Kid-friendly vacation rentals in Chesterfield

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Chesterfield kid-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Lake Placid
4.99 out of 5 average rating, 300 reviews

Cozy home Lake Placid Village

LauraRating, 5 stars1 month ago
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.
Top guest favourite
Home in Plattsburgh
5 out of 5 average rating, 9 reviews

Quiet neighborhood oasis

DianeRating, 5 stars4 months ago
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!
Guest favourite
Home in Salisbury
4.95 out of 5 average rating, 106 reviews

Lake Dunmore Home close to skiing & Middlebury

HolleyRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Lake Placid
4.91 out of 5 average rating, 114 reviews

Walk to town-Greenwood Cottage in Lake Placid

SuzanaRating, 5 stars1 month ago
I went for a winter trip with my family. The place is really well located. Extremely clean. Had all the amenities that I needed.
Guest favourite
Home in South Burlington
4.9 out of 5 average rating, 184 reviews

3 BR House near Burlington

DianeRating, 5 stars7 months ago
Great house and location was easy to get to, close to airport, and events.
Superhost
Home in Grand Isle
4.87 out of 5 average rating, 156 reviews

Gorgeous 1835 Farmhouse w. Lake/MTN Views!

Maria Del CarmenRating, 5 stars4 months ago
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.
Guest favourite
Home in Rochester
4.95 out of 5 average rating, 196 reviews

The McKinley House

GarethRating, 5 stars2 months ago
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!
Top guest favourite
Home in Wilmington
4.98 out of 5 average rating, 160 reviews

Hardy Rd Adventure House-50acres & private trails!

JackeyRating, 5 stars2 months ago
Emily was an amazing host with easy and clear instructions. The views were amazing and the location was spacious

Family-friendly apartment rentals

Guest favourite
Apartment in Lake Placid
4.95 out of 5 average rating, 146 reviews

Private apartment

KbRating, 5 stars2 months ago
Great location. Short walk to the Main Street. House was clean.
Guest favourite
Apartment in Burlington
4.93 out of 5 average rating, 199 reviews

Central Lair

BrettRating, 5 stars2 months ago
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.
Top guest favourite
Apartment in Lake Placid
4.94 out of 5 average rating, 101 reviews

Bright & Modern Near Main St – Perfect Location!

AdamRating, 5 stars2 months ago
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 :)
Guest favourite
Apartment in Burlington
4.96 out of 5 average rating, 136 reviews

Cozy NNE 5 Star Apartment

LaurieRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Burlington
4.97 out of 5 average rating, 218 reviews

Lake Champlain and Adirondack Views

NumanRating, 5 stars6 months ago
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.
Superhost
Apartment in Burlington
4.85 out of 5 average rating, 343 reviews

Funky apartment near Lake Champlain

EricaRating, 5 stars2 months ago
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. :)
Top guest favourite
Apartment in Lake Placid
4.96 out of 5 average rating, 233 reviews

Olympic Village 2 Bedroom Apartment

CarolineRating, 5 stars1 month ago
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!
Top guest favourite
Apartment in Lake Placid
4.91 out of 5 average rating, 353 reviews

Whiteface View Retreat STR # -200022

CaseyRating, 5 stars1 month ago
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

Superhost
Condo in Stowe
4.81 out of 5 average rating, 284 reviews

Spacious Stowe condo Amzing views w/shared hot tub

JeffRating, 5 stars1 month ago
great place close to Stowe.
Guest favourite
Condo in Warren
4.92 out of 5 average rating, 147 reviews

Another Day in Paradise at Sugarbush Mountain

MorganRating, 5 stars1 month ago
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!
Guest favourite
Condo in Stowe
4.86 out of 5 average rating, 153 reviews

2 bed, 2Bath, fireplace, pool, amazing location!

RichardRating, 5 stars1 month ago
We had a great visit to Stowe. Danielle’s place was great, great location, easy logistics and perfect for a few days of skiing.
Top guest favourite
Condo in Warren
4.97 out of 5 average rating, 128 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

PedroRating, 5 stars2 months ago
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
Top guest favourite
Condo in Stowe
4.96 out of 5 average rating, 114 reviews

Renovated 4-bedroom House: Hot Tub & Outdoor Space

ToskaRating, 5 stars2 weeks ago
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!!
Guest favourite
Condo in Richmond
4.92 out of 5 average rating, 37 reviews

Family condo ski in/ski out Bolton main lodge!

StephenRating, 5 stars1 month ago
Great view of the mountains across from the trails! Beautiful sunset from the balcony. Jetted bathtubs were appreciated too!
Superhost
Condo in Warren
4.83 out of 5 average rating, 23 reviews

Renovated Condo(unit #10) 3 Miles from Mtn

JohnRating, 5 stars2 months ago
We had a great weekend getaway! Close to Sugarbush for skiing, surrounding towns and restaurants! Would highly recommend a stay here.
Guest favourite
Condo in Cambridge
4.92 out of 5 average rating, 113 reviews

Family Friendly Large Condo at Smuggler Notch

TroyRating, 5 stars1 month ago
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.

Destinations to explore