Book Holiday Homes in Boston

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Featured Holiday Homes in Boston

WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment

WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment

Salem
Stay at this vacation home in Salem. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Salem Witch Museum and Salem Common are ...
WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment
Peaceful 2Br House in Cambridge

Peaceful 2Br House in Cambridge

2 out of 5
Cambridge
Stay at this vacation home in Cambridge. Enjoy air conditioning. Popular attractions Harvard Square and Fenway Park are located nearby.
Peaceful 2Br House in Cambridge
Historic 1686 Home Near Downtown l 5BR Retreat

Historic 1686 Home Near Downtown l 5BR Retreat

2 out of 5
Beverly
Stay at this vacation home in Beverly. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Salem Common and Salem Witch Museum ...
Historic 1686 Home Near Downtown l 5BR Retreat
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New 5B3B Single Family  with Central AC

New 5B3B Single Family with Central AC

Arlington
Stay at this vacation home in Arlington. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Harvard Square and Encore Boston Harbor are ...
New 5B3B Single Family with Central AC
Spacious & Convenient 1BR unit-20min to Boston

Spacious & Convenient 1BR unit-20min to Boston

2 out of 5
Melrose
Stay at this vacation home in Melrose. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Encore Boston Harbor and LEGOLAND® ...
Spacious & Convenient 1BR unit-20min to Boston
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Salem
Stay at this vacation home in Salem. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Salem Witch Museum and Salem Custom House are ...
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Newly renovated home, top of the line appliances.

Newly renovated home, top of the line appliances.

Malden
Stay at this vacation home in Malden. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Encore Boston Harbor and TD Garden are located ...
Newly renovated home, top of the line appliances.
Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs

Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs

Stoughton
Stay at this vacation home in Stoughton. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Stoughton Book Shop and Brockton Fire Museum ...
Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs
CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA

CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA

2 out of 5
Chelsea
Stay at this vacation home in Chelsea. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Encore Boston Harbor and TD Garden are located ...
CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA
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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.

Boston 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 Boston vacation homes are the perfect way for you to wing it.

Holiday houses in Boston 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 Boston 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 Boston adventures, obvs.

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

Boston Holiday Homes essential information

Accommodation
441 Holiday Homes
Lowest Price
NZ$340
Highest Price
NZ$457
Popular accommodation
WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment, Peaceful 2Br House in Cambridge, Historic 1686 Home Near Downtown l 5BR Retreat, New 5B3B Single Family with Central AC, Spacious & Convenient 1BR unit-20min to Boston, Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC , Newly renovated home, top of the line appliances., Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs, CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA

Top trending hotels in Boston

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NZ$340 per night from 24 Nov to 25 Nov
NZ$340
includes taxes & fees
24 Nov - 25 Nov
Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
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$346 per night from 25 Nov to 26 Nov
NZ$346
includes taxes & fees
25 Nov - 26 Nov
Book a stay at this eco-certified hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Omni Parker House
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NZ$362 per night from 28 Nov to 29 Nov
NZ$362
includes taxes & fees
28 Nov - 29 Nov
Stay at this 4-star historic hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in ...
The Dagny Boston
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Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4.5 out of 5
450 Summer Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is NZ$457 per night from 25 Nov to 26 Nov
NZ$457
includes taxes & fees
25 Nov - 26 Nov
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
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See all available properties in Boston
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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.

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^Subject to availability and chosen travel dates.