Book Holiday Homes in Chelsea

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Featured Holiday Homes in Chelsea

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

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

Salem
With a stay at this vacation home, you'll be centrally located in Salem, within a 5-minute walk of Salem Common and Salem Witch Museum.
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
With a stay at this vacation home in Cambridge (Neighborhood Nine), you'll be within a 5-minute drive of Harvard University and Harvard Square.
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
The price is AU$965 per night from 11 Nov to 12 Nov
AU$965
includes taxes & fees
11 Nov - 12 Nov
With a stay at this vacation home, you'll be centrally located in Beverly, within a 5-minute drive of 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
With a stay at this vacation home in Arlington, you'll be within a 10-minute drive of Harvard University and Harvard Square.
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
The price is AU$661 per night from 3 Nov to 4 Nov
AU$661
includes taxes & fees
3 Nov - 4 Nov
With a stay at this vacation home in Melrose, you'll be within a 15-minute drive of Encore Boston Harbor and TD Garden.
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
With a stay at this vacation home in Salem, you'll be by the sea, a 4-minute walk from Salem Common and 5 minutes by foot from Salem Witch Museum.
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
With a stay at this vacation home, you'll be centrally located in Malden, within a 10-minute drive of Encore Boston Harbor and Tufts University.
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
A stay at this vacation home places you in the heart of Stoughton, within a 5-minute drive of 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
The price is AU$793 per night from 4 Nov to 5 Nov
AU$793
includes taxes & fees
4 Nov - 5 Nov
With a stay at this vacation home, you'll be centrally located in Chelsea, a 5-minute drive from Encore Boston Harbor and 5 minutes from TD Garden.
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.

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

Holiday houses in Chelsea 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 Chelsea 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 Chelsea adventures, obvs.

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

Chelsea Holiday Homes essential information

Accommodation
420 Holiday Homes
Lowest Price
AU$220
Highest Price
AU$965
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 Chelsea

Hampton Inn Boston Logan Airport Chelsea

Hampton Inn Boston Logan Airport Chelsea

2.5 out of 5
200 2nd Street, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is AU$220 per night from 24 Nov to 25 Nov
AU$220
includes taxes & fees
24 Nov - 25 Nov
When you stay at Hampton Inn Boston Logan Airport Chelsea in Chelsea, you'll be near the airport, a 4-minute drive from Encore Boston Harbor and 5 minutes from ...
Hampton Inn Boston Logan Airport Chelsea
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane, Boston, MA
The price is AU$309 per night from 24 Nov to 25 Nov
AU$309
includes taxes & fees
24 Nov - 25 Nov
Located in Boston (Seaport District), Seaport Hotel Boston is a 3-minute walk from Liberty Wharf and 8 minutes by foot from Institute of Contemporary Art.
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 AU$315 per night from 25 Nov to 26 Nov
AU$315
includes taxes & fees
25 Nov - 26 Nov
Omni Parker House is centrally located in Boston, a 3-minute walk from Boston City Hall and 7 minutes by foot from Quincy Market.
Omni Parker House
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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 AU$329 per night from 28 Nov to 29 Nov
AU$329
includes taxes & fees
28 Nov - 29 Nov
With a stay at The Dagny Boston, you'll be centrally located in Boston, within a 10-minute walk of New England Aquarium and Faneuil Hall Marketplace.
The Dagny Boston
Don't see what you're looking for?
See all available properties in Chelsea
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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.