Chelsea Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Chelsea holiday rentals

Smart TV, video games, computer monitors, printers

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
10.0 out of 10, Exceptional, (3 reviews)
"Very happy with our stay here! The place was clean, warm, and comfortable. I really appreciated the easy check in/out procedures. I loved that we weren’t expected to complete a long list of cleaning tasks before checking out. Crib, pack n play, and high chair were available which is awesome for traveling with a baby. "
United States
Amna S.
The price is HK$1,677
HK$3,588 total
includes taxes & fees
4 May - 5 May
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Interior

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Chelsea
9.4 out of 10, Exceptional, (104 reviews)
"host was so welcoming and we enjoyed they stay"
United States
Roshawn D.
The price is HK$2,820
HK$5,400 total
includes taxes & fees
4 May - 5 May
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
TV, offices

Unit 34 Stylish 1BR Apartment Long-term stays

Unit 34 Stylish 1BR Apartment Long-term stays
Downtown Chelsea
Unit 34 Stylish 1BR Apartment Long-term stays
TV, offices

Unit 22 Luxurious 1BR Apartment Long-term stays

Unit 22 Luxurious 1BR Apartment Long-term stays
Downtown Chelsea
Unit 22 Luxurious 1BR Apartment Long-term stays
Exterior

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Charlestown
9.8 out of 10, Exceptional, (201 reviews)
"Perfect host, perfect spot, WORTH EVERY PENNY "
Canada
Jennifer E.
The price is HK$968
HK$3,994 total
includes taxes & fees
4 May - 5 May
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Interior

Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (92 reviews)
"Great location, very clean, very safe, beautiful view of the city when walking. Definitely would recommend ~"
United States
Tracey
The price is HK$1,340
HK$4,161 total
includes taxes & fees
31 May - 1 Jun
Fun houseboat. Walk to Boston attractions WIFI
TV

Endless Summer: Oceanside Views

Endless Summer: Oceanside Views
Boston
10.0 out of 10, Exceptional, (42 reviews)
"Fun family adventure!"
United States
Jay
The price is HK$2,499
HK$4,263 total
includes taxes & fees
25 May - 26 May
Endless Summer: Oceanside Views
TV

Blissful South End Studio

Blissful South End Studio
Back Bay
9.4 out of 10, Exceptional, (3 reviews)
"Great place on a quiet street convenient to everything!"
United States
Penelope D.
The price is HK$783
HK$1,999 total
includes taxes & fees
6 May - 7 May
Blissful South End Studio
Living area

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.4 out of 10, Very good, (30 reviews)
"This was a perfect stay. Exactly how described. Highly recommend. "
United States
Yanmarie
The price is HK$1,382
HK$2,985 total
includes taxes & fees
4 May - 5 May
The Chester Hotel
Exterior

Free Parking at 1 Bed Basement Apt, Near BU & MIT

Free Parking at 1 Bed Basement Apt, Near BU & MIT
Fenway–Kenmore
8.0 out of 10, Very good, (14 reviews)
"Great location, check in and check out was easy. Clean space. Great value "
United States
David
The price is HK$744
HK$1,708 total
includes taxes & fees
5 May - 6 May
Free Parking at 1 Bed Basement Apt, Near BU & MIT
1 bedroom, desk, iron/ironing board, WiFi

Perfect One Bedroom Stay In Downtown Boston!

Perfect One Bedroom Stay In Downtown Boston!
Downtown Boston
8.6 out of 10, Excellent, (18 reviews)
"Came to Boston to take a few college tours and this was a pretty central location. This property was also very close to several other places we were hoping to see while in town. Communication was great and check in was seamless. The property was clean and perfect for our stay. "
United States
elena d.
The price is HK$932
HK$1,868 total
includes taxes & fees
4 May - 5 May
Perfect One Bedroom Stay In Downtown Boston!
Exterior

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (10 reviews)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
The price is HK$956
HK$2,316 total
includes taxes & fees
5 May - 6 May
Stylish Back Bay Retreat, Steps from Prudential
1 bedroom, iron/ironing board, WiFi, bed sheets

Primo North End Studio

Primo North End Studio
North End
9.2 out of 10, Wonderful, (13 reviews)
"Great place, amazing location!"
United States
Christopher W.
The price is HK$1,489
HK$3,143 total
includes taxes & fees
7 May - 8 May
Primo North End Studio
1 bedroom, desk, iron/ironing board, WiFi

Studio Awaits Your Next Stay!

Studio Awaits Your Next Stay!
Bay Village
9.2 out of 10, Wonderful, (5 reviews)
"Would stay again"
United States
mark p.
The price is HK$1,355
HK$2,312 total
includes taxes & fees
7 May - 8 May
Studio Awaits Your Next Stay!
TV, offices

Come Visit Boston and Stay In Our Homey Studio

Come Visit Boston and Stay In Our Homey Studio
Downtown Boston
8.6 out of 10, Excellent, (4 reviews)
"Common areas outside of the room needed some work but overall was a good experience."
United States
Byron S.
The price is HK$1,645
HK$2,808 total
includes taxes & fees
2 Jun - 3 Jun
Come Visit Boston and Stay In Our Homey Studio
TV

Prime Central 1brm in North End Boston

Prime Central 1brm in North End Boston
North End
9.6 out of 10, Exceptional, (25 reviews)
"Location was ideal and property was well-kept and organized. Definitely would recommend for future visits."
United States
Taye A.
The price is HK$1,293
HK$2,990 total
includes taxes & fees
25 May - 26 May
Prime Central 1brm in North End Boston
Front of property

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.0 star property
Beacon Hill
7.6 out of 10, Good, (112 reviews)
"A phenomenal stay at maverick suites! The location was fantastic, the room was spotless and cozy, and the check-in/out process was a breeze. I’d happily stay here again and recommend to anyone taking a trip to Boston!"
United States
Kendra
The price is HK$1,262
HK$2,171 total
includes taxes & fees
4 May - 5 May
Maverick Suites at 40 Temple St
1 bedroom, desk, iron/ironing board, Internet

Cozy Studio Steps from Boston Common and Theaters

Cozy Studio Steps from Boston Common and Theaters
Bay Village
8.0 out of 10, Very good, (12 reviews)
"Was clean and the location was perfect for my stay. "
United States
Laurie F.
The price is HK$736
HK$2,239 total
includes taxes & fees
4 May - 5 May
Cozy Studio Steps from Boston Common and Theaters
Exterior

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very good, (165 reviews)
"Great location. Well priced. Its appeals to a specific type of traveler. Overall clean, quiet, solid WiFi services. I had some initial challenges getting in the building, but that was my fault for not checking in and providing the required documents. I would definitely stay again. PS The pizza place right across the street makes a great thin crust pie. "
United States
James
The price is HK$1,206
HK$2,107 total
includes taxes & fees
4 May - 5 May
Maverick Suites at 245 Newbury St
Front of property

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (357 reviews)
"Great stay. "
United States
Anna
The price is HK$1,044
HK$1,965 total
includes taxes & fees
4 May - 5 May
Maverick Suites at 28 Fenway
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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Top Chelsea Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

6/10 Okay
"It's in a great location near a T stop and walkable to the Prudential Center and other cool shops on Newbury. The place smelled a little funky, and the room was a bit cramped (there was maybe 8 inches between the foot of the bed and the dresser). The breakfast was pretty sad, just a few packaged pastries and some apples."
Jacob 5-night trip
Posted 6 hours ago
The Midtown Hotel MOD Collection by Sonesta

Find out more about Chelsea

Search for holiday rentals in Chelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Chelsea using one of the methods below:

  • View our selection of featured holiday rentals in Chelsea
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  • Enter your travel dates to view the best deals on holiday rentals in Chelsea while they last

Look no further and take a look at our great range of rental properties in Chelsea!

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Frequently asked questions

Can I find holiday rentals in Chelsea?

Yes, we have holiday rentals where you'll be only 2.4 mi (3.9 km) from New England Aquarium, providing a more remote option if you want a quieter place to stay. Visitors like the top-notch restaurants and shops in Chelsea. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Chelsea has to offer?

Centrally located in the heart of Boston near T: This holiday home rental outside of Chelsea has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Chelsea?

Choose from 4 Expedia holiday rentals in Chelsea for a memorable holiday.

What’s there to see and do in Chelsea?

While exploring the area, visit family-friendly sights like New England Aquarium, or get outside and enjoy nature at Boston Common. In the wider area, you’ll find popular places such as Fenway Park and Encore Boston Harbor.

What’s a holiday rental in Chelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chelsea. Holiday rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.