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

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2,179 Holiday homes

Home rental in Massachusetts

Marblehead house

3 bedrooms • 2 bathrooms • sleeps 6

from £293 / night

£2,091 / week

1 / 18

Holiday home in South Chatham

South Chatham house

3 bedrooms • 2 bathrooms • sleeps 10

from £232 / night

£1,346 - £4,415 / week

1 / 52

Holiday home in Massachusetts

Plum Island house

4 bedrooms • 2 bathrooms • sleeps 8

from £332 / night

£2,616 / week

1 / 23

Holiday home in Eastham

Eastham house

4 bedrooms • 2 bathrooms • sleeps 8

from £170 / night

£1,187 / week

1 / 19

Massachusetts holiday home rental

Nantucket house

4 bedrooms • 3 bathrooms • sleeps 7

from £644 / night

£4,503 / week

1 / 20

Apartment rental in Massachusetts

Cambridge apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £9 / night

£59 / week

1 / 4

Massachusetts holiday townhouse rental

Edgartown townhouse

3 bedrooms • 2 bathrooms • sleeps 8

from £736 / night

£5,141 / week

1 / 6

Holiday home letting

Oak Bluffs house

4 bedrooms • 2 bathrooms • sleeps 7

from £505 / night

£3,362 - £3,803 / week

1 / 5

Apartment accommodation in Massachusetts

Chelsea apartment

3 bedrooms • 1 bathroom • sleeps 6

from £210 / night

£1,470 / week

1 / 20

Home rental in Newbury

Newbury house

3 bedrooms • 3 bathrooms • sleeps 5

from £342 / night

£2,390 / week

1 / 4

Holiday condo rental

Dennis Port condo

1 bedroom • 1 bathroom • sleeps 4

from £127 / night

£1,096 - £1,180 / week

1 / 16

Holiday home in Marstons Mills

Marstons Mills house

4 bedrooms • 2 bathrooms • sleeps 8

from £145 / night

£1,016 - £1,451 / week

1 / 14

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..

from £156 / night

£1,088 / week

1 / 14

Holiday b&b rental

Arlington b&b

1 bedroom • 1 bathroom • sleeps 2

from £63 / night

£416 / week

1 / 8

Home rental in Eastham

Eastham house

3 bedrooms • 1 bathroom • sleeps 6

from £50 / night

£351 / week

1 / 35

Holiday home in Falmouth

Falmouth house

3 bedrooms • 4 bathrooms • sleeps 8

from £467 / night

£3,264 / week

1 / 25

Monterey holiday cottage rental

Monterey cottage

1 bedroom • 1 bathroom • sleeps 4

from £95 / night

£663 / week

1 / 25

Holiday home in South Orleans

South Orleans house

3 bedrooms • 4 bathrooms • sleeps 8

from £892 / night

£6,244 / week

1 / 4

Holiday condo in Dennis Port

Dennis Port condo

1 bedroom • 1 bathroom • sleeps 4

from £127 / night

£1,096 - £1,180 / week

1 / 56

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.

from £105 / night

£841 - £1,345 / week

1 / 14

Holiday home in Massachusetts

Nantucket house

4 bedrooms • 3 bathrooms • sleeps 8

from £1,009 / night

£7,064 / week

1 / 21

Chatham holiday home rental

Chatham house

2 bedrooms • 2 bathrooms • sleeps 5

from £414 / night

£2,901 / week

1 / 20

Holiday home in Harwich Port

Harwich Port house

3 bedrooms • 1 bathroom • sleeps 7

from £156 / night

£1,088 / week

1 / 20

Home rental in Wellfleet

Wellfleet house

2 bedrooms • 1 bathroom • sleeps 5

from £70 / night

£488 / week

1 / 30

Wareham holiday home rental

Wareham house

1 bedroom • 1 bathroom • sleeps 2

from £119 / night

£832 / week

1 / 10

Chatham holiday home accommodation

Chatham house

4 bedrooms • 2 bathrooms • sleeps 8

from £394 / night

£2,756 / week

1 / 14

Massachusetts holiday home rental

Nantucket house

3 bedrooms • 2 bathrooms • sleeps 8

from £547 / night

£3,826 / week

1 / 9

Holiday cottage with golf nearby in West Chatham

West Chatham cottage

1 bedroom • 1 bathroom • sleeps 4

from £146 / night

£790 / week

1 / 16

Holiday home in Centerville

Centerville house

4 bedrooms • 2 bathrooms • sleeps 6

from £314 / night

£2,510 / week

1 / 34

Monterey holiday cottage rental

Monterey cottage

2 bedrooms • 1 bathroom • sleeps 2

from £155 / night

£1,081 / week

1 / 24

Chatham holiday home rental

Chatham house

4 bedrooms • 3 bathrooms • sleeps 8

“Slice of paradise” Beautiful, well-maintained and cared for home. Exactly as pictured online. Very spacious and clean. Plenty of room to spread out. Nice, quiet neighborhood to walk around. Very close to jackknife beach (plenty of parking, no parking fees) and a short drive to other area beaches. We loved having coffee in the morning on the deck while enjoying the river views. We had a fantastic vacation and would highly recommend staying here. Joy and Bill are wonderful hosts!

from £380 / night

£2,659 / week

1 / 20

Home rental in Wellfleet

Wellfleet house

2 bedrooms • 1 bathroom • sleeps 4

from £74 / night

£513 / week

1 / 29

Sagamore Beach holiday cottage rental

Sagamore Beach cottage

3 bedrooms • 1 bathroom • sleeps 6

from £104 / night

£653 - £726 / week

1 / 11

Farmhouse rental in East Sandwich

East Sandwich farmhouse

3 bedrooms • 2 bathrooms • sleeps 8

from £153 / night

£871 - £1,161 / week

1 / 12

Holiday home in West Brookfield

West Brookfield house

4 bedrooms • 2 bathrooms • sleeps 10

from £255 / night

£1,785 / week

1 / 27

Cottage rental in Eastham

Eastham cottage

2 bedrooms • 1 bathroom • sleeps 4

“Had another amazing vacation in the cute cottages by the bay!” This year, my sister and her family, and me and mine, rented two of the three cottages. We really enjoyed being so close to the beach and having a quiet, shady welcoming place to return to when we needed a break from the sun. The kids loved playing in the grassy area between the cottages.The trees are really beautiful. It was a great space for family picnics. As last time, loved the grills, the outdoor showers, and the peace and beauty of the place. Our days were dictated by the tides! Had two delicious meals at Arnold's, played mini-golf, biked on the rail trail, fished and swam in the kettle ponds, walked and jogged on the beach, slept, read, etc. A perfect vacation. Already planning the next!

from £110 / night

£769 / week

1 / 11

Home rental in Orleans

Orleans house

3 bedrooms • 2 bathrooms • sleeps 6

from £80 / night

£559 / week

1 / 25

East Wareham holiday home rental

East Wareham house

4 bedrooms • 2 bathrooms • sleeps 10

from £203 / night

£1,419 / week

1 / 26

Cottage rental in East Orleans

East Orleans cottage

1 bedroom • 1 bathroom • sleeps 4

from £93 / night

£649 / week

1 / 10

Holiday private room in Somerville

Somerville private room

1 bedroom • 2 bathrooms • sleeps 1

from £50 / night

£350 / week

1 / 5

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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

Skip to beach! Condo across from beach!
Paradise

Great Location the beach is right out your front door ...condo quaint and comfortable...well cared for ... centrally located to island ferries and Provincetown....heated pool outside door with no pool noise heard in condo...will definitely make this a regular favorite destination … see more
Classic Cape Cod cottage on a quiet lane
Perfect summer vacation

Our family of 4, 2 adults and 2 children, had an amazing time at the cottage. The location is perfect- we walked or rode bikes to the nearby bay beach, which is lovely during the day and in the evening to see the sunset. We also walked to the fresh water pond and playground. Lots of food options nearby on Route 6, and ocean beaches and other attractions can be reached by car within 10-15 min. We also enjoyed the dirt road the cottage is on for bike and scooter riding, and the yard. The cottage has everything we needed for a week-long stay. Thank you, Fred!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
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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