Vacation Rentals & Cabins in Massachusetts

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6,446 cabins

(4) Excellent 

10

Great Vacation House in the Berkshires on Richmond Pond

Berkshires / Richmond

Richmond house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$186

Price per night from

$186

25

Charming Pocasset House w/ Patio - Walk to Beach!

Cape Cod / Bourne

Bourne house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$195

Responds fast!
avg. 8 minutes

Price per night from

$195

(8) Excellent 

39

Ocean View Condo across from Beach with pool!

Dennis / Dennis Port

Dennis Port condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

Price per night from

$125

Responds fast!
avg. 2 hours 47 minutes

Price per night from

$125

(5) Excellent 

10

Oceanfront Home with Private Beach!

Cape Cod / Sandwich

Sandwich apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
“Very nice place to stay.” My family had a great time at this beach house. Grandkids loved it. Beach was a bit rocky but they made it work. The house had everything we needed. Thank you. One suggestion would be screens on the windows.
…see more

Price per night from

$554

Responds fast!
avg. 3 hours 18 minutes

Price per night from

$554

29

#304: Beachy keen cottage! Across from Mayo Beach, and short walk to downtown.

Cape Cod / Wellfleet

Wellfleet house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$120

Price per night from

$120

5

Cozy Modern Condo for the Berkshires

Berkshires / West Stockbridge

West Stockbridge condo

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$252

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$252

24

Oceanview Buzzards Bay 3BR Getaway w/ Wraparound Deck – Steps to the Beach

Bourne / Buzzards Bay

Buzzards Bay house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Ask about children

Price per night from

$117

Price per night from

$117

(1) Average 

8

Room with double bed minutes from Harvard Square

Massachusetts / Arlington

Arlington b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

Price per night from

$75

Price per night from

$75

(28) Excellent 

10

Classic, Quiet, Private Dennisport Cottage

Dennis / Dennis Port

Dennis Port cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Perfect Cape Cod Vacation Cottage” We just returned from our week-long stay at this beautiful, immaculately clean cottage. We fell in love with it online, and it certainly did not disappoint! I can honestly say that there was not one thing lacking fro
…see more

Price per night from

$125

Price per night from

$125

12

3 Wigwam Road, Nantucket, MA

Nantucket / Siasconset

Siasconset house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$500

Price per night from

$500

11

244 Phillips Rd

Bourne / Sagamore Beach

Sagamore Beach cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$129

Price per night from

$129

(4) Excellent 

24

Waterfront Cottage - 10 Mins to Great Barrington!

Berkshires / New Marlborough

New Marlborough cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ski
  • Suitable for children age 5+

Price per night from

$180

Responds fast!
avg. 8 minutes

Price per night from

$180

(2) Very Good 

26

#403: Beautiful bay 1 min away. Nothing to pack but a bathing suit & kayak.

Cape Cod / Eastham

Eastham house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$70

Price per night from

$70

4

Topside MainHouse

Cape Cod / South Orleans

South Orleans house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+

Price per night from

$1,071

Price per night from

$1,071

(6) Excellent 

14

114 Long Pond Rd

Cape Cod / Marstons Mills

Marstons Mills house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$129

Price per night from

$129

(1) Excellent 

24

#309: Charming Victorian home on the bay in Wellfleet - walk to water!

Cape Cod / Wellfleet

Wellfleet house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$121

Price per night from

$121

17

7 Mallard Drive 49614

Cape Cod / Orleans

Orleans house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$271

Price per night from

$271

6

5 Folgers Court , Nantucket, MA

Nantucket / Siasconset

Siasconset house

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$314

Price per night from

$314

28

246 Wianno Circle

Cape Cod / Osterville

Osterville house

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Ask about children
  • Ask about pets

Price per night from

$428

Price per night from

$428

15

8325 Kane, Catherine

Cape Cod / Chatham

Chatham house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

(1) Excellent 

28

#306: Absorb the sun and salt air in your private cottage! The perfect getaway.

Cape Cod / Wellfleet

Wellfleet house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$139

Price per night from

$139

19

132425

Harwich / Harwich Port

Harwich Port house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$421

Price per night from

$421

19

51 Finway - SD2666

Cape Cod / New Seabury

New Seabury house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$575

Price per night from

$575

15

Skip to beach! Condo across from beach!

Dennis / Dennis Port

Dennis Port condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$100

Responds fast!
avg. 2 hours 47 minutes

Price per night from

$100

4

Summer Beach Home Seasonal or year lease! Beach community, walk to warm water b

Massachusetts / Wareham

Wareham house

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min

Price per night from

$143

Price per night from

$143

14

7442 Bevan

Cape Cod / Chatham

Chatham house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$200

Price per night from

$200

12

225 Wianno Circle

Cape Cod / Osterville

Osterville house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Ask about children
  • Ask about pets

Price per night from

$385

Price per night from

$385

(2) Very Good 

9

Nantucket Cottage Abuts Bird Santuary

Massachusetts / Nantucket

Nantucket house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$600

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$600

(3) Excellent 

26

Waterfront home on cedar lake in Sturbridge mass for rent 2 BR beautiful view

Massachusetts / Sturbridge

Sturbridge house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$250

Price per night from

$250

(1) Excellent 

6

One Bedroom Loft Apartment B at Cedar Hill Farm B & B

Cape Ann / Essex

Essex apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$176

Price per night from

$176

25

Cape Cod Area House w/Hot Tub - Walk to the Beach!

Cape Cod / Dennis

Dennis house

5 13 min stay varies

  • 5 bedrooms
  • sleeps 13
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$503

Responds fast!
avg. 8 minutes

Price per night from

$503

(2) Very Good 

8

Little Harbor 1 Bedroom

Falmouth / Woods Hole

Woods Hole studio

Studio 3 min stay varies

  • Studio
  • sleeps 3
  • min stay varies
  • Nearest beach 0.6 mi
  • Child Friendly
  • Car not necessary

Price per night from

$157

Price per night from

$157

(2) Excellent 

24

HUGE POOL HOUSE 4 BedRooms 2.5 Bathrooms ,3 Parking spots & a POOL!

Massachusetts / Arlington

Arlington house

5 16 1 night min

  • 5 bedrooms
  • sleeps 16
  • 1 night min
  • Child Friendly

Price per night from

$402

Responds fast!
avg. 25 minutes

Price per night from

$402

11

71 Baxter Road, Siasconset, MA

Nantucket / Siasconset

Siasconset house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$1,078

Price per night from

$1,078

(1) Excellent 

20

Enjoy horses and the largest recreational lake in Massachusetts

Berkshires / East Otis

East Otis apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$111

Price per night from

$111

(8) Excellent 

Certificate of Excellence

21

Nantucket Colonial Abuts Conservation Area

Massachusetts / Nantucket

Nantucket house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 4 mi
  • Child Friendly
  • Car not necessary

Certificate of Excellence

Price per night from

$900

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$900

24

Waterfront New England House on Wickaboag Lake!

Massachusetts / West Brookfield

West Brookfield house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$235

Responds fast!
avg. 42 minutes

Price per night from

$235

19

466 Parker Road

Cape Cod / Osterville

Osterville house

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Ask about children
  • Pet Friendly

Price per night from

$257

Price per night from

$257

About Massachusetts

Home of Plymouth Rock, the Kennedys and the Red Sox, Massachusetts is the epitome of a New England experience. With the dense wilderness, balmy beaches of Cape Cod in the southeast and the bustling metropolis of Boston on the coast, there are plenty of sights and sounds to engage visitors. Indulge in a luscious bowl of New England Clam Chowder followed by the savory flavors of a freshly caught lobster. With every season bringing something special, from the crisp, brilliant leaves of autumn to the warm summertime beaches, there's no bad time to vacation in Massachusetts.

Some of the most storied and popular regions of the state include:

  • Cape Cod: Including both the cape itself and the offshore islands, which include famous Nantucket and Martha's Vineyard, Cape Cod is a vacation unto itself. Splendorous in summer, scenic in autumn and a joy in spring, Cape Cod is a must-see for visitors to Massachusetts.
  • Boston: One of the most historic and famed cities on the east coast and the capital, Boston is home to a world-class Museum of Fine Arts, the Harvard campus and a plethora of historical sites, beautiful streets and fascinating scenery. It's not an accident that over 16 million people visit the city each year. If you're with the family, many water parks in Massachusetts and amusement parks in Massachusetts are in the Boston area. In addition, most Massachusetts National Parks are a short drive from the city.
  • Pioneer Valley: Home to the historic counties of Franklin, Hampden and Hampshire, Pioneer Valley is the perfect place to chase down the fascinating secrets of the state's complex and lengthy history.
  • Berkshire Hills: The state's westernmost region is among its most beautiful. Some of the best camping in Massachusetts is in the Berkshire Hills area, and its quiet, out-of-the-way location greatly appeals to those seeking to slow life down a gear.
  • Provincetown: A hotspot of the arts, booming Provincetown was once a well-kept secret but is becoming a fashionable place for vacationers to visit.

During the summer and fall, both Boston and the Cape Cod area are alive with activity. It's a vibrant time of year to visit, with the beautiful beaches attracting thousands of patrons on a hot summer day and the legendary New England foliage making every turn a photo opportunity come fall.

A vacation rental is a more private, spacious and quiet alternative to getting a hotel room. Staying in a cabin is a perfect way to commune with nature if you're outside the city, and a condo or apartment rental is perfect if you're staying in the Boston area.

Explore more of New England by checking out the autumn leaves in neighboring Vermont, the rich history of New Hampshire and the colorful capital of Rhode Island, Providence. All these destinations are a short journey from Boston and offer memorable ways to round out your vacation.