Family-friendly holiday rentals in Weston

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Weston family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars3 months ago
Nice place thanks Mike
Top guest favourite
Home in Colrain
4.94 out of 5 average rating, 179 reviews

Secluded Farmhouse Retreat - stunning views

ColinRating, 5 stars1 week ago
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.
Guest favourite
Chalet in Ludlow
4.95 out of 5 average rating, 129 reviews

Okemo Ski Chalet with Hot Tub

WillRating, 5 stars1 month ago
Stop scrolling, you found your next vacation. Bob is a fantastic host with a stunning home. We have stayed with Bob many times and he continues to invest in the property and ensures your stay is nothing short of fantastic. Cannot recommend the ski chalet enough.
Superhost
Home in Cavendish
4.83 out of 5 average rating, 151 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

LilyRating, 5 stars3 months ago
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.
Guest favourite
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars3 months ago
We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.
Top guest favourite
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars3 months ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.
Guest favourite
Loft in Ludlow
4.95 out of 5 average rating, 814 reviews

Spacious Renovated Barn Apt on 100 acres!

RichardRating, 5 stars1 week ago
Very clean and well equipped. Comfortable bed and bedding. Great hot tub! Convenient location for our needs. Very cute! We had 5 adults stay comfortably. Wonderful sound system.
Guest favourite
Home in Wilmington
4.9 out of 5 average rating, 147 reviews

Martin Ski Barn - 4BR Ski House, 15 min to Mt Snow

KrystleRating, 5 stars3 weeks ago
We had a wonderful stay at this property on Memorial Day Weekend! Everything in the home was exactly as described and comfortable. We didn’t have that much time to enjoy the clubhouse but we hope to return for a longer stay and take advantage of all it had to offer. The staff there were so wonderful and accommodating and gave us a wonderful tour.

Family- and pet-friendly home rentals

Superhost
Chalet in Readsboro
4.84 out of 5 average rating, 325 reviews

The King's Cottage

Carla RaeRating, 5 stars3 weeks ago
We were very comfortable at King’s Cottage. We had everything we needed. It was so quiet, private, comfortable and well appointed. Messages from the host were friendly and helpful. Great stay in a beautiful spot!
Superhost
Cabin in Cavendish
4.95 out of 5 average rating, 159 reviews

The Cozy Little Red Cabin

LaurenRating, 5 stars3 months ago
Marinas little red cabin was perfect for our ski trip! The WiFi is a little rough but we didn’t spend much time on our phones Bring dvd’s (the collection is solid but more the better) Perfect distance to okemo, Stowe is less than two hours so it was great! The cabin felt so cozy and felt right at home! Would def book again!
Superhost
Home in Mount Tabor
4.92 out of 5 average rating, 184 reviews

Mtn Treasures Waiting Lt/Ap Little rock pond

MichaelRating, 5 stars3 months ago
Very responsive host who went above and beyond to display hospitality. Clear instructions and let us enjoy the place in peace. Space itself was warm and inviting and perfect for a couple's weekend away.
Guest favourite
Home in Grafton
4.96 out of 5 average rating, 153 reviews

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

CarolRating, 5 stars3 weeks ago
Wonderful place with great family room with fireplace especially when your weather doesn’t cooperate. The house is well kept and the instructions for everything were placed all around where needed. Fenced yard was great for the dog. The bed in the master is super comfortable with great linens. Loved the house-would live in it in a heart beat. Plenty of games, air hockey table, darts and another game table…grill, firewood- even poop scoops for the dog! Well done!
Top guest favourite
Guest house in Hartland
4.95 out of 5 average rating, 993 reviews

Yurt In The Woods - Private Refuge

KristieRating, 5 stars5 days ago
It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.
Top guest favourite
Flat in Newfane
4.97 out of 5 average rating, 455 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars2 weeks ago
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.
Top guest favourite
Cabin in Pawlet
4.94 out of 5 average rating, 156 reviews

Hickory Ridge, Vermont Log Cabin, no cleaning fee

ReneeRating, 5 stars6 days ago
Fantastic and authentic Vermont experience. Top 3 AirB&Bs I’ve stayed in. Off the beaten path, but close enough to everything you need. Rik is great host and makes it easy. Book if you can find availability.
Guest favourite
Cottage in Jamaica
4.83 out of 5 average rating, 529 reviews

Cottage 7min to Ski Stratton-WoodStove,Views,DogOK

EmmaRating, 5 stars1 day ago
Jason’s place was excellent! Exactly what we were looking for in a country getaway-cozy cabin in the woods, full of charm and close to farms, hiking and swimming. we loved listening to the records while cooking. Perfect spot, perfect vacation!

Family-friendly home rentals with a pool

Guest favourite
Home in Salem
4.98 out of 5 average rating, 192 reviews

Magical Farm Getaway - a must visit!

BriannaRating, 5 stars2 weeks ago
We had a wonderful & relaxing weekend here with a large group for my sister's lowkey bachelorette party. Even with a day of non-stop pouring rain, we were perfectly content with staying in and enjoying the coziness of the house. We had a blast watching the chickens roam around and hanging out with the overly-friendly barn cats while we sat outside. The goats & pigs were happy to greet us at the fence every time. The hot tub and pool were perfect! Highly recommend staying here if you're looking for a beautifully scenic and peaceful getaway. Thanks, Sarah & BBVF team!
Guest favourite
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

NikkiRating, 5 stars4 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Guest favourite
Guest suite in Killington
4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

JoshRating, 5 stars3 months ago
Amazing stay. Loved how close it was to the mountain. The pool also looked amazing so sad it was winter. Definitely recommend staying there were 4 beds and can comfortably fit 5-6 people.
Guest favourite
Apartment in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favourite
Apartment in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars2 months ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Superhost
Apartment in Killington
4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars3 weeks ago
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!
Superhost
Apartment in Killington
4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

IanRating, 5 stars5 months ago
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.
Guest favourite
Apartment in Killington
4.93 out of 5 average rating, 456 reviews

Hike bike golf 1 bedroom 1 nght Ok shuttle

DouglasRating, 5 stars4 days ago
We enjoyed the stay. Good weather so did not need AC. Good thick towels.

Quick stats about holiday rentals that are family-friendly in Weston

  • Total rentals

    50 properties

  • Nightly prices starting at

    $167 SGD before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

Destinations to explore