Family-friendly holiday rentals in Chelsea

4.86 out of 5 average rating, 165 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

Studio Close to Beach, Boston, Airport & Train

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.

Indoor spacesFamilyCheckout

4.88 out of 5 average rating, 323 reviews

A light gray living space features a comfortable sofa adorned with decorative pillows. A round coffee table sits in the center, complemented by a soft area rug. Two windows, including a skylight, provide natural light and views of the exterior.

Apartment in Everett

Huge 1BR w/King Bed near Airport, Boston, Salem

Location: Quick 10-20 mins to the center of Boston, 25 mins to Salem. Easy access via multiple major highways, or walk 0.7mi (HILL) to bus, taking you directly into the city. This unit is an upper-level apartment of our home (i.e., STAIRS). Enjoy self-check-in and a reserved parking spot. Living room: Roku enabled TV. Mini-kitchen: Two burner stovetop, microwave, a 4 cu. sqft fridge, and a Keurig. Bedroom: king-sized bed with down alternative pillows and tempur-pedic memory foam topper.

Indoor spacesFamilyHospitality

4.78 out of 5 average rating, 238 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.

FamilyIndoor spacesAccess

4.88 out of 5 average rating, 149 reviews

A modern kitchenette is featured with stainless steel appliances, including an oven and refrigerator. A spacious gray sectional sofa is positioned on a geometric patterned area rug. Bright windows allow natural light to illuminate the room, complemented by decorative mirrors and a potted plant.

Apartment in Woburn

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

KitchenFamilyLaundry

4.92 out of 5 average rating, 297 reviews

Townhouse in Everett

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

Stay in this stylish 2-story home 3 Comfy Bedrooms + 1.5 Baths! Ideal for families or groups, it comfortably fits 6+ guests. Enjoy a fully stocked kitchen, dedicated workspace, and a private backyard with a gas BBQ & fire pit. Perfectly located for exploring Boston, Cambridge, and Salem with free private parking. Your memorable stay with experienced Superhosts awaits! 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🌆 Easy Access to Local Attractions

KitchenIndoor spacesCondition

4.98 out of 5 average rating, 304 reviews

Apartment in Medford

Hipster Basecamp | Deck • Design • 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)

Indoor spacesFamilyCheck-in

4.89 out of 5 average rating, 119 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 spacesLaundry

4.95 out of 5 average rating, 100 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.

KitchenFamilyEV charging

4.96 out of 5 average rating, 204 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.

KitchenIndoor spacesCleanliness

4.94 out of 5 average rating, 190 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.

Indoor spacesKitchenCheckout

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.

FamilyKitchenNearby

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!

Welcome to this modern and cozy apartment, steps away from the first public beach in America. Perfectly located, 1 min to the Revere Beach T station, minutes from the airport, Salem, Encore casino, Universities, only 15 mins to Downtown Boston, and ideal location for quick access to all Boston has to offer. Perfect for families and groups.

Indoor spacesFamilyValue

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, 280 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 spacesAmenities

4.92 out of 5 average rating, 234 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

Indoor spacesFamilyAccuracy

4.98 out of 5 average rating, 217 reviews

A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.

Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

FamilyKitchenHospitality

4.78 out of 5 average rating, 358 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!

FamilyIndoor spacesCheckout

4.87 out of 5 average rating, 30 reviews

Apartment in Chelsea

Modern 2BR Retreat Minutes from Boston

Indoor spacesFamilyCheck-in

5.0 out of 5 average rating, 31 reviews

Home in Wellesley

Wellesley Spacious and Modern

Indoor spacesKitchenHospitality

5.0 out of 5 average rating, 14 reviews

Home in Medford

Hot tub - Arcade - Boston themed rooms

KitchenIndoor spacesBackyard

Guest suite in Marblehead

5.0 out of 5 average rating, 81 reviews

Headers’ Haven

KitchenFamilyBathroom

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 237 reviews

Condo in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

Indoor spacesKitchenAccess

4.87 out of 5 average rating, 204 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

KitchenFamilyLayout

4.98 out of 5 average rating, 117 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

KitchenFamilyNearby

4.92 out of 5 average rating, 1396 reviews

A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.

Guest suite in Winthrop

Licensed Boston airport studio 5 stars, subway

FamilyKitchenWalkability

4.96 out of 5 average rating, 162 reviews

A spacious bedroom features a large bed dressed in white sheets and a light blue blanket. Nightstands with lamps are positioned on either side of the bed. A subtle area rug adds warmth, while a painting hangs on the wall, complementing the calm color scheme.

Apartment in Revere

Spacious 3 Bedroom Apartment with King Bed

KitchenFamilyView

4.89 out of 5 average rating, 101 reviews

Home in Malden

Across the Subway · TD Garden · Concerts · Games F

FamilyIndoor spacesDecor

4.94 out of 5 average rating, 253 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

KitchenIndoor spacesHospitality

4.94 out of 5 average rating, 177 reviews

A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.

Apartment in Nahant

Ocean view studio with hot tub & access to Boston

Indoor spacesFamilyBiking

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 344 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

Indoor spacesFamilyBackyard

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, 215 reviews

Country Cottage in the City

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 163 reviews

Cottage in Marblehead

Pool Is Open! Steps from Harbor + Walk to Old MHD

Indoor spacesKitchenCleanliness

4.96 out of 5 average rating, 157 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

Indoor spacesFamilyGetting around

4.97 out of 5 average rating, 443 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!

Indoor spacesKitchenLaundry

4.97 out of 5 average rating, 118 reviews

The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.

Home in Weston

Spacious vacation unit in premium suburban town

FamilyKitchenLocation

Apartment in Manchester-by-the-Sea

4.91 out of 5 average rating, 194 reviews

Private Pool Retreat w/Fire Pit Near Singing Beach

Indoor spacesKitchenOutdoor spaces