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Houses in Massachusetts and Holiday rentals - Holiday Lettings - Holiday Rentals Massachusetts

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3,433 Holiday homes

Home rental in Massachusetts

Marblehead house

3 bedrooms / 2 bathrooms / sleeps 6

from £307 / night

£2,191 / week

Holiday home in South Chatham

South Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

from £230 / night

£1,336 - £4,382 / week

Holiday home in Massachusetts

Plum Island house

4 bedrooms / 2 bathrooms / sleeps 8

from £330 / night

£2,606 / week

Holiday home in Eastham

Eastham house

4 bedrooms / 2 bathrooms / sleeps 8

14

from £169 / night

£1,181 / week

Massachusetts holiday home rental

Nantucket house

4 bedrooms / 3 bathrooms / sleeps 7

from £641 / night

£4,483 / week

Apartment rental in Massachusetts

Cambridge apartment

2 bedrooms / 2 bathrooms / sleeps 4

from £10 / night

£66 / week

Massachusetts holiday townhouse rental

Edgartown townhouse

3 bedrooms / 2 bathrooms / sleeps 8

from £832 / night

£5,813 / week

Holiday home letting

Oak Bluffs house

4 bedrooms / 2 bathrooms / sleeps 7

from £377 / night

£2,514 - £2,954 / week

Apartment accommodation in Massachusetts

Chelsea apartment

3 bedrooms / 1 bathroom / sleeps 6

from £236 / night

£1,647 / week

Home rental in Newbury

Newbury house

3 bedrooms / 3 bathrooms / sleeps 5

from £365 / night

£2,556 / week

Holiday home in Eastham

Eastham house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 minutes

from £376 / night

£2,627 / week

Holiday b&b in Massachusetts

Cambridge b&b

1 bedroom / 1 bathroom / sleeps 3

from £91 / night

£636 - £1,883 / week

Holiday b&b in Cambridge

Cambridge b&b

1 bedroom / 1 bathroom / sleeps 4

from £91 / night

£636 - £1,883 / week

Holiday b&b in Massachusetts

Cambridge b&b

1 bedroom / 1 bathroom / sleeps 3

from £91 / night

£636 - £1,883 / week

Holiday condo rental

Dennis Port condo

1 bedroom / 1 bathroom / sleeps 4

4

Responds fast! avg. 1 hour 25 minutes

from £125 / night

£1,076 - £1,159 / week

Holiday home in Marstons Mills

Marstons Mills house

4 bedrooms / 2 bathrooms / sleeps 8

6

from £145 / night

£1,012 - £1,662 / week

Holiday cottage in Sagamore Beach

Sagamore Beach cottage

3 bedrooms / 1 bathroom / sleeps 5

“Beach House-343 Phillips Rd” The location couldnt have been better...right on the beach.. Great outdoor shower, Updated kitchen, Very nice.. would definitely stay again..

11

from £156 / night

£1,084 - £2,529 / week

Holiday b&b rental

Arlington b&b

1 bedroom / 1 bathroom / sleeps 2

1

from £71 / night

£470 / week

Home rental in Eastham

Eastham house

3 bedrooms / 1 bathroom / sleeps 6

3

from £78 / night

£547 / week

West Stockbridge holiday condo rental

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 35 minutes

from £210 / night

£1,217 / week

Massachusetts holiday home rental

Siasconset house

5 bedrooms / 3 bathrooms / sleeps 10

from £517 / night

£3,615 - £8,675 / week

Holiday home in Falmouth

Falmouth house

3 bedrooms / 4 bathrooms / sleeps 8

from £465 / night

£3,252 / week

West Chatham holiday home rental

West Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

3

from £354 / night

£2,470 / week

Monterey holiday cottage rental

Monterey cottage

1 bedroom / 1 bathroom / sleeps 4

1

Responds fast! avg. 5 minutes

from £95 / night

£661 / week

Holiday home in South Orleans

South Orleans house

3 bedrooms / 4 bathrooms / sleeps 8

from £1,009 / night

£7,059 / week

Massachusetts holiday home let

Siasconset house

2 bedrooms / 2 bathrooms / sleeps 4

from £138 / night

£962 - £1,817 / week

Essex holiday apartment rental

Essex apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £154 / night

£964 - £1,271 / week

Holiday condo in Dennis Port

Dennis Port condo

1 bedroom / 1 bathroom / sleeps 4

14

Responds fast! avg. 1 hour 23 minutes

from £126 / night

£1,086 - £1,170 / week

Holiday cottage in Dennis Port

Dennis Port cottage

2 bedrooms / 1 bathroom / sleeps 5

“A cozy 'home from home'.” We were delighted with our stay in this relaxing, well decorated and very comfortable Cape Cod cottage. It is perfectly located being close to the beach, shops and restaurants and ideal for exploring the beautiful Cape. Clearly a lot of thought has gone into making sure that everything one could possibly wish for is provided. Arriving after our long journey we at once settled in and felt at home. The warm house, welcoming chocolates and bottle of wine were much appreciated as well as the paper and pen waiting for us in the kitchen drawer the following morning just as our thoughts had turned to shopping. The sun shone and the glorious cherry tree in the garden put on a wonderful flowering display during our visit. From the peaceful deck we were able to watch the squirrels in the trees whilst having lunch. So much praise should go to Mark and Lynn for creating this 'home from home' to which we very much hope to return before too long.

29

Responds fast! avg. 3 hours 32 minutes

from £104 / night

£826 - £1,197 / week

Holiday home in Massachusetts

Nantucket house

4 bedrooms / 3 bathrooms / sleeps 8

8

from £1,000 / night

£6,997 / week

Home rental in Massachusetts

Nantucket house

2 bedrooms / 2 bathrooms / sleeps 4

from £239 / night

£1,668 / week

Home rental in Siasconset

Siasconset house

3 bedrooms / 3 bathrooms / sleeps 8

from £209 / night

£1,462 / week

Chatham holiday home rental

Chatham house

2 bedrooms / 2 bathrooms / sleeps 5

1

from £362 / night

£2,529 / week

Holiday home in Harwich Port

Harwich Port house

3 bedrooms / 1 bathroom / sleeps 7

from £145 / night

£1,012 - £1,084 / week

Holiday home in Siasconset

Siasconset house

3 bedrooms / 17 bathrooms / sleeps 26

from £433 / night

£3,032 / week

Home rental in Wellfleet

Wellfleet house

2 bedrooms / 1 bathroom / sleeps 5

from £87 / night

£607 / week

Holiday farmhouse in Massachusetts

Belchertown farmhouse

6 bedrooms / 3 bathrooms / sleeps 14

from £377 / night

£1,883 / week

Wareham holiday home rental

Wareham house

1 bedroom / 1 bathroom / sleeps 2

from £135 / night

£942 / week

Chatham holiday home accommodation

Chatham house

4 bedrooms / 2 bathrooms / sleeps 8

from £331 / night

£2,312 / week

Siasconset holiday home rental

Siasconset house

2 bedrooms / 2 bathrooms / sleeps 4

from £334 / night

£2,335 / week

Viewing 40 of 3,433
rentals in Massachusetts

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Massachusetts holidays

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 savoury flavours 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 holiday 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 naantucket and Martha's Vineyard, Cape Cod is a holiday 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 amongst 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 holidayers 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 holiday 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 neighbouring Vermont, the rich history of New Hampshire and the colourful capital of Rhode Island, Providence. All these destinations are a short journey from Boston and offer memorable ways to round out your holiday.

Top Destination reviews

Charming Cape Cod Cabin
Peaceful, a great spot

We had a wonderful time staying in this house and particularly enjoyed the peaceful location - sitting out on the porch in the evening all you could hear was the wind in the trees and the crickets. The local town of Orleans is a 15 minute cycle away on the Cape Cod Rail Trail and has some wonderful spots for ice cream & thrift stores - highly recommend a visit to the Ice Cream Cafe & the Local Colour Boutique. It was great to be able to cycle to most places from this location, there were several small ponds nearby that were quieter for a swim than some of the larger ones - though Wellfleet Long Pond is a must. The house itself was large and comfortable, the kitchen was a great spot where we could all chat whilst making dinner, we got a lot of use out of the basement tv room as it was one of the coolest spots in the house. All in all, it made for a lovely base to come back to at the end of a long day at the beach!see more
Barnstable Village Private Pool
Great home, garden and location

Located at the end of a quiet road. Pool and garden outstanding - surrounded on all sides by trees with plenty of bird life - Blue Jays the stars. Barnstable is an ideal location to explore all of Cape Cod. Close to Barnstable Harbour with it's Whale Watching boat - an exciting trip. Good restaurants within a few minutes drive, Rob the owner provides information on the best places to visitsee more
Blissful Cape Cod Cottage with Waterviews
Fantastic location

A great location for all the family. We had a full itinerary of day trips on Cape Cod but ended up spending most of our time on the beach and in the pond. No need to go any further afield ! … see more
#102: NEW Renovation, Modern; Private Patio; Walk to Town!
Great location

Great location and lovely modern decor. Main living area/kitchen is a bit small for family life, with not enough storage in kitchen or bedrooms. Would better suit adults who mostly eat out. Car parking space was also a little narrow meaning a big car blocks access to the neighbor below. We managed in the end with a large SUV, but needed some tight parking manoeuvres. Having said all that we had a great week and enjoyed the short strolls to town and everything Provincetown has to offer.see more

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