Family-friendly holiday rentals in Dorchester

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Top-rated family-friendly rentals in Dorchester

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious living area features a comfortable gray sofa with decorative cushions and a wooden coffee table. Natural light streams through multiple windows, highlighting gleaming hardwood floors. A dining table with white chairs is visible, alongside an air conditioning unit and a wall-mounted art piece.
Flat in North Quincy
4.98 out of 5 average rating, 105 reviews

Home Away from Home | Next to Boston & Beach, EV+

Enjoy a comfortable stay in this beautiful, newly renovated 2 bedroom apartment less than a 10 min walk to the beach and convenient access to Boston by car (15-25min) or public transportation (30-45min). It's a spacious 1200 sqft, was just fully remodeled, retains plenty of character and boasts loads of windows and light. Recharge from your trip in style with a fully equipped kitchen, two comfortable king beds, 55" smart TV, new sofas, work & dining area, sun porch, AC and free street parking.

Top guest favourite
A bright and airy room features a comfortable bed adorned with colorful bedding. Two wooden desks with chairs are positioned thoughtfully, along with various seating options. Natural light filters through a window, accentuating the room's warm wood flooring and blue walls.
Guest suite in Boston
4.9 out of 5 average rating, 172 reviews

Boston arbor oasis - cute one bedroom suite

Upbeat, beautiful one bedroom with attached bathroom. Have the ground floor / lower level of our home to yourself. Your own private entrance, come and go as you like. Located on a quiet, dead end street in a very safe, residential Boston neighborhood, with big beautiful evergreen trees. Convenient to 93. Five minute Uber or short bus ride to Ashmont station, from here take the train downtown Boston. Free off street parking. Easy walk to coffee shops, restaurants, bars, and Neponset River trail!

Top guest favourite
The kitchen features white cabinetry and stainless steel appliances, with a spacious layout for cooking. A game table is shown with a pool table in the background. A cozy living area includes a light blue accent wall and comfortable seating. The backyard displays a grassy area with a slide and a playset.
Home in South Boston
4.99 out of 5 average rating, 213 reviews

Family Friendly City Oasis! Free Parking, King Bed

Welcome to The Southie House! An epic private home for a family vacation or conference in the Heart of Boston! Close to the Red line T for access to downtown, Cambridge & local universities, and short ride to the BCEC. At the same time a short walk to the beach for relaxing. Enjoy the back yard oasis with the whole group! This home provides you with a private place to relax after a full day of exploring, ensuring you have all the comforts of home while traveling. COME SEE OUR NEW GAME-ROOM & GYM

Top guest favourite
A spacious master bedroom is depicted, featuring a large bed with crisp white linens. Rich, dark curtains frame tall windows, complementing the soft pink walls. A modern television is mounted on the wall, and mirrored doors reflect the inviting decor, enhancing the room's brightness.
Guest suite in Ashmont
4.96 out of 5 average rating, 269 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A unique master bedroom and a cozy 2nd bedroom adjacent to a marble spa bathroom (with heated floor and a large shower & built-in bench). With a clean, glass-tiled kitchen & granite-top counters, you’ll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood. Enjoy the feel of a downtown hotel without the high price. Note: There’s no separate living room, but comfortable seating is available in the 2nd bedroom & kitchen

Superhost
An inviting entryway is adorned with a decorative mirror and a houseplant next to a console table. The living area is visible in the background, featuring a comfortable black sofa, a patterned area rug, and a mounted television on the wall.
Home in Dorchester
4.9 out of 5 average rating, 146 reviews

New Spacious Home in Boston

Welcome to our spacious urban retreat in the heart of Boston. This well maintained 4 bedroom unit is conveniently located near many city attractions. Enjoy quiet patio, backyard and free coffee bar. Great for a quick getaway or special gathering. 5 min walk to access bus and train 10 min drive to UMass Boston and JFK Library 20 min drive to Fenway Park and TD garden sports 10 min drive to the famous Franklin Park Zoo/Golf Course 20 min drive to Historical Downtown Boston and Prudential Shopping

Top guest favourite
A spacious living room is showcased with large windows offering natural light. Comfortable seating includes a light green sectional sofa and a white couch. A wooden coffee table sits atop a colorful area rug. A flat-screen television is mounted on the wall, providing entertainment options.
Apartment in Dorchester
4.97 out of 5 average rating, 157 reviews

1st floor, free parking off street, 3 min to train

1BR private first floor condo that has it all. Suitable for families, vacationing, and remote work. *Please note we live on the 2nd Floor (separate entrance) - FREE PARKING off-street driveway for 1 vehicle - PUBLIC TRANSIT 2 short blocks from Red Line, downtown in 15 min - SMART HOME High Speed dedicated Wi-Fi, smart speakers and lighting - WALKERS PARADISE Walk score 91 , many bars & restaurants & conveniences - PARKS Savin Hill & Beach within 10 min walk, near Carson Beach & Harbor walk

Guest favourite
A modern kitchen features white cabinetry and stainless steel appliances. A large island with seating is positioned centrally, complemented by pendant lighting above. Natural light streams in through the nearby window, illuminating the sleek countertops and stylish backsplash.
Flat in Ashmont
4.84 out of 5 average rating, 255 reviews

🎖The Ashmont Apartment | Close to Subway/Downtown

This unique 2 bed/2 bath apartment is brand new, along with all the furnishings and amenities. The unit includes 1 Queen + 1 Full size en-suite bedrooms. The unit is extremely clean and beautifully decorated. Only a 5 minute walk to Ashmont T station (red line), which takes you directly into Downtown Boston, Harvard, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Guest favourite
A micro studio space features a wall-mounted television positioned near a built-in bookcase. Natural light enters through two large windows, illuminating the minimalist decor and a cozy, spacious bed with crisp white bedding. A small white table and chair enhance the functionality of the room.
Flat in Fort Hill
4.9 out of 5 average rating, 940 reviews

AKBrownstone: cozy private studio by T

🏠 Live like a local: designed micro studio, in a classic Boston Brownstone 🌳 Your very own cozy 170sqft (15sqm) pied-à-terre on the ground level, overlooking Victorian homes on a tree lined street 🚇 5 mins walk to the T (subway), 3rd stop to Back Bay city center or go on bike & walking path 👣 Walk to Longwood Medical Area (Harvard Medical, etc), Museums (MFA, Gardner), Northeastern, & Fenway Park 🇺🇸 Located in residential & historic Fort Hill/Highland Park, free street parking

Superhost
The living room features a dark couch adorned with light blue pillows, positioned opposite a mounted 65-inch television. Natural light filters through two windows, and a small side table is placed next to the couch, creating a functional and open space.
Flat in Dorchester
4.91 out of 5 average rating, 209 reviews

1-Bedroom Apt (7B1) 20-Minuite To Downtown Boston

Prime Location: Located just a 10-minute walk from buses and the commuter rail, our guests enjoy a swift 15-minute train ride to downtown Boston. With Fenway Park, TD Garden, and Boston Logan Airport within a short distance, our apartment serves as your gateway to the best of Boston. Our newly built 1-BR lower-unit apartment is perfectly near the vibrant heart of Boston. For both leisure and business travelers, offering a serene stay with easy access to Boston’s bustling city life.

Top guest favourite
A well-maintained front yard showcases a variety of plants and flowers, with stone steps leading to the entrance. The entryway features a welcoming door adorned with a wreath, complemented by a decorative planter filled with yellow flowers. A smooth, dark asphalt pathway is visible.
Guest house in Ashmont
4.9 out of 5 average rating, 140 reviews

Prime City Location: Private Suite-separate entry.

This quiet residential neighborhood has easy access to a transportation hub (subway/bus/trolley/taxi), is 7 miles from the airport and has restaurants and services nearby - many within easy walking distance. My Codman Hill neighborhood is a premium area and represents the best of suburbia in the city. The neighborhood hosts primarily single family homes with double and triple deckers but the huge Victorian houses dating back to the 1700 and 1800's are within this community.

Top guest favourite
The open kitchen and dining area feature a round dining table surrounded by four chairs. Natural light fills the space through large windows, illuminating the glossy stained hardwood floors. A decorative plant adds a touch of greenery, enhancing the overall inviting ambiance.
Flat in Wollaston
4.96 out of 5 average rating, 211 reviews

Short Train 2 Boston, Luxury prvt unit w parking

Enjoy a comfortable stay in this private entrance, beautiful, newly renovated 1 bedroom apartment only a short 4 minute walk to Wollaston train station- 5 stops to downtown Boston. Convenient access to Boston by car (15-20min) as well. Full gut-renovation, open floor kitchen/dining room. Gorgeous bathroom. New HVAC system. W&D in unit. Off street parking spot right next to separate, private entrance. Great neighborhood, beautiful park across the street.

Guest favourite
A cozy bedroom is presented with a full bed dressed in vibrant patterned bedding. A mirror is mounted on the wall, reflecting natural light that brightens the space. The flooring features a large area rug, adding warmth to the room's ambiance.
Flat in Dorchester
4.81 out of 5 average rating, 222 reviews

Victorian 3rd Floor Unit

We are a 15-minute drive to Downtown Boston, Logan Airport, major Universities, historical sites like Castle Island, the beach, museums, State Parks, and major shopping malls. It is easily accessible by trains or buses (5-minute walk to the T and a 15-minute train ride to Downtown Boston). Steps away from local restaurants, cafes, bakeries, and markets on the main street. Free on-street parking.

Popular amenities for Dorchester family-friendly rentals

When is the best time to visit Dorchester?

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Avg. price$246 SGD$248 SGD$264 SGD$316 SGD$330 SGD$317 SGD$312 SGD$292 SGD$302 SGD$326 SGD$281 SGD$251 SGD
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Quick stats about holiday rentals that are family-friendly in Dorchester

  • Total holiday rentals

    Explore 410 holiday rentals in Dorchester

  • Nightly prices starting at

    Dorchester holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 20,840 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wifi availability

    410 of Dorchester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Dorchester rentals

  • 4.8 Average rating

    Dorchester stays are highly rated by guests – averaging 4.8 out of 5!

  • Nearby attractions

    Dorchester’s top spots include Franklin Park Zoo, University of Massachusetts Boston and Roxbury Community College