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

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5,308 Holiday homes

Home rental in Massachusetts

Marblehead house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 35 minutes

from £311 / night

£2,175 / week

Holiday home in South Chatham

South Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

from £257 / night

£1,492 / week

Holiday home in Massachusetts

Plum Island house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 55 minutes

from £376 / night

£2,965 / week

Holiday home in Eastham

Eastham house

4 bedrooms / 2 bathrooms / sleeps 8

14

Responds fast! avg. 3 hours 15 minutes

from £192 / night

£1,344 / week

Cottage rental in Dennis Port

Dennis Port cottage

2 bedrooms / 1 bathroom / sleeps 6

from £226 / night

£1,412 / week

Holiday home in Centerville

Centerville house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 57 minutes

from £265 / night

£1,853 - £3,111 / week

Massachusetts holiday home rental

Nantucket house

4 bedrooms / 3 bathrooms / sleeps 7

from £725 / night

£5,074 / week

Home rental in Orleans

Orleans house

4 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 59 minutes

from £280 / night

£1,863 / week

Home rental in Somerville

Somerville house

3 bedrooms / 2 bathrooms / sleeps 10

from £330 / night

£2,306 / week

Apartment rental in Massachusetts

Cambridge apartment

2 bedrooms / 2 bathrooms / sleeps 4

from £10 / night

£66 / week

Home rental in Massachusetts

Siasconset house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 47 minutes

from £752 / night

£6,586 / 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 £372 / night

£2,353 - £2,847 / week

Holiday apartment in Massachusetts

Boston apartment

1 bedroom / 1 bathroom / sleeps 4

1

Pricing unknown

Holiday home rental

New Seabury house

4 bedrooms / 2 bathrooms / sleeps 8

from £800 / night

£5,601 / week

Apartment accommodation in Massachusetts

Chelsea apartment

3 bedrooms / 1 bathroom / sleeps 6

from £236 / night

£1,647 / week

Holiday home in Eastham

Eastham house

3 bedrooms / 2 bathrooms / sleeps 6

from £423 / night

£2,960 / week

Provincetown holiday yacht rental

Provincetown yacht

3 bedrooms / 3 bathrooms / sleeps 6

1

from £2,024 / night

£14,164 / week

Cottage rental in Osterville

Osterville cottage

3 bedrooms / 2 bathrooms / sleeps 6

from £565 / night

£3,954 / week

Holiday home in Brewster

Brewster house

4 bedrooms / 2 bathrooms / sleeps 9

from £424 / night

£2,824 / week

Holiday home in Williamstown

Williamstown house

4 bedrooms / 2 bathrooms / sleeps 6

from £123 / night

£857 / 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 apartment in Massachusetts

Boston apartment

1 bedroom / 1 bathroom / sleeps 4

from £1,026 / night

£5,131 / week

Holiday home in Boston

Boston house

1 bedroom / 1 bathroom / sleeps 3

from £1,145 / night

£5,725 / week

Holiday condo rental

Dennis Port condo

1 bedroom / 1 bathroom / sleeps 4

3

Responds fast! avg. 2 hours 45 minutes

from £142 / night

£1,318 / week

Osterville holiday home rental

Osterville house

3 bedrooms / 3 bathrooms / sleeps 6

from £185 / night

£1,296 / week

Holiday home in Marstons Mills

Marstons Mills house

4 bedrooms / 2 bathrooms / sleeps 8

6

from £112 / night

£730 - £1,754 / 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 £170 / night

£1,099 - £2,740 / week

Holiday b&b rental

Arlington b&b

1 bedroom / 1 bathroom / sleeps 2

1

from £71 / night

£470 / week

Holiday home in Dennis

Dennis house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 5 minutes

from £575 / night

£4,023 / week

Home rental in Eastham

Eastham house

3 bedrooms / 1 bathroom / sleeps 6

3

from £50 / night

£346 / week

West Stockbridge holiday condo rental

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

from £236 / night

£1,365 / week

Holiday home in Massachusetts

Nahant house

3 bedrooms / 1 bathroom / sleeps 6

2

from £256 / night

£1,788 / week

Holiday home in Richmond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

4

from £175 / night

£1,222 / week

Massachusetts holiday home rental

Siasconset house

5 bedrooms / 3 bathrooms / sleeps 10

from £588 / night

£4,111 - £7,399 / week

Holiday home rental

East Orleans house

1 bedroom / 1 bathroom / sleeps 3

1

Responds fast! avg. 0 minutes

from £105 / night

£734 / week

Holiday home in Falmouth

Falmouth house

3 bedrooms / 4 bathrooms / sleeps 8

from £521 / night

£3,644 / week

West Chatham holiday home rental

West Chatham house

3 bedrooms / 2 bathrooms / sleeps 10

3

Responds fast! avg. 3 hours 16 minutes

from £402 / night

£2,812 / week

Viewing 40 of 5,308
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

Sweet Seaside cottage... love nest or family haven
Lovely holiday

The area is lovely and had a very relaxing holiday. Swimming pool was a big plus as we have a four year old.. Some lovely beaches near by especially veterans beach.. … see more
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
Hyannis Retreat
Excellent location and very comfortable

Mu husband and I are both retired and stayed here for 4 nights as part of our tour of New England. Hyannis is a good base for exploring Cape Cod and the Retreat is well located close to the port where you will find plenty to watch and of course the seafood restaurants. You will need a car to get to the port, but you can walk to the beach for a swim or a stroll. We had everything we needed for our short stay.see 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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