Book Holiday Homes in Massachusetts

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Featured Holiday Homes in Massachusetts

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
The price is NZ$447 per night from 27 May to 28 May
NZ$447
per night
27 May - 28 May
Stay at this vacation home in Dennis Port. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Our guests praise the clean rooms in our reviews. Popular ...
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths

Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths

Mashpee
Book a stay at this beach vacation home in Mashpee. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Popponesset Beach and Cape Cod Children's ...
Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths
Oceanfront hotel suite at beachfront Sandbars Inn with balcony, AC & firepit

Oceanfront hotel suite at beachfront Sandbars Inn with balcony, AC & firepit

North Truro
Book a stay at this beach vacation home in North Truro. Enjoy a beach locale, balconies, and cable/satellite TV service. Our guests praise the clean rooms in ...
Oceanfront hotel suite at beachfront Sandbars Inn with balcony, AC & firepit
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Beautiful, Cozy Ultra Convenient Salem Home

Beautiful, Cozy Ultra Convenient Salem Home

Salem
The price is NZ$551 per night from 3 Jun to 4 Jun
NZ$551
per night
3 Jun - 4 Jun
Stay at this vacation home in Salem. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Witch House and Salem Witch Museum are located ...
Beautiful, Cozy Ultra Convenient Salem Home
2 Blocks to Main Street Hyannis Sleeps 6.  3 bed 2 full baths

2 Blocks to Main Street Hyannis Sleeps 6. 3 bed 2 full baths

Barnstable
Stay at this vacation home in Hyannis. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Cape Cod Melody Tent and ...
2 Blocks to Main Street Hyannis Sleeps 6. 3 bed 2 full baths
Peaceful cottage with deck, screened porch, grill, & firepit - walk to beach

Peaceful cottage with deck, screened porch, grill, & firepit - walk to beach

Eastham
Stay at this vacation home in Eastham. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Nauset Beach and Cape Cod National Seashore are ...
Peaceful cottage with deck, screened porch, grill, & firepit - walk to beach
Lake Access 4 Bed 3 Full Bath

Lake Access 4 Bed 3 Full Bath

Billerica
The price is NZ$1,225 per night from 27 May to 28 May
NZ$1,225
per night
27 May - 28 May
Stay at this vacation home in Billerica. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Burlington Mall and Nutting Lake Conservation ...
Lake Access 4 Bed 3 Full Bath
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Oak Bluffs
Stay at this vacation home in Oak Bluffs. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Inkwell Beach and Oak Bluffs ...
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Peace and quiet on the lake

Peace and quiet on the lake

Becket
Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and patios. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry are located ...
Peace and quiet on the lake
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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.

Massachusetts Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Massachusetts vacation homes are the perfect way for you to wing it.

Holiday houses in Massachusetts let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Massachusetts in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Massachusetts adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Massachusetts with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Massachusetts vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Massachusetts Holiday Homes essential information

Accommodation
4485 Holiday Homes
Lowest Price
NZ$289
Highest Price
NZ$1,225
Popular accommodation
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Popponesset Waterfront - Private Deeded Beachfront Home, 3 bedrooms, 2 baths, Oceanfront hotel suite at beachfront Sandbars Inn with balcony, AC & firepit, Beautiful, Cozy Ultra Convenient Salem Home, 2 Blocks to Main Street Hyannis Sleeps 6. 3 bed 2 full baths, Peaceful cottage with deck, screened porch, grill, & firepit - walk to beach, Lake Access 4 Bed 3 Full Bath, Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard, Peace and quiet on the lake

Top trending hotels in Massachusetts

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4.5 out of 5
450 Summer Street, Boston, MA
The price is NZ$315 per night from 27 May to 28 May
NZ$315
per night
27 May - 28 May
Stay at this 4.5-star luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
Omni Boston Hotel at the Seaport
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
The price is NZ$520 per night from 27 May to 28 May
NZ$520
per night
27 May - 28 May
Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Seaport Hotel Boston
Omni Parker House

Omni Parker House

4 out of 5
60 School St, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 27 May to 28 May
NZ$379
per night
27 May - 28 May
Book a stay at this eco-certified hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Omni Parker House
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The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NZ$289 per night from 27 May to 28 May
NZ$289
per night
27 May - 28 May
Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful ...
The Revolution Hotel
Don't see what you're looking for?
See all available properties in Massachusetts
View all properties
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.

More ways to explore Massachusetts

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^Subject to availability and chosen travel dates.