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 stars2 weeks 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
Condo in Killington
4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars4 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!
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.
Top Guest favourite
Home in Ludlow
4.97 out of 5 average rating, 160 reviews

Ski Chalet with Hot Tub on Okemo Mountain

ImanRating, 5 stars4 weeks ago
Had an awesome weekend here with the family! The cabin had everything we needed, super comfy and well-stocked. The hot tub was a huge bonus, and the hosts were super friendly. Would definitely come back!
Guest favourite
Loft in Ludlow
4.95 out of 5 average rating, 815 reviews

Spacious Renovated Barn Apt on 100 acres!

BillRating, 5 stars4 days ago
My wife and I have visited twice already and hope to go back again soon. We met the owner and her wonderful fiancé while we were visiting. Wonderful people. Very private and beautiful location. If you need to unwind and relax this is the location for you. Thank you for hosting us and congratulations..

Family- and pet-friendly home rentals

Superhost
Chalet in Readsboro
4.84 out of 5 average rating, 326 reviews

The King's Cottage

Lynzi And DaveRating, 5 stars2 weeks ago
Really lovely Airbnb in a beautiful location! I came with my dogs and they were right at home. This spot was truly a dog friendly location. They even provided dog bowls and beds! There was also a ton of room to run and play with them. You really can’t beat the location and view if you want to get away. I love that there are chairs both on the patio and in the lawn to enjoy the view. My husband and I were looking for a place to truly check out and get away from work and this was the perfect spot for that. The bed and couches were really comfy, the kitchen had all the basics and I love that there was a fireplace option, even if we didn’t need it. It rained a ton while we were there and the yard gets pretty soggy, so if you’re planning for outdoor playtime on a rainy day, bring your rainboots! 10/10 stay and we’re already talking about booking another weekend there.
Guest favourite
Cabin in Mount Holly
4.92 out of 5 average rating, 196 reviews

Cozy Vermont Cabin near Okemo.

MarlaRating, 5 stars3 months ago
A very clean, cozy, and comfortable home! We came to ski at Okemo and were pleased that the house is only about a 10 minute drive from the resort and the town of Ludlow where there are great restaurants and shops. The living area of the home is spacious and great for hanging out - there were tons of movies on DVD and video games to enjoy. The kitchen was well-equipped and perfect for cooking meals at home. The beds were comfy. Overall a wonderful stay! We hope to be back in the future.
Guest favourite
Cabin in West Windsor
4.96 out of 5 average rating, 144 reviews

Cowshed Cabin Farm

JefferyRating, 5 stars1 week ago
Great host, great location. Very relaxing and close to many attractions. Loved watching all the birds coming into the yard
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
Apartment in Town of Rockingham
4.83 out of 5 average rating, 186 reviews

Apartment on Main Street

CraigRating, 5 stars1 month ago
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.
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 stars4 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
Guesthouse in Hartland
4.95 out of 5 average rating, 993 reviews

Yurt In The Woods - Private Refuge

KristieRating, 5 stars1 week ago
It’s very well maintained and private. Everything was as in the pictures and it was a breeze to take care of.

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 stars3 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, 146 reviews

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

DiannaRating, 5 stars1 day ago
all around the house was so pretty! flowers and felt like you're in the middle of the forest, the house standing on a small hill and the only exit is through one driveway on a mini bridge, which is very cute and secluded. The only downside is sooooo many mosquitoes, but thats honestly everywhere especially if you're in the forest. This place gives off you're visiting your grandparents home, which felt very nice and refreshing especially since we're from a rowdy city.
Guest favourite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars3 months ago
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!
Guest favourite
Condo 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
Condo 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
Condo in Killington
4.89 out of 5 average rating, 162 reviews

Modern Killington Farmhouse Condo: Close to Resort

RodneyRating, 5 stars4 months ago
Great home near the mountain, exactly how described and shown in pictures. We had a wonderful stay.
Guest favourite
Condo in Killington
4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

MichaelRating, 5 stars3 months ago
Great spot near the mountain. nice community pool and hot tub.

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

  • Total rentals

    50 properties

  • Nightly prices starting at

    $217 NZD 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

  • Wi-Fi availability

    50 properties include access to Wi-Fi

Destinations to explore