
Family-friendly holiday rentals in Weston
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Weston
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Cozy Private Studio Unit w/ Laundry and Parking!
Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

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.

Country Charm minutes from the Hub - 1st Floor Apt
Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

Cozy en suite w/ high ceilings
 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of 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. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Entire Apartment in Newton, Close to Boston!
Come stay in this comfortable one bedroom apartment with large open space living room, kitchen area, bathroom, Wi-Fi, parking, and a private entrance onto a gorgeous backyard garden. Centrally located in a quiet neighborhood equidistant from Moody St. in Waltham and West Newton Sq. -- a 15 minute walk from excellent restaurants and an independent movie theater in both directions. Two dance studios with regular weekend dances nearby. To protect guests with allergies, no pets allowed.

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. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

New Super Modern 2 bed in Waltham
A tastefully decorated unit on the 1st floor. Just across from the Waltham Watch Factory. 10-min walk to Moody St. and Charles River path. Built in 2014, open living, dining, and kitchen areas are ideal for working or entertaining. Stainless steel appliances and high class kitchenware. Spacious 2 bedrooms and 1 bathroom. Private deck. In unit washer/dryer. Baby friendly. Parking spot#1. Tax of 11.7% starts 7/1/19. Open and no-contact fire stairway is accessible from the parking lot.

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...

Water front cabin-like guest suite on a quiet pond
Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

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

Sunny apartment in gracious Victorian
Relax into your Boston stay! We offer a sunny in-law apartment on the first floor of a gracious owner-occupied Victorian house. Quiet, safe residential neighborhood. Private entrance. Spacious bedroom, living room with sofabed, kitchenette & bath. Strong Wi-fi. Driveway parking. Contactless check-in, Easy access to Boston, Cambridge, Rts. 128 & 90, and Charles River bike path. Let us welcome you!

Entire guest suite in Stoneham
Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.
Popular amenities for Weston family-friendly rentals
Family-friendly home rentals with a hot tub

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

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

Manomet Boathouse Station #31

Winery Studio w/ Private Hot Tub+Fireplace+Tasting

Heart of Southie - Hot Tub + Walk to Top Bars

Lakeside apartment, patio, hot tub, outside shower

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views
Family- and pet-friendly home rentals

Newly Built En Suite

Recently Renovated 2 BR Close to Boston w/Parking!

2bed/2bath Apt at Waltham Landing. Corner Unit

Ocean Park Retreat

Tiny farm house on horse farm

White Pine Cottage – Cozy 3BR w/ Fireplace

Renovated Cozy City Getaway

Cozy, historic 3 bedroom home close to Boston!
Family-friendly home rentals with a pool

Peaceful suite in Boston with city views

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Triggers Cabin

Cozy Private Suite halfway between Cape & Boston

Stylish and Cozy at Revere Beach

Country Cottage in the City

Antique Home - Steps from Harbor - Private Pool

In-law Apartment, Full Kitchen, Near Mt Wachusetts
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 $251 NZD per night before taxes and fees

Verified guest reviews
Over 460 verified reviews to help you choose

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!
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- Family-friendly rentals Middlesex County
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- Family-friendly rentals United States
- Hampton Beach
- TD Garden
- Fenway Park
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Freedom Trail
- Boston University
- New England Aquarium
- MIT Museum
- Boston Seaport
- Canobie Lake Park
- Boston Convention and Exhibition Center
- Crane Beach
- Duxbury Beach
- Museum of Fine Arts
- Gillette Stadium
- Quincy Market
- North Hampton Beach
- Prudential Center
- Roger Williams Park Zoo
- Roxbury Crossing Station
- Boston Children's Museum




