A coastal village with houses, a lighthouse, and boats on the water.

Holiday Homes in Massachusetts

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Top Cities in Massachusetts

A historic building with "QUINCY MARKET" sign, surrounded by modern buildings and a clock tower.
Holiday HomesHoliday Homes

Boston

Boston

Our top choices for Massachusetts holiday homes

A modern kitchen with a central island, stainless steel appliances, and a dining area with a glass table and chairs.

1. Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport

Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport
Newburyport
9.8 out of 10, Exceptional, (147 reviews)
"We enjoyed our stay at this property. It was very clean and comfortable and exceeded our expectations. Newburyport is a beautiful town!"
United States
Jean G.
Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport
A cozy living room with a fireplace, wooden ceiling, and a dining area with a table and chairs.

2. Luxury Loft Historic Center Oak Bluffs

Luxury Loft Historic Center Oak Bluffs
Oak Bluffs
9.6 out of 10, Exceptional, (51 reviews)
"This was my second time staying in this house, everything is perfect! Tons of space, responsive host, walking distance to everything.. Thank you Kim!"
United States
Julia K.
Luxury Loft Historic Center Oak Bluffs
A two-story house with a white picket fence, a front door, and a garage.

3. Cozy 4 bedroom cottage in town, with parking

Cozy 4 bedroom cottage in town, with parking
Nantucket Town
8.6 out of 10, Excellent, (35 reviews)
"Pictures are accurate and check in was smooth. The bathrooms are pretty outdated and both are on the 1st floor whereas 3 of the 4 bedrooms are on the 2nd floor, so that wasn’t ideal. Communal space and kitchen were lovely. Bedrooms were tight and beds pretty uncomfortable. All that said, you’re paying a super reasonable rate for proximity to town. We weren’t expecting a luxury experience and the space worked well for our two families - would definitely stay here again."
United States
Ashley D.
Cozy 4 bedroom cottage in town, with parking
A hallway with wooden flooring, white walls, and a bed in the background.

4. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is €379
includes taxes & fees
20 Oct - 21 Oct
Cozy private 2 bed apartment in Shelburne Falls
A spacious living room with a large window overlooking a scenic view, a wooden staircase, and a cozy seating area.

5. Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!
Dennis
9.6 out of 10, Exceptional, (133 reviews)
"Amazing house and place. It was incredible. We had the best vacation ever. We will definitely be back."
United States
Kelli A.
Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!
A hotel room with two beds, a flat-screen TV, a fireplace, and a ceiling fan.

6. Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots
Salem
9.4 out of 10, Exceptional, (3 reviews)
"Clean ,friendly neighbors and a great community"
United States
Nia F.
The price is €1,360
includes taxes & fees
12 Oct - 13 Oct
Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots
A stone building with a central entrance, surrounded by lush greenery and flowering plants.

7. Beautiful House Minutes from Town, on Bike Path

Beautiful House Minutes from Town, on Bike Path
Nantucket Town
10.0 out of 10, Exceptional, (63 reviews)
"Very clean and hosts provided great communication"
United States
Kellee C.
Beautiful House Minutes from Town, on Bike Path
A beach with a sandy shore, a few scattered rocks, and a calm sea.

8. Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Falmouth Heights
10.0 out of 10, Exceptional, (209 reviews)
"We had a great little weekend away and the house was perfect. "
United States
Katie S.
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

9. Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking

Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
Dorchester
9.2 out of 10, Wonderful, (7 reviews)
"Great location near the Red Line, clean, and exactly what we were hoping for. Highly recommend!"
United States
Wynn
The price is €188
includes taxes & fees
22 Oct - 23 Oct
Modern Boston Stay, Full-Sized Kitchen, Electric Sauna, Added Driveway Parking
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

10. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (59 reviews)
"Nice home with great kitchen and all the amenities."
United States
rick b.
The price is €321
includes taxes & fees
20 Oct - 21 Oct
Beach Life Bliss - steps to the beach
A dining area with a wooden table and chairs, a radiator, a window with curtains, and a door.

11. Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking
South Medford
9.2 out of 10, Wonderful, (15 reviews)
"Clean rooms and comfortable beds "
United States
camilo r.
Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking
A beach with a wooden fence, sand, and the ocean.

12. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
9.8 out of 10, Exceptional, (7 reviews)
"I booked a last minute stay for some time at the ocean. The booking/check in process was so easy with very detailed instructions sent the day of my arrival. The place was exactly as pictured, a well-appointed, clean cottage, with everything I needed. The host also left a welcome gift that was thoughtful and useful. I walked the few blocks to the ocean everyday, multiple times a day to walk for hours on the beaches. I got food from a nice little Italian restaurant (Capri) just a block away. The...
United States
Maura
The price is €414
includes taxes & fees
14 Oct - 15 Oct
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
A circular stone arrangement in a forested area with trees and greenery around.

13. Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA
Goshen
9.6 out of 10, Exceptional, (19 reviews)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA
An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

14. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
10.0 out of 10, Exceptional, (206 reviews)
"Great location and great host!! We’ll be back!!!"
United States
Patrick T.
The price is €281
includes taxes & fees
14 Oct - 15 Oct
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A modern kitchen with a wooden dining table, wicker chairs, a stainless steel refrigerator, and white cabinetry.

15. Beautifully Renovated Main Street Cottage- Great Location

Beautifully Renovated Main Street Cottage- Great Location
Nantucket Town
10.0 out of 10, Exceptional, (133 reviews)
"We had an excellent stay & Peter could not have been more helpful! The location is perfect, excellent communication with host, super clean & comfortable beds. Check-in and check-out were super smooth. Hope to book again next year. Highly recommend!"
United States
Lauren K.
Beautifully Renovated Main Street Cottage- Great Location
A beach with waves lapping onto the shore, a clear sky, and a sandy landscape.

16. Lovely Dog Friendly Beach Home Close to Everything. 5 and 6 day stay open July

Lovely Dog Friendly Beach Home Close to Everything. 5 and 6 day stay open July
Eastham
10.0 out of 10, Exceptional, (246 reviews)
"Fabulous place to stay with your pup!!! Always have a great time!!!"
United States
Christine J.
The price is €476
includes taxes & fees
24 Oct - 25 Oct
Lovely Dog Friendly Beach Home Close to Everything. 5 and 6 day stay open July
A staircase with a white railing leading to a landing with a bench and a shelf with books.

17. Beachy right near “Children’s” Beach, near town and walking distance from Ferry.

Beachy right near “Children’s” Beach, near town and walking distance from Ferry.
Nantucket Town
10.0 out of 10, Exceptional, (119 reviews)
"Comfortable stay for a family of 4 (2 adults, 2 kids) could fit a third family member if needed. The host was very communicative and responded within the day for most messages if not sooner."
United States
Stanford
The price is €745
includes taxes & fees
18 Oct - 19 Oct
Beachy right near “Children’s” Beach, near town and walking distance from Ferry.
A bright, well-lit room with a white sofa, a small round table, and a television mounted on the wall.

18. Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St

Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
Nantucket Town
10.0 out of 10, Exceptional, (85 reviews)
"Convenient location, sweet property, well cared for."
United States
Barbara W.
The price is €852
includes taxes & fees
9 Nov - 10 Nov
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St
A cozy living room with a grey sofa, a round wicker ottoman, a leopard print rug, and a dining area with a table and chairs.

19. Best location in Old Town, 5 minutes to everything, enjoy the difference!

Best location in Old Town, 5 minutes to everything, enjoy the difference!
Marblehead Historic District
9.2 out of 10, Wonderful, (14 reviews)
"We loved staying in this charming home that was walking distance to all of the best Marblehead spots!"
United States
Kate D.
The price is €781
includes taxes & fees
9 Nov - 10 Nov
Best location in Old Town, 5 minutes to everything, enjoy the difference!
A modern living room with a sofa, ottoman, and round coffee table. There is a fireplace with a mantel and a clock on the wall.

20. Cozy 3BD 1BA near Beach T-10 Min from Boston

Cozy 3BD 1BA near Beach T-10 Min from Boston
Revere
9.4 out of 10, Exceptional, (16 reviews)
"Very nice place!!"
United States
Anonymous traveller
Cozy 3BD 1BA near Beach T-10 Min from Boston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Massachusetts Hotel Reviews

Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"No ice machine so had to go to first floor from 12th floor to get ice or a drink"
Tina 2-night trip
Posted 3 hours ago
Hyatt Regency Boston Harbor

Find out more about Massachusetts

Massachusetts Holiday Homes information

Number of reviews
1,560
Accommodation
6005 Holiday Homes
Lowest Price
€188
Highest Price
€1,360

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