 2 on-site Bar (one is seasonal): - table tennis or ping pong, billiards
- *Sports courts: Open seasonally and weather permitting (tennis, basketball, volleyball, and more)
- A number of these units are available, and each is individually decorated. The images shown are a representation of the unit you will receive. At check-in, you will receive a unit of the same type as shown in this listing, complete with the advertised size and number of rooms, but the actual decor in the unit, view, and furniture layout may differ
- A full end-of-stay clean is included, but guests are requested to leave their units tidy
- By booking this property in Holiday Inn Club Vacations Oak n’ Spruce Resort you agree to our house rules, health & safety and cancellation policies
- You will receive a copy of an Arrival Information after confirming your reservation

Guest Reviews:

- "Check out time was too early" - "A bit worn with age Property needs a bit of maintenance" - "Love everything about this property. Very clean and lots of activities for the kiddos. Everyone there was very nice. Thanks." - "loved the outdoor table on the patio and the quality of the bedroom,bath and kitchen. Only two complaints. sharp knives are not sharp. Bring your own. It was a challenge cutting your bagel. Living room is small could you another comfortable chair. There is one 3 person couch and one lounge chair so it was not so comfortable for 4 people. Otherwise we loved this property"

Villa Rentals in Massachusetts
Indian Lake House
Villa
Proctor Street, Worcester, MA, MA 01606, USA

Indian Lake House is located in Worcester, just 2.3 miles from DCU Center Arena & Convention Center and 4.2 miles from Ecotarium A Museum Of Science Nature. Guests can benefit from a patio and an outdoor fireplace. The villa also features free Wifi, free private parking, and facilities for disabled guests. Providing access to a balcony with quiet street views, the air-conditioned villa consists of 3 bedrooms. Featuring a terrace with lake views, this villa also comes with a cable flat-screen TV, a well-equipped kitchen with an oven, a microwave, and a toaster, as well as 1 bathroom with a bath and a hair dryer. There's also a seating area and a fireplace. The villa has a picnic area where you can spend the day outdoors. Fitton Football Stadium is 4.2 miles from the villa, while Old Sturbridge Village is 24 miles from the property. Worcester Regional Airport is 5 miles away.

Guest Reviews:

- "Fun spot, perfect for our needs." - "Our family enjoyed the stay. View was gorgeous and home was comfortable" - "A quiet, serene, relaxing getaway" - "Quiet gataway" - "I would definitely stay here again" - "I would definitely book here again, when coming to visit family!" - "The location was awesome! The host was spectacular and accommodating! 100% would book again!!!" - "Perfect Disc Golf Getaway House" - "Lovely quiet place to stay in Worcester"

Villa Rentals in Massachusetts
Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance
Villa
Boston, Massachusetts, USA

The Villa at Eastie overlooks the harbor and shipping channels, early morning lobstermen can be seen from the sunroom hauling their traps, as well as the ships coming to port. Plane bugs (id book) will love the spectacular view of Logan Int. Airport. At the end of the street is Constitution Beach. There are kayaks for the adventurous or relax in the fountain garden. Smell the sea breeze and reminisce about the politics that must have been discussed in this former Senators home. Entertain in the formal dining room under the crystal chandelier or relax and read a book on one of the balconies overlooking the harbor. The Blue line (T)(public trans) is only two blocks away and offers a ride to the airport station and free shuttle bus to your terminal, a few more stops and you are downtown for world class shopping, restaurants, museums and the Swan boats ride. Ask about antiquing in the area.

Guest Reviews:

- "Everything was wonderful. Top notch. The only thing I would change is to have a shower curtain for the shower. It ended up being fine without one, but could be a shock for some people at first. But even without a shower curtain, I would stay there again! Great old house, full of character, and so fun watching the planes take off and land over the view of the water. Wonderful hosts!" - "It was great. Interesting period house. Across an inlet from the airport - kids loved watching the planes. Very convenient to the blue line (free because Sumner Tunnel is closed). We did everything on our list of Boston things to do - and more!"

Villa Rentals in Massachusetts
Cape Cod Villa
Villa
16 Olde Coach Lane, Harwich, MA, MA 02645, USA

12 miles from Nauset Lighthouse in Harwich, Cape Cod Villa features accommodations with access to spa facilities, wellness packages, and beauty services. This property offers access to a balcony, a pool table, free private parking, and free Wifi. Guests can book fitness classes or yoga classes. With direct access to a patio with garden views, the air-conditioned villa consists of 4 bedrooms. Offering a terrace with lake views, this villa also has a flat-screen TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 2 bathrooms with a bath and bathrobes. The villa offers bed linen, towels, and laundry service. There is an on-site coffee shop, and during warmer months you can make use of the barbecue facilities. For guests with children, the villa offers an indoor play area and a baby safety gate. A bicycle rental service is available at Cape Cod Villa, while cycling and hiking can be enjoyed nearby. Wellfleet Bay Wildlife Sanctuary is 13 miles from the accommodation, while Cape Cod National Seashore is 15 miles away. Cape Cod Gateway Airport is 14 miles from the property.

Guest Reviews:

- "A fairy tale dream!" - "Beautiful house and property!" - "Very comfortable property, beautifully decorated with a very responsive and helpful host." - "amazing retreat, LOVELY place" - "Natalia was over the top with exceeding expectations and on point with my daughter’s sweet 16th!" - "It was a magical experience." - "Loved house and all it has to offer ! Any wait to come back" - "Incredible experience in a beautiful villa!"

Villa Rentals in Massachusetts
VILLA at Ocean Edge Endicott Village, GOLF PRIVILEGES AND VIEW. LINENS PROVIDED
Villa
Brewster, , Massachusetts, USA

Enjoy this sun-splashed, spacious 2nd floor villa with 3 bedrooms and 2 full baths. Fantastic location at Ocean Edge resort, overlooking the golf course. Waken to the sounds of birds. Steps from the Linx Tavern which is open daily in-season for breakfast, lunch and dinner. Steps away from the Arbor pool and the Shark Bah. This beautiful unit offers cathedral ceilings, palladium windows, fireplaced living room, new sleeper sofa in living room. A/C in all living areas, 4 TVs with cable, Wi-Fi, high speed Internet, Amazon Alexa, telephone. Master bedroom has a king-size bed, new mattress/foundation for restful sleep. Second bedroom has two full size beds. Third bedroom has full size bed with new mattress and foundation. Separated bedrooms ensures privacy for multiple families or relatives. Fully applianced kitchen, washer & dryer in the unit. Beautifully appointed with a nautical theme. New kitchen cabinets with granite counter tops. There is a pack-n-play, carriage, booster seat and bed rails for the little ones. (Please bring baby's sheet and blankets.) Many activities (see list below).

*7 night minimum stay in July, and August; Saturday to Saturday only
* 5 night minimum stay in June
* 3 night minimum April, May, September and October.

Deposit of 50% is required.

We have several repeat guests. Their comments have been - "This place is beautiful. We love it, we can't wait to come back. Very clean and all updated. I saw the others but this is by far the best. Furnished in a summer beach mode that can make you feel happy. Walk to pools!"

Don't wait this condo will go quickly.

Activities:

Enjoy golf access at Ocean Edge. The clubhouse is a short walk (300 yards) from my unit. Green fees apply.

Of course, Cape Cod is famous for its beaches. There are numerous beach guides available online. My favorite is published by the Cape Cod Chamber of Commerce: https://www.capecodchamber.org/things-to-do/beaches/.

Besides the beaches and golf, the Ocean Edge resort has many on-site activities. The complete list is published on the Ocean Edge web site: https://www.oceanedge.com/activities. For the most up-to-date information on what is happening, call Ocean Edge directly: 508-896-9000

The outdoor Arbor pool is just across the street from my unit (4 minute walk). Relax there, no need to cook, your every desire will be met by the Shark Bah which is adjacent to the Arbor pool. Nothing could be more convenient for a wonderful, relaxing week. Zero driving!

All on-site activities at Ocean Edge resort require the purchase of guest passes. Daily passes cost $27 per adult (16 years or over) and $14 per child (6 to 15 years). Children under 6 are free. Weekly passes cost $80 per adult and $40 per child.

Guest Reviews:

- "What a lovely condo. The setting is "NewEngland" My family and I had a wonderful time. The condo is so spacious and most everything you need was provided. Will return." - "Great accommodations, everything as advertised. Lorin checked in with us to make sure everything was to our liking. We are looking to visit again in the future." - "Lorin’s house was exactly as it was described. It worked perfectly for my family. We had a wonderful time and would definitely return. Highly recommend this property."

Villa Rentals in Massachusetts
Peaceful Getaway Cottage on grounds of historic mid-century gem
Villa
333 Howard Street, Northborough, MA, MA 01532, USA

Peaceful Getaway Cottage on grounds of historic mid-century gem is located in Northborough, just 12 miles from DCU Center Arena & Convention Center and 25 miles from Minute Man National Historical Park. This property offers access to a terrace, a pool table, free private parking, and free Wifi. The villa features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with bathrobes. Towels and bed linen are offered in the villa. There's also a seating area and a fireplace. There is an on-site bar. Guests can swim in the outdoor swimming pool, relax in the garden, or go hiking. Worcester Regional Airport is 16 miles from the property.

Guest Reviews:

- "we loved it!" - "Perfect place for us to stay when visiting my son in Hopkinton. Definitely would stay again. Unique" - "A great stay with all the amenities you need!" - "It was an absolutely wonderful weekend at a peaceful location" - "Truly a gem!" - "Relaxing tranquil spot in a beautiful area" - "Beautiful cottage for a quiet stay or small family gathering" - "Happy, and peaceful experience" - "Needed to be cleaned more and had a real problem with ants in the kitchen and bathroom"

Villa Rentals in Massachusetts
Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
Villa
Charlton, Massachusetts, USA

Bring the whole family to this lovely villa with lots of free parking and multiple comfy King Beds. This Villa seats on 1 Acre in a really residential and quiet neighborhood in Charlton MA. The property boasts of a spacious backyard with a private play ground for kids and a private pool with a large deck. It's less than 10 minutes away from the Treehouse brewery. The Heritage Country Club golf course is about 10 minutes from the Villa. There are several lakes within 20 minutes from the Villa.

Guest Reviews:

- "This property was absolutely beautiful and spacious! The home was very accommodating for my group and we all had such a wonderful time. The views were perfect and the neighborhood was nice and quiet. Michael was extremely helpful and very available to answer any questions we had. If you plan on visiting Charlton, I would definitely recommend this place!" - "We had a wonderful time. The house was beautiful and dry clean. Michael was an attentive host….couldn’t have asked for anything more!"

Villa Rentals in Massachusetts
Mattakeese Villa
House
Yarmouth, MA, USA

17 miles from Sandwich Glass Museum in Yarmouth, Mattakeese Villa provides accommodations with access to spa facilities. The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests. The vacation home features 4 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 provided in the vacation home. The property has an outdoor dining area. Guests can also warm up near the outdoor fireplace after a day of cycling. Heritage Museums & Gardens is 17 miles from Mattakeese Villa, while Nauset Lighthouse is 25 miles away. Cape Cod Gateway Airport is 1.2 miles from the property.

Guest Reviews:

- "This was a great experience I recommend you stay at this house. Everything is very clean!" - "We had an amazing time during our stay and made many great memories." - "Very comfortable, clean and well appointed home. Great for families or friend gatherings. Excellent rental."

Villa Rentals in Massachusetts
Spacious Villa with Access to Various Amenities!
Villa
South Lee, Massachusetts, USA

This is the perfect villa for your group! Enjoy an awesome location and access to a number of exciting amenities including a fitness center, 2 pools, a hot tub, dining options on-site, and an 18-hole mini golf course when you stay in our villa! Located in central Berkshires, Massachusetts, you'll love this awesome rental in a fantastic location.

• 2 Bedrooms each with 1 King bed
• Sofa bed for additional guests
• Complimentary toiletries
• 18-hole mini golf course
• The kids will love the arcade!
• 3 on-site restaurants
• Fitness centre on-site
• Free parking is available on-site
• Just 11 minutes from the Norman Rockwell Museum

This is an excellent location for those who want to explore outside or take in the local culture. During winter, hit up Butternut or Jiminy Peak for prime powder. During the summer, go hiking, rafting, or boating. Our luxurious rentals are the ideal home base to explore this exciting area!

Our space has 2 BEDROOMS which each feature a King bed. You'll find a Sofa bed in the living room which can accommodate additional guests.

Get ready in our 2 BATHROOMS with a jacuzzi tub in the master bathroom. We provide you with a hairdryer and complimentary toiletries.

After a day spent hiking, retreat to our LIVING SPACE. Curl up on the sofa and enjoy your favourite shows on our cable TV. You can easily connect with friends and family back home, courtesy of the complimentary Wi-Fi.

In the full KITCHEN you'll find a microwave, a refrigerator, and a variety of other appliances. Start your morning with a cup of coffee, fresh from our in-suite coffee machine. When you don't feel like cooking, enjoy a meal at the on-site restaurants, Subway, Mama DeLuca's, and the Beartree Bar where you can play trivia, sing karaoke or shoot some pool while enjoying a drink.

There are a number of other amenities you're sure to enjoy when you stay at Holiday Inn Club Vacations Oak n’ Spruce Resort where our space is conveniently located. These include fitness centre access, a sauna, table tennis or ping pong, billiards, an indoor pool, an outdoor pool, an indoor whirlpool, and on-site activities for kids including an 18 hole mini golf course and an arcade. Outside, you'll find tennis, basketball, volleyball, and horseshoes.

Parking is available for free on-site.

The properties here are individually decorated, so there can be some differences in the decor and furniture layout from one condo to the next, but all are finished to a great standard! If you have a specific request, please inform our team upon booking and we will be happy to add a request to your reservation.

LOCAL FAVOURITES

This unit is located in the perfect position for day trips to Albany, NY (only an hour away), Hartford, CT (an hour away), and Boston (2 hours away). We recommend visiting the Norman Rockwell museum, just an 11 minute drive away. For some fun outside, we suggest hiking the Appalachian Trail during autumn, and skiing Butternut or Jiminy Peak during the winter.

OTHER THINGS TO NOTE:
• Unfortunately, your furry best friend will have to sit this one out as pets are not allowed in this unit
• If you’re travelling by car, we’ve got you covered with FREE parking on-site!
• Upon arrival, you will be asked for a refundable damage deposit of $115 that will be returned provided no damage or additional cleaning is required
• The properties here are individually decorated, so there can be some differences in the decor and furniture layout from one condo to the next, but all are finished to a great standard! If you have a specific request, please inform our team upon booking and we will be happy to add a request to your reservation

Guest Reviews:

- "I cannot believe I have been coming to the Berkshires for years and did not know of this great place to stay. It had all the amenities you need. Lee is the beginning of the Berkshires. The Unit was large, clean, and well stocked. Plan to come back annually." - "We had several sales attempts to sell us time shares at the facility. This was disruptive" - "All went smoothly/ many great features for family fun" - "Clean property, easy check-in, great family activities"

Villa Rentals in Massachusetts
Spacious Countryside Villa
Villa

Boasting garden views, Spacious Countryside Villa features accommodation with a tennis court and a balcony, around 13 km from DCU Center Arena & Convention Center. There is an in-house restaurant, plus free private parking and free WiFi are available. The air-conditioned villa consists of 3 bedrooms, a living room, a fully equipped kitchen with a fridge and a coffee machine, and 3 bathrooms with a shower and free toiletries. The property also has 3 bathrooms featuring a bath and a hairdryer, and towels and bed linen are provided. The villa offers a sun terrace. After a day of hiking, skiing or fishing, guests can relax in the garden or in the shared lounge area. Fitton Football Stadium is 12 km from Spacious Countryside Villa, while EcoTarium A Museum of Science Nature is 16 km from the property. The nearest airport is Worcester Regional Airport, 5 km from the accommodation.

Amenities:

Balcony/Terrace • Kitchen • Smoking • Air Conditioner • Breakfast • Child Friendly • Internet • Parking • Laundry

Villa Rentals in Massachusetts
Villa with Access to Various Amenities
Villa
South Lee, Massachusetts, USA

When you stay in our villa, you'll have access to a number of exciting amenities including a fitness center, 2 pools, a hot tub, dining options on-site, and an 18-hole mini golf course! Located in central Berkshires, Massachusetts, you'll love this awesome rental in a fantastic location.

• 1 Bedroom with 1 Queen bed
• Sofa bed for additional guests
• Complimentary toiletries
• 18-hole mini golf course
• Arcade
• 3 on-site restaurants
• Fitness centre on-site
• Free parking is available on-site
• Just 11 minutes from the Norman Rockwell Museum

This is an excellent location for those who want to explore outside or take in the local culture. During winter, hit up Butternut or Jiminy Peak for prime powder. During the summer, go hiking, rafting, or boating. Our luxurious rentals are the ideal home base to explore this exciting area!

Our space has 1 BEDROOM which features 1 Queen bed. You'll find a Sofa bed in the living room which can accommodate additional guests.

Get ready in our 1 BATHROOM. We provide you with a hairdryer and complimentary toiletries.

After a day spent hiking, retreat to our LIVING SPACE. Curl up on the sofa and enjoy your favourite shows on our cable TV. You can easily connect with friends and family back home, courtesy of the complimentary Wi-Fi.

In the KITCHEN you'll find a microwave, a refrigerator, and a variety of other appliances. Start your morning with a cup of coffee, fresh from our in-suite coffee machine. When you don't feel like cooking, enjoy a meal at the on-site restaurants, Subway, Mama DeLuca's, and the Beartree Bar where you can play trivia, sing karaoke or shoot some pool while enjoying a drink.

There are a number of other amenities you're sure to enjoy when you stay at Holiday Inn Club Vacations Oak n’ Spruce Resort where our space is conveniently located. These include fitness centre access, a sauna, table tennis or ping pong, billiards, an indoor pool, an outdoor pool, an indoor whirlpool, and on-site activities for kids including an 18 hole mini golf course and an arcade. Outside, you'll find tennis, basketball, volleyball, and horseshoes.

Parking is available for free on-site.

The properties here are individually decorated, so there can be some differences in the decor and furniture layout from one condo to the next, but all are finished to a great standard! If you have a specific request, please inform our team upon booking and we will be happy to add a request to your reservation.

LOCAL FAVORITES

This unit is located in the perfect position for day trips to Albany, NY (only an hour away), Hartford, CT (an hour away), and Boston (2 hours away). We recommend visiting the Norman Rockwell museum, just an 11 minute drive away. For some fun outside, we suggest hiking the Appalachian Trail during autumn, and skiing Butternut or Jiminy Peak during the winter.

OTHER THINGS TO NOTE:
• Unfortunately, pets are not allowed in this unit
• If you’re travelling by car, we’ve got you covered with FREE parking on-site!
• Upon arrival, you will be asked for a refundable damage deposit of $115 that will be returned provided no damage or additional cleaning is required
• The properties here are individually decorated, so there can be some differences in the decor and furniture layout from one condo to the next, but all are finished to a great standard! If you have a specific request, please inform our team upon booking and we will be happy to add a request to your reservation

Guest Reviews:

- "Perfect setup for family for camp visiting day. Space was clean and well kept." - "Incredibly impressed with the whole Place! Luckily we had a townhouse so no one was above us because I didn’t realize this was really designed for families . So clean , grounds were a pleasure to walk around with all the plantings- very well maintained. Pool and activity center was really nice and although we didn’t use the activity center, I would have loved it with a young family . All the staff were friendly and it was just a pleasure staying there."

Villa Rentals in Massachusetts
Harborview Villa
House
Harwich Port, MA, USA

Harborview Villa offers accommodations in Harwich Port, 1.3 miles from Bank Street Beach and 18 miles from Nauset Lighthouse. The property is around 19 miles from Wellfleet Bay Wildlife Sanctuary, 21 miles from Cape Cod National Seashore, and 25 miles from Sandwich Glass Museum. Heritage Museums & Gardens is 26 miles from the vacation home. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 1 bathroom. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. For guests with children, the vacation home provides a children's playground. Guests can also warm up near the outdoor fireplace after a day of cycling. Cape Cod Gateway Airport is 11 miles away.

Amenities:

Air Conditioner • Oceanfront • Pet Friendly • View • Barbecue/Outdoor Cooking • Child Friendly • Ocean View • Laundry • Guest Services • Fireplace/Heating • Security/Safety • Sports/Activities

Villa Rentals in Massachusetts
The Kemble- Built by a US Secretary of State in Lenox
Villa
Lenox, Massachusetts, USA

The Kemble Berkshires is a registered Great Estatebuilt in the 1880s for a U.S. Secretary of State and New Jersey State Senator - nownewly renovated byShared Estates with bright minimalist finishes and world-class amenities. The property has manicured landscaping with massive rolling views of the Stockbridge Bowl. Whether you want to relax in the library room with its array of books from the early 1900s, jam out in the music room, snuggle up in front of one of the home's seven fireplaces or enjoy a drink with a friend at the private bar, you will find beautiful spaces to enjoy in groups or in solitude. 100% carbon neutral.Events up to 175.

The Kemble is the top grossing, #1 vacation rental in the Berkshires out of roughly 1,000 listings. Owner's previous property was showcased on Netflix's "World's Most Amazing Vacation Rentals" series.
The property offers a dining room (including custom farmhouse dining table), a professional kitchen, herb and vegetable garden, fire pit and expansive multi-level stone patios and decks. Events up to 175 are permitted and a tent is provided for rain contingency (first weekend in May to third weekend in October), commercial kitchen items are also provided. Indoor walls are sound-insulated for privacy.
We provide a long list of amenities, for kids big and small we offer a virtual reality gaming room, PS4 gaming setup, retro arcade, foosball table, ping-pong, board games and more. For outdoors you will find bocce, croquet, tennis and badminton equipment, large Jenga, paddle board, kayakand more.
The Kemble Berkshires is an innovative social equity vehicle. Owned by 143 investors from Main Street and Wall Street through Shared Estates' equity crowdfunding model with investments ranging from $1,000 to $100,000, the property is part of a transformation that levels the real estate ownership playing field.
The Berkshires is one of the country's top cultural centers and the Kemble is steps away from many leading national institutions: Tanglewood (summer home to the Boston Symphony Orchestra), Shakespeare and Company, The Norman Rockwell Museum, Edith Wharton's The Mount, Clark Art, Jacobs Pillow and more. The Massachusetts Museum of Contemporary Art (largest in the US), Kripalu (largest yoga center), Williams College (#1 Liberal Arts College in the US) are all nearby.
The Berkshires is also home to a variety of outdoor destinations: Bousquet, Butternut, Catamount (longest zip line in the USA) and Jiminy Peak.
TVs can be found in most bedrooms. Fully ADA compliant accessibility ramps, bedrooms and baths help make entry easy for all. Safety is our top priority, with discrete sprinkler systems, fire ladders and more in every room for piece of mind for all. We provide popcorn, biscotti, teas, cocoa, candy and more. A welcome basket of local goods and fresh cut flowers greet your party.
The Kemble donates 1% of net income to The Lenox Library. You will find a variety of sculpture and original fine art installed throughout.
Most of our stays are multigenerational family trips, reunions, friends getting together or retreats, however as a registered Great Estate we host many events as well (capped at 175) - our events fees:
No amplified outdoor music:
<50 guests: $2,500
<100 guests: $5,000 (or $50 / guest)
<175 guests: $9,500 (or 54 / guest)
Amplified outdoor music (we are limited to 10 such events annually)
<100 guests: $11,500 (or $115 / guest)
<175 guests: $13,500 (or $77 / guest)
From the first weekend in May to the end ofOctober event fees also include use of our 44 foot round sailcloth tent.
We have over 5,500 square feet of dedicated parking. The three acres are very private, but you are also steps to downtown Lenox, the heart of the Berkshire hills. Lenox is home not only to a variety of leading cultural institutions, but also to many fine and farm-to-table dining experiences.

Guest Reviews:

- "We had a wonderful time at the Kemble. We were 22 adults and two children and there was so much space for everyone. The covered deck was great as an outdoor space as it was a very rainy weekend, but we even managed to get some time in the vast yard playing some wiffle ball. When we had a couple of small issues they responded quickly even though it was late in the evening. We had a fantastic time with the extended family together in this spacious home."

Villa Rentals in Massachusetts
7 Deer Run Harwich Cape Cod- -Sea Pine Villa
House
7 Deer Run, Harwich, MA, 02645, USA

7 Deer Run Harwich Cape Cod- -Sea Pine Villa offers accommodations in Harwich, 1.2 miles from Red River Beach and 1.3 miles from Forest Beach. The vacation home features both Wifi and private parking free of charge. Nauset Lighthouse is 16 miles away and Wellfleet Bay Wildlife Sanctuary is 22 miles from the vacation home. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. A TV with cable channels is featured. The accommodation has a fireplace. Cape Cod National Seashore is 23 miles from 7 Deer Run Harwich Cape Cod- -Sea Pine Villa, while Sandwich Glass Museum is 28 miles away. The nearest airport is Cape Cod Gateway Airport, 14 miles from the accommodation.

Amenities:

Other • Parking • Child Friendly • Security/Safety • Air Conditioner • Fireplace/Heating • Internet • Pet Friendly

Villa Rentals in Massachusetts
Mayflower Beach Villas - Seagull
Villa
Dennis, Massachusetts, USA

Do you want to be a few hundred yards from one of the best beaches in world? This luxurious, newly built , spacious three bedroom home is steps away from bayside beach next to Mayflower Beach (known to be the best beach on Cape Cod). Kid friendly and safe, this beach has a low tide that affords children to explore tidal pools and allow parents to relax from a distance or find their own solitude through long walks on miles of beach and dune. In the evening, the sun sets over the Cape Cod Bay to create a bucolic and romantic atmosphere. Once here, you can literally leave your car parked. The property sits between two of the Cape's most popular restaurants- 'Chapin's' which is a new and popular family restaurant with an outdoor deck and a large bar area with nightly entertainment in a neighborhood atmosphere and 'Gina's' which is famous for its intimate setting and chef-inspired Italian cuisine.

Dennis, named the All American Town in 1978, is located in the middle of the Cape and remains small and delightful to visit. All Cape attractions are easily accessible from this central location with tennis and golf courses only minutes away. The first Summer Theater in America, The Cape Playhouse, is just down the street, as well as scores of antique shops, fine clothing stores, art galleries, superb restaurants, a marine aquarium & park, harbors with boat launching, rental & charter facilities. There are two fine restaurants within walking distance. We have two PGA certified golf courses, plus public and private tennis within three miles. The Cape Cod bike trail (a lovely 21 mile trail along salt marshes, lakes, ponds, cranberry bog and sand dunes) starts in Dennis. Tobey Farm (oldest family farm on cape cod) is two miles away. The Johnny Kelly Recreation Area, named after the famous Boston Marathoner who makes his home in this 'All American Town Of Dennis' is only five miles away.

Guest Reviews:

- "perfect house in a perfect location what a pleasure thank you" - "This place was so clean, nice and close to the beach and well stocked. We will definitely be staying again." - "This is the perfect rental for 3 generations! On the 2nd level, the kids had a room, mom/dad had a room, and we shared a full bath and living room. The grandparents had the 1st floor master with private bathroom off the kitchen/living room. Even better, dual temperature controls on each level! Two great restaurants within walking distance. Our weekend stay was cold and mostly rainy (late-September/early-October) but we were able to get to the beach and have s’mores while sitting around the fire pit. Would love to come back in the summer!"

Villa Rentals in Massachusetts
Ocean Views & Private Beach 3BR Nature Escape villa
Villa
Nameloc Heights, MA, USA

Ocean Views & Private Beach 3BR Nature Escape villa offers accommodations in Nameloc Heights, 8.3 miles from Heritage Museums & Gardens and 11 miles from Plimoth Plantation. The air-conditioned accommodation is 8.2 miles from Sandwich Glass Museum, and guests can benefit from on-site private parking and complimentary Wifi. The villa features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 4 bathrooms with a hair dryer. Towels and bed linen are provided in the villa. The accommodation is non-smoking. Cape Cod Gateway Airport is 20 miles away.

Amenities:

Fireplace/Heating • Guest Services • Other • Air Conditioner • Sports/Activities • Internet • Security/Safety • Barbecue/Outdoor Cooking • Parking • Child Friendly

Villa Rentals in Massachusetts
Boston Marriott Custom House ~ Downtown Suite with views of the city and harbor
Villa
Boston, Massachusetts, USA

Marriott Vacation Club Pulse at Custom House, Boston welcomes guests with expansive suite accommodations, thoughtful amenities and a perfect location near the water. Located in downtown Boston, our property boasts unmatched views of the harbor, plus is a short distance away from some of the city's most iconic attractions, including Quincy Market, Faneuil Hall, and the Boston Opera House. Ideal for facilitating family vacations, my rental suite include complimentary Wi-Fi, a full kitchenette, separate living and sleeping areas and flat-screen TVs. Reinvigorate with a visit to the fitness center or admire the view from our 26th-floor open-air Observation Deck. Kids and adults alike will love features like an on-site movie theater and game room; dine anytime with local restaurant delivery. However you elect to spend your time in "The Hub," we're confident you'll love calling Marriott at Custom House, Boston your home away from home.

Guest Reviews:

- "The property is fabulous and in the best spot in Boston to explore the city. The accommodations are roomy and had everything we needed . We feel extremely fortunate to have found and been able to stay here. Service was impeccable and communication was great with the host. I wholeheartedly recommend staying here to everyone. Thanks so much!" - "We loved our stay! Such a special property and a great location in Boston as well." - "First visit to Boston and was impressed with the manager’s and staffs (especially Justin) exceptional customer service and attention to detail. The 18th floor room was spotless and faced the Long Wharf and bay……extremely convenient location for exploring “old town” and local restaurants, as well as commuting to and from the airport (Aquarium Station). Will reserve again during my next trip to Boston….."

Villa Rentals in Massachusetts
Gorgeous 5 bedroom Boston Home
Villa
71 Commonwealth Avenue, Chestnut Hill, MA, MA 02467, USA

Gorgeous 5 bedroom Boston Home is located in Chestnut Hill, just 4.9 miles from Boston University and 4.9 miles from John F. Kennedy Park. The air-conditioned accommodation is 4.5 miles from Fenway Park, and guests can benefit from on-site private parking and complimentary Wifi. Boston Museum of Fine Arts is 5.1 miles away and Harvard University is 5.2 miles from the villa. Offering a terrace and garden views, the spacious villa includes 5 bedrooms, 2 living rooms, cable flat-screen TV, an equipped kitchen, and 3 bathrooms with a bidet and a bath. For added privacy, the accommodation features a private entrance. Central Square is 5.1 miles from the villa, while Harvard Square is 5.1 miles from the property. Logan Airport is 10 miles away.

Amenities:

Child Friendly • Parking • Air Conditioner • Internet • Barbecue/Outdoor Cooking

Villa Rentals in Massachusetts
Beautiful 2BD Villa in Berkshires Resort
Villa
Lee, Massachusetts, USA

We're located in the beautiful Berkshire Mountains of western Massachusetts, a regional center for performing and visual arts. Enjoy its many festivals and live theater, museums, beautiful scenery and rural New England charm. The 2BR unit features (2) King size beds in the bedroom, a Queen pull-out sofa in the living room, and a fully furnished kitchen that can support most cooking needs. Pet is allowed with the proof of vaccinations. ($150 per stay per pet will be charged at registration) The Resort is situated in the beautiful Berkshire Mountains of Western Massachusetts. The Berkshires is known for its cultural attractions. Among them Lots of activities: Museums, Premium Outlets, Tanglewood, summer home of the Boston Pops, Ballet Theater (Jacob's Pillow), Crepala Yoga Center, Shakespeare Theater, and the Norman Rockwell Museum and amazing mountains. The Resort amenities include a full health club, two indoor heated pools and whirlpool, an Olympic-sized outdoor pool, miniature golf, movie theater, cocktail lounge, indoor activity center, outdoor basketball, cross-country ski trails, and activities for all ages. Nearby a trout-filled freshwater stream adds a gentle touch to the picnic area. Enjoy skiing, sledding and tubing in the winter. Vacationers will enjoy leaf-viewing in the fall and exploring the adjacent 10,000-acre state forest, which also has a lake.

Museums of interest abound in the Berkshire region. Just five miles west of Pittsfield you will find the Hancock Shaker Village featuring a 200-year-old Shaker site complete with buildings, artifacts, crafts, gardens and farm animals. In Stockbridge, visit the home of the first missionary to the Native Americans, Reverend Sergeant, circa 1739. The Norman Rockwell Museum in Stockbridge features the largest Rockwell collection in the world.
Performing arts: Tanglewood is the summer home of the Boston Symphony Orchestra. Other performing arts festivals during the season are the Berkshire Performing Arts Center in Lenox, The Berkshire Performing Theater Festival and Jacob's Pillow Dance Festival, the hub and Mecca of dancing in North America, according to Time Magazine.
Sports and outdoor activities abound in this region. Visit the Appalachian Trail with 80 miles of trails in Massachusetts; The Pleasant Valley Wildlife Sanctuary; The Tolland State Forest - for boating, hiking, fishing, camping, and swimming.
Winter activities: 15 Min Drive to Bousquet Ski Area, which is a 200-acre ski area located in on a northern summit of Yokun Ridge in Pittsfield, Massachusetts within the Berkshires cultural region. The resort features a vertical drop of 750 feet, a lift-top elevation of 1,818 feet, twenty-four trails, five lifts, one terrain park, and 75% snowmaking capacity. 20 Min Drive to Ski Butternut, also known as Butternut Basin, is a ski resort in Great Barrington, Massachusetts, located on Warner Mountain in The Berkshires. Channing and Jane Murdock took control of the area in 1963, naming the area Butternut Basin after the large groves of butternut trees located in the basin of the mountain.
Base elevation: 825′ 0″ Top elevation: 1,764′ 0″ Vertical: 1,000′ 0″ Yearly snowfall: 9′ 7″
Hours: Opens 9AM Fri Runs: 22

Guest Reviews:

- "This resort accommodated our 3 kids (oldest is 13) and large breed dog. The XL crate fit well in the master bedroom but could have also fit in the additional bedroom. The pull out couch was adequate. If we were to go again I may opt for an air mattress for added comfort. Pools and hot tub were large and clean. We skied at Butternut and visited local museums. Everything was very close. Highly recommend.." - "We arrived at the property to the owners who got us all situated. Painless process. Close to so many mountains, great pool/hot tub for after skiing. Towns around the area are so adorable as well. Will return again!"

Massachusetts Family Friendly Villa Rentals

Massachusetts Villa Rentals with Parking

Massachusetts Villa Rentals with Entertainment

Massachusetts Pet Friendly Villa Rentals

Massachusetts Villa Rentals with Spa

Massachusetts Villa Rentals with Private Pool

Massachusetts Villa-Rentals on the Map

Compare the Best Villa-Rentals in Massachusetts – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Roslindale village condos 127 Selwyn Street, Boston, MA, MA 02131, USA 674 4.0 8.9 163 Click here
Villa with Access to Amazing Amenities! South Lee, Massachusetts, USA 235 9.4 138 Click here
Indian Lake House Proctor Street, Worcester, MA, MA 01606, USA 198 4.0 8.4 27 Click here
Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance Boston, Massachusetts, USA 653 10.0 133 Click here
Cape Cod Villa 16 Olde Coach Lane, Harwich, MA, MA 02645, USA 574 4.0 9.9 13 Click here
VILLA at Ocean Edge Endicott Village, GOLF PRIVILEGES AND VIEW. LINENS PROVIDED Brewster, , Massachusetts, USA 522 9.8 81 Click here
Peaceful Getaway Cottage on grounds of historic mid-century gem 333 Howard Street, Northborough, MA, MA 01532, USA 340 4.0 9.6 11 Click here
Spacious Getaway by TreeHouse Brewery & Amazon WareHouse Charlton, Massachusetts, USA 442 8.6 24 Click here
Mattakeese Villa Yarmouth, MA, USA 468 4.0 8.6 7 Click here
Spacious Villa with Access to Various Amenities! South Lee, Massachusetts, USA 262 9.8 20 Click here
Villa with Access to Various Amenities South Lee, Massachusetts, USA 198 9.0 17 Click here
Harborview Villa Harwich Port, MA, USA 496 4.0 1 Click here
The Kemble- Built by a US Secretary of State in Lenox Lenox, Massachusetts, USA 3925 10.0 17 Click here
7 Deer Run Harwich Cape Cod- -Sea Pine Villa 7 Deer Run, Harwich, MA, 02645, USA 594 4.0 1 Click here
Mayflower Beach Villas - Seagull Dennis, Massachusetts, USA 653 10.0 11 Click here
Ocean Views & Private Beach 3BR Nature Escape villa Nameloc Heights, MA, USA 703 4.0 1 Click here
Boston Marriott Custom House ~ Downtown Suite with views of the city and harbor Boston, Massachusetts, USA 792 10.0 11 Click here
Gorgeous 5 bedroom Boston Home 71 Commonwealth Avenue, Chestnut Hill, MA, MA 02467, USA 1325 4.0 1 Click here
Beautiful 2BD Villa in Berkshires Resort Lee, Massachusetts, USA 304 9.6 10 Click here

Note: The prices for each Villa-Rentals in Massachusetts do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Villa rentals in Massachusetts that come with a private pool include:

  • Villa with Access to Amazing Amenities!.- Review Count: 138, Rating: 9.4
  • VILLA at Ocean Edge Endicott Village, GOLF PRIVILEGES AND VIEW. LINENS PROVIDED.- Review Count: 81, Rating: 9.8
  • Peaceful Getaway Cottage on grounds of historic mid-century gem.- Review Count: 11, Rating: 9.6

Villa rentals in Massachusetts offering shuttle or transport services include:

  • Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance.- Review Count: 133, Rating: 10.0
  • 52 Union.- Review Count: 0, Rating: 0.0

These villa rentals in Massachusetts provide spa or wellness facilities:

  • Villa with Access to Amazing Amenities!.- Review Count: 138, Rating: 9.4
  • Cape Cod Villa.- Review Count: 13, Rating: 9.9
  • VILLA at Ocean Edge Endicott Village, GOLF PRIVILEGES AND VIEW. LINENS PROVIDED.- Review Count: 81, Rating: 9.8

Family-friendly villa rentals in Massachusetts include:

  • Roslindale village condos.- Review Count: 163, Rating: 8.9
  • Villa with Access to Amazing Amenities!.- Review Count: 138, Rating: 9.4
  • Indian Lake House.- Review Count: 27, Rating: 8.4

Pet-friendly villa rentals in Massachusetts include:

  • Roslindale village condos.- Review Count: 163, Rating: 8.9
  • Indian Lake House.- Review Count: 27, Rating: 8.4
  • Harborview Villa.- Review Count: 0, Rating: 0.0

Villa rentals in Massachusetts that offer breakfast or chef service include:

  • Cape Cod Villa.- Review Count: 13, Rating: 9.9
  • Peaceful Getaway Cottage on grounds of historic mid-century gem.- Review Count: 11, Rating: 9.6
  • Spacious Countryside Villa.- Review Count: 3, Rating: 9.0

Villa rentals in Massachusetts with private or secure parking include:

  • Roslindale village condos.- Review Count: 163, Rating: 8.9
  • Villa with Access to Amazing Amenities!.- Review Count: 138, Rating: 9.4
  • Indian Lake House.- Review Count: 27, Rating: 8.4

Some of the best Villa Rentals in Massachusetts are:

  • Roslindale village condos.- Review Count: 163, Rating: 8.9
  • Indian Lake House.- Review Count: 27, Rating: 8.4
  • Cape Cod Villa.- Review Count: 13, Rating: 9.9

Some of the popular Villa Rentals in Massachusetts are:

  • Roslindale village condos.- Review Count: 163, Rating: 8.9
  • Villa with Access to Amazing Amenities!.- Review Count: 138, Rating: 9.4
  • Harborfront Villa, Charming Mix of Contemporary and Turn of the Century Elegance.- Review Count: 133, Rating: 10.0