
Family-friendly vacation rentals in Chelsea
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Chelsea

Total vacation rentals
Explore 110 vacation rentals in Chelsea

Nightly prices starting at
Chelsea vacation rentals start at G$14,647 GYD per night before taxes and fees

Verified guest reviews
Over 9,740 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
110 of Chelsea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chelsea rentals

4.8 Average rating
Chelsea stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Chelsea
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Eco-friendly Studio near Beach, Boston & Airport
Modern and cozy basement studio just 10 minutes drive from Logan Airport, 5 minutes from Revere Beach, and 14 minutes from Downtown Boston. Fully equipped with a kitchenette, full bathroom, high-speed internet, and a 75-inch Smart TV. Enjoy entertainment options like a foosball table, Xbox, and board games. Step outside to a private lounge area with a fireplace and grill. Free driveway parking and plenty of nearby restaurants make this the perfect home base for comfort, convenience, and fun.
4.87 out of 5 average rating, 179 reviews
Renovated Cozy City Getaway
Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.
4.78 out of 5 average rating, 246 reviews
Hipster Basecamp | Fireplace • Deck • Parking
Welcome to Hipster Basecamp, a curated space where mid-century design meets modern comfort. Enjoy bold touches like a double-sided fireplace, Smeg appliances, and a ceiling-mounted rain shower. Brew espresso or mix cocktails with everything at your fingertips, then head to the deck to unwind and take in the peaceful view. Admire original artwork throughout — and if a piece speaks to you, it's available for purchase. (*note: record player is currently out of order)
4.98 out of 5 average rating, 312 reviews
10 minutes to Airport-Boston-Casino (2G)
(2G)=Your place is on the 2nd floor and your color code is Green. Do Not include it to the address when you navigate to us. We have a beautiful victorian house built in 1858, owned by our family in 1911, big spaces and high ceilings are a blessing! You can stay here with your family and kids, we have a play room with some toys for fun, a living room, a bedroom and a private full bathroom with a pressure shower. Chelsea is a nice quiet place with a lot to offer.
4.83 out of 5 average rating, 427 reviews
Family Home + Near Downtown + Cool Backyard!
Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!
4.94 out of 5 average rating, 260 reviews
Modern Farmhouse Suite in Historic Lexington
Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests
4.97 out of 5 average rating, 189 reviews
Rio Stays
Our place is your place with a combination of modern and colonial touches, we made it thinking about you, either for fun, recreation or business, close to the casino, downtown, revere beach, and the most prestigious colleges and universities, and don't forget museums and historical places, with amazing places, with a great night and day view , and coffee maker to start or finish your day!!
4.86 out of 5 average rating, 303 reviews
Curated Designer Retreat • Pool • Gym • Dining
Experience modern Everett living in this bright 2BR/2BA home! Enjoy a fully equipped kitchen with stainless steel appliances, in-unit laundry, and spacious sunlit living areas. Relax by the courtyard pool, stay active in the 24/7 fitness center, or unwind in the outdoor lounges and fire pits. Close to Encore, Assembly Row and major highways for easy access to Greater Boston.
4.96 out of 5 average rating, 116 reviews
Modern Suite Near Boston, Airport & Downtown
Enjoy a spacious, private suite with its own entry and free parking on Admiral's Hill. Nestled in a secure, gated community, this peaceful retreat offers stunning city views and direct access to Mary O'Malley State Park. Perfectly located minutes from Logan Airport. Easy access to downtown Boston via public transit, it’s ideal for both relaxation and convenience.
4.96 out of 5 average rating, 224 reviews
Comfort apartment 3bed/2bath near Boston
Recently renovated apartment with new supplies, sheets, and 3 new mattresses!! My apartment is located near Boston in a very quiet, safe, and peaceful neighborhood. Great Location! 15 minutes from the Airport! 10 minutes away from the new Casino!! 15 minutes away from Downtown Boston! Very Close to Whidden Hospital in case of an emergency. NO PARTIES ALLOWED.
4.87 out of 5 average rating, 208 reviews
Modern 2-bedroom w/parking near Encore and Logan
Modern two bedroom with free parking, conveniently located 7 minutes from Boston Logan Airport, 5 minutes from Revere Beach and only 12 minutes to Encore Casino and downtown Boston. No parties or events are allowed in the unit. Penalties apply. DISCLAIMER: For your safety and the safety of others, surveillance cameras are installed outdoors at this property.
4.94 out of 5 average rating, 196 reviews
Convenient Cozy Clean Public Trans Free parking
THE CHELSEA HOUSE: A charming 1900s third-floor (24 steps) apartment in a quiet, clean three-family brick building on a one-way street. Features include hardwood floors, exposed brick, and sloped loft-style ceilings that create a warm, cozy feel. Parking included. This is our home away from home, and we’re happy to share it with you. Thank you for staying.
4.94 out of 5 average rating, 436 reviewsPopular amenities for Chelsea family-friendly rentals
Family-friendly home rentals with a hot tub

Lakeside apartment, patio, hot tub, outside shower
4.98 out of 5 average rating, 221 reviews
Oceanfront Pool. Close to Boston. Free Parking.
4.96 out of 5 average rating, 285 reviews
Romantic Getaway w/private Jacuzzi• Fire Pit•
4.93 out of 5 average rating, 242 reviews
Modern, Spacious 1BR for 4 - Easy Marathon Access!
4.78 out of 5 average rating, 359 reviews
Modern 2BR Retreat Minutes from Boston
4.89 out of 5 average rating, 35 reviews
Hot tub - Arcade - Boston themed rooms
5.0 out of 5 average rating, 17 reviews
Headers’ Haven
5.0 out of 5 average rating, 89 reviews
Luxury lake retreat- pool, fire pit, trails
4.76 out of 5 average rating, 38 reviewsFamily- and pet-friendly home rentals

The Day-Burrill-Wadsworth-La Voix House
4.98 out of 5 average rating, 123 reviews
#9 Modern Home 15 min to Boston w/ Yard & Parking
4.92 out of 5 average rating, 301 reviews
Designer 3-BR Apt in Historic Charlestown, Boston
4.98 out of 5 average rating, 106 reviews
Sunny 3 bedroom on beach
4.84 out of 5 average rating, 133 reviews
Cozy Apt, minutes from Boston!
4.83 out of 5 average rating, 101 reviews
Private apartment near Boston/Airport/Beach/Train
4.8 out of 5 average rating, 145 reviews
Private Cozy Third Floor Space
4.95 out of 5 average rating, 143 reviews
Boston Country Landing / Logan Airport/Train 3Bed
4.89 out of 5 average rating, 491 reviewsFamily-friendly home rentals with a pool

Charming 2-story private Guesthouse
4.94 out of 5 average rating, 257 reviews
Pool Is Open in Sept! Steps from Harbor + Old Town
4.99 out of 5 average rating, 169 reviews
Country Cottage in the City
4.95 out of 5 average rating, 218 reviews
Private Suite• Pool • Sleeps 4 • Boston • Airport
4.97 out of 5 average rating, 348 reviews
Cozy Private Studio Unit w/ Laundry and Parking!
4.97 out of 5 average rating, 450 reviews
The Drew : Vibrant • Comfortable • W/D • City View
4.8 out of 5 average rating, 124 reviews
Private Pool Retreat w/Fire Pit Near Singing Beach
4.91 out of 5 average rating, 202 reviews
Cozy Private Suite halfway between Cape & Boston
4.87 out of 5 average rating, 114 reviewsWhen is the best time to visit Chelsea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,386 GYD | G$29,921 GYD | G$31,595 GYD | G$40,592 GYD | G$44,149 GYD | G$51,891 GYD | G$43,103 GYD | G$42,894 GYD | G$43,940 GYD | G$45,405 GYD | G$38,918 GYD | G$35,780 GYD |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
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- Fenway Park
- Hampton Beach
- Harvard University
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- Onset Beach
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- Duxbury Beach
- North Hampton Beach
- MIT Museum
- Harvard Square
- Tufts University
- Crane Beach
- Quincy Market
- Snhu Arena





