Top Vacation Homes in Massachusetts in 2026

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

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Top Cities in Massachusetts

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

Boston

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

Provincetown

Our top choices for Massachusetts holiday homes

A circular stone arrangement in a forested area with trees and greenery around.

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

A colorful, multi-level house with a porch and a large wheel, surrounded by lush greenery.

A bedroom with a bed, a nightstand, a wall-mounted shelf, and two paintings.

1. Experience Three Sisters Sanctuary in Goshen, MA

Experience Three Sisters Sanctuary in Goshen, MA

Goshen

9.6 out of 10, Exceptional, (22 reviews)

9.6/10

Exceptional

(22 reviews)

"This is a magical stay!"

Ryan B.

Experience Three Sisters Sanctuary in Goshen, MA

A modern kitchen with a stainless steel refrigerator, a microwave, a sink, and a stove.

A dining area with a table, chairs, a cabinet, and a fireplace.

A dining area with a chandelier, a white door, and a view of the outside through a glass door.

A dining room with a chandelier, a fireplace, and a view through a glass door.

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)

10/10

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"

James B.

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

A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

A tent, a playhouse, and a swing set in a grassy area with trees in the background.

A living room with a sofa, a dining table with chairs, and a kitchen area visible through an open door.

A compact living space with a sofa, armchairs, a dining table, a refrigerator, and a window with sheer curtains.

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)

9.2/10

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."

Gregory C.

The price is HK$1,154

HK$1,154

HK$1,465 total

includes taxes & fees

27 Oct - 28 Oct

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

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

A brown leather armchair with a striped pillow, a hanging wall clock, and a potted plant.

A two-story house with a front porch, a red door, and a small garden with red flowers.

A neatly made bed with a textured white blanket and pillows, a wooden headboard, a bedside lamp, and a small plant on a wooden nightstand.

4. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield

10.0 out of 10, Exceptional, (71 reviews)

10/10

Exceptional

(71 reviews)

"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"

Jane P.

The price is HK$1,200

HK$1,200

HK$1,962 total

includes taxes & fees

27 Oct - 28 Oct

Lovely 2nd Floor Apartment

A hallway with wooden flooring, white walls, and a bed in the background.

A spacious living area with a sofa, coffee table, and a kitchen counter with mugs.

A living room with a sofa, coffee table, and dining table set with plates and glasses.

A two-story house with a gabled roof, a chimney, and a front porch.

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."

maureen

The price is HK$1,578

HK$1,578

HK$3,270 total

includes taxes & fees

27 Oct - 28 Oct

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.

A modern bathroom with a white bathtub, toilet, and sink.

A kitchen with a stainless steel refrigerator, a brick wall, a white door, and a plant.

6. Bright Contemporary Escape, Near the T

Bright Contemporary Escape, Near the T

Roxbury

9.8 out of 10, Exceptional, (56 reviews)

9.8/10

Exceptional

(56 reviews)

"Close to everything, great place to stay"

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.

A rustic wooden cabin with a stone floor, a wicker sofa with a blue cushion, and a purple door.

A living room with a sofa, a coffee table with books, a large vase, and a lamp.

A kitchen with wooden cabinets, granite countertops, and a wooden ceiling.

7. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester

9.8 out of 10, Exceptional, (63 reviews)

9.8/10

Exceptional

(63 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!"

Nicole

The price is HK$3,882

HK$3,882

HK$6,456 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.

Outdoor seating with blue umbrellas, tables, and potted plants.

A modern kitchen with a central island, wooden flooring, and large windows with curtains.

A beach with a pier extending into calm waters, a clear sky, and a distant city skyline.

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)

9.2/10

Wonderful

(125 reviews)

"Overall great stay, loved the location"

Anthony E.

The price is HK$1,490

HK$1,490

HK$3,364 total

includes taxes & fees

23 Nov - 24 Nov

Renovated Beach House Close to Everything, Minutes to Boston

A modern kitchen with a stainless steel refrigerator, double sink, and wooden flooring.

A red door with a white frame, two wall-mounted lights, and a welcome mat with a striped design.

A dining area with a wooden table and chairs, a central decorative piece, and large windows with curtains.

A compact kitchen with a stainless steel refrigerator, a microwave, and a built-in oven. It features white cabinetry, a wooden floor, and a window providing a view of the outside.

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)

9.8/10

Exceptional

(23 reviews)

"Great, clean location to stay."

Mike O.

The price is HK$2,157

HK$2,157

HK$4,030 total

includes taxes & fees

27 Oct - 28 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.

A white wooden gate with a metal latch, a gravel path, and a green bush.

A harbor with boats docked, a red building, and a house with a window.

A coastal scene with a stone pier leading to a small gazebo, a sandy beach, and a house in the background.

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)

10/10

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."

Mark E.

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

An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

A living room with two sofas, a coffee table, and a chair. There is a door with a blue frame and a window with curtains.

A living room with a fireplace, sofas, a coffee table, and a television.

A residential house with a front yard, a driveway, and a wooden fence.

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)

10/10

Exceptional

(209 reviews)

"Great location and perfect home for overnight stay!"

Betsy D.

The price is HK$699

HK$699

HK$2,442 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.

A dining area with a table, chairs, a bench, and a cabinet.

A kitchen with a central island, a microwave, cabinets, and a trash bin with a recycling symbol.

A two-story house with a front porch, black shutters, and a small tree in front.

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)

10/10

Exceptional

(274 reviews)

"Clean big house was a perfect home base for our group’s weekend"

Steven S.

Leslie's Retreat: Spacious home ideally located to everything

A staircase with a wooden handrail, a potted plant, a chandelier, and a framed picture on the wall.

A living room with a sofa, two armchairs, a coffee table, a chandelier, and large potted plants.

A deck with a table and chairs, a sliding glass door, and a white fence.

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)

9.6/10

Exceptional

(5 reviews)

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.

A living room with a black leather sofa, a wooden coffee table, a patterned rug, and a view through large glass doors to an outdoor deck.

A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a chandelier.

A rustic wooden chest with a 'Perch' label, placed on a table with a framed picture of a building in the background.

14. Waterview Westend Townhouse

Waterview Westend Townhouse

Provincetown

9.4 out of 10, Exceptional, (102 reviews)

9.4/10

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"

Glen A.

Waterview Westend Townhouse

A spacious living area with a large sectional sofa, a glass dining table, and multiple windows providing natural light.

A green bridge spanning a river with a marina and residential buildings in the foreground.

A large brick building with a central entrance, steps leading up to it, and a well-maintained lawn.

A brick building with a covered patio, outdoor seating, and a well-maintained garden.

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)

9.4/10

Exceptional

(129 reviews)

"Great stay for a couple of nights. Great location."

Kevin C.

The price is HK$2,950

HK$2,950

HK$5,670 total

includes taxes & fees

27 Oct - 28 Oct

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.

A living room with a leather sofa, a hanging lamp, and a brick fireplace.

A two-story building with a balcony, a name sign, and a flag decoration.

A cozy room with a fireplace, a dining table with chairs, and a hanging light fixture.

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)

9.6/10

Exceptional

(47 reviews)

"Beautiful home close to the ocean for our trip, incredibly happy I chose it!"

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.

A compact kitchen with a dining area, a refrigerator, and a sink.

A guest entrance with two white doors, one with a wooden frame and the other with a black handle.

A room with a bed, a TV, a patterned rug, and a door leading to a staircase.

17. Salem Getaway - Cozy 1BR Near Downtown

Salem Getaway - Cozy 1BR Near Downtown

Salem

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Perfect little place for a quick quaint stay."

Annette A.

The price is HK$1,372

HK$1,372

HK$2,505 total

includes taxes & fees

3 Nov - 4 Nov

Salem Getaway - Cozy 1BR Near Downtown

A deck with a table and chairs, overlooking the ocean.

A beach with large rocks and pebbles, a clear blue sky, and calm water.

A modern kitchen with stainless steel appliances, a large island with bar stools, and a window with floral curtains.

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, (27 reviews)

10/10

Exceptional

(27 reviews)

"Beautiful location and, even better, our Host thought about all the small details that make the home stand out."

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.

A modern kitchen with white cabinetry, stainless steel appliances, and a large dining table with wicker chairs.

A bedroom with a bed, two bedside tables, a desk, and a chair.

A wooden patio table set for six with white chairs, a stone pathway, and a wooden fence in the background.

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)

10/10

Exceptional

(63 reviews)

"This property is located perfectly between town, the beaches , bike paths and shopping access.House is adorable!"

Richard L.

Beautiful House Minutes from Town, on Bike Path

A dining area with a wooden table, chairs, and a ceiling fan.

A two-story house with a wrap-around porch, a fenced yard, and a driveway leading to the house.

A staircase with a wooden handrail and a white wall with a light switch.

A kitchen with wooden cabinets, a black countertop, a window with a view, and a hanging bag.

20. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires

Great Barrington

9.6 out of 10, Exceptional, (29 reviews)

9.6/10

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."

Kelly B.

The price is HK$1,376

HK$1,376

HK$2,212 total

includes taxes & fees

27 Oct - 28 Oct

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

Four Points by Sheraton Boston Newton

8/10 Good

"I"

Patricia 3-night trip

Posted 5 hours ago

Four Points by Sheraton Boston Newton

Encore Boston Harbor

10/10 Excellent

"Excellent service"

praneeth 2-night trip

Posted 6 hours ago

Encore Boston Harbor

The Godfrey Hotel Boston

10/10 Excellent

"The hotel is gorgeous with a great location. Our room was beautiful with a very comfortable bed. Just neatly, the staff were friendly, kind, gracious, and were there with whatever I might need or want. I will be staying here over and over again!"

Elisabeth M 1-night trip

Posted 10 hours ago

The Godfrey Hotel Boston

The Dagny Boston

10/10 Excellent

"This was one of the nicest hotels we have ever stayed in, and I highly recommend it. The rooms were fantastic, clean, and the staff was exceptional. The location is great and the restaurants are some of the best. 5 stars here!"

Brad 3-night trip

Posted 12 hours ago

The Dagny Boston

Harborside Inn Of Boston

10/10 Excellent

"We loved the hotel. Great location."

Robyn 3-night trip

Posted 12 hours ago

Harborside Inn Of Boston

Hyatt Regency Boston

10/10 Excellent

"Clean. Nice staff. Nice bar."

Richard 3-night trip

Posted 12 hours ago

Hyatt Regency Boston

Bedford Plaza Hotel - Boston

8/10 Good

"Staff was great, building and room were good, it’s an older basic building that needs an update but it was good for what it was. The staff working there are going above and beyond. Shower was clogged when we got there."

Eric 2-night trip

Posted 16 hours ago

Bedford Plaza Hotel - Boston

Find out more about Massachusetts

Massachusetts Vacation Homes information

Number of reviews	1,077
Accommodation	6129 Vacation Homes
Lowest Price	HK$1,465
Highest Price	HK$6,456

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Vacation Homes in Massachusetts

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Massachusetts

Boston

Provincetown

Our top choices for Massachusetts holiday homes

1. Experience Three Sisters Sanctuary in Goshen, MA

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

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

4. Lovely 2nd Floor Apartment

5. Shelburne Falls on Main

6. Bright Contemporary Escape, Near the T

7. Beach Life Bliss - steps to the beach

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

9. Spacious 4-bedroom with four and half bathrooms

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

11. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

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

14. Waterview Westend Townhouse

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

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

17. Salem Getaway - Cozy 1BR Near Downtown

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

19. Beautiful House Minutes from Town, on Bike Path

20. Leaf-Peeper Paradise in the Berkshires

Find holiday rentals that suit your style

Top Massachusetts Hotel Reviews

Four Points by Sheraton Boston Newton

Find out more about Massachusetts

Massachusetts Vacation Homes information

Explore a world of travel with Expedia