
Family-friendly holiday rentals in Weston
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Weston

Total holiday rentals
Explore 10 holiday rentals in Weston

Nightly prices starting at
Weston holiday rentals start at $368 NZD per night before taxes and fees

Verified guest reviews
Over 460 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Weston holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Weston rentals

5 Average rating
Weston stays are highly rated by guests—averaging 5 out of 5!
Top-rated family-friendly rentals in Weston
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

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.

Just Renovated, Private & Quiet 2 Bedroom Condo
Keep it simple and comfortable at this peaceful, centrally located getaway. Set at the very end of a private, ultra-quiet dead-end road, the home feels tucked away This newly renovated 2-bedroom unit is an ideal home base for your Boston-area stay You’ll have easy access to public transportation, parks, dining, shopping, and major highways including I-95, I-90, and Route 2. Enjoy your own private outdoor deck, a spacious yard, in-unit laundry, central AC, and off-street parking for two cars

2bed/2bath Apt at Waltham Landing. Middle Unit
This apartment complex was built in 2016. It is 1 block from The Charles River and Waltham's famous Moody Street, aka "Restaurant Row." Across the street from Waltham Station: Fitchburg Line - Commuter Rail. Bentley and Brandeis are 1 mile away. Monthly rentals accepted (inquire for best rate), discounts for groups and long-term rentals. Perfect for business travelers, families, anyone in between housing or visiting town! Free parking in the parking lot. Yes there is an Elevator.

Lovely one bedroom apartment condo, with parking
The whole group will enjoy easy access to everything from this centrally located place. Entire unit. In the heart of Waltham Large and comfortable one bedroom apartment in quite condominium style place. Great location 5 minutes walk to train or bus to Boston, 6 minutes walk to Moody street where all the restaurants and attractions are currently open. Also 7 minutes drive from Brandeis university or Bentley College . We are located near everything you would need to do in Waltham. The

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.

Spacious vacation unit in premium suburban town
Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Spacious 4 bedroom home with large yard
Private and clean renovated 4 bedroom house in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 8 comfortably in 4 bedrooms. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Kids will enjoy the swingset. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27, and many colleges and MetroWest office parks.

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!

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

Beautiful, Clean & Quiet 2 BR- 15 min to BOSTON
SUNNY, CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College. FREE PARKING, WiFi and WASHER & DRYER.

Private apartment with driveway parking in Woburn
Enjoy your private retreat in this spacious 1-bedroom lower-level apartment, comfortably accommodating up to 4 guests. Features a fully equipped kitchen, a cozy living room with a 65" Smart TV, and access to a beautiful, enclosed backyard. Located minutes from shops and restaurants, it's the perfect blend of comfort and convenience for your stay.
Popular amenities for Weston family-friendly rentals
Family-friendly home rentals with a hot tub

Lakeside apartment, patio, hot tub, outside shower

1790 Stone Manor Farm

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Romantic Getaway w/private Jacuzzi• Fire Pit•

Hopkinton Mass 3+ Bedrooms - Great location!

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

Rustic Farmette Studio w/yearround Hot Tub

Nana-tucket Inn
Family- and pet-friendly home rentals

White Pine Cottage – Cozy 3BR w/ Fireplace

Conveniently Located Private Garden Apartment

Near Boston Beautiful 3 Bedroom in Framingham, MA

Cozy, historic 3 bedroom home close to Boston!

Scandi-Modern Apartment

Modern Cozy 2 Bed Near Cambridge

Newly renovated, spacious, clean, 3 bedroom home.

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10
Family-friendly home rentals with a pool

Cozy Private Studio Unit w/ Laundry and Parking!

Country Cottage in the City

The Franklin: Wellness • Aesthetic • W/D • Gym

Farmhouse Guest Apartment

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

Curated Designer Retreat • Pool • Gym • Dining

Pool Is Open! Steps from Harbor + Walk to Old MHD

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace
Destinations to explore
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Seaport
- Boston Common
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Canobie Lake Park
- Boston College
- Northeastern University
- Duxbury Beach
- MIT Museum
- North Hampton Beach
- Crane Beach
- Tufts University
- Quincy Market
- Harvard Square
- Roger Williams Park Zoo
- Saquish Beach





