
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.

All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Private & Remote, Enjoy Outdoors, Sleep in Luxury
Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

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.

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.

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

Newly Renovated Lovely 2 bedroom unit - Newton MA
Only a 10 minute drive to the heart of Boston's downtown area and other central Boston colleges and universities. This is a newly renovated 2 bedroom unit with 2 bathrooms on the first floor for parties up to 7 people (convertable couches) in a quiet and peaceful Irish suburban community. Driveway and street parking is always available. About an 11 minute walk to the nearest commuter rail line. Laundry access in the basement. No indoor smoke and no open flames, fines will be issued if caught.

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

White Pine Cottage – Cozy 3BR w/ Fireplace
Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

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

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.
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

Oceanfront Pool. Close to Boston. Free Parking.

Winery Studio w/ Private Hot Tub & Wine Tasting

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

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

Harvard House-The Gathering Place.

Sunny & private cottage in Lanesville Village

Farm Living

Newly renovated, spacious, clean, 3 bedroom home.

Lakefront, view of ski mtn, fireplace, sauna

Near Boston Beautiful 3 Bedroom in Framingham, MA
Family-friendly home rentals with a pool

The Murthy : Bright • Spotless • W/D

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Private Pool Retreat w/Fire Pit Near Singing Beach

Cozy Private Suite halfway between Cape & Boston

Country Cottage in the City

Historic 1 Bed/In Town/Best Location/Hot tub/deck

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

Luxury Grand Oasis | Pool · Gym · Parking · 2BR
Quick stats about holiday rentals that are family-friendly in Weston

Total holiday rentals
Explore 20 holiday rentals in Weston

Nightly prices starting at
Weston holiday rentals start at $170 NZD per night before taxes and fees

Verified guest reviews
Over 430 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
20 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Rentals with a washing machine and dryer Weston
- Apartment rentals Weston
- Pet-friendly rentals Weston
- House rentals Weston
- Rentals with a patio Weston
- Fitness-friendly rentals Weston
- Rentals with pools Weston
- Hotel rooms Weston
- Family-friendly rentals Middlesex County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- New England Aquarium
- Revere Beach
- Boston Seaport
- Boston University
- Gillette Stadium
- Northeastern University
- Boston Convention and Exhibition Center
- Freedom Trail
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Roxbury Crossing Station
- Quincy Market
- North Hampton Beach
- Museum of Fine Arts
- Prudential Center
- Roger Williams Park Zoo





