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Dog Friendly Accommodation in Massachusetts - Holiday Lettings

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3,882 dog friendly and pet friendly properties

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Holiday home in West Hyannisport

West Hyannisport house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £162 / night

£1,134 / week

1 / 17

Belmont holiday apartment rental

Belmont apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £129 / night

£994 - £1,477 / week

1 / 28

Holiday cottage letting

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £227 / night

£1,588 / week

1 / 18

Holiday home in Barnstable

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,058 / night

£7,405 / week

1 / 20

Holiday home in Falmouth

Falmouth house

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

from £632 / night

£4,351 - £7,289 / week

1 / 25

Holiday farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £139 / night

£833 / week

1 / 4

Holiday farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £139 / night

£833 / week

1 / 4

Holiday cottage with golf nearby in Rockport

Rockport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £273 / night

£1,912 / week

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Holiday apartment with golf nearby in Rockport

Rockport apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £227 / night

£1,588 / week

1 / 18

Holiday apartment rental

Rockport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £246 / night

£1,717 / week

1 / 19

Holiday cottage in Truro

Truro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £265 / night

£1,852 / week

1 / 16

Falmouth holiday home rental

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £255 / night

£1,944 - £3,240 / week

1 / 24

Holiday cottage in Truro

Truro cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £265 / night

£2,037 / week

1 / 22

Truro holiday cottage rental

Truro cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £397 / night

£2,777 / week

1 / 13

Holiday cottage accommodation

Gloucester cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £12 / night

£14 / week

1 / 4

Holiday cottage rental

Nantucket cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Wonderful Cottage for Nantucket Getaway!!” My boyfriend and I (and our dog, Tyson) needed to getaway from the hustle and bustle of home and we could not have picked a better place to stay! I have absolutely no complaints about this listing. It was clean and stocked with everything you would need. We got groceries the first night and spent most of our time relaxing and grilling on the deck. The location is great because it is just a short drive into town but also just far enough away to get some private time in the Tom Nevers area. We took Tyson to the beach nearby which he LOVED and we enjoyed exploring the island. Lauren and Ron were amazing in all aspects of the rental process. They were easy to reach for any questions or concerns and Lauren provided me with a ton of helpful information about the island and our stay at the cottage. I HIGHLY recommend this listing to any couple looking for some R & R. Would definitely stay here again!!

from £463 / night

£3,240 / week

1 / 94

Holiday bungalow in Marshfield

Marshfield bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £232 / night

£1,620 / week

1 / 19

Holiday bungalow in Marshfield

Marshfield bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from £482 / night

£3,369 / week

1 / 13

Massachusetts holiday apartment rental

Belmont apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £148 / night

£994 - £1,477 / week

1 / 28

Home rental in Chatham

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £320 / night

£2,772 - £5,549 / week

1 / 55

Holiday home in South Chatham

South Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £320 / night

£2,772 - £5,549 / week

1 / 52

Holiday home in Plymouth

Plymouth house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £1,389 / night

£5,831 - £6,479 / week

1 / 29

Holiday home with golf nearby in Massachusetts

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

from £5,554 / night

£38,874 / week

1 / 49

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 £1,124 / night

£7,868 / week

1 / 48

Holiday home with golf nearby in Massachusetts

Nantucket house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from £648 / night

£4,536 / week

1 / 52

Holiday home in Chatham

Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £320 / night

£2,772 - £5,549 / week

1 / 56

Holiday home rental

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

“Fantastic place to stay in the Berkshires” Elaine was a very gracious host, and the...accommodations were lovely and in a great location. The historic house has a lot of charm and many nice updates, especially the clean, updated bathrooms and the huge screened-in porch. ... We had room to spare, and everyone had a room to themselves. The kitchen was well stocked, and the living room very cozy... This would be a great place for skiers. We loved the area and highly recommend Elaine and her charming farmhouse!

from £241 / night

£1,435 - £2,893 / week

1 / 20

Holiday home in Hawley

Hawley house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £176 / night

£1,019 / week

1 / 22

Home rental in Becket

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £255 / night

£1,111 / week

1 / 20

Holiday cottage in Eastham

Eastham cottage

  • 1 bathroom
  • sleeps 2

from £93 / night

£556 / week

1 / 15

Holiday cottage in Massachusetts

Plymouth cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

“Peaceful, relaxing and comfortable stay” We stayed at the cottage in Manomet for one week and it was wonderful! We loved the home...quaint New England at it's best. Everything you need (except towels, sheets) for a fabulous week at the beach. Only reason I didn't give it 5 stars was because you had to bring your own linens. Will book again. Thank you Marywinne for allowing us this time at your summer home.

from £278 / night

£1,666 / week

1 / 43

Cottage rental in Truro

Truro cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £278 / night

£1,944 / week

1 / 28

Mashpee holiday cottage rental

Mashpee cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

“Best family vacation spot!!!!” Our stay overall was excellent! Our kids played on the beach for hours catching crabs/ minnows and swimming. We enjoyed exploring the bay by paddle board and kayak. By boat, we went on exciting adventures. We anchored at Washburn island where we relaxed and walked on the sandbar. The vacation rental is about 7 miles away from Marthas Vineyard by boat. We had a wonderful day trip on the Vineyard. We thoroughly recommend this vacation spot.

from £278 / night

£1,342 / week

1 / 14

Great Barrington holiday home rental

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from £139 / night

£880 / week

1 / 14

Cottage rental in Wellfleet

Wellfleet cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Perfect Vacation Spot” My boyfriend and I were looking for a get away during the holiday we found the house and absolutely fell in love with it. This hidden gem of a spot is fabulous! The deck that wraps around the house and facing the water is a wonderful place to sit out for the day or have dinner on the deck as the sun goes down. The house on the water allows you to feel like your at the beach without even leaving the house. Once the tide goes out there is such great walking beach and so many shells and sea creatures. Drew was great helping us find the house and all that was available once we got settled. My boyfriends favorite part was watching the fireworks from all the surrounding towns while sitting on the deck. And he loved the outdoor shower! The town of Wellfleet is a great destination for anybody! And this little house is the best place in town!

from £250 / night

£1,551 - £5,253 / week

1 / 24

Holiday home in Chatham

Chatham house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £795 / night

£5,554 / week

1 / 47

North Truro holiday apartment rental

North Truro apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £232 / night

£1,296 / week

1 / 8

Massachusetts holiday home rental

Nantucket house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £787 / night

£5,507 / week

1 / 25

Holiday home in Falmouth

Falmouth house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

from £405 / night

£2,830 - £4,042 / week

1 / 24

West Harwich holiday home rental

West Harwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Great place to stay and play” A great place to stay for a vacation on Cape Cod. The rooms were comfortable and of good size. There was a relaxing atmosphere and all the comforts of home. Plenty of games and videos for adults and kids and a large screen TV. Parking was ample and easy to come and go. The kitchen was more than expected. The back yard and spacious rear deck and furnishings made outdoor meals and barbecuing a pleasure. I especially liked the covered outdoor shower (with hotwater) to wash away beach sand and ocean salt. Speaking of ocean salt, the beach is just a short walk away.

from £93 / night

£463 - £2,129 / week

1 / 25

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