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Chelsea, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Chelsea, MA

Compare Vacation Rentals for Families in Chelsea, MA

These kid-friendly vacation rentals in Chelsea, MA keep you close to top city attractions for a stress-free family vacation.

3br2bth Td Garden/mit/harvard/bos/3 Parking Spaces - Chelsea, MA
10 23 reviews
Chelsea, MA
09/14 – 09/18
$537/nighttotal: $2148 (4 )

3br2bth Td Garden/mit/harvard/bos/3 Parking Spaces

3 2
apartment , Somerville
This East Somerville rental is conveniently located near the Sullivan Square T station (a 7-minute walk), Assembly Row (a 10-minute walk), and offers easy access to Kendall Square, MIT, and Harvard.
The four-bedroom, two-bathroom apartment sleeps eight guests, features a fully equipped kitchen with dishwasher, in-unit laundry, free parking for two vehicles, and family-friendly amenities like a high chair and crib available upon request.
Private Luxury Retreat | Pool · Gym · Parking - Chelsea, MA
9.9 94 reviews
Chelsea, MA
08/20 – 11/19
$206/nighttotal: $18746 (91 )

Private Luxury Retreat | Pool · Gym · Parking

1 2
apartment , Everett
This Everett apartment rental, located in the Commercial Triangle, offers easy access to downtown Boston via the Silver Line and Route 1.
The two-bedroom, two-bathroom unit sleeps six, boasting a modern kitchen with quartz countertops, in-suite laundry, a 55-inch smart TV, and resort-style amenities including a pool, fitness center, and pet spa.
Luxury South End Apartment With City Views - Chelsea, MA
10 1 review
Chelsea, MA
06/27 – 07/04
$1053/nighttotal: $7371 (7 )

Luxury South End Apartment With City Views

1 2
apartment , Boston
This South End Boston rental is conveniently located near the Museum of Fine Arts, Boston, and offers easy access to shopping on Newbury Street and Harvard Square.
The 750-square-foot apartment features one bedroom, one bathroom, sleeps five, and includes a fully equipped kitchen, in-unit laundry, and a swimming pool.
Gorgeous Apt Near Boston/assembly/encore/harvard - Chelsea, MA
9.9 242 reviews
Chelsea, MA
09/14 – 09/18
$358/nighttotal: $1432 (4 )

Gorgeous Apt Near Boston/assembly/encore/harvard

3 2
apartment , Somerville
This Somerville apartment is located in Assembly Row, a short walk from shops and restaurants, and less than a 10-minute drive to Faneuil Hall, the North End, and downtown Boston. The apartment has excellent user, location, and cleanliness ratings.
The three-bedroom unit comfortably accommodates six guests with queen-size beds in each room and a desk. Enjoy modern amenities like central air conditioning, free parking, a washer and dryer, a fully equipped kitchen, and a large smart TV.

Best Chelsea, MA vacation rentals with parking

Cozy 3bd 1ba Near Beach T-10 Min From Boston - Chelsea, MA
9.4 6 reviews
Chelsea, MA
09/14 – 09/18
$387/nighttotal: $1548 (4 )

Cozy 3bd 1ba Near Beach T-10 Min From Boston

3 2
apartment , Revere
This Revere condo offers proximity to major attractions, situated just a 7-minute drive from Encore Boston Harbor and TD Garden, with other Boston landmarks like the New England Aquarium and Museum of Science easily accessible.
This 3-bedroom, 1-bathroom rental accommodates up to 8 guests and features a private terrace with outdoor furniture, complimentary Wi-Fi, a fully equipped kitchen with an oven and stovetop, and on-site parking.
Beacon Hill Charm - Chelsea, MA
Chelsea, MA
06/27 – 07/04
$327/nighttotal: $2289 (7 )

Beacon Hill Charm

1 2
apartment , Boston
This private apartment in a historic Beacon Hill brownstone is located a short walk from Boston Common and the Charles River, offering convenient access to Boston's restaurants, shops, and historic sites.
This studio flat accommodates up to two guests and features a kitchenette with a microwave and mini-fridge, a full-sized bed, an ensuite bathroom, and a desk, with amenities including air conditioning, internet, and parking.
Modern 2br Home Close To Campus & 10 Min Boston - Chelsea, MA
9.6 16 reviews
Chelsea, MA
09/14 – 09/18
$298/nighttotal: $1192 (4 )

Modern 2br Home Close To Campus & 10 Min Boston

3 2
apartment , Medford
This Medford house rental is conveniently located 1.1 miles from Assembly Row, 2.4 miles from Encore Boston Harbor, and under 3 miles from LEGOLAND Discovery Center, offering easy access to public transportation and Boston via Wellington and Malden Center train stations.
This three-bedroom, one-bathroom home sleeps five guests and features a fully equipped kitchen with a refrigerator, microwave, oven, and stovetop, a Smart TV, in-house games and books, and a terrace/balcony.
Beautiful 1br Near Encore Boston 8387 - Chelsea, MA
8.0 1 review
Chelsea, MA
06/27 – 07/04
$269/nighttotal: $1883 (7 )

Beautiful 1br Near Encore Boston 8387

1 2
apartment , Everett
This Everett apartment rental is conveniently located near the Encore Boston Harbor casino, a 10-minute walk away, offering easy access to Boston's Seaport district and major universities.
This 700-square-foot unit features one bedroom, one bathroom, and sleeps up to three guests with a queen bed and queen-size sofa bed; amenities include free on-site parking, in-unit laundry, and a fully equipped kitchen.

Frequently Asked Questions about vacation rentals in Chelsea, MA

  • What are the top family-friendly attractions in Chelsea, MA?

    Chelsea is a great place for families. The Chelsea Public Library has a great children's section and often hosts family-friendly events. The Chelsea Soldiers Home offers a peaceful walk through its grounds and a chance to learn about the history of the military. The Chelsea Creek Park is a nice place to have a picnic or play with the kids.
  • What are the best Airbnb and vacation rentals in Chelsea, MA?

  • When is the best time to book a vacation rental in Chelsea, MA?

    The best time to book a vacation rental in Chelsea depends on what you're looking for. If you want to avoid the crowds, book in the shoulder seasons, like spring or fall. If you want to experience the city's festivals, book during the summer months.
  • What are the most popular Airbnbs in Chelsea, MA?

  • What are the best budget-friendly activities in Chelsea, MA?

    Chelsea has plenty of budget-friendly activities. You can walk or bike along the Chelsea Creek, visit the Chelsea Historical Society Museum, or explore the Chelsea Public Library. You can also find some great deals on food at the local restaurants.
  • What are the best vacation rentals with a pool in Chelsea, MA?

  • What are the best restaurants with local dishes in Chelsea, MA?

    Chelsea has a great variety of restaurants. For local dishes, try the seafood at The Landing Restaurant or the Italian food at La Cucina. If you're looking for something more casual, try the burgers at The Chelsea Diner.
  • What are the best rentals for families and kids in Chelsea, MA?

  • What are the best walking or cycling routes in Chelsea, MA?

    Chelsea is a great place to explore on foot or by bike. You can walk or bike along the Chelsea Creek, which offers beautiful views of the city and the Boston skyline. You can also bike the Tobin Bridge for a scenic ride.
  • What are the best rentals or Airbnbs with a jacuzzi in Chelsea, MA?

  • Are there pet-friendly attractions in Chelsea, MA?

    Chelsea has a few pet-friendly attractions. The Chelsea Creek Park is a great place to walk your dog, and the Chelsea Soldiers Home has a designated pet-friendly area.
  • What are the benefits of choosing a vacation rental in Chelsea, MA?

    Vacation rentals offer more space and privacy than hotels. They can also be a more affordable option, especially for families or groups. Many rentals are located in residential neighborhoods, which can give you a more authentic experience of the city.
  • What are the top sports attractions and facilities in Chelsea, MA?

    Chelsea is home to the Chelsea High School athletic facilities, which include a football field, a track, and a baseball field. The city also has a few parks with basketball courts and playgrounds. You can also find a few gyms and fitness centers in the area.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Chelsea, MA

Enjoy your own private terrace with city skyline views at these vacation rentals in Chelsea, MA.

98 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests - Chelsea, MA
Chelsea, MA
08/20 – 11/19
$545/nighttotal: $49595 (91 )

98 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests

2 2
apartment , Boston
Vacation rental listing for 5 people. You will be based in Boston.
Services and facilities include a kitchen, air conditioning and an elevator.
Prime Seaport 2br Steps To Convention Center - Chelsea, MA
Chelsea, MA
06/27 – 07/04
$1210/nighttotal: $8470 (7 )

Prime Seaport 2br Steps To Convention Center

2 2
apartment , Boston
This 2-bedroom, 2-bathroom condo offers a prime Seaport district location in Boston, steps from the Convention Center and within 1.7 miles of the Old State House and Custom House.
This air-conditioned rental includes Wi-Fi, on-site parking, a full kitchen, and a terrace, accommodating up to 7 guests with a check-out between 8 AM and 11 AM.
Peace In The City - Humble Luxury Minutes From Boston, Beach & Casino - Chelsea, MA
10 2 reviews
Chelsea, MA
07/15 – 07/19
$498/nighttotal: $1992 (4 )

Peace In The City - Humble Luxury Minutes From Boston, Beach & Casino

2 1
apartment , Everett
This Everett vacation home offers easy beach access and is located 2 miles from Encore Boston Harbor and within 6 miles of the TD Garden and Boston Harbor.
The 1190-square-foot property features three bedrooms, one bathroom, a sofa bed, and accommodates up to six guests with amenities including free parking, Wi-Fi, and a private balcony.
3br2bth Parking Cambridge Boston W&d Subway Ac - Chelsea, MA
9.6 14 reviews
Chelsea, MA
09/14 – 09/18
$487/nighttotal: $1948 (4 )

3br2bth Parking Cambridge Boston W&d Subway Ac

3 2
house , Somerville
This Somerville vacation home is conveniently located near Inman Square, 1.2 miles from the Central Square Theater, 1.4 miles from MIT, and close to Cambridge College and the Peabody Museum.
This 1,100-square-foot house features three bedrooms, two bathrooms, free parking, and accommodates up to 13 guests, offering amenities such as a fully equipped kitchen, air conditioning, and a terrace.

Discover Pet-Friendly Vacation Rentals in Chelsea, MA

Experience a pet-friendly stay in Chelsea, MA with vacation rentals located steps away from city dog parks and walking trails.

Cedar & Brick On The Hill - Chelsea, MA
10 18 reviews
Chelsea, MA
06/27 – 07/04
$262/nighttotal: $1834 (7 )

Cedar & Brick On The Hill

1 2
apartment , Boston
This Beacon Hill guesthouse provides a prime Boston location, situated a short walk from Boston Common and offering convenient access to the Charles River, as well as the city's premier dining, shopping, and historic sites.
This 1-bedroom, 1-bathroom accommodation for two guests includes essential amenities such as air conditioning, internet, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, making it an ideal base for exploring Boston.
Unit 22 Luxurious 1br Apartment Long-term Stays - Chelsea, MA
10 1 review
Chelsea, MA
07/15 – 07/19
$258/nighttotal: $1032 (4 )

Unit 22 Luxurious 1br Apartment Long-term Stays

1 1
apartment , Chelsea
This 1-bedroom Chelsea apartment is located 1.9 miles from Logan Airport, 2.9 miles from TD Garden, and 3 miles from Old North Church.
This 780-square-foot unit accommodates up to 5 guests and features a fully equipped kitchen with a dishwasher and oven, air conditioning, and complimentary WiFi.
Simple 1br |  Financial District | Keyless Entry - Chelsea, MA
Chelsea, MA
07/15 – 07/19
$381/nighttotal: $1524 (4 )

Simple 1br | Financial District | Keyless Entry

1 1
apartment , Boston
This 1-bedroom apartment is located in downtown Boston, 3 minutes on foot from public transportation and approximately 1.1 miles from Mass General Hospital.
This downtown Boston condo offers a fully stocked kitchen, air conditioning, and in-building laundry, ideal for 2 guests with self-check-in and close proximity to Faneuil Hall Marketplace and the New England Aquarium.
Beauty In Back Bay, 1br W/ Gym, Close To The Common By Blueground - Chelsea, MA
10 1 review
Chelsea, MA
08/20 – 11/19
$325/nighttotal: $29575 (91 )

Beauty In Back Bay, 1br W/ Gym, Close To The Common By Blueground

1 2
apartment , Boston
This Bay Village rental is ideally located a short walk from Boston Common, Copley Square, and Boylston Street, providing easy access to major Boston attractions and public transportation (Arlington and Boylston stations within an 8-minute walk).
The one-bedroom apartment sleeps two, features a fully equipped kitchen with dishwasher, in-unit laundry, and a fitness center onsite, plus nearby access to an arcade/game room.
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