A busy street with a large clock, brick buildings, and cars.

Chelsea Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chelsea vacation rentals

Room

1. Family-Friendly 1BR | Sleeps 6

Family-Friendly 1BR | Sleeps 6
Chelsea
$251 nightly
The price is $277
Nov 2 - Nov 3
Total with taxes and fees
Family-Friendly 1BR | Sleeps 6
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.

2. 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, (8 reviews)
"It was close to Boston and the airport"
United States
Lewis
$348 nightly
The price is $388
Nov 1 - Nov 2
Total with taxes and fees
Charming 2-bedroom condo in delightful Chelsea with WiFi, AC
A bed with a headboard, a bedside table, and a wall-mounted light fixture.

3. 3 bdrm Apt next to Airport/2

3 bdrm Apt next to Airport/2
Chelsea
$219 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
3 bdrm Apt next to Airport/2
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.

4. Mezzanine Apt near Airport Private Parking

Mezzanine Apt near Airport Private Parking
Chelsea
$246 nightly
The price is $250
Nov 1 - Nov 2
Total with taxes and fees
Mezzanine Apt near Airport Private Parking
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.

5. Modern Apt Near Airport 7 Min to Downtown

Modern Apt Near Airport 7 Min to Downtown
Chelsea
$259 nightly
The price is $263
Nov 9 - Nov 10
Total with taxes and fees
Modern Apt Near Airport 7 Min to Downtown
A modern kitchen with wooden cabinets, a stove, a microwave, and a dining table with chairs.

6. 3bdrm Apt next to Airport/Downtown 7 min drive

3bdrm Apt next to Airport/Downtown 7 min drive
Chelsea
8.4 out of 10, Very good, (8 reviews)
"We only stayed a night for an early flight out the next morning. But, it was comfortable. The place was clean, fresh towels. Very easy to get into. It was also close to a good amount of eateries and conveniences."
United States
Maryah M.
$333 nightly
The price is $338
Nov 2 - Nov 3
Total with taxes and fees
3bdrm Apt next to Airport/Downtown 7 min drive
A living room with two dark sofas, a wooden coffee table, a clock, and a plant.

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

Home for Families | Sleeps 11 | 5 min Downtown
Chelsea
$417 nightly
The price is $423
Nov 2 - Nov 3
Total with taxes and fees
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, (127 reviews)
"The dedicated parking spots was a huge plus."
United States
Ted W.
$695 nightly
The price is $776
Oct 27 - Oct 28
Total with taxes and fees
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
A modern kitchen with stainless steel appliances, granite countertops, and a built-in oven.

9. Modern 1BR | Sleeps 6 + Parking

Modern 1BR | Sleeps 6 + Parking
Chelsea
$260 nightly
The price is $288
Nov 1 - Nov 2
Total with taxes and fees
Modern 1BR | Sleeps 6 + Parking
A modern living room with a sofa, dining table, chairs, a coffee table, and a TV displaying streaming services.

10. 1BR for 6 | Parking + Easy Transit

1BR for 6 | Parking + Easy Transit
Chelsea
$246 nightly
The price is $271
Nov 5 - Nov 6
Total with taxes and fees
1BR for 6 | Parking + Easy Transit
A hotel room with a bed, a wall-mounted TV displaying streaming services, and a neatly made bed with a folded towel.

11. Comfortable 1BR | Fast WiFi + Parking

Comfortable 1BR | Fast WiFi + Parking
Chelsea
$249 nightly
The price is $275
Nov 9 - Nov 10
Total with taxes and fees
Comfortable 1BR | Fast WiFi + Parking
A hotel room with a bunk bed, a single bed, and a large window with curtains.

12. 1BR for 6 | Parking + Full Kitchen

1BR for 6 | Parking + Full Kitchen
Chelsea
$253 nightly
The price is $280
Nov 9 - Nov 10
Total with taxes and fees
1BR for 6 | Parking + Full Kitchen
A modern kitchen with a bar area, two bar stools, and a refrigerator.

13. Spacious 1BR | Sleeps 6 + Parking

Spacious 1BR | Sleeps 6 + Parking
Chelsea
$345 nightly
The price is $388
Oct 22 - Oct 23
Total with taxes and fees
Spacious 1BR | Sleeps 6 + Parking
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.

14. Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront
East Boston
9.8 out of 10, Exceptional, (47 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
$301 nightly
The price is $346
Nov 2 - Nov 3
Total with taxes and fees
Bright 2BR by Boston Waterfront
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, (210 reviews)
"Such a quaint and quiet location. We loved staying on the pier. The boat was clean and tidy!! We would definitely stay there again!!"
United States
Angela L.
$436 nightly
The price is $501
Nov 9 - Nov 10
Total with taxes and fees
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
A room with a large window overlooking a marina with boats and buildings.

16. Fun houseboat. Walk to Boston attractions WIFI

Fun houseboat. Walk to Boston attractions WIFI
Boston
9.8 out of 10, Exceptional, (116 reviews)
"Rustic boathouse in a great central location ."
United States
William M.
$417 nightly
The price is $479
Nov 9 - Nov 10
Total with taxes and fees
Fun houseboat. Walk to Boston attractions WIFI
A modern living room with a black leather sofa, grey armchairs, a coffee table, and a large window offering a city view.

17. Kasa Boston at Fenway

Kasa Boston at Fenway
4.0 star property
Fenway–Kenmore
8.8 out of 10, Excellent, (329 reviews)
"Absolutely gorgeous apartments! Concierge was very friendly!"
United States
Kelly
$270 nightly
The price is $310
Nov 4 - Nov 5
Total with taxes and fees
Kasa Boston at Fenway
A row of brick townhouses with fire escapes, a brick sidewalk, and potted plants.

18. 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, (156 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
$252 nightly
The price is $290
Nov 1 - Nov 2
Total with taxes and fees
Maverick Suites at 40 Temple St
A bedroom with a bed, a round table with chairs, a TV, and a large mirror.

19. The Concord Hotel

The Concord Hotel
2.0 star property
South End
8.0 out of 10, Very good, (33 reviews)
"Great location, great Apartment"
United States
Carla Patricia
$300 nightly
The price is $344
Oct 12 - Oct 13
Total with taxes and fees
The Concord Hotel
A hotel room with a bed, two bedside lamps, a window with blinds, and a framed picture on the wall.

20. Temple Place Suites

Temple Place Suites
2.5 star property
Downtown Boston
7.2 out of 10, Good, (500 reviews)
"Great location, good value and comfortable beds"
United States
Deborah
$162 nightly
The price is $186
Nov 2 - Nov 3
Total with taxes and fees
Temple Place Suites
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

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"I have been waiting to stay at one of these properties the Wynn or encore. I was so impressed and floored, the room was perfect the view was spectacular I didn’t want to leave the room. The gym was great with amazing machines. I was really impressed with the hospitality I can’t wait to stay at another."
Ronald 2-night trip
Posted 6 hours ago
Encore Boston Harbor

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chelsea in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.