
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.

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
4.91 out of 5 average rating, 176 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
4.86 out of 5 average rating, 361 reviews
Peaceful Country Home, Dover, Ma: Private Entrance
Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.
4.98 out of 5 average rating, 346 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
4.95 out of 5 average rating, 224 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.
5.0 out of 5 average rating, 120 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.
4.95 out of 5 average rating, 217 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!
4.98 out of 5 average rating, 360 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.
4.95 out of 5 average rating, 111 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
4.86 out of 5 average rating, 237 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.
4.98 out of 5 average rating, 303 reviews
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.
4.96 out of 5 average rating, 116 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!
4.85 out of 5 average rating, 150 reviewsPopular amenities for Dedham family-friendly rentals
Family-friendly home rentals with a hot tub

1790 Stone Manor Farm
4.96 out of 5 average rating, 166 reviews
Modern, Spacious 1BR for 4 - Easy Marathon Access!
4.78 out of 5 average rating, 359 reviews
Lakeside apartment, patio, hot tub, outside shower
4.98 out of 5 average rating, 221 reviews
Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views
4.96 out of 5 average rating, 156 reviews
Romantic Getaway w/private Jacuzzi• Fire Pit•
4.91 out of 5 average rating, 242 reviews
Hopkinton Mass 3+ Bedrooms - Great location!
4.95 out of 5 average rating, 179 reviews
Oceanfront Pool. Close to Boston. Free Parking.
4.96 out of 5 average rating, 285 reviews
Newly renovated, close to Foxboro and Boston
4.72 out of 5 average rating, 137 reviewsFamily- and pet-friendly home rentals

Flower Farm Getaway 2BR, 20 Min To Boston
5.0 out of 5 average rating, 211 reviews
Charming 2-story private Guesthouse
4.94 out of 5 average rating, 256 reviews
Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod
4.96 out of 5 average rating, 234 reviews
Conveniently Located Private Garden Apartment
4.92 out of 5 average rating, 417 reviews
Modern home 22 min Boston, 20 min Gillette Stadium
4.92 out of 5 average rating, 160 reviews
Entire home 3 miles from Gillette, sleeps 7.
4.89 out of 5 average rating, 114 reviews
Cozy en suite w/ high ceilings
4.98 out of 5 average rating, 141 reviews
Spacious 4 bedroom home with large yard
4.89 out of 5 average rating, 133 reviewsFamily-friendly home rentals with a pool

Cozy Private Studio Unit w/ Laundry and Parking!
4.97 out of 5 average rating, 450 reviews
Pool Is Open in Sept! Steps from Harbor + Old Town
4.99 out of 5 average rating, 167 reviews
Amazing studio
4.87 out of 5 average rating, 208 reviews
The Secret Garden 4 Bedroom, 7 Bed 3 Baths
4.9 out of 5 average rating, 199 reviews
The Murthy : Bright • Spotless • W/D
4.95 out of 5 average rating, 161 reviews
Spacious vacation unit in premium suburban town
4.97 out of 5 average rating, 120 reviews
Exquisite 1 Bedroom Suite-Charming,W/Private Entry
4.78 out of 5 average rating, 104 reviews
Private Pool Retreat w/Fire Pit Near Singing Beach
4.91 out of 5 average rating, 202 reviewsWhen is the best time to visit Dedham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €186 | €192 | €183 | €209 | €222 | €302 | €180 | €180 | €188 | €194 | €192 | €192 |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 14°C | 19°C | 22°C | 22°C | 18°C | 11°C | 6°C | 0°C |
Destinations to explore
- Fenway Park
- Hampton Beach
- Harvard University
- TD Garden
- Boston Seaport
- Gillette Stadium
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- Onset Beach
- New England Aquarium
- Boston College
- Northeastern University
- Canobie Lake Park
- Duxbury Beach
- MIT Museum
- Harvard Square
- Tufts University
- Crane Beach
- Quincy Market
- Massachusetts Institute of Technology
- Saquish Beach





