Chelsea Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Chelsea holiday rentals

A modern living room with a sofa, coffee table, and a small table with books and a lamp. There is a kitchen area with cabinets, a refrigerator, and a microwave. A welcome sign is on the wall, and a basketball arcade game is visible.

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

Chelsea

Cooper D.

HK$3,561 total

includes taxes & fees

28 Sept - 29 Sept

A spacious living area with a large sectional sofa, a glass dining table, and multiple windows providing natural light.

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

Chelsea

Ted W.

HK$5,407 total

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a bed, a window, and a wall with vertical wooden slats.

3. 3bdrm Apt next to Airport/Downtown 7 min drive

Chelsea

Aslin

HK$2,443 total

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a sofa, two bar stools, a round wooden coffee table, and a television.

4. Spacious 1BR | Sleeps 6 + Parking

Chelsea

HK$3,616 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with white cabinetry, a black stove, and a microwave.

5. Home for Families | Sleeps 11 | 5 min Downtown

Chelsea

HK$3,843 total

includes taxes & fees

29 Sept - 30 Sept

A living room with a grey sofa, a beige armchair, a world map pillow, a clock on the wall, and a door leading to another room.

6. Mezzanine Apt near Airport Private Parking

Chelsea

HK$2,314 total

includes taxes & fees

24 Sept - 25 Sept

A bedroom with a bed, a sofa, a potted plant, and a window with blinds.

7. Modern Apt Near Airport 7 Min to Downtown

Chelsea

HK$2,140 total

includes taxes & fees

27 Sept - 28 Sept

A neatly made bed with a striped bedspread, a wooden headboard, and a nightstand with a drawer.

8. 3 bdrm Apt next to Airport/2

Chelsea

HK$1,812 total

includes taxes & fees

23 Sept - 24 Sept

A closet with a white interior, a hanging rod, and a carpeted floor.

9. Modern 1BR | Sleeps 6 + Parking

Chelsea

HK$2,738 total

includes taxes & fees

12 Oct - 13 Oct

A hotel room with a bed, a nightstand, a window with a view of buildings, and a framed picture on the wall.

10. 1BR for 6 | Parking + Full Kitchen

Chelsea

HK$2,297 total

includes taxes & fees

29 Sept - 30 Sept

A modern living room with a sofa, a round wooden coffee table, and a kitchen in the background.

11. Comfortable 1BR | Fast WiFi + Parking

Chelsea

HK$2,608 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a view of the outdoors through large windows.

12. 1BR for 6 | Parking + Easy Transit

Chelsea

HK$2,386 total

includes taxes & fees

7 Oct - 8 Oct

A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

13. Marriott Vacation Club® at Custom House, Boston

Downtown Boston

Brittany

HK$5,703 total

includes taxes & fees

8 Oct - 9 Oct

An outdoor patio with round tables and chairs, surrounded by green umbrellas.

14. Crescent Suites Hotel

South Side

Mark

HK$1,412 total

includes taxes & fees

27 Sept - 28 Sept

A marina with numerous boats docked, a large building with a green roof, and a cityscape in the background.

15. Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat

Boston

Gale P.

HK$4,831 total

includes taxes & fees

28 Sept - 29 Sept

A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

16. Maverick Suites at 40 Temple St

Beacon Hill

Jerrold

HK$2,609 total

includes taxes & fees

4 Oct - 5 Oct

A modern lobby with a wooden panel wall, a beige sofa, a patterned rug, and a large abstract painting.

17. Global Luxury Suites Downtown Boston

Chinatown

Myah

HK$3,855 total

includes taxes & fees

30 Sept - 1 Oct

A deck with wicker furniture and a table, overlooking a marina with boats.

18. Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

Thompson Square - Bunker Hill

Jeremy H.

HK$4,775 total

includes taxes & fees

30 Sept - 1 Oct

A spacious living room with a dining area, wooden columns, and a large window providing natural light.

19. Near Boston Historic two-bedroom with Modern Amenities

Malden

Jenn K.

HK$2,254 total

includes taxes & fees

24 Sept - 25 Sept

A living room with a grey sofa, a black armchair, a coffee table, and a blue rug. There are two windows with blinds, a bookshelf, and a potted plant.

20. Bright 2BR by Boston Waterfront

East Boston

Bridget

HK$2,605 total

includes taxes & fees

28 Sept - 29 Sept

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Top Chelsea Hotel Reviews

Doubletree By Hilton Boston Logan Airport Chelsea

10/10 Excellent

"Shuttle drivers friendly and helpful. Food in restaurant surprisingly good. Beds comfortable. Pool lovely and not overly chlorinated,"

Harborside Inn Of Boston

10/10 Excellent

"I loved how conveniently located the hotel is. Everything is so close by, and it’s right in the middle of everything, so you really don’t need to rent a car to get around. What I liked most was the staff , everyone was so friendly and helpful. The hotel has an older, more historic feel inside, but I think that actually gives it a lot of character and makes it really charming."

Hyatt Regency Boston Harbor

10/10 Excellent

"We stayed for 7 nights and enjoyed our time there. We knew we selected a hotel that was across the water from downtown, but we really wanted a good view. It was a great decision! We took transportation to the Boston Waterfront, Boston Common and the Seaport district daily. This is a GREAT place for a “home base”. It was convenient to have a restaurant in our hotel. We had dinner there three times and the food is really good. They also give you free clam chowder daily if you stay there. it’s good chowder too. The view of Boston from the restaurant is the same as our room, amazing. Although I gave a five star rating there were a couple drawbacks: The hotel sits kind of alone out by the airport and we couldn’t get Uber Eats or Door Dash deliveries. The hotel store is very limited. The ice machine was broken on our floor the entire time. They don’t have a lot of ice in this hotel as it is and that was a bummer. My wife likes ice and taking the elevator to get it twice per day was not ideal. Like I mentioned previously, this was not enough to detract from our 5 star rating. The view was awesome and the location worked well, we just had to plan ahead. If you are visiting Boston this is a great option."

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:

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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.

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

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This holiday home rental outside of Chelsea offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and a selection of books.

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.

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Check prices for these dates

Our top choices for Chelsea holiday rentals

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

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

3. 3bdrm Apt next to Airport/Downtown 7 min drive

4. Spacious 1BR | Sleeps 6 + Parking

5. Home for Families | Sleeps 11 | 5 min Downtown

6. Mezzanine Apt near Airport Private Parking

7. Modern Apt Near Airport 7 Min to Downtown

8. 3 bdrm Apt next to Airport/2

9. Modern 1BR | Sleeps 6 + Parking

10. 1BR for 6 | Parking + Full Kitchen

11. Comfortable 1BR | Fast WiFi + Parking

12. 1BR for 6 | Parking + Easy Transit

13. Marriott Vacation Club® at Custom House, Boston

14. Crescent Suites Hotel

15. Boston Harbor Waterfront Yacht Escape near Freedom Trail 2B/2B sleeps 6 AC/Heat

16. Maverick Suites at 40 Temple St

17. Global Luxury Suites Downtown Boston

18. Spacious & Comfy 2BR/2Bath Yacht -Toasty Heat- On Freedom Trail-Walk to Downtown

19. Near Boston Historic two-bedroom with Modern Amenities

20. Bright 2BR by Boston Waterfront

Find holiday rentals that suit your style

Top Chelsea Hotel Reviews

Doubletree By Hilton Boston Logan Airport Chelsea

Harborside Inn Of Boston

Hyatt Regency Boston/Cambridge

The Dagny Boston

The Westin Copley Place, Boston, a Marriott Hotel

Omni Boston Hotel at the Seaport

Hyatt Regency Boston Harbor

The Revolution Hotel

citizenM Boston North Station

Find out more about Chelsea

Frequently asked questions

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