Chelsea Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chelsea vacation 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

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
Chelsea
8.6 out of 10, Excellent, (10 reviews)
"It was close to Boston and the airport"
United States
Lewis
The price is CA $213
CA $504 total
includes taxes & fees
Nov 9 - Nov 10
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

2. Family-Friendly 1BR | Sleeps 6

Family-Friendly 1BR | Sleeps 6
Chelsea
The price is CA $195
CA $394 total
includes taxes & fees
Nov 8 - Nov 9
Family-Friendly 1BR | Sleeps 6
A modern living room with a flat-screen TV, a grey sofa, and a wooden accent wall.

3. 3 bdrm Apt next to Airport/2

3 bdrm Apt next to Airport/2
Chelsea
The price is CA $320
CA $351 total
includes taxes & fees
Nov 30 - Dec 1
3 bdrm Apt next to Airport/2
A bedroom with a bed, a nightstand with a lamp, and wall art depicting cityscapes.

4. Mezzanine Apt near Airport Private Parking

Mezzanine Apt near Airport Private Parking
Chelsea
The price is CA $285
CA $313 total
includes taxes & fees
Dec 1 - Dec 2
Mezzanine Apt near Airport Private Parking
A bedroom with a large bed, two chairs, a potted plant, and a bay window with blinds.

5. 3bdrm Apt next to Airport/Downtown 7 min drive

3bdrm Apt next to Airport/Downtown 7 min drive
Chelsea
8.0 out of 10, Very good, (11 reviews)
"We stayed here overnight for a show at TD Garden. Great price and location for our needs."
United States
Nicole D.
The price is CA $320
CA $351 total
includes taxes & fees
Nov 30 - Dec 1
3bdrm Apt next to Airport/Downtown 7 min drive
A modern living room with a flat-screen TV on a white stand, a grey sofa, a wooden accent wall, and a hanging light fixture.

6. Modern Apt Near Airport 7 Min to Downtown

Modern Apt Near Airport 7 Min to Downtown
Chelsea
The price is CA $259
CA $283 total
includes taxes & fees
Nov 30 - Dec 1
Modern Apt Near Airport 7 Min to Downtown
A bedroom with a bed, a bedside table with a lamp, a wall-mounted shelf, and a potted plant.

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

Home for Families | Sleeps 11 | 5 min Downtown
Chelsea
10.0 out of 10, Exceptional, (1 review)
The price is CA $355
CA $386 total
includes taxes & fees
Nov 8 - Nov 9
Home for Families | Sleeps 11 | 5 min Downtown
A spacious living area with a large sectional sofa, a glass dining table, and multiple windows providing natural light.

8. 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, (129 reviews)
"Great stay for a couple of nights. Great location."
United States
Kevin C.
The price is CA $527
CA $955 total
includes taxes & fees
Nov 8 - Nov 9
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
A modern living room with a sofa, dining table, chairs, a coffee table, and a TV displaying streaming services.

9. 1BR for 6 | Parking + Easy Transit

1BR for 6 | Parking + Easy Transit
Chelsea
The price is CA $172
CA $365 total
includes taxes & fees
Nov 8 - Nov 9
1BR for 6 | Parking + Easy Transit
A modern living room with a sofa, a dining table with chairs, a coffee table with a plant, and a TV mounted on the wall.

10. 1BR for 6 | Parking + Full Kitchen

1BR for 6 | Parking + Full Kitchen
Chelsea
The price is CA $189
CA $385 total
includes taxes & fees
Nov 8 - Nov 9
1BR for 6 | Parking + Full Kitchen
A modern living room with a sofa, chairs, a round table, and a large window with a view.

11. Spacious 1BR | Sleeps 6 + Parking

Spacious 1BR | Sleeps 6 + Parking
Chelsea
The price is CA $233
CA $441 total
includes taxes & fees
Nov 17 - Nov 18
Spacious 1BR | Sleeps 6 + Parking
A modern living room with a sofa, chairs, a coffee table, and a TV mounted on the wall.

12. Comfortable 1BR | Fast WiFi + Parking

Comfortable 1BR | Fast WiFi + Parking
Chelsea
The price is CA $195
CA $394 total
includes taxes & fees
Nov 8 - Nov 9
Comfortable 1BR | Fast WiFi + Parking
A modern living room with a sofa, chairs, a coffee table, and a painting on the wall.

13. Modern 1BR | Sleeps 6 + Parking

Modern 1BR | Sleeps 6 + Parking
Chelsea
The price is CA $190
CA $388 total
includes taxes & fees
Nov 11 - Nov 12
Modern 1BR | Sleeps 6 + Parking
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

14. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (120 reviews)
"The houseboat was great! Everyone was super friendly and helpful. Can’t wait for our next stay!"
United States
Frank M.
The price is CA $173
CA $655 total
includes taxes & fees
Nov 30 - Dec 1
Fun houseboat. Walk to Boston attractions WIFI
A marina with boats docked, a red brick building, and modern high-rise apartments in the background.

15. 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, (213 reviews)
"Wonderful brief stay!"
United States
Marie T.
The price is CA $170
CA $708 total
includes taxes & fees
Dec 7 - Dec 8
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A waterfront building with a sign reading "Turtle," featuring a dock with red chairs and potted plants.

16. Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC

Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
Thompson Square - Bunker Hill
9.8 out of 10, Exceptional, (79 reviews)
"Great communication. The atmosphere was beautiful. Love all the baked goods"
United States
VIaney
The price is CA $377
CA $645 total
includes taxes & fees
Nov 13 - Nov 14
Unique Boston Harbor Houseboat Suite 2 - Experience near the Freedom Trail -AC
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

Global Luxury Suites Downtown Boston
4.0 star property
Chinatown
8.0 out of 10, Very good, (772 reviews)
"Great room: new and spacious. The kitchenette has everything i needed and more."
United States
Yelitza
The price is CA $138
CA $324 total
includes taxes & fees
Nov 29 - Nov 30
Global Luxury Suites Downtown Boston
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.

18. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.6 out of 10, Exceptional, (51 reviews)
"7 min from the airport, seamless check in and entry and a spotless, welcoming place- with coffee! Great rental- perfect if you’re coming/going from Logan"
United States
Bridget
The price is CA $135
CA $404 total
includes taxes & fees
Nov 9 - Nov 10
Bright 2BR by Boston Waterfront
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

19. Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St
2.5 star property
Beacon Hill
8.0 out of 10, Very good, (165 reviews)
"Great property in a great location. Tons of food options nearby. Walking distance to Target and Whole Foods. Easy access to the Blue line. The neighborhood was quiet and clean. Boston common is just a block away. Definitely would stay again and highly recommend."
United States
TommyWallace
The price is CA $142
CA $294 total
includes taxes & fees
Nov 9 - Nov 10
Maverick Suites at 40 Temple St
A balcony with a city view, featuring a table with wine glasses and a bottle, and a chair.

20. Marriott Vacation Club® at Custom House, Boston

Marriott Vacation Club® at Custom House, Boston
3.5 star property
Downtown Boston
9.4 out of 10, Exceptional, (680 reviews)
"I can’t believe this property is a hotel and not a historic landmark. If you like historical places this is the place to stay in Boston."
United States
Benny
The price is CA $321
CA $369 total
includes taxes & fees
Nov 22 - Nov 23
Marriott Vacation Club® at Custom House, Boston
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

A modern bar area with a long counter, multiple seating options, and large windows providing views of the outside.
Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville

Cambria Hotel Boston Somerville
Spring Hill

10/10 Excellent

Nice and quiet rooms, comfortable beds, and very nice shower rooms.
Canada
Li
Reviewed October 25, 2026
Cambria Hotel Boston Somerville

Find out more about Chelsea

Everything you need to know about Chelsea vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chelsea vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chelsea vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chelsea vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chelsea vacation rentals we have selected for you start as low as CA $118 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chelsea rentals

At Expedia, we put the best Chelsea vacation 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 vacation.

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 vacation rentals in Chelsea?

Yes, we give you a choice of vacation rentals near the most popular sights in Chelsea, or you can go with a secluded option if you're looking for relaxation. 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's the top vacation rental that Chelsea has to offer?

Lovely Bright and Spacious 4-bedroom house with 6 off-street parking spots: This vacation home rental near 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

How many vacation rentals will I find in Chelsea?

Choose from 5 Expedia vacation rentals in Chelsea for a memorable vacation.

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 larger area, you’ll find popular places like Fenway Park and Encore Boston Harbor.

What’s a vacation rental in Chelsea like?

A vacation rental is a private property you can book for a long or short time in Chelsea. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips.