
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 $102 NZD per night before taxes and fees

Verified guest reviews
Over 4,740 verified reviews to help you choose

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Dedham holiday rentals include Wi-Fi 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.

Cozy en suite w/ high ceilings
 Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. Natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. Just 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Very safe walkable neighborhood

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 abundance on-street parking. Pet friendly!

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.

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod
Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

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

~*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

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.

Conveniently Located Private Garden Apartment
Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

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

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.

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.

Private apartment close the city!
New couch! New towels and linens! Fresh paint! New flooring coming soon. This private apartment is part of my home but has a separate entrance, full bath, living room and private bedroom. We're in a family neighborhood close to the city, and very convenient for those visiting with a car.
Popular amenities for Dedham family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Lakeside apartment, patio, hot tub, outside shower

Romantic Getaway w/private Jacuzzi• Fire Pit•

1790 Stone Manor Farm

Hopkinton Mass 3+ Bedrooms - Great location!

Oceanfront Pool. Close to Boston. Free Parking.

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Modern, Spacious 1BR for 4 - Easy Marathon Access!
Family- and pet-friendly home rentals

Charming 2-story private Guesthouse

Cozy Guesthouse Near T-Station - Family Friendly

Newly Finished Guest Haven in Woburn

Scandi-Modern Apartment

Entire home 3 miles from Gillette, sleeps 7.

Flower Farm Getaway 2BR, 20 Min To Boston

Peaceful Garden Apartment

Recently Renovated 2 BR Close to Boston w/Parking!
Family-friendly home rentals with a pool

Amazing studio

Curated Designer Retreat • Pool • Gym • Dining

Cozy Private Studio Unit w/ Laundry and Parking!

The Murthy : Bright • Spotless • W/D

Cozy Private Suite halfway between Cape & Boston

Spacious vacation unit in premium suburban town

Private Suite• Pool • Sleeps 4 • Boston • Airport

Pool Is Open! Steps from Harbor + Walk to Old MHD
When is the best time to visit Dedham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $364 NZD | $374 NZD | $357 NZD | $408 NZD | $434 NZD | $589 NZD | $352 NZD | $352 NZD | $367 NZD | $379 NZD | $374 NZD | $374 NZD |
| 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
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Portland Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Newport Holiday rentals
- Atlantic City Holiday rentals
- Providence Holiday rentals
- Bar Harbor Holiday rentals
- Salem Holiday rentals
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Seaport
- Boston Common
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- Canobie Lake Park
- Boston College
- Northeastern University
- Duxbury Beach
- MIT Museum
- Crane Beach
- Tufts University
- Quincy Market
- Harvard Square
- Roger Williams Park Zoo





