
Kid-friendly holiday rentals in Winhall
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Top-rated family-friendly rentals in Winhall
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Kid-friendly house rentals

Entire Chalet in Winhall, Vermont
We enjoyed the stay, the accommodations were perfect for our family, four adults and two young children. The home is very well organized and comfortable, with things to do for the kids. Recommended.

Highland Haus: stunning ski getaway with hot tub
The home and location are great, but the hosts are what make this place. They go above and beyond to make your stay special.

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home
I can only say wonderful things about this property! Everything was beautiful both inside and out. The house was very clean and organized and was also extremely well stocked. Anything that we needed we found in this house. And everyone in our group said the beds were very comfortable… which is very important to me! Erik was great with communication and very proactive. He sent us a note about a week before we checked in that had everything we needed to know; it was quite helpful. I highly recommend this home….and as an added bonus, the view is spectacular! You will not be disappointed if you stay here!

Vermont Botanical Studio Apartment
The place was quaint and peaceful. It was cleaned after we arrived which was not a problem. Oliver is very friendly. It could use new towels. Coffee and tea would be a nice touch.

Stratton; 8 min! Swimming, 2 min. Pet friendly
Kelly was very responsive and helpful. She went out of her way to get us a last minute booking and it didn’t disappoint! It was clean, well stocked and very comfortable! I will definitely book this again when its available!!!

Comfortable farmhouse with stunning views
Such a cool house. We loved the charm of the older section of the house. So many private spaces to cozy up and read a book. Then there is the more modern portion of the house. It was perfect for the folks to watch tv and enjoy the VT scenery out of the large windows. The road is quiet and the area is lovely. We easily drove into Manchester for groceries and dinner. Really loved it!!

Lawrence Cottage
We loved staying at this cozy home. It had beautiful grounds and we enjoyed sledding and walking around thoroughly and made a cozy fire to warm up after being outdoors. The hosts left fresh eggs, milk, coffee and other treats. Overall it was an excellent experience.

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs
We LOVED our stay here! The lake is so peaceful and the house has the perfect view. Andrew was very helpful and accommodating and we would highly recommend staying here!
Family-friendly apartment rentals

Private Apt. on Farm, Hot Tub with views!
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!

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.

Private Hilltop farm apartment
What a lovely and serene spot to spend a few days in the Mountains of Vermont! Loved waking up to views of horses in the field by the private deck and a breathtaking mountain view. The hosts were kind and communicative. The space was clean and had just the right amount of amenities. Definitely recommend and hope to stay again!

The Beer Diviner Brewery Apartment
Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!

Cozy Poultney Village Apartment
We had an exceptional stay at this Airbnb! It was perfect for two people with plenty of room. It was so cozy. We loved the Vermont specific decor. The ingredients for pancakes and the basic ingredients in the fridge were a thoughtful touch. I could not recommend staying here more!!!

Peace Street Guest Apartment
Awesome location and very spacious place with plenty of room and seating. Awesome bath tub

Yellow Door Inn
The Yellow Door Inn was exactly what I needed for my little getaway from the craziness of my life!! You are surrounded by art, and comfort that is difficult to find. I felt at peace the moment I arrived and my doggos also loved the large yard and access to the Salem Art Works!! Klara and Greg are great hosts, they responded very quickly and were so so kind to me during my stay. If you are staying in Salem, I would 1000% recommend the Yellow Door Inn. You will not regret it! I know I will most definitely be back next time I stay in the area. It was hard for me to leave and head back home, because I felt I was already home…

Rock River Retreat: VT Oasis Pet Friendly
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.
Family-friendly apartment rentals

Main St Escape | Explore Downtown Ludlow
Clean, great location, easy check in/out, and friendly host - would definitely stay again.

Summer Dream! The Handle Lodge at Snowtree Condos
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

Okemo Clock Tower Base Ski-in/Ski-out Condo
We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

Updated Ski in/Ski out Stratton Condo!
Caitlyn An excellent host quick to respond despite moving with her babies the same day as my trip! She was accommodating and provided a clear quick easy in from my late night travel. Her space is large and spacious with great set up lighting and comfortable and clean bedding. Loved the couch bedding set up! The entrance allowed ease to store the ski stuff so roomy keeping the living space free of the typical ski vacay clutter! The bathroom shower temp and pressure with soft towel and wash cloths provided with soap, and shampoo and conditioner gave a nice end of the day relax. Plenty of blankets for layering that may be needed. Kitchen appointed well with a good stove and oven easy to use and to easy prepare with pans and utensils for cooking, plenty of silver ware and plates glasses and plates that i truly appreciated. Couldn't use the ski in/ ski out as that lift was this late int eh season but how easy was it to scoot down in 2 min! Will be my stratton stay always onward!

Great 2 bedroom condo at Stratton Mountain
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

Cozy condo within walking distance to the slopes.
You really can’t beat this location. It’s across the steet from the lifts and the village with lots of restaurants/bars/stores. The space was perfect for our family of four. Our two young children stayed on the pullout and we thought the king bed was quite comfy. We would def stay here again!

Walk to Mt. Snow-Spa-Summer Pool
Great little studio spot to use as your Basecamp for activities in the area!

Private & Quiet Studio Apt. in Vermont
We are repeat visitors. Staying here is always a pleasure. The apartment is wonderful. Just as described and perfect for day trips or just staying in. Mary and Lance are friendly and courteous. Hope to be able to stay here again when in the area.
Quick stats about holiday rentals that are kid-friendly in Winhall
Total rentals
80 properties
Nightly prices starting at
₹11,191 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
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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
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Lake George Expedition Park
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area