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

Total vacation rentals
Explore 50 vacation rentals in Weston

Nightly prices starting at
Weston vacation rentals start at G$23,006 GYD per night before taxes and fees

Verified guest reviews
Over 2,430 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 of Weston vacation rentals include wi-fi access

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

4.9 Average rating
Weston stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Weston
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Little Cabin on the Ridge
Classic Vermont cabin.This cozy home is perfect for singles, couples and families.The well-designed space offers sleeping for 4 in two bedrooms and an open loft space. Wrap around porch has 4 rockers for taking in the mountain air, coffee or tea, or reading in a cozy quilt. Fiber optic wifi 1000 mbps.Very efficient forced hot air heating and Central Air cooling.Peaceful, quiet,relaxing, great place to unwind with all kinds of activities nearby. due to health and safety concerns no animals please

Spacious King Spa Suite Weston Hills
Spacious 750 sqft guest suite king bed, table & chairs, kitchenette & sitting area & large, private spa bathroom featuring walk through mosaic shower area 4 shower heads, jets, wands & two person roman jacuzzi tub featuring aroma & chroma therapy & heated back rests. Ensuite bidet, elongated toilet & urinal. Pull-out sofa & comfy king bed with views from 5 glass doors to private deck. Xfinity high speed Internet and streaming TV. Private entrance from deck or shared entrance via front door.

Glamping Cabin with Hot Tub on Flower Farm
<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

4 Bedroom Family Ski House w/ WiFi, cable!
This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

The Owl’s Nest in Landgrove
Our recently renovated cabin is the perfect escape during any season! Located within minutes of Bromley, Magic, and Stratton, Wild Wings, and Viking. Also nestled in an amazing network of hiking, biking and ski trails. Guests will never be more than a few minutes away from outdoor adventure. With two bedrooms and one bonus loft, guests can enjoy the comforts of our cozy cabin, including a full kitchen, bathroom, outdoor shower, HOT TUB, fire pit, WiFi and FREE EV CHARGING. @owlsnestvt

Modern Okemo Smart Cabin - As Seen On DIY Channel
This is a brand new modern timber frame smart cabin in Ludlow (~5 min from Okemo). The house was recently featured on DIY / Discovery’s acclaimed TV show, Building Off The Grid. Warm up after a day of skiing or riding with heated floors and a walk-in shower. Charge up your electric vehicle in the private garage. Directly access the VAST snowmobile trail from the backyard or sit back on the porch and soak up the views. Message host about renting for next winter season!

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub
Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.
Popular amenities for Weston family-friendly rentals
Family-friendly home rentals with a hot tub

Log Cabin: Amazing Views, River Frontage, Hot Tub

Cozy Log Cabin with Hot Tub | 1/2 mile to Okemo

Romantic Ski Cabin in VT, Hot Tub, Fire Pit, Charm

Schoolhouse Spa Retreat on a Vermont Farm

Vermont Mirror House

Secluded tiny house resort - DOG FRIENDLY

Modern Cabin with Outdoor Spa on Vermont Farm

Private Ski Cabin On Okemo Mt. With New Hot Tub!
Family- and pet-friendly home rentals

The Post Haus: one-of-a-kind modern VT experience

Classic Vermont A-Frame | Fire Pit | Near Stratton

Modern 3-bedroom A-frame in Londonderry w/ Pond

Private Cabin/PetsOK/AC/Minutes to Okemo/Fast Wifi

Apple Blossom Cottage: A Tiny House

Stylish Vermont Cabin | Views · Trails · Luxe

Vermont Country Cottage(Near Village w/Magic View)

Love Shack Yurt on Star Lake (100% off grid)
Family-friendly home rentals with a pool

Moon Valley Country Retreat no clean fee pets yes

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Dream Catcher Farm

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Hollywood Bungalow in the Berkshires #C0191633410
When is the best time to visit Weston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$83,240 GYD | G$84,913 GYD | G$78,011 GYD | G$61,489 GYD | G$60,025 GYD | G$61,489 GYD | G$69,855 GYD | G$63,999 GYD | G$63,789 GYD | G$64,626 GYD | G$72,574 GYD | G$77,384 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Québec City Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Providence Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- Rentals with a patio Weston
- Pet-friendly rentals Weston
- Rentals with a fireplace Weston
- Rentals with outdoor seating Weston
- House rentals Weston
- Rentals with a fire pit Weston
- Rentals with a washer and dryer Weston
- Family-friendly rentals Windsor County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Dartmouth College
- West Mountain Ski Resort
- Killington Resort
- Ragged Mountain Resort
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Montshire Museum of Science
- Mount Monadnock
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Trout Lake
- Camp Plymouth State Park





