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

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2,031 Holiday homes

Holiday b&b in Massachusetts

Revere b&b

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from £270 / night

£1,370 - £1,946 / week

1 / 12

Gloucester holiday home rental

Gloucester house

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 10

from £522 / night

£3,654 / week

1 / 18

Holiday boathouse in South Orleans

South Orleans boathouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £392 / night

£2,740 / week

1 / 10

Holiday home in South Orleans

South Orleans house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £979 / night

£6,850 / week

1 / 4

Home rental in Chatham

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £316 / night

£2,736 - £5,476 / week

1 / 55

Holiday home in South Chatham

South Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £316 / night

£2,736 - £5,476 / week

1 / 52

Holiday hotel apartment in Massachusetts

Winthrop hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £173 / night

£1,209 / week

1 / 4

Holiday hotel apartment in Winthrop

Winthrop hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £237 / night

£1,656 / week

1 / 4

Holiday home in Massachusetts

Milton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £179 / night

£1,128 / week

1 / 25

Townhouse rental in South Yarmouth

South Yarmouth townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £92 / night

£640 / week

1 / 27

Somerville holiday home rental

Somerville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £328 / night

£2,329 / week

1 / 12

Home rental in Massachusetts

Middleborough house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £115 / night

£594 / week

1 / 17

Holiday home in Dennis Port

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £160 / night

£1,119 / week

1 / 22

Holiday home in Dennis Port

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Cozy and minutes from the beach” Quiet and cozy cottage. Decent for 2 and a child. We brought our 2 dogs and it got a bit tight but manageable. Would do it again but this time w/o the dogs:) Definitely recommend the place.

from £160 / night

£1,119 / week

1 / 11

Oak Bluffs holiday cottage rental

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £1,566 / night

£10,960 / week

1 / 26

Holiday cottage in Sandwich

Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £120 / night

£878 - £1,835 / week

1 / 15

Holiday cottage in Falmouth

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £392 / night

£2,740 / week

1 / 5

Home rental in New Seabury with golf nearby

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £297 / night

£2,740 / week

1 / 30

Holiday home rental

Rockport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

from £548 / night

£4,339 / week

1 / 46

Holiday home rental

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £261 / night

£1,827 / week

1 / 20

Sagamore Beach holiday cottage rental

Sagamore Beach cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £136 / night

£958 - £1,755 / week

1 / 11

Dennis Port holiday home rental

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £496 / night

£3,471 / week

1 / 16

Holiday apartment in Sandwich

Sandwich apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £274 / night

£1,915 - £3,032 / week

1 / 17

Holiday cottage in Massachusetts

Westford cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £177 / night

£1,233 / week

1 / 20

Home rental in Eastham

Eastham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

from £255 / night

£1,781 / week

1 / 15

Holiday apartment in East Otis

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £101 / night

£640 / week

1 / 20

Gloucester holiday home rental

Gloucester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £320 / night

£2,238 / week

1 / 68

Holiday home in Dennis

Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £118 / night

£825 / week

1 / 8

Holiday home in Massachusetts

Nantucket house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

from £1,370 / night

£9,590 / week

1 / 27

Home rental in Massachusetts

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £503 / night

£3,517 / week

1 / 14

Holiday home in West Hyannisport

West Hyannisport house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £160 / night

£1,119 / week

1 / 17

Lynn holiday apartment rental

Lynn apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

from £23 / night

£160 / week

1 / 9

Holiday home in North Truro

North Truro house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,109 / night

£7,764 / week

1 / 30

Belmont holiday apartment rental

Belmont apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £127 / night

£981 - £1,457 / week

1 / 28

Holiday cottage letting

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £224 / night

£1,567 / week

1 / 18

Provincetown holiday cottage rental

Provincetown cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £252 / night

£2,101 / week

1 / 14

Holiday home in Brewster

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

from £393 / night

£2,740 / week

1 / 24

Holiday home in Barnstable

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,044 / night

£7,307 / week

1 / 20

Holiday home in Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £320 / night

£2,284 - £2,603 / week

1 / 24

Holiday home in Falmouth

Falmouth house

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

from £623 / night

£4,293 - £7,193 / week

1 / 25

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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
The Pagodas -Unit 7 - Studio Steps from Bay Beach!
Very nice - great value

Unit 7 at the Pagodas was as advertised: convenient to everything Truro/Provincetown and to the beach “ a few steps away”. Partial view of the Bay, good view over the conservation lands. Unit was immaculate and well-stocked for self-catering. Owner very responsive. Very quiet - deck great for reading, for breakfast, etc. We would return.see more
Gartner House, a charming home in Lenox
Nice spot, great for a small group

Lenox is charming and very walkable. Even has a great yarn store! Five of us spent the weekend there very comfortably. Knit and chatted in the living room — plenty of space and good light. Kitchen very well stocked and easy to use. Bedrooms were very nice. Easy to go for walks. Great old place with character and yet convenient. We didn’t get to any of the trails in that area, but maybe next time.see more
Charming Condo 1 with Easy Access to Boston
Great place to be!

It was great staying in this wonderful location. There are many stores and restaurants within walking distance, also the bus is very easy to reach which brings you in no time to the T (subway) at Harvard Square. The house and the neighborhood are beautiful and we enjoyed interesting and meaningful conversations with Mont and the other guests. Mont was very good at offering suggestions on places to visit or check out based on interests he heard us mention during our conversations with him. We highly recommend this home and host and would stay here again.see more
Mariner Motor Lodge
Mariner Hotel

Great place to stay. Lots of improvements underway so that's a bit of a pain but it is great value and very centrally located. Very clean and nice people. I recommend it highly. … see more

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