Chelsea Holiday Rentals

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Holiday Rentals in Chelsea

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

Chelsea
10.0 out of 10, Exceptional, (1)
"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 AU$650
includes taxes & fees
1 Jan - 2 Jan 2026
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

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

Chelsea
9.4 out of 10, Exceptional, (94)
"Beautiful location! We definitely return. "
United States
Michelle N.
The price is AU$824
includes taxes & fees
9 Dec - 10 Dec
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

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

Charlestown
9.8 out of 10, Exceptional, (200)
"My husband and I had an excellent stay! It was very comfortable! I would highly recommend staying on The Blue Pearl and hope to stay there again. "
United States
Stacey W.
The price is AU$708
includes taxes & fees
9 Dec - 10 Dec
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep

Fun houseboat. Walk to Boston attractions WIFI

Boston
9.8 out of 10, Exceptional, (89)
"It was unique way to stay in the city"
United States
brian m.
The price is AU$670
includes taxes & fees
9 Dec - 10 Dec
Fun houseboat. Walk to Boston attractions WIFI

Charlestown Houseboat Walk to attractions Be rocked to sleep

Thompson Square - Bunker Hill
9.6 out of 10, Exceptional, (99)
"Location is great, houseboat is nice, we enjoyed our stay very much. "
United States
Ellen C.
The price is AU$670
includes taxes & fees
4 Jan - 5 Jan 2026
Charlestown Houseboat Walk to attractions Be rocked to sleep

Bay Village Suites

2.0 star property
Bay Village
6.4 out of 10, (249)
"Great location nice neighborhood "
United States
Jose
Bay Village Suites

Maverick Suites at 245 Newbury St

2.0 star property
Back Bay
8.2 out of 10, Very good, (154)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
Maverick Suites at 245 Newbury St

Maverick Suites at 40 Temple St

2.0 star property
Beacon Hill
7.6 out of 10, Good, (102)
"Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌"
United Kingdom
Jordan Elizabeth Marie
Maverick Suites at 40 Temple St

Maverick Suites at 400 Columbus Ave

2.0 star property
South End
7.4 out of 10, Good, (133)
"I thoroughly enjoyed my stay. Great property in a nice neighborhood in Back Bay. Bonus: it's also near the Logan Express bus stop for easy airport access. "
United States
Mark
Maverick Suites at 400 Columbus Ave

Global Luxury Suites Downtown Boston

4.0 star property
Chinatown
8.0 out of 10, Very good, (628)
"This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. "
United States
Lily
The price is AU$216
includes taxes & fees
18 Dec - 19 Dec
Global Luxury Suites Downtown Boston

Temple Place Suites

2.5 star property
Downtown Boston
7.0 out of 10, Good, (324)
"Pretty clean room, good location, resonable price."
Canada
Beiyu
The price is AU$251
includes taxes & fees
9 Dec - 10 Dec
Temple Place Suites

Best Location Studio In Downtown Boston

Downtown Boston
10.0 out of 10, Exceptional, (1)
"In town to celebrate a special event."
United States
Pam P.
The price is AU$331
includes taxes & fees
11 Dec - 12 Dec
Best Location Studio In Downtown Boston

Maverick Suites at 28 Fenway

3.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (324)
"Spotless room, spotless building, great staff, comfortable bed. "
United States
Patricia
The price is AU$298
includes taxes & fees
16 Dec - 17 Dec
Maverick Suites at 28 Fenway

The Chester: Urban Chic Retreat In South End

2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!"
United States
Chad T.
The price is AU$573
includes taxes & fees
18 Dec - 19 Dec
The Chester: Urban Chic Retreat In South End

Premier Suites - Bay Village

2.0 star property
Bay Village
6.4 out of 10, (251)
"Clean room, good location, check in check out easily!"
United States
HIEN T
The price is AU$203
includes taxes & fees
11 Dec - 12 Dec
Premier Suites - Bay Village

Come Visit Boston and Stay In Our Homey Studio

Downtown Boston
8.8 out of 10, Excellent, (3)
"Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!"
United States
Dean and Courtenay M.
The price is AU$327
includes taxes & fees
9 Dec - 10 Dec
Come Visit Boston and Stay In Our Homey Studio

The Chester Hotel

4.0 star property
South End
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is AU$534
includes taxes & fees
9 Dec - 10 Dec
The Chester Hotel

Modern North End Studio

North End
9.0 out of 10, Wonderful, (10)
"Convenient location. Great restaurants. Perfect apatment for a couple. "
United States
Holly V.
The price is AU$478
includes taxes & fees
29 Dec - 30 Dec
Modern North End Studio

Studio Awaits Your Next Stay!

Bay Village
9.2 out of 10, Wonderful, (5)
"Would stay again"
United States
mark p.
The price is AU$327
includes taxes & fees
16 Dec - 17 Dec
Studio Awaits Your Next Stay!

Walk to Boston Common, Safe & Central Stay

Beacon Hill
7.2 out of 10, Good, (17)
"Property was excellent. Transportation was easy and communication with host was great. Thanks for a great vacation in beautiful Boston."
United States
john
The price is AU$452
includes taxes & fees
8 Jan - 9 Jan 2026
Walk to Boston Common, Safe & Central Stay
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

Find out more about Chelsea

Everything you need to know about Chelsea holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chelsea holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chelsea holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chelsea holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chelsea. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chelsea holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chelsea holiday rentals we have selected for you start as low as AU$203 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chelsea rentals

At Expedia, we put the best Chelsea holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chelsea rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chelsea holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chelsea. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy Salem Getaway. Historic Home Near All the Sights: This holiday home rental outside of Chelsea offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals will I find in Chelsea?

Choose from 3 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 TD Garden.

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.