
Kid-friendly holiday rentals in Bennington County
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Top-rated kid-friendly rentals in Bennington County
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Child-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 .

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.

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.

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!

The Gate House--Experience Vermont!
What an amazing place! We were struck by its charm the moment we arrived. Everything was so well appointed and beautiful. We just wish we could have stayed longer and explored Bennington more! We came for a Williams College graduation and so the weekend was busy but we had some wonderful meals together at the house and also a little time to explore the countryside around. We hope to come back to this magical place sometime soon!😊

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!!!

Summit View Ski and Golf Retreat w/hot tub & Sauna
The home is gorgeous - thoughtfully decorated, cozy and clean. The location is perfect for access to Stratton and to Manchester. The host, Jason, provided very clear and helpful instructions for check-in, check-out and use of the home and is friendly and attentive. This is a wonderful place to stay!

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.
Kid-Friendly apartment rentals

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!

**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!

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.

Walk To Wilmington Village
We had a great weekend here! The listing was accurate and the place was cozy and quiet. Just what is needed after a long day at the mountain. Shawn was super helpful and very nice! I highly recommend Shawn and this location.

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.

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.

Globetrotter Retreat - Minutes to the Mountain
We had a great 4 day stay at Nina’s place. The apt is exactly as pictured and described on Airbnb. The space was a nice size, the furniture comfortable with the bed on the softer side, really good Water pressure in the shower, good amount of kitchen ware To create breakfast and lunches and light dinners. We loved the proximity to town and yet how quiet the place was, and there is a river directly in back. Nina was very prompt in responding to questions and gave us great recommendations for hikes in the area. There is a great bookstore and a number of really wonderful gift stores with Vermont artist’s works a block from the apt. And about a mile down the road starfire bakery with truly amazing baked goods. Make it a priority to Go there and try lots of things! We really loved our stay at Nina’s place and hope we can return in the fall or winter.

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!
Child-Friendly Holiday Condos

Mount Snow Ski Chalet
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

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!

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!

3 Bedroom, 2 Bathroom Condo, 2 Mins to Mount Snow!
Great location and perfect house to stay in

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