50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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Vacation rentals Cape Cod
3,446 properties
Martha's Vineyard
754 properties
Apartments Nantucket
523 properties
Apartments Boston
278 properties
Vacation rentals Cape Ann
149 properties
Apartments Berkshires
125 properties
Apartments Cambridge
51 properties
Apartments Somerville
30 properties
Apartments Plymouth
27 properties
Ipswich
17 properties
Waltham
16 properties
Brookline
15 properties
Apartments Marshfield
13 properties
Hampshire County
12 properties
Apartments Scituate
11 properties
Beach rentals Salisbury
10 properties
Apartments Marion
9 properties
Apartments Wareham
6 properties
Apartments Hull
6 properties
Revere
6 properties

Massachusetts

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5,771 Vacation rentals

(7) Very Good 

24

Vacation cottage with golf nearby in New Seabury

Cape Cod / New Seabury

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • 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 $185 / night

$1295 - $1695 / week

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from $185 / 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

$1600 - $4495 / week

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avg. 1 hour 45 minutes

from $275 / 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

$1300 / week

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from $235 / 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 $284 / night

$1988 - $2788 / week

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from $284 / night

(11) 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

$1428 / week

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Responds fast!
avg. 3 hours 47 minutes

from $204 / night

12

Vacation home in Dennis Port

Cape Cod / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
Enjoy your vacation just steps away from a private, family friendly beach on Nantucket Sound. The cottage is located a few houses away from the Oak Street Private Beach. Cottage includes flat screen TV, cable, wi-fi, window AC unit, full kitchen, indoor/outdoor shower, …see more

from $150 / night

$1050 / week

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from $150 / night

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

(22) Excellent 

65

Apartment rental in Boston

Massachusetts / Boston

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Contemporary One Bedroom, One Bath fully furnished condominium home (711 SF) at a Luxury Condominiums Building at the Boston/Charlestown historic Navy Yard, on the waterfront of Boston Harbor, situated right on the freedom trail and historic attractions such as the USS …see more

from $165 / night

$1050 - $1595 / week

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Responds fast!
avg. 2 hours 33 minutes

from $165 / night

14

Vacation home in Massachusetts

Massachusetts / Plum Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

$3150 - $3450 / week

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Responds fast!
avg. 2 hours 47 minutes

from $399 / night

17

Vacation home in Dennis Port

Cape Cod / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Child friendly
Enjoy your vacation just steps away from a private, family friendly beach on Nantucket Sound. The cottage is located a few houses away from the Oak Street Private Beach. Cottage includes flat screen TV, cable, wi-fi, window AC unit, full kitchen, indoor/outdoor shower, …see more

from $215 / night

$1500 / week

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from $215 / 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 $736 / night

$5150 - $5400 / week

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from $736 / night

13

Vacation guest house in Vineyard Haven

Martha's Vineyard / Vineyard Haven

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden
This property is in downtown Vineyard Haven within the historic district. The barn has a sleeping loft, open living, dining & kitchen area. The efficiency kitchen has a two burner cooktop,under counter refrigerator,coffee maker,microwave and large capacity convection …see more

from $245 / night

$1715 / week

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Responds fast!
avg. 1 hour 57 minutes

from $245 / 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

$3400 / week

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Responds fast!
avg. 1 hour 25 minutes

from $486 / 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

$1800 / week

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Responds fast!
avg. 3 hours 43 minutes

from $250 / 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

$4900 / week

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from $700 / 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

(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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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

$1225 / week

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from $175 / 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

$6176 / week

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from $883 / night

13

Vacation apartment accommodation

Massachusetts / Fall River

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
This is a private, two bedroom apartment that has WIFI, cable, sleeping for 6! TWO bedrooms! One full bed, two twins and a sleeper couch! Hardwood floors, granite counter-tops, appliances, bathtub, shower, modern kitchen and supplies ...perfect for a couple, single, gro …see more

from $92 / night

$525 / week

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from $92 / night

7

Vacation home accommodation

Massachusetts / Milford

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Air conditioning
Welcome to our home right in the middle of the Beautiful downtown of Milford.The scenery is relaxing in the evenings for a walk in the park or the bicycle trail past the historic Cathedral.The room is furnished with a Queen size sofa bed, a queen size futton,spacious Cl …see more

from $89 / night

$623 / week

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from $89 / night

(1) Very Good 

24

Mashpee Vacation home rental

Cape Cod / Mashpee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
*Please note you must be 30 years of age or older and this property does not allow parties or large gatherings of any kind. Mashpee is a charming coastal town on Massachusetts' southern coast that offers travelers a change of pace from the hustle and bustle of everyday …see more

from $275 / night

$1925 - $2800 / week

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Responds fast!
avg. 22 minutes

from $275 / night

41

Vacation home in Falmouth

Cape Cod / Falmouth

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Style, elegance, and an abundance of New England atmosphere come together in this two-bedroom Falmouth home, a lakefront lodge with a gorgeously designed interior, an outdoor entertaining area with a private hot tub, and a wonderful location on the edge of Jenkins Pond. …see more

from $115 / night

$805 / week

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from $115 / night

(17) Excellent 

20

Apartment rental in Hyannis

Cape Cod / Hyannis

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This cozy one bedroom, one bath cottage is just steps to Sea Street and Keyes Beach. Cottage features a newly renovated open living room, fully equipped kitchen, dining area and spacious bedroom. AC in the bedroom and living room. Enjoy the lovely water views and breath …see more

from $135 / night

$1265 / week

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from $135 / night

24

Home rental in Dennis Port

Cape Cod / Dennis Port

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
#902 Sea Stars Cottage: Adorable! This updated cottage is centrally located by Nantucket Sound beaches, shopping and restaurants. Sweet little neighborhood lined with quaint beach cottages, perfect area for bike riding and outdoor entertaining. Immediate feeling of CLEA …see more

from $125 / night

$765 - $1699 / week

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from $125 / night

(1) Excellent 

41

Vacation home in Chatham

Cape Cod / Chatham

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of q …see more

from $600 / night

$4000 - $5200 / week

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from $600 / night

(3) Excellent 

11

Vacation home in Sagamore Beach

Bourne / Sagamore Beach

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Perfect turn-key Sagamore Beach rental home that is a 2-minute walk to the beach. This 4 bedroom home features tons of light, a large finished basement perfect for kids and still holds that "new" home, sparkling clean factor since it was built in 2004. Features a wonde …see more

from $300 / night

$2000 - $2300 / week

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from $300 / night

5

West Stockbridge Vacation condo rental

Berkshires / West Stockbridge

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in t …see more

from $250 / night

$1400 / week

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from $250 / night

(1) Very Good 

6

Vacation apartment in Massachusetts

Martha's Vineyard / Edgartown

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.8 mi
  • Car not necessary
  • Air conditioning
Small studio in a great location close to everything on quiet street in downtown Edgartown. Sleeps 1-2 in queen bed with shower bath and small but complete kitchen. Easy walking access to shopping, dining, beaches, bike path, tennis and public transportation. Attached …see more

from $250 / night

$1800 / week

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Responds fast!
avg. 2 hours 35 minutes

from $250 / night

7

Home rental in Wellfleet

Cape Cod / Wellfleet

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
#304 Beachfront One: 50-feet to the water and directly across from Mayo beach, you'll walk to everything (beach, town, restaurants)!  Classic Cape Cod charm awaits you in this sweet cottage on the water.  Located directly across the street from Cape Cod Bay, its view wi …see more

from $135 / night

$945 - $2099 / week

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from $135 / night

(15) Very Good 

10

Cottage accommodation in Lanesboro

Berkshires / Lanesboro

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. We are about 8 minutes …see more

from $155 / night

$1100 - $1626 / week

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from $155 / night

25

Vacation home in Oak Bluffs

Martha's Vineyard / Oak Bluffs

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and …see more

from $218 / night

$1520 / week

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from $218 / night

(14) Excellent 

16

Vacation apartment in Truro

Cape Cod / Truro

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Adorable free standing cottage at Stones Throw Condominiums offers you all the modern comforts of home. Situated just off Shore Road, this cottage offers you the privacy of North Truro, with the convenience of a 5 minute drive or catch the Shuttle to Provincetown. There …see more

from $165 / night

$650 - $1426 / week

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from $165 / night

(1) Very Good 

45

Vacation home in Massachusetts

Massachusetts / Martha's Vineyard

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
With a spacious interior ranging from formal to casual, a separate play room for the kids, and a large lawn, this Martha's Vineyard vacation home is a great choice for your next family trip. Located in the town of Tisbury, this home is just a short distance away from th …see more

from $127 / night

$889 / week

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from $127 / night

7

Condo rental in Massachusetts

Massachusetts / Natick

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Air conditioning
Light and contemporary 2 bedrooms, 2 bathrooms condo with everything you need for a comfortable stay. Perfect for a family with up to 4 kids or for 2 couples. Spacious master bedroom, additional bedroom, and bathroom. Both rooms have large closets. Enjoy the pool and te …see more

from $140 / night

$899 / week

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from $140 / night

25

Vacation home in Wellfleet

Cape Cod / Wellfleet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Experience peace and comfort at this two-bedroom-plus-loft townhouse on Cape Cod. Perfect for a family or other groups of up to six guests, it offers a charming cabin ambiance in a woodland setting that's far from the hustle and bustle of city living. Welcome to Wellfle …see more

from $99 / night

$693 / week

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from $99 / night

(1) Very Good 

9

Vacation cottage in East Sandwich

Sandwich / East Sandwich

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Set in an association of 9 stand alone cottages is this 3 bedroom Gambrel. First floor bedroom with queen sized bed, first floor full bathroom with tub and shower, open living room  and eat in kitchen. Spiral staircase to 2nd floor with 2 bedrooms, both with twin beds a …see more

from $93 / night

$650 - $1550 / week

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from $93 / night

(10) Excellent 

Certificate of Excellence

14

Apartment rental in Scituate

Massachusetts / Scituate

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Air conditioning
Small efficiency studio with private entrance,deck and bath. Walk to everything in Scituate Harbor. Restaurants, shopping, boating and beach. Sit on your private deck and patio to enjoy the views of the harbor and all the activity. Queen size sleeper sofa allows yo …see more

Certificate of Excellence

from $135 / night

$850 - $1000 / week

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Responds fast!
avg. 2 hours 6 minutes

from $135 / night

(7) Excellent 

25

Truro Vacation home rental

Cape Cod / Truro

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
A wonderful home for family gatherings on your own private beach. A large modern home (3800 square feet!) on over an acre of land provides ample space and an amazing degree of seclusion. The house is both steps from the beach, and situated so that just about every room …see more

from $714 / night

$3200 - $14000 / week

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Responds fast!
avg. 3 hours 33 minutes

from $714 / night

16

Vacation home in Massachusetts

Martha's Vineyard / Oak Bluffs

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
Bright, airy contemporary home located in the wonderful East Chop neighborhood. The first floor features an open concept living room and kitchen. The kitchen has a large island that can seat seven. First floor bedroom is located off of the living room and has access to …see more

from $257 / night

$1800 - $2900 / week

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from $257 / night