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
The dining area features a wooden table with six chairs, complemented by a striped table runner. A stylish vase with dried stems is placed at the center. A cozy couch, adorned in rich upholstery, is located beside the table, with a cityscape wall art piece above a dark cabinet.
Home in Hyde Park
4.86 out of 5 average rating, 360 reviews

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

Top guest favourite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston
5.0 out of 5 average rating, 211 reviews

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

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

Top guest favourite
A living area features a large wall adorned with natural-themed artwork, complemented by two windows allowing ample light. A flat-screen TV is mounted on the wall opposite a small table with a woven texture. A plush gray sofa enhances the inviting space.
Flat in Newton
5.0 out of 5 average rating, 120 reviews

Inn at Newton Highlands, Suite 2, Apartment-Hotel

This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

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 living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 360 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. NEW in 2022: Mini-split AC!

Top guest favourite
A dining area with a dark wooden table is set for four, featuring a colorful table runner. Natural light filters through windows adorned with light curtains, illuminating a cozy living room space beyond, furnished with a sectional couch, decorative pillows, and houseplants.
Guest suite in Newton
4.95 out of 5 average rating, 159 reviews

New Markdown! Lovely 3 Bedroom Unit with Garage

Planning your World Cup trip? Boston host of 7 World Cup matches. Enjoy the comfort of a fully equipped home perfect for watching every game This beautiful sunlit second floor unit with private garage has 3 bedrooms, full bathroom, splendid modern kitchen, gracious dining room, an elegant living room and a dedicated pleasant office room . Enjoy the shared backyard with a patio and playground for the kids. Registration: STR - 24 - 12

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.

Top guest favourite
Apartment in Norwood
4.85 out of 5 average rating, 150 reviews

The Plant Haus

A peaceful oasis with easy access to Rt 1, Rt 128, and walking distance from Norwood Center and the Norwood Depot commuter rail stop that goes to South Station. 30 mins from Providence and Boston and less than 20 mins to Gillette Stadium. My place is located in a quiet community. I am just a phone call or text away should you need me!

Popular amenities for Dedham family-friendly rentals

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