Family-friendly vacation rentals in Chelsea

4.97 out of 5 average rating, 247 reviews

The living room is furnished with a beige leather sofa and a dark brown armchair, complemented by warm wood flooring. A ceiling fan is mounted above, and natural light filters through two windows adorned with sheer curtains. A flat-screen TV and a coffee table are also visible.

Apartment in East Boston

Apartment w/Parking, minutes to airport / Downtown

Spacious 3 Bedroom apartment in Boston. Great for vacation, business or layover. -Modern and clean with lots of light. -Great for families and groups. -Minutes to subway and Downtown Boston. -Affordable and convenient location. -All amenities included plus free parking. -Easy access to and from airport. Recently renovated first floor apartment fully furnished with all amenities including washer, dryer, wifi, tv, full kitchen and parking. Convenient location just minutes to all area amenities.

KitchenIndoor spacesBeach

4.93 out of 5 average rating, 136 reviews

The kitchen features modern white cabinetry, stainless steel appliances, and a spacious island. Pendant lights hang from the ceiling, illuminating the area. A window allows natural light to fill the space, highlighting the plants and decorative items arranged throughout.

Apartment in Everett

Boston Luxury home +Free Parking 5 mins to Casino

Welcome to The Cottage 1925, The Best home on the East Coast! , luxury vacation rental with Game Room and Bonus Den. Enjoy your family reunion, Friendsgiving, Couples retreats and more at The Cottage. This two level home has plenty of space to relax, unique decor , plenty of off street parking and a car on site to rent for your convenience. Enjoy the Scenes of Downtown Boston , “Little Italy” in the North End and of course the state of the art Encore Casino. 13 minutes away from the airport.

FamilyIndoor spacesHeating

4.87 out of 5 average rating, 175 reviews

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.

KitchenIndoor spacesCleanliness

4.78 out of 5 average rating, 245 reviews

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.

KitchenIndoor spacesGetting around

4.88 out of 5 average rating, 123 reviews

A multi-story home features a distinctive architectural design with a pointed turret. A welcoming entrance is flanked by neatly trimmed shrubs, with a wrought iron fence partially surrounding the front yard. The exterior showcases composite siding and a well-maintained stairway leading to the door.

Home in Everett

Charming 4R Boston home w/parking, 5 min to Casino

• Bus stop in front with big parking • Short drive or public transit to downtown Boston, Fenway, Encore Casino, tourist spots • 4 renovated cozy bedrooms and office with height adjustable desk • Master bedroom on third floor with privacy bathroom • 3 bedrooms on second floor share renovated bathroom with washlet • Open floor connect living room, dining room, kitchen • Entertainment room and Laundry in basement • Covered-front deck, relax patio backyard • Nearby public park Came

FamilyKitchenAccess

4.83 out of 5 average rating, 425 reviews

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 spacesKitchenBeach

4.9 out of 5 average rating, 125 reviews

A living area is presented with a wall-mounted television and a small wooden table. A light-colored armchair and a decorative plant enhance the space. Dark curtains frame a window, and a patterned rug adds texture to the dark hardwood floor.

Apartment in Revere

Apartment in Revere near the airport

Enjoy the simplicity of this quiet and central accommodation. Located in a strategic area. Close to the airport, beaches, shopping malls, train station, Downtown Boston, etc. The apartment has a bedroom, large kitchen, living-dining room, full bathroom and an outside terrace overlooking the interior of the property. The living-dining room has the peculiarity of having a door with a lock so it can be used as an additional private room if required.

FamilyIndoor spacesComfort

4.87 out of 5 average rating, 302 reviews

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!!

Indoor spacesKitchenLayout

4.95 out of 5 average rating, 111 reviews

Apartment in Everett

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.

KitchenIndoor spacesBeach

4.96 out of 5 average rating, 219 reviews

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.

FamilyKitchenOutdoor spaces

4.94 out of 5 average rating, 192 reviews

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.

KitchenIndoor spacesAir conditioning

4.94 out of 5 average rating, 435 reviews

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 spacesKitchenWalkability

Popular amenities for Chelsea family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 284 reviews

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.

FamilyIndoor spacesHot tub

4.98 out of 5 average rating, 221 reviews

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

FamilyIndoor spacesCheckout

4.92 out of 5 average rating, 237 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

KitchenIndoor spacesLayout

4.78 out of 5 average rating, 359 reviews

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!

Indoor spacesKitchenNearby

4.88 out of 5 average rating, 34 reviews

Apartment in Chelsea

Modern 2BR Retreat Minutes from Boston

Indoor spacesFamilyWalkability

5.0 out of 5 average rating, 34 reviews

Home in Wellesley

Wellesley Spacious and Modern

FamilyIndoor spacesHospitality

Guest suite in Marblehead

5.0 out of 5 average rating, 85 reviews

Headers’ Haven

Indoor spacesFamilyLayout

5.0 out of 5 average rating, 6 reviews

Home in Hull

Luxury Bayfront Stay | Beach + Firepit

Indoor spacesFamilyBathroom

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 299 reviews

Townhouse in Everett

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

FamilyIndoor spacesComfort

4.87 out of 5 average rating, 206 reviews

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

Indoor spacesKitchenQuiet

4.8 out of 5 average rating, 144 reviews

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

KitchenFamilyTV

4.83 out of 5 average rating, 100 reviews

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 spacesKitchenWalkability

4.94 out of 5 average rating, 258 reviews

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!

KitchenIndoor spacesCheckout

4.88 out of 5 average rating, 234 reviews

The spacious living area features warm wooden flooring and a central table with seating. Natural light enters through a nearby door, complemented by modern pendant lighting. A kitchenette is visible with a stylish shelf displaying decorative items, creating a functional yet inviting environment.

Apartment in Arlington

Dixie’s House, 1BD in Arlington

FamilyIndoor spacesHeating

4.98 out of 5 average rating, 121 reviews

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

Indoor spacesKitchenCheckout

4.89 out of 5 average rating, 104 reviews

Home in Malden

Across the Subway · TD Garden · Concerts · Games F

Indoor spacesFamilyParking

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 167 reviews

Cottage in Marblehead

Pool Is Open in Sept! Steps from Harbor + Old Town

FamilyIndoor spacesWalkability

4.97 out of 5 average rating, 346 reviews

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

KitchenIndoor spacesHospitality

4.94 out of 5 average rating, 255 reviews

A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.

Guesthouse in Newton

Charming 2-story private Guesthouse

Indoor spacesFamilyNearby

Guesthouse in West Roxbury

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.

4.95 out of 5 average rating, 217 reviews

Country Cottage in the City

Indoor spacesKitchenAmenities

4.95 out of 5 average rating, 161 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Apartment in Brighton

The Murthy : Bright • Spotless • W/D

FamilyKitchenQuiet

4.97 out of 5 average rating, 448 reviews

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!

KitchenIndoor spacesCondition

Apartment in Manchester-by-the-Sea

4.91 out of 5 average rating, 200 reviews

Private Pool Retreat w/Fire Pit Near Singing Beach

FamilyIndoor spacesLong stay