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

Vacation Homes in Massachusetts

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Top Cities in Massachusetts

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

Boston

Boston
A white house with a red roof on a grassy hill.
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Provincetown

Provincetown

Our top choices for Massachusetts holiday homes

A cozy living room with a sofa, a coffee table, and a window with a view of trees.

1. Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA
Goshen
9.6 out of 10, Exceptional, (22 reviews)
"This is a magical stay!"
United States
Ryan B.
Experience Three Sisters Sanctuary in Goshen, MA
A modern kitchen with a stainless steel refrigerator, a microwave, a sink, and a stove.

2. Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fenway–Kenmore
10.0 out of 10, Exceptional, (100 reviews)
"This house was clean and has what you need to have a great stay. It is close by to public transportation and walkable to shops"
United States
James B.
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
A round metal fire pit with grilling tools and a red chair in the background.

3. Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
9.2 out of 10, Wonderful, (12 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is HK$1,280
HK$1,614 total
includes taxes & fees
29 Oct - 30 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

4. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is HK$1,200
HK$1,954 total
includes taxes & fees
2 Nov - 3 Nov
Lovely 2nd Floor Apartment
A hallway with wooden flooring, white walls, and a bed in the background.

5. Shelburne Falls on Main

Shelburne Falls on Main
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 HK$1,579
HK$3,271 total
includes taxes & fees
2 Nov - 3 Nov
Shelburne Falls on Main
A bedroom with a large bed, a bedside table with a lamp, and a view of the outdoors through the window.

6. Bright Contemporary Escape, Near the T

Bright Contemporary Escape, Near the T
Roxbury
9.8 out of 10, Exceptional, (56 reviews)
"Close to everything, great place to stay"
United States
Julio M.
Bright Contemporary Escape, Near the T
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

7. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (64 reviews)
"Very nice little house with all amenities you can ask for. Unfortunately we only had a quick over night stay. Beautiful location. The drive way is a challenge to get out if you are backing out. We certainly would stay again!"
United States
Nicole
The price is HK$3,883
HK$6,458 total
includes taxes & fees
1 Nov - 2 Nov
Beach Life Bliss - steps to the beach
A view of a beach with cars parked on the side of the road, a pedestrian crossing, and a wooden fence.

8. Renovated Beach House Close to Everything, Minutes to Boston

Renovated Beach House Close to Everything, Minutes to Boston
Quincy
9.2 out of 10, Wonderful, (125 reviews)
"Overall great stay, loved the location"
United States
Anthony E.
The price is HK$1,491
HK$3,409 total
includes taxes & fees
2 Nov - 3 Nov
Renovated Beach House Close to Everything, Minutes to Boston
A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

9. Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean location to stay."
United States
Mike O.
The price is HK$2,157
HK$4,031 total
includes taxes & fees
29 Oct - 30 Oct
Spacious 4-bedroom with four and half bathrooms
A modern kitchen with wooden cabinets, a large island, a stove, and hanging wicker light fixtures.

10. Cozy Coastal Holiday Getaway! Gas Fireplace! Walk to Town, Beach & Train!🍂🎄❄️

Cozy Coastal Holiday Getaway! Gas Fireplace! Walk to Town, Beach & Train!🍂🎄❄️
Rockport
10.0 out of 10, Exceptional, (17 reviews)
"The property is comfortable and beautifully decorated. The main attractions within Rockport are all within walking distance and nothing on the entirety of Cape Ann felt more than a 15 min drive away. Great rental and great place to visit."
United States
Mark E.
Cozy Coastal Holiday Getaway! Gas Fireplace! Walk to Town, Beach & Train!🍂🎄❄️
A living room with a fireplace, sofas, a coffee table, and a television.

11. 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, (209 reviews)
"Great location and perfect home for overnight stay!"
United States
Betsy D.
The price is HK$699
HK$2,443 total
includes taxes & fees
7 Nov - 8 Nov
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
A hallway with a white door, a hanging light fixture, and a potted plant on a stand.

12. Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything
Salem
10.0 out of 10, Exceptional, (274 reviews)
"Clean big house was a perfect home base for our group’s weekend"
United States
Steven S.
Leslie's Retreat: Spacious home ideally located to everything
A spacious hallway with a dining area, a staircase, and a large plant.

13. 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
9.6 out of 10, Exceptional, (5 reviews)
The price is HK$3,515
HK$6,494 total
includes taxes & fees
2 Nov - 3 Nov
Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots
A living room with a television, wooden cabinet, fireplace, clock, and a lamp.

14. Waterview Westend Townhouse

Waterview Westend Townhouse
Provincetown
9.4 out of 10, Exceptional, (102 reviews)
"Great place, very spacious, reserved parking spaces (2) right outside the front door, nice deck off the living room, and fantastic location - you can easily walk to everything"
United States
Glen A.
Waterview Westend Townhouse
A spacious living area with a large sectional sofa, a glass dining table, and multiple windows providing natural light.

15. Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (129 reviews)
"Great stay for a couple of nights. Great location."
United States
Kevin C.
The price is HK$2,951
HK$5,671 total
includes taxes & fees
2 Nov - 3 Nov
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
A covered outdoor patio with a wooden deck, a table with chairs, and a view of the neighborhood.

16. 2 Story Beach House with full screen porch - Short walk to beach

2 Story Beach House with full screen porch - Short walk to beach
Marshfield
9.6 out of 10, Exceptional, (47 reviews)
"Beautiful home close to the ocean for our trip, incredibly happy I chose it!"
United States
Brandon R.
2 Story Beach House with full screen porch - Short walk to beach
A shed with a door open, revealing an interior with a wooden floor and a rug.

17. Salem Getaway - Cozy 1BR Near Downtown

Salem Getaway - Cozy 1BR Near Downtown
Salem
10.0 out of 10, Exceptional, (1 review)
"Perfect little place for a quick quaint stay."
United States
Annette A.
The price is HK$1,530
HK$2,708 total
includes taxes & fees
2 Nov - 3 Nov
Salem Getaway - Cozy 1BR Near Downtown
A deck with a table and chairs, overlooking the ocean.

18. 2-bedroom ocean-front Fairhaven home overlooking Buzzards Bay

2-bedroom ocean-front Fairhaven home overlooking Buzzards Bay
Fairhaven
10.0 out of 10, Exceptional, (29 reviews)
"Beautiful location and, even better, our Host thought about all the small details that make the home stand out."
United States
Scott M.
2-bedroom ocean-front Fairhaven home overlooking Buzzards Bay
A stone building with a central entrance, surrounded by lush greenery and flowering plants.

19. 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)
"This property is located perfectly between town, the beaches , bike paths and shopping access.House is adorable!"
United States
Richard L.
Beautiful House Minutes from Town, on Bike Path
A dining area with a wooden table, chairs, and a ceiling fan.

20. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is HK$1,589
HK$2,484 total
includes taxes & fees
3 Nov - 4 Nov
Leaf-Peeper Paradise in the Berkshires
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

The Dagny Boston

The Dagny Boston

10/10 Excellent
"👍"
matthew 1-night trip
Posted 4 hours ago
The Dagny Boston

Find out more about Massachusetts

Massachusetts Vacation Homes information

Number of reviews
1,082
Accommodation
6129 Vacation Homes
Lowest Price
HK$1,614
Highest Price
HK$6,494

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