Family-friendly holiday rentals in Dedham

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Dedham

  • Total holiday rentals

    Explore 60 holiday rentals in Dedham

  • Nightly prices starting at

    Dedham holiday rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 4,740 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Dedham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Dedham rentals

  • 4.9 Average rating

    Dedham stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated family-friendly rentals in Dedham

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

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Guest favourite
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
4.91 out of 5 average rating, 174 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

Guest favourite
A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.
Home in Stoughton
4.93 out of 5 average rating, 159 reviews

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and limited on-street parking. Pet friendly!

Top guest favourite
The exterior of a red house is framed by a well-maintained garden comprising various flowers and greenery. The house features a welcoming entryway, a chimney, and a grassy area. Sunlight illuminates the scene, highlighting the vibrant colors of the surrounding landscape.
Flat in Dedham
4.95 out of 5 average rating, 223 reviews

Two bedrooms, full bathroom, and breakfast room

We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

Guest favourite
The living room features a comfortable couch adorned with a soft throw blanket. A large piece of artwork hangs on the wall, showcasing a vibrant floral design. Two stylish glass tables are positioned in front of the couch, accompanied by a decorative rug.
Home in Hyde Park
4.9 out of 5 average rating, 391 reviews

~*30min to Downtown*~ THE COSMOPOLITAN

Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

Guest favourite
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.
Guest house in West Roxbury
4.95 out of 5 average rating, 217 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

Top guest favourite
A spacious dining area is presented with a wooden table surrounded by black chairs. A modern kitchen with granite countertops and stainless steel appliances is visible. Natural light fills the room through large windows adorned with light curtains, creating a bright and inviting setting.
Hotel room in Newton
5.0 out of 5 average rating, 102 reviews

Inn at Newton Highlands, Suite 1, Apartment-Hotel

This gorgeous 2 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is pure luxury. It features a large and inviting living room, spacious bedrooms with private bathrooms, a private 500 sq.ft. deck, and everything else to make your stay comfortable and memorable. The suite has its own HVAC system. This suite is one of several luxury suites in a small boutique Inn which is located in the heart of Newton Highlands in a beautiful, fully remodeled historic building.

Guest favourite
A bright living area features a cozy sofa and a small coffee table, with a colorful rug underneath. A sleek media console holds a television, while a glass cabinet displays decorative items. Light is provided by recessed ceiling fixtures, creating an open and airy atmosphere.
Flat in Roslindale
4.95 out of 5 average rating, 106 reviews

Forever Boston-5 mil Fenway, FreePrkg

Relax with the whole family at this peaceful neighborhood . The fully renovated first floor unit, offers plenty of space for an entire family with 3 bedroom and 1 full bathroom. Conveniently located on Jamaica Plain/Roslindale line. It is 2 min walk to the bus line, 10 min walk to Bellevue commuter rail, Roslindale Village and to the famous Museum of trees Arnold Arboretum. 6 miles to downtown Boston, 5 miles to Fenway Park and only 2 miles from Jamaica Pond.

Top guest favourite
A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.
Guest suite in Lexington
4.97 out of 5 average rating, 185 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

Guest favourite
A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. Two lamps provide soft lighting. Mirrored closet doors reflect the room, and artwork hangs on the wall, adding a touch of character. Warm wooden flooring complements the neutral decor.
Home in Canton
4.94 out of 5 average rating, 109 reviews

Gorgeous 2nd Floor Home with Private Entry

Welcome to your home away from home! This beautiful second-floor 2 BR unit keyless self check in offers a private entrance and private stairs. Features: · Newly Installed AC · Fully Kitchen: Equipped with smart utilities, including an oven, microwave, dishwasher, washer, and dryer. · High-speed internet. · Comfortable Sleeping Arrangements: 2 beds & a sofa bed, perfect for accommodating up to 4 guests.

Guest favourite
The kitchen area features vibrant red cabinetry and a white tiled backsplash. A small wooden table is set for two with black chairs, complemented by a bottle of wine and two glasses. Natural light filters through a large window, enhancing the inviting atmosphere.
Flat in Roslindale
4.86 out of 5 average rating, 237 reviews

1bd Boston apt - convenient & quiet

Small, private 1bd apt in Boston city neighborhood of Roslindale. - 5 mins walk to Roslindale Square for dining, groceries, bakeries and coffee shops - Trains to downtown (15min journey) just 2 mins away.  - Green space on your doorstep. Harvard's tree museum, the beautiful Arnold Arboretum - Full kitchen, wifi, unrestricted on-street parking. Washer/Dryer. Shared outdoor space. - Value option in an expensive city  

Top guest favourite
A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.
Home in Dedham
4.98 out of 5 average rating, 303 reviews

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

Guest favourite
An open-concept kitchen features a large marble countertops with two stylish bar stools. Modern appliances are available, including a refrigerator and a gas stove. Floating shelves display decorative elements and small plants, while soft overhead lighting enhances the clean, contemporary design.
Apartment in Roslindale
4.84 out of 5 average rating, 99 reviews

Modern Stay | Clean, Cozy & Stylish!

Come enjoy your stay with us at the Beech House! You will have 3 rooms available within our recently renovated home. The property is one of two apartments, where you will have your own private entrance and parking space. Local Transportation Info: 0.3 miles from bus stop 1.1 miles from Roslindale Village 2.2 miles from Forest Hills Our family welcomes you to our home!

Popular amenities for Dedham family-friendly rentals

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