Chelsea Vacation Rentals from CA $253: Short-Term Rentals for 2026

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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

Chelsea

Cooper D.

CA $635 total

includes taxes & fees

Sep 28 - Sep 29

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.

CA $965 total

includes taxes & fees

Oct 4 - Oct 5

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

CA $435 total

includes taxes & fees

Sep 29 - Sep 30

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

CA $661 total

includes taxes & fees

Oct 18 - Oct 19

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

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

Chelsea

CA $684 total

includes taxes & fees

Sep 29 - Sep 30

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

CA $439 total

includes taxes & fees

Sep 27 - Sep 28

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

CA $383 total

includes taxes & fees

Sep 27 - Sep 28

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

CA $349 total

includes taxes & fees

Sep 29 - Sep 30

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

9. Modern 1BR | Sleeps 6 + Parking

Chelsea

CA $480 total

includes taxes & fees

Oct 12 - Oct 13

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

CA $408 total

includes taxes & fees

Sep 29 - Sep 30

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

CA $457 total

includes taxes & fees

Oct 12 - Oct 13

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

CA $420 total

includes taxes & fees

Oct 7 - Oct 8

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

CA $1,020 total

includes taxes & fees

Oct 8 - Oct 9

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

14. Crescent Suites Hotel

South Side

Mark

CA $253 total

includes taxes & fees

Sep 27 - Sep 28

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.

CA $827 total

includes taxes & fees

Sep 30 - Oct 1

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

16. Maverick Suites at 40 Temple St

Beacon Hill

Jerrold

CA $384 total

includes taxes & fees

Sep 27 - Sep 28

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

CA $661 total

includes taxes & fees

Sep 30 - Oct 1

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.

CA $832 total

includes taxes & fees

Sep 30 - Oct 1

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.

CA $396 total

includes taxes & fees

Sep 24 - Sep 25

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

CA $464 total

includes taxes & fees

Sep 28 - Sep 29

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Top Chelsea Hotel Reviews

Encore Boston Harbor

10/10 Excellent

"Great"

Harborside Inn Of Boston

10/10 Excellent

"Perfect location! Clean hotel, not too far from the parking garage. We had a room on the 1st floor, the dumpsters were located literally outside our window - garbage pick up is around 4am woke us all up not a big deal for us but if you’re a light sleeper request a room away from that area otherwise no issues"

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 $253 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.

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Check prices for these dates

Our top choices for Chelsea vacation 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 vacation rentals that suit your style

Top Chelsea Hotel Reviews

Encore Boston Harbor

Harborside Inn Of Boston

Doubletree By Hilton Boston Logan Airport Chelsea

Hyatt Regency Boston/Cambridge

Omni Parker House

citizenM Boston North Station

Arcadian Hotel

The Westin Copley Place, Boston, a Marriott Hotel

Find out more about Chelsea

Frequently asked questions

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