
Kid-friendly vacation rentals in Chesterfield
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Top-rated kid-friendly rentals in Chesterfield
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Popular amenities for Chesterfield kid-friendly rentals
Kid-friendly house rentals

Cozy home Lake Placid Village
The house was cheerful and pristine. It was well stocked and the linens & bedding were great quality. The house size was perfect for 5 or 6 people and we enjoyed it immensely. The house was very clean and well kept. There was a nice outside deck area with a fire pit and chairs, and we found it very pleasant.

Quiet neighborhood oasis
This was our first stay in the Leonard Ave location. Kevin met us at the house and showed us everything. There were a few items that were needed and Kevin took care of those immediately. His communication was excellent and we enjoyed our stay. There were 9 of us and the accommodations were exactly what we needed! We will absolutely book again!

Lake Dunmore Home close to skiing & Middlebury
This is our third stay at Kevin’s place. It is a home that has brought wonderful family memories for us over the years. The stunning lakefront views, large porch area and sleeping arrangements are perfect for two small families. The game area is perfect for a few drinks and dock on the lake perfect for fishing!

Walk to town-Greenwood Cottage in Lake Placid
I went for a winter trip with my family. The place is really well located. Extremely clean. Had all the amenities that I needed.

3 BR House near Burlington
Great house and location was easy to get to, close to airport, and events.

Gorgeous 1835 Farmhouse w. Lake/MTN Views!
It is a beautiful house where you can smell the family and we liked that a lot. It is close to the ski slopes, very clean and comfortable. Lidsa and Tom have very good communication, excellent service.

The McKinley House
We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!

Hardy Rd Adventure House-50acres & private trails!
Emily was an amazing host with easy and clear instructions. The views were amazing and the location was spacious
Family-friendly apartment rentals

Private apartment
Great location. Short walk to the Main Street. House was clean.

Central Lair
Relaxing, elegant, like a peaceful forest. There's games and toys, things to read and listen to, everything we needed to make and serve food from the markets right nearby. Beautiful space in a beautiful place.

Bright & Modern Near Main St – Perfect Location!
Lovely place to spend a snowy week w/ our toddler in Lake Placid. Second time staying here and Angela was very responsive in making our stay cozy. Easy walk to downtown shops and restaurants :)

Cozy NNE 5 Star Apartment
Our two night stay at Kent’s was absolutely wonderful! Kent was charming, friendly, and gave us great recommendations for places to eat. The apartment was cozy and welcoming, with great attention to meeting guests’ needs. We could not have asked for a better place to spend the weekend and have every intention of going back again!

Lake Champlain and Adirondack Views
June’s place is nice and cozy, great amenities including washer/dryer, beautiful views of Lake Champlain and Adirondack mountains. June was a responsive host and helped us get in to her place last minute with ease.

Funky apartment near Lake Champlain
Cozy space, lovely hosts! Our arrival was perfectly timed with a snow storm. Our hosts were kind, flexible, friendly, and very easy to communicate with. The space is warm and colorful, with a nicely functional kitchen. The area is easily walkable from lakeside to Church St shops, even in snow. As others have mentioned, there is a decent amount of sound bleed between the guest and host spaces, but it was not a problem for us. Pretty typical for an older house, and adds to the coziness. :)

Olympic Village 2 Bedroom Apartment
Great stay! Close to town, easy to find with plenty of parking. Friendly and responsive host with easy check-in and check-out instructions. Cozy in winter, kitchen has everything you need small but cute. Bathroom was fine, all the basics and a little heater, which was great. Beds were comfy and it was quiet. Would definitely stay again!

Whiteface View Retreat STR # -200022
We had a wonderful stay. The apartment was perfect for 4 people and a dog for a weekend trip. Having a place right down the stairs to take the dog to use the bathroom made it much more convenient than a hotel. We spent most our weekend outside or exploring downtown Lake Placid which was just a few minutes away so the location was perfect. The apartment was clean and well maintained.
Family-friendly condo rentals

Spacious Stowe condo Amzing views w/shared hot tub
great place close to Stowe.

Another Day in Paradise at Sugarbush Mountain
What an awesome place!! This is the perfect spot for a great weekend at Sugarbush. I can’t wait to stay here again next year!

2 bed, 2Bath, fireplace, pool, amazing location!
We had a great visit to Stowe. Danielle’s place was great, great location, easy logistics and perfect for a few days of skiing.

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO
Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy

Renovated 4-bedroom House: Hot Tub & Outdoor Space
The condo was excelent. Plenty of space, clean, and well organized. The condo has lots of dishes, pots, pans, cups which made it easy to cook. The grill was in good condition and located perfectly on the balcony. Josh was very responsive and flexible. He gave very clear instructions and the expectations for checkout were very reasonable and easy to complete. Great place to book if you are bringing children and pets! Plenty of yard space for them to play. The location is a close to drive stowe for skiing and to ben and jerrys factory for a fun family acitivty. I highly recommend this location!!

Family condo ski in/ski out Bolton main lodge!
Great view of the mountains across from the trails! Beautiful sunset from the balcony. Jetted bathtubs were appreciated too!

Renovated Condo(unit #10) 3 Miles from Mtn
We had a great weekend getaway! Close to Sugarbush for skiing, surrounding towns and restaurants! Would highly recommend a stay here.

Family Friendly Large Condo at Smuggler Notch
We had a great stay. The condo is spacious, and the toys were a big hit with the kids. The location is as advertised - right in the heart of Smuggler's Notch and a short walk to the village and Morse Mountain chairlifts. Getting to / from any part of the resort is a breeze with shuttle service available right outside the building. Having access to the unit's ski locker at the ground level is a big help, and there are plenty of coat hangers as well as ample space to store boots, helmets, etc. It's an ideal place and set-up for a Smuggler's notch ski trip.
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- Sugarbush Resort
- Smugglers' Notch Resort
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