Search holiday homes in Massachusetts

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Featured holiday home destinations

Destination inspiration for your trip – find a holiday home

Chatham

96 holiday homes

Eastham

88 holiday homes

Orleans

71 holiday homes

Wellfleet

67 holiday homes

Harwich

66 holiday homes

South Yarmouth

65 holiday homes

Dennis

61 holiday homes

East Sandwich

53 holiday homes

Yarmouth

50 holiday homes

Barnstable

49 holiday homes

Falmouth

44 holiday homes

Brewster

43 holiday homes

Provincetown

43 holiday homes

Oak Bluffs

40 holiday homes

Mashpee

39 holiday homes

Dennis Port

38 holiday homes

The best holiday homes in Massachusetts

Check out our pick of great holiday homes in Massachusetts

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The Fairview

Peabody

Featuring air-conditioned accommodation with a patio, The Fairview is situated in Peabody. This property offers access to a terrace, tennis at the tennis court, free private parking and free WiFi.

Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 14 reviews
Price from
US$337.50
1 night, 2 adults

Cape Cod Hyannis Rendezvous'

Barnstable

A recently renovated holiday home situated in Barnstable, Cape Cod Hyannis Rendezvous' features a garden.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 9 reviews
Price from
US$439.20
1 night, 2 adults

Brand New 4BR House 20Min Downtown Boston

Boston

Featuring air-conditioned accommodation with a balcony, Brand New 4BR House 20Min Downtown Boston is located in Boston. This property offers access to a terrace, free private parking and free WiFi.

V
Vasco
From
Portugal
Nice spot, a bit farway on rush hours but very confortable, clean and full of stuff to do inside.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 26 reviews
Price from
US$285.12
1 night, 2 adults

Waterfront Oasis in Yarmouth, Cape Cod

Yarmouth

Set in Yarmouth, 2.4 km from Colonial Acres Beach and 25 km from Sandwich Glass Museum, Waterfront Oasis in Yarmouth, Cape Cod offers a private beach area and air conditioning.

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 6 reviews
Price from
US$325
1 night, 2 adults

Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak

Hancock

Featuring a hot tub, Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak is set in Hancock.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 9 reviews
Price from
US$447.55
1 night, 2 adults

Cape Cod Villa

Harwich

Featuring air-conditioned accommodation with a patio, Cape Cod Villa is set in Harwich. This property offers access to a balcony, a pool table, free private parking and free WiFi.

G
Giulia
From
France
Incredible location ! The house is gorgeous and well equipped with a very cozy decoration !
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 16 reviews
Price from
US$481.95
1 night, 2 adults

An authentic, rustic luxurious little single family home in Old Town. All yours.

Marblehead

Located in Marblehead, 1.6 km from Gas House Beach and 6.2 km from Peabody Essex Museum, An authentic, rustic luxurious little single family home in Old Town. All yours.

O
Our former Wheaten.....
From
United Kingdom
The style of furnishings, a very well equipped kitchen with small things like oil and herbs provided, good linen enable a very comfortable stay. Natasha was chatty by e-mail as she was on vacation but provided speedy replies and information to any requests that I had. I will certainly return as the best thing about the place....it was really quiet and had a great king sized bed.
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 27 reviews
Price from
US$236.25
1 night, 2 adults

41 - 3BR Quincy - Lovely Townhouse near Adams

Quincy

Boasting air-conditioned accommodation with a patio, 41 - 3BR Quincy - Lovely Townhouse near Adams is set in Quincy. This holiday home offers free private parking, a 24-hour front desk and free WiFi.

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 24 reviews
Price from
US$299.70
1 night, 2 adults

Enchanting Hidden Door Escape

Stoneham

Located in Stoneham, Enchanting Hidden Door Escape is a recently renovated accommodation, 15 km from Inman Square and 15 km from Brattle Theatre.

R
Rod
From
United Kingdom
Kitchen facilities Bed comfort Security
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 5 reviews
Price from
US$364.50
1 night, 2 adults

LakeAccess 4 Bed 3 Full Bath HOT TUB

Billerica

Set in Billerica, the recently renovated LakeAccess 4 Bed 3 Full Bath HOT TUB offers accommodation 17 km from Minute Man National Historical Park and 24 km from Peabody Museum.

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 6 reviews
Price from
US$472.50
1 night, 2 adults
All holiday homes in Massachusetts

Most booked holiday homes in Massachusetts this month

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Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 12 reviews

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 26 reviews

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 31 reviews

Popular with guests booking holiday homes in Massachusetts

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 10 reviews

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 22 reviews

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 22 reviews

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 31 reviews

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 10 reviews

Popular with guests booking holiday homes in Massachusetts

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 6 reviews

FAQs about holiday homes in Massachusetts

Holiday homes that guests love in Massachusetts

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Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 11 reviews
Tranquil, quiet location. The cottage provides all the comfort one can ask for. The interior design is artful and appealing. It was very clean throughout. As the weather was lovely we spent two days sitting in the spacious grounds underneath the canopy of the beautiful trees, reading and recuperating. A great place of the world.
Guest review by
Wiebke
Young couple
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 14 reviews
We had a lovely time with our family with two small children. The location perfectly located and was very clean and had a lot of space.
Guest review by
Wouter
Family with young children
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews
Very comfy, very charming, very clean, well-equipped and well-localized place. We spent a great time there.
Guest review by
julien
Solo traveller
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 8 reviews
The Location is absolutely perfect. The place was very clean and just as described. We very much enjoyed our stay and had everything we needed.
Guest review by
Melissa
Solo traveller
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 5 reviews
Our stay at this Gloucester gem was nothing short of magical! From the cozy interiors to the breathtaking ocean views, every detail was perfection. The hosts' hospitality made us feel right at home, and the proximity to local attractions added an extra layer of convenience. If you're looking for a picturesque retreat, this vacation home is an absolute dream. Can't wait to come back and create more unforgettable memories!
Guest review by
Courtney Mozingo
Family with young children
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews
Superb holiday home . Lovely quiet location yet easy access to shops,restaurants and beaches.great base to explore Cape Cod. Home was clean,well equipped and plenty of space for our family of 4. Would highly recommend.
Guest review by
Lucy
Solo traveller
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 8 reviews
The house is beautiful, very clean and well equipped, with a large backyard.
Guest review by
Gil
Solo traveller
Scored out of 10, guest rating 8.5
Very good - What previous guests thought, 4 reviews
The house was very clean, well equipped, and comfortable. We loved the privacy of the woods surrounding the house but even more, the wildlife that accompanied it. It was so lovely that we didn't mind staying in when it rained.
Guest review by
June
Solo traveller
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 18 reviews
This is a well designed cottage with beautiful landscaping right near a forest. The inside is retro/mid-century modern and it was very comfortable and filled with information about local activities. Every morning I ate out on the screened-in porch and the feeders attracted everything from eastern Bluebirds to wild turkeys. The kitchen had everything I needed. The place is very clean. It was only 20 minutes to downtown Greenfield.
Guest review by
Amy
Solo traveller