Become a host

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$14,645 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.

1 of 1 pages1 / 1
Top guest favorite
A wooden table featuring a natural, textured surface holds a decorative bowl and a small green plant. A softly lit lamp and a vase with white flowers are also visible. The wall art depicts two silhouettes of deer amid foliage, adding a serene touch.
Guest suite in Revere

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.

FamilyKitchenShared spaces

4.87 out of 5 average rating, 179 reviews
Guest favorite
A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.
Home in East Boston

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.

FamilyKitchenLong stay

4.78 out of 5 average rating, 247 reviews
Top guest favorite
A welcoming living area features a marble-topped coffee table surrounded by comfortable seating. A decorative fireplace with a herringbone pattern adds warmth. Natural light filters through the space, highlighting a large mirror and a simple bouquet on the table. The kitchen is visible in the background.
Apartment in Charlestown

Designer 3-BR Apt in Historic Charlestown, Boston

Enjoy this beautifully appointed home in the historic Boston neighborhood of Charlestown. The space was designed and renovated to highlight historic details while incorporating modern finishes & amenities. The unit is conveniently located near shops, restaurants, the MBTA, Whole Foods, Freedom Trail, and USS Constitution. We are a family who prioritizes wellness, is passionate about our community, and loves traveling. Our hope is that we incorporate pieces of these into your stay.

KitchenFamilyPets

4.98 out of 5 average rating, 106 reviews
Top guest favorite
Apartment in Medford

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)

KitchenFamilyDecor

4.98 out of 5 average rating, 314 reviews
Superhost
A spacious bedroom is shown, featuring a black bed with a textured bedding set displaying ocean waves. A cozy armchair sits beside a radiator, and a small folding table is placed nearby. Natural light enters through a window with patterned curtains.
Home in Chelsea

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.

Indoor spacesKitchenWifi

4.83 out of 5 average rating, 427 reviews
Top guest favorite
The living area features two gray sofas positioned around a round wooden coffee table on a vibrant blue area rug. A cozy fireplace is situated against a striking red wall, complemented by a bookshelf filled with books. Natural light enters through a nearby window.
Condo in East Boston

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!

Indoor spacesKitchenOutdoor spaces

4.94 out of 5 average rating, 262 reviews
Guest favorite
Apartment in Everett

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

Indoor spacesFamilyWifi

4.92 out of 5 average rating, 130 reviews
Guest favorite
A comfortable sleeping area is equipped with a spacious bed layered with plush bedding and decorative pillows. A cozy seating area features a light-colored couch beside a bedside table with a lamp. Soft natural light streams through windows dressed in sheer and dark curtains.
Home in Revere

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!!

KitchenIndoor spacesSleep quality

4.87 out of 5 average rating, 304 reviews
Guest favorite
The entrance to the suite is adorned with lush greenery, creating a welcoming facade. A door leads into the unit, framed by railings and planters. The area is bordered by stone pathways and garden beds, enhancing the natural appeal of the space.
Guest suite in Chelsea

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.

Indoor spacesKitchenOutdoor spaces

4.96 out of 5 average rating, 224 reviews
Superhost
A spacious bed is adorned with soft white linens and accent pillows in warm tones. Flanking the bed are two nightstands topped with stylish lamps, providing a calming glow. A neatly folded towel is placed at the foot of the bed, enhancing the overall comfort.
Apartment in Everett

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.

Indoor spacesFamilyAir conditioning

4.87 out of 5 average rating, 208 reviews
Top guest favorite
The living area features a glass dining table surrounded by wooden chairs. A comfortable gray sofa is positioned nearby, complemented by decorative cushions. Natural light floods in through multiple large windows, enhancing the airy and bright ambiance of the space.
Home in Revere

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.

Indoor spacesFamilyWalkability

4.94 out of 5 average rating, 198 reviews
Guest favorite
A living room is featured with hardwood floors and exposed brick walls, creating a cozy ambiance. A large TV sits atop a white media console. A comfortable blue chair with a patterned cushion provides seating, while a coffee table enhances the space. Artwork decorates the walls.
Apartment in Chelsea

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.

Indoor spacesKitchenLaundry

4.94 out of 5 average rating, 437 reviews

Popular amenities for Chelsea family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

FamilyKitchenNearby

4.98 out of 5 average rating, 221 reviews
Top guest favorite
A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.
Apartment in Winthrop

Oceanfront Pool. Close to Boston. Free Parking.

Indoor spacesKitchenLong stay

4.96 out of 5 average rating, 286 reviews
Guest favorite
Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

Indoor spacesFamilySleep quality

4.93 out of 5 average rating, 242 reviews
Superhost
A modern open-concept living space features a well-equipped kitchen with stainless steel appliances and a large island with seating for five. A cozy living area displays a sectional couch facing a wall-mounted TV, with large windows allowing natural light to brighten the room.
Home in South Boston

Heart of Southie - Hot Tub + Walk to Top Bars

KitchenIndoor spacesGetting around

4.93 out of 5 average rating, 116 reviews
Guest favorite
The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.
Apartment in Roxbury

Modern, Spacious 1BR for 4 - Easy Marathon Access!

FamilyIndoor spacesQuiet

4.78 out of 5 average rating, 359 reviews
Superhost
Apartment in Chelsea

Modern 2BR Retreat Minutes from Boston

FamilyKitchenCondition

4.89 out of 5 average rating, 35 reviews
Top guest favorite
Guest suite in Marblehead

Headers’ Haven

FamilyKitchenPool

5.0 out of 5 average rating, 90 reviews
Guest favorite
Home in Canton

Luxury lake retreat- pool, fire pit, trails

KitchenIndoor spacesBathroom

4.76 out of 5 average rating, 38 reviews

Family- and pet-friendly home rentals

Top guest favorite
The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.
Condo in Winthrop

The Day-Burrill-Wadsworth-La Voix House

FamilyKitchenEV charging

4.98 out of 5 average rating, 123 reviews
Top guest favorite
Townhouse in Everett

#9 Modern Home 15 min to Boston w/ Yard & Parking

Indoor spacesKitchenQuiet

4.92 out of 5 average rating, 301 reviews
Guest favorite
A historic clock stands prominently by the waterfront, marking the time against a beautiful sunset. The horizon features vibrant oranges and yellows as the sun descends. An open pavilion structure is visible in the background along the calm beach, reflecting a peaceful atmosphere.
Apartment in Revere

Cozy Apt, minutes from Boston!

Indoor spacesFamilyAccuracy

4.83 out of 5 average rating, 101 reviews
Guest favorite
A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.
Apartment in Winthrop

Sunny 3 bedroom on beach

Indoor spacesFamilyBeach

4.84 out of 5 average rating, 134 reviews
Guest favorite
The living area includes a dark sofa and a comfortable armchair, complemented by a wooden coffee table featuring an assortment of items. A map hangs on the wall, and a fireplace adds character. Light from nearby windows illuminates the space.
Apartment in Revere

Private apartment near Boston/Airport/Beach/Train

Indoor spacesKitchenPets

4.8 out of 5 average rating, 145 reviews
Guest favorite
Apartment in Woburn

Newly Finished Guest Haven in Woburn

Indoor spacesFamilyHeating

4.88 out of 5 average rating, 172 reviews
Guest favorite
Home in Malden

Across the Subway · TD Garden · Concerts · Games F

Indoor spacesKitchenHiking

4.89 out of 5 average rating, 104 reviews
Top guest favorite
A stylish living room features a green sectional sofa complemented by colorful throw pillows. A round coffee table rests on a patterned area rug. Art pieces adorn the walls, and natural light enters through windows, illuminating the warm wooden flooring and brick fireplace.
Home in Arlington

The Brickhouz at Arlington !

Indoor spacesKitchenAmenities

4.99 out of 5 average rating, 120 reviews

Family-friendly home rentals with a pool

Top guest favorite
Cottage in Marblehead

Steps from Harbor + Walk to Old Town + Restaurants

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 169 reviews
Guest favorite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury

Country Cottage in the City

KitchenIndoor spacesBathroom

4.95 out of 5 average rating, 218 reviews
Top guest favorite
The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.
Apartment in Winthrop

Private Suite• Pool • Sleeps 4 • Boston • Airport

FamilyKitchenHeating

4.97 out of 5 average rating, 348 reviews
Top guest favorite
A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.
Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

Indoor spacesFamilyDecor

4.97 out of 5 average rating, 451 reviews
Superhost
Apartment in Brighton

The Drew : Vibrant • Comfortable • W/D • City View

KitchenIndoor spacesBathroom

4.8 out of 5 average rating, 124 reviews
Guest favorite
A spacious room features a full-sized bed with light bedding. A euro lounger is positioned in front, decorated with a soft throw. Mirrors on the opposite wall reflect the room's layout, and a window offers natural light, contributing to the overall bright atmosphere.
Guest suite in Rockland

Cozy Private Suite halfway between Cape & Boston

Indoor spacesFamilyBackyard

4.87 out of 5 average rating, 114 reviews
Guest favorite
Apartment in Manchester-by-the-Sea

Private Pool Retreat w/Fire Pit Near Singing Beach

FamilyKitchenNearby

4.91 out of 5 average rating, 203 reviews
Top guest favorite
A spacious living area features hardwood flooring and large glass doors that provide natural light and views of the outdoors. Two comfortable sofas are positioned around a coffee table, with a dining area visible in the background. Wall sconces add soft illumination.
Home in Weston

Spacious vacation unit in premium suburban town

Indoor spacesKitchenHeating

4.97 out of 5 average rating, 120 reviews

When is the best time to visit Chelsea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,383 GYDG$29,918 GYDG$31,592 GYDG$40,588 GYDG$44,145 GYDG$51,886 GYDG$43,099 GYDG$42,890 GYDG$43,936 GYDG$45,401 GYDG$38,915 GYDG$35,776 GYD
Avg. temp-1°C0°C4°C9°C15°C20°C23°C23°C19°C13°C7°C2°C

Destinations to explore