Book Holiday Homes in Massachusetts

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Featured Holiday Homes in Massachusetts

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth
The price is NZ$531 per night from 29 Apr to 30 Apr
NZ$531
includes taxes & fees
29 Apr - 30 Apr
Stay at this vacation home in Plymouth. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Manomet Beach and Ellisville Harbor State Park ...
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

West Roxbury
Book a stay at this golf vacation home in Boston. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Fenway Park and Copley Square ...
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
LUXURIOUS New Cottage!  5-min. walk to Main St. And Harbor Beaches

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Nantucket
The price is NZ$1,039 per night from 28 Apr to 29 Apr
NZ$1,039
includes taxes & fees
28 Apr - 29 Apr
Stay at this vacation home in Nantucket. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Greater Light Garden and Fire Hose Cart House are ...
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
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Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
The price is NZ$753 per night from 5 May to 6 May
NZ$753
includes taxes & fees
5 May - 6 May
Stay at this vacation home in Chatham. Enjoy a water park, a garden, and patios. Popular attractions Hardings Beach and Ridgevale Beach are located nearby.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Boston
Stay at this vacation home in Boston. Enjoy balconies, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Boston Common and New England ...
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T

Boston
Stay at this vacation home in Boston. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Fenway Park and Copley Square are located ...
Clean, Contemporary Escape | Near T
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

Chelsea
Book a stay at this family-friendly vacation home in Chelsea. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Boston Harbor ...
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Salem
Stay at this vacation home in Salem. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Salem Witch Museum and New England Pirate ...
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

Quincy
Stay at this vacation home in Quincy. Enjoy free WiFi, a fitness center, and a garden. Popular attractions New England Aquarium and Faneuil Hall Marketplace ...
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
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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
6209 Holiday Homes
Lowest Price
NZ$201
Highest Price
NZ$1,039
Popular accommodation
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay, West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy, LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches, Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi, Clean, Contemporary Escape | Near T, 2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything , Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

Top trending hotels in Massachusetts

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street, Newton, MA
The price is NZ$201 per night from 27 Apr to 28 Apr
NZ$201
includes taxes & fees
27 Apr - 28 Apr
Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Four Points by Sheraton Boston Newton
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$331 per night from 27 Apr to 28 Apr
NZ$331
includes taxes & fees
27 Apr - 28 Apr
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
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NZ$409 per night from 25 Apr to 26 Apr
NZ$409
includes taxes & fees
25 Apr - 26 Apr
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...
citizenM Boston Back Bay
Save an average of 15% on thousands of hotels when you're signed in
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
The price is NZ$350 per night from 27 Apr to 28 Apr
NZ$350
includes taxes & fees
27 Apr - 28 Apr
Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in ...
Harborside Inn Of Boston
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.