
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 $315 AUD 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 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.

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, 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. Safe walkable neighborhood.

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.

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

Comfy-Spacious-private 1BR conveniently located
This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

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

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

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 Two Bedroom Apartment
Private and clean renovated 2 bedroom apartment in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 6 comfortably in 2 queen beds and 1 futon. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27. Close to many colleges and MetroWest office parks.

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.
Popular amenities for Weston family-friendly rentals
Family-friendly home rentals with a hot tub

Nana-tucket Inn

Hopkinton Mass 3+ Bedrooms - Great location!

Romantic Getaway w/private Jacuzzi• Fire Pit•

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

Winery Studio w/ Private Hot Tub & Wine 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

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10

Harvard House-The Gathering Place.

White Pine Cottage – Cozy 3BR w/ Fireplace

Newly renovated, spacious, clean, 3 bedroom home.

Private Studio w/ Loft Center Historic Carlisle

Near Boston Beautiful 3 Bedroom in Framingham, MA

The Brickhouz at Arlington !

2bed/2bath Apt at Waltham Landing. Corner Unit
Family-friendly home rentals with a pool

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

The Weiss : Modern Gallery • Historic Property!

the house of id; vintage shop, accessible space

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

Cozy Private Suite halfway between Cape & Boston

Country Cottage in the City

Private/Quiet Single Family Home

Pool Is Open! Steps from Harbor + Walk to Old MHD
Destinations to explore
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- Family-friendly rentals Middlesex County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Boston Common
- Boston Seaport
- Gillette Stadium
- Revere Beach
- Brown University
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Canobie Lake Park
- MIT Museum
- Duxbury Beach
- North Hampton Beach
- Crane Beach
- Boston College
- Northeastern University
- Quincy Market
- Tufts University
- Harvard Square
- Roger Williams Park Zoo





