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

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2,014 Holiday homes

Holiday home in Falmouth

Falmouth house

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

from £627 / night

£4,321 - £7,239 / week

1 / 25

Holiday home in East Sandwich

East Sandwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £201 / night

£1,445 - £1,686 / week

1 / 12

Holiday farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £138 / night

£828 / week

1 / 4

Holiday farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £138 / night

£828 / week

1 / 4

Holiday home with swimming pool in Barnstable

Barnstable house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

from £366 / night

£2,561 / week

1 / 24

Holiday apartment in Chatham

Chatham apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £483 / night

£3,378 / week

1 / 26

Holiday home in Dennis

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £421 / night

£2,942 / week

1 / 10

Home rental in Mashpee

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £1,314 / night

£9,192 / week

1 / 5

Williamstown holiday condo rental

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £210 / night

£1,471 / week

1 / 6

Holiday home in Dennis

Dennis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Long Weekend” Great location to beach and local places to eat and drink. Easy access to the rest of the Cape. Pet friendly was a plus. The only downer was it stated it slept 6 but only room for 4, this made for some unhappy campers

from £161 / night

£1,126 / week

1 / 16

Holiday home in Orleans

Orleans house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

from £591 / night

£4,137 / week

1 / 15

Holiday home in East Sandwich

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £257 / night

£1,847 - £4,175 / week

1 / 15

Dennis holiday home rental

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £473 / night

£3,309 / week

1 / 17

Falmouth holiday home rental

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £506 / night

£3,447 - £4,734 / week

1 / 27

Massachusetts holiday home rental

Martha's Vineyard house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £828 / night

£5,791 / week

1 / 18

Home rental in Provincetown

Provincetown house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £368 / night

£2,574 - £3,700 / week

1 / 38

Holiday apartment with golf nearby in Rockport

Rockport apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £226 / night

£1,577 / week

1 / 18

Holiday cottage with golf nearby in Rockport

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £272 / night

£1,899 / week

1 / 17

Holiday apartment rental

Rockport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £244 / night

£1,705 / week

1 / 19

Wellfleet holiday home rental

Wellfleet house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £263 / night

£1,839 / week

1 / 6

Sandwich holiday home rental

Sandwich house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

from £193 / night

£1,365 - £1,686 / week

1 / 10

Holiday cottage in Centerville

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £276 / night

£1,931 / week

1 / 25

Holiday home in Dennis Port

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £198 / night

£1,384 / week

1 / 15

Holiday cottage in Truro

Truro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £263 / night

£1,839 / week

1 / 16

Falmouth holiday home rental

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £253 / night

£1,931 - £3,218 / week

1 / 24

Holiday home in Mashpee

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £677 / night

£4,734 / week

1 / 13

Holiday home rental

Nantucket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,117 / night

£7,813 / week

1 / 20

Holiday home in Massachusetts

Westport Point house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £434 / night

£3,034 / week

1 / 6

Chatham holiday home rental

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £276 / night

£1,747 / week

1 / 19

Holiday home in New Seabury

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

from £665 / night

£4,656 / week

1 / 13

Holiday home in Hyannis Port

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

from £297 / night

£1,931 / week

1 / 20

Holiday home letting

Hull house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £414 / night

£2,758 / week

1 / 24

Holiday home in Massachusetts

Chilmark house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £723 / night

£5,056 / week

1 / 43

Holiday home in Eastham

Eastham house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £460 / night

£3,218 / week

1 / 38

Holiday home with golf nearby in Massachusetts

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

from £5,515 / night

£38,606 / week

1 / 49

Holiday home in Massachusetts

Vineyard Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Fantastic Weekend Getaway” When my three girlfriends and I wanted to do a short getaway to the Vineyard, I started researching our options for where we could stay - and I am so thrilled I found this little bungalow! David was fantastic, and he was super flexible, organized and just a dream to work with. The home itself was very nice, and comfortable, for the four of us ladies to stay for one evening. I think it would be ideal for for a small family, too. The walk into Vineyard Haven was lovely - not too long, not too short - and that made for a wonderful experience for all four of us. My friends hand't been to the Vineyard, so being able to experience the very best of Vineyard Hospitality from David made our stay that much more enjoyable. Thanks for everything!!

from £212 / night

£1,393 - £2,298 / week

1 / 41

Holiday home rental

Nantucket house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Perfect place for a large family reunion” It was the perfect place for 4 siblings and spouse to hang out. The rooms are spacious though we draw cards to decide who gets that gorgeous room that walks out to the deck. We won, and that makes the stay more perfect for my husband and I. Having 4 bikes gave us so much freedom to explore. Nantucket is a perfect place to bike, relatively flat except 1 day we had to fight against strong wind. It was a bit hard to find at first, but it is quite convenient to get to the main road. It is not walking distance to any business, so it provides the quiet and seclusion one might look for in vacation. There is everything you need in the kitchen: we boil lobsters and grilled fish, meat and vegetable outside. We feast out and in for 5 days. In case we want to get away from the group to do some work or are fighting for bathroom, we can also spread to the "outhouse" - a very lovely self contained carriage house. Lastly, I really appreciate how helpful Bob has been before our stay and after, ensuring us with a wonderful stay. Though I have never met him, I felt like I know him from our email exchanges. Only complaint, kitchen utensils not always thoroughly cleaned.

from £1,117 / night

£7,813 / week

1 / 48

Holiday home with golf nearby in Rockport

Rockport house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £782 / night

£5,470 - £9,652 / week

1 / 20

Holiday home in Bourne

Bourne house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from £506 / night

£3,218 / week

1 / 22

Holiday apartment in Lee

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £299 / night

£2,092 - £2,735 / week

1 / 12

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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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