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

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North America Holidays
174603 properties
United States Holidays
130862 properties
Holiday rentals Cape Cod
2,859 properties
Houses Nantucket
1,167 properties
Holiday rentals Martha's Vineyard
828 properties
Apartments Boston
517 properties
Brookline
149 properties
Apartments Cape Ann
137 properties
Berkshires
130 properties
Cambridge
59 properties
Somerville
26 properties
Plymouth
26 properties
Scituate
16 properties
Houses Ipswich
14 properties
Hampshire County
14 properties
Houses Marshfield
10 properties
Salem
7 properties
Beach rentals Marblehead
7 properties
Cottages Wareham
7 properties
Salisbury
7 properties
Apartments Newburyport
6 properties

Massachusetts

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6,018 Holiday homes

(9) Very Good 

24

Holiday cottage with golf nearby in New Seabury

Cape Cod / New Seabury

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £179 / night

£1,072 - £1,965 / week

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from £179 / night

23

Holiday home in Massachusetts

Massachusetts / Plum Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning

from £285 / night

£2,250 / week

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Responds fast!
avg. 2 hours 0 minutes

from £285 / night

(3) Excellent 

24

Holiday apartment rental

Massachusetts / Plymouth

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £168 / night

£929 / week

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Responds fast!
avg. 2 hours 5 minutes

from £168 / night

45

Holiday home in South Chatham

Chatham / South Chatham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 0.6 km
  • Child friendly
  • Air conditioning

from £197 / night

£1,143 - £3,750 / week

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Responds fast!
avg. 1 hour 22 minutes

from £197 / night

20

Home rental in Orleans

Cape Cod / Orleans

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning

from £179 / night

£1,286 / week

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from £179 / night

(12) Very Good 

19

Holiday home in Eastham

Cape Cod / Eastham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £146 / night

£1,020 / week

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Responds fast!
avg. 3 hours 39 minutes

from £146 / night

13

Cottage rental in Dennis Port

Dennis / Dennis Port

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £172 / night

£1,072 / week

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from £172 / night

31

Holiday home with golf nearby in Stockbridge

Berkshires / Stockbridge

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £179 / night

£1,393 - £2,250 / week

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from £179 / night

18

Home rental in Massachusetts

Massachusetts / Marblehead

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £229 / night

£1,600 - £1,625 / week

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from £229 / night

20

Massachusetts holiday home rental

Massachusetts / Nantucket

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £551 / night

£3,858 / week

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from £551 / night

14

Provincetown holiday condo rental

Cape Cod / Provincetown

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

from £347 / night

£2,429 / week

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from £347 / night

52

Holiday home in Centerville

Cape Cod / Centerville

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £268 / night

£1,870 - £2,125 / week

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Responds fast!
avg. 3 hours 43 minutes

from £268 / night

4

Home rental in Somerville

Massachusetts / Somerville

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from £179 / night

£1,250 / week

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from £179 / night

4

Apartment rental in Massachusetts

Massachusetts / Cambridge

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min

from £8 / night

£50 / week

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from £8 / night

19

B&b rental in Massachusetts

Nantucket / Siasconset

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning

from £179 / night

£1,250 / week

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Responds fast!
avg. 57 minutes

from £179 / night

9

Holiday home in Teaticket

Falmouth / Teaticket

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £215 / night

£1,500 - £2,500 / week

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from £215 / night

(1) Average 

6

Holiday apartment in Massachusetts

Massachusetts / Boston

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Air conditioning

Pricing unknown

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Pricing unknown

6

Holiday home in Massachusetts

Massachusetts / Boston

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

Pricing unknown

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Pricing unknown

17

Apartment rental in Orleans

Cape Cod / Orleans

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £125 / night

£875 / week

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from £125 / night

29

Home rental in Massachusetts

Nantucket / Siasconset

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £500 / night

£3,500 / week

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Responds fast!
avg. 57 minutes

from £500 / night

6

Massachusetts holiday townhouse rental

Martha's Vineyard / Edgartown

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly

from £631 / night

£4,411 / week

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from £631 / night

5

Holiday home letting

Martha's Vineyard / Oak Bluffs

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly

from £215 / night

£1,786 - £1,858 / week

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Responds fast!
avg. 3 hours 29 minutes

from £215 / night

4

Holiday apartment in Massachusetts

Massachusetts / Boston

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly

from £878 / night

£4,386 / week

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from £878 / night

4

Holiday home in Boston

Massachusetts / Boston

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning

from £1,000 / night

£5,000 / week

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from £1,000 / night

(2) Excellent 

21

Holiday home in South Yarmouth

Cape Cod / South Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £233 / night

£1,800 / week

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Responds fast!
avg. 1 hour 14 minutes

from £233 / night

(27) Excellent 

21

Holiday apartment in Lenox

Berkshires / Lenox

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets

from £108 / night

£643 - £858 / week

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from £108 / night

31

Holiday home in Massachusetts

Martha's Vineyard / Vineyard Haven

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £215 / night

£1,500 - £3,965 / week

Enquire View

from £215 / night

25

Holiday home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £204 / night

£1,429 - £1,858 / week

Enquire View

from £204 / night

22

Holiday home in Massachusetts

Martha's Vineyard / Edgartown

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £235 / night

£1,643 - £2,858 / week

Enquire View

from £235 / night

35

Provincetown holiday home rental

Cape Cod / Provincetown

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning

from £203 / night

£1,447 - £3,214 / week

Book View

from £203 / night

46

Massachusetts holiday studio rental

Massachusetts / Cambridge

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning

from £59 / night

£410 / week

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Responds fast!
avg. 26 minutes

from £59 / night

11

Massachusetts ski apartment to rent.

Massachusetts / Conway

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Ski
  • Suitable for children age 5+

from £118 / night

£697 / week

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from £118 / night

5

Holiday condo with shared pool in Dennis Port

Dennis / Dennis Port

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £154 / night

£929 / week

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from £154 / night

12

Chilmark holiday home rental

Martha's Vineyard / Chilmark

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask owner if suitable for children

from £235 / night

£1,643 - £2,233 / week

Enquire View

from £235 / night

(1) Excellent 

11

Holiday cottage in Massachusetts

Massachusetts / Plymouth

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £225 / night

£1,572 / week

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Responds fast!
avg. 2 hours 42 minutes

from £225 / night

27

Holiday home in Massachusetts

Martha's Vineyard / Oak Bluffs

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask owner if suitable for children

from £409 / night

£2,858 - £4,643 / week

Enquire View

from £409 / night

22

Holiday home in Woods Hole

Falmouth / Woods Hole

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £307 / night

£2,143 / week

Enquire View

from £307 / night

26

Holiday home in Eastham

Cape Cod / Eastham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning

from £67 / night

£492 - £1,214 / week

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from £67 / night

(1) Excellent 

10

Hancock holiday hotel apartment rental

Berkshires / Hancock

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £325 / night

£2,275 / week

Book View

from £325 / night

14

Holiday home in South Chatham

Chatham / South Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £164 / night

£1,143 / week

Enquire View

from £164 / night

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
LetGo.Rentals/Plymouth
Lovely Holiday Home

This apartment was so much bigger and nicer than the photographs indicate. It was clean , spacious,very comfortable and so well equipped., even condiments, herbs and oil were provided for cooking, as well as detergent and dish washer tablets for the washing machines. The view from the living room window over the bay was lovely and the owners were friendly and helpful without being intrusive. Plymouth is a smashing town with a lot of history and knowledgeable guides who seem to know the answer to every question. It has good restaurants, cafes and walks. It is easy to drive to Province Town, Taunton and Boston. Close by is the Miles Standish Memorial Forest , good for longer treks and picnics.The Whale Watch Boat was 5 minutes walk from the flat and a great experience. We stayed at Plymouth Harbour View for wonderful eight days and have wholeheartedly recommended it to family and friends.see more
New lux. Apt.private roof deck harbor/skyline
Fabulous Apartment

I cannot recommend this enough. The apartment was exactly as described, only better. Very clean, new, spacious. All facilities were there and more. Pure luxury stay. Theresa, the owner, emailed me with directions which were perfect. The restaurant she recommended was the best we went to during our whole stay in the US. The bakery and deli were also excellent. Thank you for a great apartment with fabulous views, great facilities, information and pure comfort.see more
Affordable Luxury -3bd/3ba -$2,300 w/Linens Incl
A fabulous home from home in Cape Cod with beautiful beach close by and access to shared pool, loved it!!!

We have had a brilliant stay in a lovely home on Cape Cod. A very well equipped house close to a beautiful sandy beach and with access to a shared pool. Owners were extremely accommodating, giving lots of help with bike hire etc. Ideally situated for visiting Martha's Vineyard and Nantucket as well as other lovely towns. Our teenage sons particularly enjoyed the basketball hoop at the end of the drive. A fantastic week, one we will never forget!see more
Luxury 3 story with private roof deck 6 month min rental
Fabulous, superbly well equipped condo off the beaten track

We stayed here for a 3 night city break in early September and the accommodation is fully set up and very well equipped for up to six people in 3 double rooms. There are great views over to the city from both the kitchen/living room/deck and from the roof terrace and some great sunsets to be appreciated. Teresa the owner is very helpful and able to provide great pointers and guidance for your Boston trip. There is a lovely Italian restaurant within easy walking distance along with a bakery and wine/beer store, it is also easy to walk to the nearest T station for transfer to downtown. No car is required for a stay here and we easily walked to the supermarket to stock up on items for our stay. Boston is an expensive city to stay in and this is a luxury and cost effective option for anyone looking for accommodation near to the city but away from the immediate hustle and bustle.see more