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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chelsea holiday rentals

Rooftop terrace

1. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (667 reviews)
"The hotel was beautiful and so unique. Staff was amazing and it was in a great location."
United States
Brittany
The price is ฿21,072
฿24,222 total
includes taxes & fees
8 Oct - 9 Oct
Marriott Vacation Club® at Custom House, Boston
Lobby lounge

2. Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (745 reviews)
"Friendly sat at Front and the property is very nice it was useful for a quick work trip. Easy to get around well lit and maintained"
United States
Christopher
The price is ฿10,823
฿16,595 total
includes taxes & fees
30 Sept - 1 Oct
Global Luxury Suites Downtown Boston
Lobby

3. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (319 reviews)
"Excellent property upscale amenities full kitchen perfect in every way and my room was only a studio I’ll definitely be back next time to try a larger room just to see what they’re like"
United States
Dirk
Kasa Boston at Fenway
Exterior

4. 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, (203 reviews)
"Right in the heart of the shopping district, easy walking and central to Fenway/downtown Boston"
United States
Jennifer
The price is ฿7,197
฿11,337 total
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 245 Newbury St
Front of property

5. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
7.8 out of 10, Good, (148 reviews)
"There only a few things I require from a hotel. Hotel Maverick Suites at 40 are clean, quiet and reasonably priced. I enjoyed my stay there immensely. A bonus was their convenient location."
United States
Jerrold
The price is ฿6,972
฿11,079 total
includes taxes & fees
4 Oct - 5 Oct
Maverick Suites at 40 Temple St
Studio | Iron/ironing board, free WiFi

6. The Concord Hotel

The Concord Hotel
2.0 star property
South End
7.6 out of 10, Good, (24 reviews)
"Great room! Cool place to stay. We walked everywhere and stuff was close by. Woud stay here again"
United States
Cotie
The price is ฿9,206
฿14,796 total
includes taxes & fees
30 Sept - 1 Oct
The Concord Hotel
42-inch TV with satellite channels

7. Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.6 out of 10, Good, (172 reviews)
"Well located"
United States
Evelyn
The price is ฿4,858
฿8,648 total
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 400 Columbus Ave
Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services

8. The Monty Boston

The Monty Boston
2.5 star property
Downtown Boston
9.6 out of 10, Exceptional, (40 reviews)
"This place is absolutely stunning I would definitely book again. "
United States
Klaudia
The price is ฿25,065
฿34,558 total
includes taxes & fees
4 Oct - 5 Oct
The Monty Boston
Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets

9. Premier Suites - Bay Village

Premier Suites - Bay Village
2.0 star property
Bay Village
6.4 out of 10, (345 reviews)
"Location is great"
United States
Eria
The price is ฿4,378
฿6,756 total
includes taxes & fees
30 Sept - 1 Oct
Premier Suites - Bay Village
Terrace/patio

10. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,277 reviews)
"Great location, close to restaurants and stores. Beautiful rooms. Close enought to Boston without all the traffic. Close to Mass Pike."
United States
Mark
The price is ฿5,368
฿5,996 total
includes taxes & fees
27 Sept - 28 Sept
Crescent Suites Hotel
Front of property

11. Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (425 reviews)
"Comfortable room, walkable area, beautiful park across the road, and easy to work with."
United States
Amber
The price is ฿5,368
฿9,426 total
includes taxes & fees
30 Sept - 1 Oct
Maverick Suites at 28 Fenway
1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, free WiFi, bed sheets

12. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (478 reviews)
"Clean, good location, all what I need for short stay"
United States
Julia
The price is ฿4,018
฿6,726 total
includes taxes & fees
28 Sept - 29 Sept
Temple Place Suites
Premium Studio Suite | Premium bedding, desk, iron/ironing board, free WiFi

13. Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.2 out of 10, Wonderful, (237 reviews)
"Great location if you go to the BCH"
Mexico
Ana
The price is ฿8,230
฿15,206 total
includes taxes & fees
30 Sept - 1 Oct
Charlesgate Suites
Premium Apartment | Living area | 24-inch Smart TV with digital channels

14. The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.8 out of 10, Excellent, (38 reviews)
"It was in a great neighbourhood and beautiful decorated"
United Kingdom
Shanida
The price is ฿6,417
฿11,590 total
includes taxes & fees
30 Sept - 1 Oct
The Chester Hotel
Interior entrance

15. Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner
8.4 out of 10, Very good, (314 reviews)
"Room was clean, neat area."
United States
Keir
The price is ฿3,868
฿7,299 total
includes taxes & fees
27 Sept - 28 Sept
Maverick Suites at 89 Marion
Indoor pool, pool umbrellas, pool loungers

16. Global Luxury Suites East Boston

Global Luxury Suites East Boston
4.0 star property
East Boston
6.8 out of 10, (210 reviews)
"Cozy, comfy and cute✨. Would def rent again❤️"
United States
Erica
The price is ฿10,094
฿15,433 total
includes taxes & fees
30 Sept - 1 Oct
Global Luxury Suites East Boston
30-inch flat-screen TV with satellite channels, TV

17. Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
8.0 out of 10, Very good, (87 reviews)
"It was very close to stores to go shopping and amazing spot to get last minute reservations for dinner"
United States
Talyciah
The price is ฿4,723
฿8,493 total
includes taxes & fees
28 Sept - 29 Sept
Maverick Suites at 402 Columbus Ave
Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down duvets, memory-foam beds

18. Symple Live

Symple Live
4.5 star property
Fenway–Kenmore
9.0 out of 10, Wonderful, (22 reviews)
"Great location, close to the T line, grocery store nearby. Clean, quiet and very comfortable accommodations, especially the best bed I’ve slept in at a rental location. Had everything we needed, looking forward to coming back!"
United States
Lori
The price is ฿13,261
฿18,883 total
includes taxes & fees
18 Oct - 19 Oct
Symple Live
Apartment | Interior

19. Furnished Apartment Near Longwood

Furnished Apartment Near Longwood
3.0 star property
North Brookline
7.6 out of 10, Good, (7 reviews)
"Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities."
United States
Sujiang
Furnished Apartment Near Longwood
House (SeaCity View) | Exterior

20. Seacity View

Seacity View
2.0 star property
Swampscott
7.0 out of 10, Good, (2 reviews)
"Beautiful house!"
United States
carla n
The price is ฿16,006
฿27,277 total
includes taxes & fees
4 Oct - 5 Oct
Seacity View
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 Dagny Boston

The Dagny Boston

10/10 Excellent
"None"
Patrice 2-night trip
Posted 1 hour ago
The Dagny Boston

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
  • Use the map to find apartments and other holiday homes in the Chelsea neighbourhood you prefer
  • 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!

Frequently asked questions

Can I find holiday rentals in Chelsea?

Yes, there are holiday rentals close to the most popular sights in Chelsea, or you can select a more secluded option if you're looking for a relaxing 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.

How many holiday rentals will I find in Chelsea?

Choose from 5 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 USS Constitution Museum, 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.