
Family-friendly holiday rentals in Stratton
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Top-rated family-friendly rentals in Stratton
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Family-friendly home rentals with a hot tub

2 Doors Down - Modern Farmhouse in Downtown Ludlow
We are fishermen from CT who stay at Bob’s place every year. This place accommodates us comfortably. We are able to walk to restaurants and love the location. Bob is so proactive making our stay so easy. He always communicates well and responds quickly to our needs. Until next year.🎣

Top of the World! Jacuzzi! Private Hiking Trails!
Nice place thanks Mike

Country Getaway Lodge / Ranch
Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.

Secluded Farmhouse Retreat - stunning views
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.

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.

Okemo-Ludlow, fireplace, hottub, sleeps 13
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.

Ski Chalet with Hot Tub on Okemo Mountain
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!

Expansive Lakehouse with Jacuzzi
My family and I had a wonderful time! Larry is very sweet, gave us a tour, offered to help with docking our boat and even offered my husband the tools to fix the bunk on our trailer. The house is big and beautiful!! Very clean, the beds are comfortable, the kitchen has everything you need!! The hot tub is definitely a bonus as we used it everyday!! The dock was perfect, we had room for our pontoon boat and jet skis. All around the perfect place for some R&R!!! My family and I love Cossayuna Lake as we are semi local and it was our first experience with an Airbnb. Thank you Larry for sharing your home!! Highly recommend this for your next vacation!!
Family- and pet-friendly home rentals

Cottage
A great spot, only a short drive from downtown Brattleboro. The host was friendly and responsive. It’s a lovely cabin and the surrounding nature is very peaceful. It’s a cozy, quiet spot.

400+ Airbnb Visits: Incredible Mountain Cabin
We had a wonderful stay at Ali and Carson’s cabin! They were incredibly helpful and welcoming hosts. The Mountain View from the cabin is absolutely stunning, even with the rainy weather, it was breathtaking. We also enjoyed exploring the charming nearby towns, and our two dogs had a great time as well. Despite the rain, we loved our stay and are already looking forward to coming back when the weather is better. Highly recommend!

Quaint cozy vermont apartment
Mariann has a great space in a great location. Very accommodating and friendly, made you feel very welcome . Very responsive. Really nice area. Would highly recommend.

Apartment on Main Street
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.

The Carriage Barn
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.

Comfortable farmhouse with stunning views
This was the perfect place for a peaceful Vermont getaway! The house is unique and a great balance of historical farmhouse and modern comfort. Very clean and easy to use amenities. Would love to stay again!

Sunrise Cabin
Susan and Carmen's place was just as advertised. We really appreciated their flexibility on check-in and it was nice meeting Carmen to show us around. The space is very cozy and comfortable. The cabin is well equiped with all the items you need for a stay, as well as some toys that my young daughter enjoyed playing with. There was a sulfur smell with the hot water, but I know Carmen is working to resolve that and we were told the water is safe to drink. Beautiful views and close to Magic MTN and Ludlow. I'd love to stay there again.

Adorable home in Newfane
We had a great stay at Saskia's house. Directions were perfect and everything was as described. The home is on a dirt road (but you only have to drive on the dirt road for less than a minute), our non-4 wheel drive car handled it with no problem. We loved the secluded and relaxing atmosphere and the bed was really comfortable too. Saskia was a great host, very communicative and welcoming, she left a great guide to the house and area. Highly recommended if you’re looking for a private getaway. We would definitely stay again. A+++
Family-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
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!

Bear's Den - Mt Snow Townhome w/ Heated Pool!
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

Mt Snow Ski In/Out at Seasons
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.

Moon Valley Country Retreat no clean fee pets yes
This is a wonderful place to stay. It’s very clean and the hosts have prepared for everything. It feels like your own cabin in the woods. Plus there are so many activities in a short distance of the place.

Cozy Bear- 1 mile to Mt Snow Ski Home
We really loved staying here. The location was perfect and the accommodations were fantastic. Our host was exceptional in making sure we were comfortable and informed. We will definitely try to book again.

One Bedroom Suite Near Okemo
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

1st Fl Condo 3BR @ Stratton Sleeps 7 Pool, Hot Tub
Our stay at Carl’s listing was more than we could ask. The location is perfect to the mountain and the shops and restaurants in the village. Carl was very helpful for the check in process and was very responsive. The space was very large and clean. We had the best time and I would certainly stay here again in the future!! The amenities at the lodge were amazing and the lodge manager was so incredibly helpful and friendly as well. A happy and fun vacation!!

Hollywood Bungalow in the Berkshires #C0191633410
Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.
Quick stats about holiday rentals that are family-friendly in Stratton
Total rentals
150 properties
Nightly prices starting at
₹7,740 before taxes and fees
Total number of reviews
3.9K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- West Mountain Ski Resort
- Saratoga Spa State Park
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Stratton Mountain Resort
- The Shattuck Golf Club
- Lake George Expedition Park
- Magic Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Pineridge Cross Country Ski Area
- Bretwood Golf Course
- Fox Run Golf Club