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
This vacation home is in the heart of Salem, within a 5-minute walk of Salem Witch Trials Memorial 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$1,026 per night from 1 Dec to 2 Dec
AU$1,026
includes taxes & fees
1 Dec - 2 Dec
With a stay at this vacation home, you'll be centrally located in Beverly, within a 5-minute drive of Salem Witch Museum and John Cabot House.
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$666 per night from 24 Nov to 25 Nov
AU$666
includes taxes & fees
24 Nov - 25 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
When you stay at this vacation home in Salem, you'll be by the sea, within a 10-minute walk of Salem Witch Museum and Salem Custom House.
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 15-minute drive of Encore Boston Harbor and TD Garden.
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$797 per night from 2 Dec to 3 Dec
AU$797
includes taxes & fees
2 Dec - 3 Dec
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
424 Holiday Homes
Lowest Price
AU$178
Highest Price
AU$1,026
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$178 per night from 1 Dec to 2 Dec
AU$178
includes taxes & fees
1 Dec - 2 Dec
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
Fully refundableReserve now, pay when you stay
The price is AU$294 per night from 22 Dec to 23 Dec
AU$294
includes taxes & fees
22 Dec - 23 Dec
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
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$289 per night from 22 Dec to 23 Dec
AU$289
includes taxes & fees
22 Dec - 23 Dec
With a stay at Hilton Boston Park Plaza, you'll be centrally located in Boston, steps from Boston Public Garden and within a 5-minute walk of Newbury ...
Hilton Boston Park Plaza
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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$333 per night from 25 Nov to 26 Nov
AU$333
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
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.