
Kid-friendly holiday rentals in Bennington County
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Top-rated family-friendly rentals in Bennington County
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Kid-friendly house rentals

Modern meets Country Cottage in Manchester Village
Great location to the town center and Shaw supermarket; the Equinox Resort was walkable. We were welcomed with a bottle of wine and a couple of beers, and informative note. The host was communicative and addressed any of our needs. The cottage was neat, well stocked with essentials, and the Queen bed comfortable; we only used 1 of 2 bedrooms . We brought our dogs and we appreciated that .

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

Quaint One-Story Vermont House with Mountain View
This is a great place to stay convenient to Bennington, Manchester and Brattleboro plus Williams and the Clark Museum and it’s a quick drive to a great coffee shop in North Bennington Pangaea which has homemade donuts on Sunday mornings.

Modern 3-bedroom A-frame in Londonderry w/ Pond
We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

Vermont Sugar House Retreat
This home is certainly one that feels like home when you walk in the door! The warmth of the wood and decor, and little touches throughout, let us know how loved this home is. We had everything we needed for our 2-plus week stay, and our hosts were incredibly responsive and kind. It was lovely to hear the owls and running water at night, and I can imagine how lovely the fireplace would be to use during the colder months! Thank you for a lovely stay!!!

The Gate House--Experience Vermont!
Pictures don't do Peter & Monique's listing justice. The home, the grounds & the surroundings are gorgeous in a way that isn't just picturesque but is peaceful & rejuvenating. Our family of 4 were staying here to attend the Williams reunion so we didn't get as much time as we would have liked to take full advantage of all the hikes, walks etc that the property location offered & almost wish we'd had more time. The AirBnb is exceptionally stocked, we've stayed in AirBnbs in the country & abroad & rarely do hosts provide things (like linens, coffee supplies etc) in adequate amounts let alone in excess of what might be needed for the number of guests X days being spent there. Not only were the hosts extremely generous but the quality of everything was excellent. We have family in different parts of MA and we asked the hosts if it was OK for our family to visit us at the property during the day & they graciously allowed that. Peter was extremely responsive & thoughtful in communications.

Wilmington. Easy walk to center of town.
This place was very clean and matched the photos. It was a great deal for 3 bedrooms with large beds in each room. It’s very comfortable. I got a quick response when I wanted to double check about parking. Wilmington is a nice area and much more affordable than northwest Massachusetts. It’s the perfect location to get to so many areas up that way. This is a main road, like described, and the trucks can be a little loud going by, it does shake the house a little. You don’t really hear it unless you’re in the living room or front bedroom. My mom is a senior and was a bit nervous about walking to the center of town, it’s just minutes away but there is no sidewalk and people do drive fast here. Just something to keep in mind if you have small children or seniors with you. You can drive, there are public lots so it’s no big deal.

Wilmington A-Frame- Cozy and Convenient
This spot is absolutely perfect to be on a quite spot to enjoy nature but still right within walking distance of the center of Wilmington. The cabin itself is beautifully appointed, gorgeous, and super comfortable. Due to rain we ended up spending most of our time inside relaxing and watching movies, and have zero regrets about it. The host was also extremely friendly, helpful and responsive. I'll definitely be coming back again and recommend this for a Wilmington get away weekend!
Family-friendly apartment rentals

**Happy Hour! Gorgeous & Modern Downtown Retreat**
This place was absolutely awesome!! There’s a lake right down the street, we got in some good fishing over there😁 there’s also a dispensary and liquor store downstairs. Hands down the coolest dispensary I’ve ever been in. Also, love the golden retriever in the liquor store!! The flea market was right down the street as well as a small pink colored coffee shack. They had the best iced lattes and they use espresso cubes for ice! Can’t wait to go back!

Arrowhead Stays - Downtown Manchester Vermont
We had another great stay (our third) for a weekend in Manchester. We love the walkability of the location, and the weather even turned out to be better than the forecast. It was nice and cool inside, despite being quite hot for mid-May. We will be back!

Quiet Getaway in Equinox Valley
If anyone is looking for a quiet stay in the country with beautiful views, large apartment, fully stocked kitchen and a comfy bed, then this is the place to stay! The view from the living room is spectacular! We loved our stay here, close to beautiful Manchester VT with its restaurants and bars, art, etc. Mark is very responsive to all questions, even helping us find local music to enjoy during our stay. We especially enjoyed driving through a local farm on the quiet road to the Airbnb, even encountering the mama sow pig and her piglets in the road one time! Thank you Mark and Allison. You are great hosts. We wish we could have stayed longer.

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.

Globetrotter Retreat too - Minutes to the Mountain
Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

Peace Street Guest Apartment
We have booked this place to stay for a friends wedding. Place was close to location, easy to find, cute and clean. We had a wonderful stay. Would highly recommend.

Style and Comfort- Perfect Year Round Location
We loved everything about this place!! We arrived after setting up an outdoor event so we were slightly disappointed that the A/Cs weren’t in yet but it was nice and cool anyway and we didn’t miss them all weekend. Overall a wonderful stay and will absolutely be on our list of possible places for next year!

Vermont barn apartment
This is a return visit to Pam's place. It was exactly as I remembered it. A magnificent setting in a beautiful part of VT. The space is sweetly decorated and accessorized in an appropriate horse theme. Everything is in pristine condition. The cleanliness is matchless. Fully equipped as described. A bed that's hard to get out of in the morning!! Pam takes this business seriously and is a consummate professional - at the same time warm and welcoming.
Family-friendly apartment rentals

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim
We stayed at Julia's vacation rental for a 3-day weekend with our four children under the age of 12. The things that were great: 1) the unit is 150 foot walk in ski boots from a ski trail that will take you to the Mount Snow lift, which was great because we didn't have to shlep 4 kids ski gear, 2) the four kids loved the bunk bed room and were comfortable, 3) there are two large shelves of board games the kids enjoyed, 4) the access to the Sports Center which has a heated indoor pool and hot tubs were a great way to end the day after skiing, 5) the outdoor locker was a great place to dump all the ski gear (much better storage location than inside the car or inside the unit) and 6) very nice fluffy towels and bed sheeting was comfortable. A combined liquid shampoo and body soap is provided in each bathroom, which is the same that we use to bath our kids at home.

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.

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!

Condo w/ great amenities 4-seasons! Ski in Ski out
Christine was a great host. The condo was as described. The place was clean and well organized, very cute and cozy. Christine was very responsive and helpful. I will definitely stay here again.

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!!

Stratton Mountain vacation spot
We had a great stay at this cozy condo, perfectly located on a shuttle route to Stratton Mountain. The convenience of being just minutes from the slopes made our ski trip stress-free.

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!
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pico Mountain Ski Resort
- West Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Lake George Expedition Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Bousquet Mountain Ski Area
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area
- Canterbury Farm