Book Holiday Homes in Chelsea

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Featured Holiday Homes in Chelsea

Modern & Walkable to city sights.  A 4-bedroom house in wonderful Boston

Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston

Boston
With a stay at this vacation home in Boston (Charlestown), you'll be within a 5-minute drive of TD Garden and New England Aquarium.
Modern & Walkable to city sights. A 4-bedroom house in wonderful 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
The price is AU$512 per night from 2 Feb to 3 Feb
AU$512
includes taxes & fees
2 Feb - 3 Feb
Located in Salem, this vacation home is by the sea, within a 5-minute walk of Salem Maritime National Historic Site and New England Pirate Museum.
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Charming home with deck- walkable to transit, shops & restaurants

Charming home with deck- walkable to transit, shops & restaurants

Newton
With a stay at this vacation home in Newton (Newton Upper Falls), you'll be within a 15-minute drive of Boston College and Boston University.
Charming home with deck- walkable to transit, shops & restaurants
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Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Swampscott
With a stay at this vacation home in Swampscott, you'll be within a 5-minute drive of Salem Harbor and Salem State College.
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
OLD TOWN CHARM.  
Sleeps 4- 2 bedrooms - 2.5 baths

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

Marblehead
Located in Marblehead, this vacation home is by the sea, a 3-minute walk from Marblehead Museum & Historical Society and within a 5-minute drive of Fort ...
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
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
A stay at this vacation home places you in the heart of Salem, steps from Salem Witch Trials Memorial and New England Pirate Museum.
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

Waltham
With a stay at this vacation home in Waltham (South Side), you'll be within a 15-minute drive of Boston College and Harvard University.
Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston
A stay at this vacation home places you in the heart of Boston, within a 15-minute walk of Fenway Park and Boston University.
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
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
With a stay at this vacation home, you'll be centrally located in Boston, within a 5-minute drive of Boston Convention and Exhibition Center and Northeastern ...
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
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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
472 Holiday Homes
Lowest Price
AU$198
Highest Price
AU$512
Popular accommodation
Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston, Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC , Charming home with deck- walkable to transit, shops & restaurants, Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace, OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV, Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston, Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Top trending hotels in Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

4 out of 5
201 Everett Ave, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is AU$204 per night from 6 Feb to 7 Feb
AU$204
includes taxes & fees
6 Feb - 7 Feb
In the heart of Chelsea, Doubletree By Hilton Boston Logan Airport Chelsea is within a 5-minute drive of Encore Boston Harbor and TD Garden.
Doubletree By Hilton Boston Logan Airport 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$204 per night from 17 Feb to 18 Feb
AU$204
includes taxes & fees
17 Feb - 18 Feb
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
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea

2.5 out of 5
200 Maple St, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is AU$205 per night from 9 Feb to 10 Feb
AU$205
includes taxes & fees
9 Feb - 10 Feb
When you stay at Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea in Chelsea, you'll be near the airport, within a 5-minute drive of Encore Boston ...
Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea
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TownePlace Suites Boston Logan Airport/Chelsea

TownePlace Suites Boston Logan Airport/Chelsea

3 out of 5
30 Eastern Avenue, Chelsea, MA
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 9 Feb to 10 Feb
AU$198
includes taxes & fees
9 Feb - 10 Feb
When you stay at TownePlace Suites Boston Logan Airport/Chelsea in Chelsea, you'll be on a river, within a 10-minute drive of TD Garden and New England ...
TownePlace Suites Boston Logan Airport/Chelsea
Don't see what you're looking for?
See all available properties in Chelsea
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.

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^Subject to availability and chosen travel dates.