50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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2,938 properties
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806 properties
Apartments Boston
359 properties
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133 properties
Apartments Berkshires
128 properties
Apartments Cambridge
53 properties
Brookline
34 properties
Apartments Somerville
28 properties
Apartments Plymouth
25 properties
Ipswich
15 properties
Apartments Scituate
15 properties
Hampshire County
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Apartments Marshfield
10 properties
Apartments Salem
8 properties
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7 properties
Beach rentals Salisbury
7 properties
Revere
6 properties
Brimfield
6 properties

Massachusetts

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5,867 Vacation rentals

23

Vacation home in Massachusetts

Massachusetts / Plum Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Coveted Oceanfront at the Entrance of the Merrimac River. Enjoy 3 levels of decks as you watch the boats pass thru the Breakers. Enjoy panoramic views from the rooftop deck from the coastline of Maine & New Hampshire North to the Isles of Shoal East to Rockport & Glouce …see more

from $399 / night

$3,150 / week

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avg. 2 hours 0 minutes

from $399 / night

(3) Excellent 

24

Vacation apartment rental

Massachusetts / Plymouth

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
A beautiful one-bedroom with additional queen sleep-sofa in the heart of historic Plymouth harbor is waiting for you. Not more than 15 yards to the water and a 3-minute walk to the Mayflower and Plymouth Rock, this location couldn't be better for a vacation rental in P …see more

from $235 / night

$1,300 / week

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avg. 3 hours 4 minutes

from $235 / night

(9) Very Good 

24

Vacation cottage with golf nearby in New Seabury

Cape Cod / New Seabury

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Lovely open-plan home furnished in comfortable, casual style. Fully-equipped kitchen with counter seating, dining area and sitting area with TV, flow into second step-down sitting area which opens with sliding glass doors onto deck and back yard. Master bedroom (with …see more

from $250 / night

$1,500 - $2,750 / week

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from $250 / night

45

Vacation home in South Chatham

Chatham / South Chatham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 0.6 mi
  • Child friendly
  • Air conditioning
Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are brig …see more

from $275 / night

$1,600 - $4,495 / week

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avg. 2 hours 19 minutes

from $275 / night

4

Home rental in Somerville

Massachusetts / Somerville

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Our 3 bed, 2 bath, townhouse is business ready with wifi, 50inch tv with full cable, keurig & coffee/tea and flexible check-ins. We have a stock of DVDs, blowdryer, iron, universal charging station, a collection of frequent forgettables from all our travels, and hand w …see more

from $250 / night

$1,750 / week

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from $250 / night

4

Apartment rental in Massachusetts

Massachusetts / Cambridge

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
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from $10 / night

$70 / week

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from $10 / night

20

Home rental in Orleans

Cape Cod / Orleans

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Rel …see more

from $250 / night

$1,800 / week

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Responds fast!
avg. 3 hours 57 minutes

from $250 / night

20

Massachusetts Vacation home rental

Massachusetts / Nantucket

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This classic and historic Nantucket sea captain's house (part of Nantucket's Historic Registry) was built in 1807 is located on Nantucket Island lying east of Cape Cod, Massachusetts, easily accessible from Boston. Carefully restored by its owners, the home is a short …see more

from $772 / night

$5,400 / week

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from $772 / night

(12) Very Good 

19

Vacation home in Eastham

Cape Cod / Eastham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Cosy, welcoming home in South Eastham on the outer Cape. The property is well equipped and with lots of space for families or groups. Our traditional Cape Cod house features 4 bedrooms, 2 baths, a generous open plan living/dining/kitchen leading out to a deck. The hous …see more

from $204 / night

$1,428 / week

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Responds fast!
avg. 3 hours 45 minutes

from $204 / night

17

Apartment rental in Orleans

Cape Cod / Orleans

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
2 bedroom 1 bath apartment with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Queen bed in one room and a double bed in the other room. Optional air mattress can be set up in living room to sleep 2 more if needed. Window AC units in b …see more

from $175 / night

$1,225 / week

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from $175 / night

31

Vacation home with golf nearby in Stockbridge

Berkshires / Stockbridge

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. Skiing - Butternut 9 miles, Catamount 14 miles, Jiminy Peak 23 miles -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwe …see more

from $250 / night

$1,950 - $3,150 / week

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from $250 / night

7

Massachusetts Vacation apartment rental

Massachusetts / Cambridge

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
Beautiful loft apartment in the heart of Cambridge at Kendall Square. The apartment is fully equipped with washing machine, dryer, dish washer, microwave, and balcony with stunning view. Rental also includes amenities such as gym, pool, parking space, video room, concie …see more

from $250 / night

$1,747 / week

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from $250 / night

9

Vacation home in Teaticket

Falmouth / Teaticket

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home offers 5 bedrooms, 3 full baths, spacious full kitchen and dining area, washer and dryer, family room with TV,  WIFI, outdoor gas grill, heated pool, space to lounge, sandy area with fire pit and hammock under the trees.     Create lasting memories in our compl …see more

from $300 / night

$2,100 - $3,500 / week

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from $300 / night

14

Provincetown Vacation condo rental

Cape Cod / Provincetown

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
A rare historic gem located in Provincetown's Gallery District at the top of Pearl St. This exclusive unit is one of two redeveloped from a 19th-century barn that later served as the Cape School of Art and the studio and residence of the American painter Edwin Dickinson …see more

from $486 / night

$3,400 / week

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avg. 1 hour 40 minutes

from $486 / night

6

Massachusetts Vacation townhouse rental

Martha's Vineyard / Edgartown

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
The K-4 Duplex is part of the Winnetu Oceanside Resort - the only Resort at South Beach. It's a 10-minute walk to the beach and is situated at the bicycling/jogging path leading to charming Edgartown. This 'Silver Level' home offers three bedrooms, two-and-a-half bathro …see more

from $883 / night

$6,175 / week

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from $883 / night

29

Home rental in Massachusetts

Nantucket / Siasconset

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Nantucket is a magical little island located 30 miles off the shores of Cape Cod. It's steeped in the history of its whaling founding fathers. Grey shingled houses dot the coastline, the streets in town are paved in cobblestones, and the harbor is filled with boats well …see more

from $700 / night

$4,900 / week

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from $700 / night

52

Vacation home in Centerville

Cape Cod / Centerville

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Close your eyes and imagine the perfect beach house .Well that's what Mc's Shack Beach House . Situated down a leafy lane right on the beach, on your own private stretch of beach. Mc's Shack Beach House is approx 1700 sq ft ,it has 2 large bedrooms ,a large livingro …see more

from $399 / night

$2,788 - $3,138 / week

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from $399 / night

19

B&b rental in Massachusetts

Nantucket / Siasconset

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
Sea Lion is a 4 bedroom house located in the heart of Tom Nevers. In the summer it's a holiday rental house, in the winter I transform it into a Bed & Breakfast, and live on-site as your hostess. Space Sea Lion is a classic Tom Nevers Upside Down House with 4 decks and …see more

from $250 / night

$1,750 / week

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from $250 / night

(1) Good 

6

Vacation apartment in Massachusetts

Massachusetts / Boston

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Air conditioning
Large, bright apartment located steps from Coolidge Corner. 1 bed/1 bath. Fully equipped kitchen with dishwasher. There is also a gym and laundry located in the building. Across the street from a T stop and walking distance to the heart of Coolidge Corner. …see more

Pricing unknown

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6

Vacation home in Massachusetts

Massachusetts / Boston

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Quiet but just a minute off the interstate, a great place to stay for a few days. Easy access to Newton, Cambridge or Boston. Lovely deck and backyard to relax in the summer. 3 bedrooms and a playroom spread over 3 floors, a garage. A BBQ and a backyard make your stay v …see more

Pricing unknown

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Pricing unknown

18

Home rental in Massachusetts

Massachusetts / Marblehead

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Home originally built in 1923. Purchased and completely renovated in 2004. 1600 sq. ft. As you step onto a mahogany front porch, you open a walnut wood front door into a spacious open floor plan. Diningroom, livingroom and kitchen are bright and cheerful. First floor …see more

from $320 / night

$2,240 - $2,275 / week

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from $320 / night

4

Vacation apartment in Massachusetts

Massachusetts / Boston

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Great one bedroom apartment with lots of living space and large full bathroom. Complete kitchen including dishwasher and microwave. Free internet and cable access. 24 doorman and paid parking available in lower garage. Many nearby restaurants, bars and a Walgreens. Also …see more

from $1,241 / night

$6,206 / week

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from $1,241 / night

4

Vacation home in Boston

Massachusetts / Boston

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
Beautiful one bedroom penthouse apartment with small balcony overlooking Boston harbor and airport. Walk-able to all major tourist destinations including Fanueil Hall and Quincy market. Many nearby restaurants and bars. Right next to the blue and orange line T stops. Do …see more

from $1,410 / night

$7,050 / week

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from $1,410 / night

20

Vacation home in Osterville

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden
Desired location on Cape Cod! It's always nice to be a short stroll to the village with it's shops and great restaurants and not far from the beach. This Osterville rental home has these qualities and more. Walk into a large Living room with TV, eat in Kitchen with …see more

from $300 / night

$2,100 / week

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from $300 / night

9

Vacation home in Nantucket

Massachusetts / Nantucket

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets
Monomoy Village Cottage: Adorable fully renovated and nicely decorated. Open floor plan - fully equipped kitchen. The cottage is a short walk to a secluded harbor beach. Warm, charming, and a short distance to downtown Nanttucket. Additional amenities include: beach to …see more

from $458 / night

$3,200 / week

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from $458 / night

23

Vacation home in Massachusetts

Martha's Vineyard / Edgartown

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
MVVR EXCLUSIVE: Situated on a quiet tree lined cul de sac, this lovely home has everything to assure families a wonderful Vineyard vacation experience. Charm abounds in this tastefully decorated 3 level home with A/C, 3 TV's, WiFi, large mahogany deck, outdoor shower …see more

from $258 / night

$1,800 - $3,900 / week

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from $258 / night

12

Woods Hole Vacation home rental

Falmouth / Woods Hole

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
This private getaway is located right on pristine Quissett Harbor. Dine inside or out on an elevated deck with a retractable awning permitting all weather eating straight from the outdoor grill. Enjoy a 500 yd stroll to two swimming beaches (The Knob or Crescent Beach …see more

from $429 / night

$3,000 / week

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from $429 / night

20

Vacation apartment rental

Cape Cod / Brewster

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
This street level garden villa for 6 guests has a definite beachy feel, and is located within walking distance to Fletcher or Arbor pool complexes as well as the tennis courts and the Linx Tavern. The nautical décor in the air-conditioned living and dining area is an in …see more

from $161 / night

$1,125 - $1,712 / week

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from $161 / night

24

West Stockbridge Vacation home rental

Berkshires / West Stockbridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provi …see more

from $165 / night

$1,155 - $1,435 / week

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avg. 45 minutes

from $165 / night

20

Oak Bluffs Vacation home rental

Martha's Vineyard / Oak Bluffs

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step in …see more

from $243 / night

$1,700 - $2,500 / week

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from $243 / night

34

Vacation home with swimming pool in Massachusetts

Martha's Vineyard / Edgartown

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Stunning tri level vacation home bordered by professionally landscaped grounds with Gunite pool, located in a quiet Katama neighborhood, walk or bike to South Beach. This spacious home is perfect for extended families and features multiple living areas on both the first …see more

from $650 / night

$4,550 - $14,050 / week

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from $650 / night

(2) Very Good 

16

Vacation apartment in Hancock

Berkshires / Hancock

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everyt …see more

from $199 / night

$1,393 / week

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from $199 / night

12

Massachusetts Vacation home rental

Massachusetts / Nantucket

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Featured in the April 2010 design issue of Nantucket Today, this adorable Nantucket country cottage is an ideal spot to enjoy an island vacation; a short distance from downtown and conveniently located to shopping, markets and beaches. 1st fl: Living room, dining area, …see more

from $658 / night

$4,600 / week

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from $658 / night

(1) Excellent 

23

Vacation home in Massachusetts

Martha's Vineyard / Edgartown

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
Enjoy your vacation at "Second Heaven", a brand new remodeled three-bedroom contemporary cape. Conveniently located 3 miles into Edgartown Center and 3.5 miles to State Beach. Adjacent to bike path. Enjoy the summer cottage feel in this tastefully decorated home with al …see more

from $247 / night

$1,725 - $2,525 / week

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from $247 / night

29

Home rental in Edgartown

Martha's Vineyard / Edgartown

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Pristine summer home, centrally located in Dodger's Hole neighborhood offers a private setting surrounded by beautifully landscaped yard. The home features a wrap around deck, deck dining area and a spacious screened porch with outdoor living room and overlooks the gor …see more

from $315 / night

$2,200 - $3,500 / week

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from $315 / night

31

Massachusetts Vacation home rental

Martha's Vineyard / West Tisbury

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely, fully equipped contemporary 5 bedroom, 4 bathroom home with distant waterviews over the North Shore and beautiful private association beach access. Luxuries include gourmet kitchen with breakfast bar seating for eight, open pantry, stainless appliances, two …see more

from $858 / night

$6,000 - $9,000 / week

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from $858 / night

31

Vacation home in Massachusetts

Martha's Vineyard / Vineyard Haven

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Nestled in the lovely private community of homes and condos, this lovely two bedroom 2 and a half bath unit is just a five minute walk to the association pool and tennis courts and just two miles from Vineyard Haven Village Center. Relax on the large back deck with …see more

from $215 / night

$1,500 - $2,900 / week

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from $215 / night

26

Massachusetts Vacation home rental

Martha's Vineyard / Edgartown

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Traditional and delightful Cape style home features 3 bedrooms and 2.5 baths. Sunny open floor plan on the main living level consists of kitchen, dining area and comfortable living room which opens to deck area and large yard. There is an additional TV/Office room wit …see more

from $190 / night

$1,325 - $3,835 / week

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from $190 / night

12

Vacation home in Massachusetts

Martha's Vineyard / Edgartown

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Centrally located mid island this beautifully appointed home features open design kitchen, dining and living areas for easy entertainment with family and friends. French doors off of living area open onto a comfortably furnished screened porch with dining table. Glass …see more

from $322 / night

$2,250 - $3,650 / week

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from $322 / night

18

Vacation home in Massachusetts

Martha's Vineyard / Vineyard Haven

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
MVVR Exclusive: Beautifully appointed with a mix of Asian and Tibetan antique furniture, furnishings from Napa Valley, Sundance and Pottery Barn, and original art work, this highly desirable townhouse provides a luxurious but comfortable setting for a memorable Vineyard …see more

from $286 / night

$2,000 - $3,400 / week

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from $286 / night