
Kid-friendly holiday rentals in Chesterfield
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Top-rated family-friendly rentals in Chesterfield
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Popular amenities for Chesterfield family-friendly rentals
Kid-friendly house rentals

"Beau Overlook" Enjoy 2 states from 1 great spot!
Where do I start...from before I arrived, up until my departure...Joanne was attentive in every way possible. All my questions were answered with an immediate response. The home was extraordinary. The effort Joanne has put in to making it just like home shows. With an abundance of whimsical touches. Up until the day I left, I would see a new thing. As if the enchanting home wasn't enough, the back patio is a place of serenity...with the sounds and view of the river extraordinary. I could go on and on, but I will just say, "it was the best vacation I have ever had". One word describes this Airbnb...AMAZING!!!🩷. I will return next year! Didn't want to leave!!! 😊 Thank you Joanne for your exemplary hospitality!

Quiet Adirondack Retreat with MASSIVE Views
We stayed at Roger’s property over the holidays and couldn’t be happier with our choice! Beautiful views, the house was incredible with all amenities. Roger was an incredible host who was the most responsive and helpful owner I have ever dealt with on Air BnB. Thank you Roger for a wonderful stay!

Cozy Adirondack Home w/Private Backyard
We had a great stay overall—this Airbnb was cozy, comfortable, and located in a beautiful, quiet neighborhood. The host was responsive and check-in was seamless. The amenities were as promised, and we truly enjoyed our time there.

Adirondack Home on Fern Lake : The Murphy House
Very spacious, clean, comfortable. Bathrooms and amenities were perfect. This set my standards high for future ski cabins at this price range !

The Blue Jay Aframe
Incredible stay at this beautiful A-frame. The hosts went above and beyond to make us feel at home. They thought of every single detail to make the house feel special. The location was incredible, in the heart of the Adirondack! Really recommend this incredible place!

Adirondack Panther Mountain Retreat
We loved David's home and felt at home during our stay. The area is beautiful, peaceful, and quiet. We felt the hosts were responsive, accessible, and helpful. The home is clean, comfortable, and cozy. We would definitely stay again!

Magical Augur Lake Retreat-Great for Large Groups!
The house was amazing. Enough space for everyone in my group. It was also very cozy, made us feel at home! Gabrielle was an amazing host, communicated well with us. She checked in to make sure everything was okay and if we checked in smoothly.

Enjoy every season in the Lake Champlain Region
Dana is a wonderful home owner. She has a beautiful home in a quiet neighborhood. Its out of town, but close to everything. And has everything you need to make you feel right at home.
Family-friendly apartment rentals

Charlotte Private Studio Apartment with a View
Wonderful place to stay. The place was exactly what we needed for our stay in the area. The unit was very clean, quiet, and the location was great. The host's were very quick to respond to our messages. Highly recommend and would definitely stay again!

Cedar View
My husband and I only stayed 2 nights at Carson's apartment, but it was exactly as described, very clean and looked like the pictures posted. Beautifully decorated and had everything you could need in the cute little kitchen. The bed was comfortable and there were even extra chargers in the bedroom. The mini split heat in the apartment was nice, as it was raining and cold our first night. The location is ideal - quiet neighborhood but short drive to downtown.

River Stone Retreat
The location is perfect with easy access to the Ausable river with brown trout fishing within 100 yards. Meg was friendly and responsive and made sure everything was smooth. Highly recommend for anyone looking for a peaceful Adirondack getaway!

Bright & adorable 1 bedroom studio with parking
Had a great stay—exactly what I was looking for. The place was extremely quiet, very clean, and easy to access. It felt cozy and calming from the moment I arrived. The bed was super comfortable—probably one of the best I’ve slept on. Overall, a peaceful and comfortable experience. Would definitely stay again.

Purple Door Annex
We have visited Burlington and stayed in various Airbnb's several times since our daughter started at UVM 3 years ago. I did not have the pleasure to stay at Chris and Kara's but this was my husbands absolute favorite place!

Sunny, 1 bedroom studio, walk to downtown.
We loved the cozy Airbnb!! Very close to attractions and restaurants. We enjoyed our stay!

Adirondack Backwoods Elegance
We have been there before and really like the setting and the accommodations. The apartment is nicely furnished and Shir has thought of all the essentials. We live in the country too and really value the backwoods setting. It is close to hiking and cross country ski opportunities. There is also a wonderful screened-in porch, though our visits in late October and late February have not been good times to enjoy it. There was also a barred owl around one morning and we were able to get some pictures. It was a perfect place to get away for a few days.

The Bright Space.
We had a great holiday weekend in Charlotte at Robert's apartment. It was close to the mountains we wanted to climb and a nature preserve where we skied. Close to Burlington and Middlebury where we found dinner each night. The apartment is cozy and comfortable; really a delightful place. We also met Robert who was funny and the perfect host. We stayed during a massive winter storm that dumped so much snow on the area and Robert was always very interested in making sure we could get out of the driveway! There were also thoughtful snacks and what not for us when we arrived which is such a nice bonus. We will definitely check to see if the apartment is available the next time we come to VT. Thank you so much, Robert! We hope to stay with you again soon.
Family-friendly apartment rentals

Black Bear's Den in Historic Stowe Center
Cute little place that was a perfect location for our visit to Stowe. Walkable restaurants and stores and even the places we had to drive weren’t far either. The place was very clean and perfect for our group. Would definitely come again!

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!

The maple leaf retreat at Smugglers' Notch Resort
Great place to stay. Beautiful walking trails and very peaceful in the off season. Enjoyed the over the mountain ride into Stowe each morning.

Adirondack Studio Retreat–Cozy Lake Placid Escape!
Nicest bnb we have stayed at in placid! We had the grounds to ourselves and enjoyed sitting by the lake the first night before it rained the rest of the weekend. The place was cozy and the fireplace was nice for the rainy days. I appreciated the snacks and drinks in the room too!

Modern Farmhouse Condo: fast WiFi+close to it ALL!
Great, quiet getaway - perfect home base to explore Stowe from!

Slopeside Condo - Elegant & Cozy - Bike/Hike
My husband and I loved our stay at the slopeside condo. The chair lift is right next to the condo for easy ski access (AMAZING skiing btw). Inside, the condo is so clean and cozy. Emily (the co-host) was very nice and responsive with great local restaurant recommendations. We're already thinking of coming back next year!

Cozy Condominium for Couples @ whiteface lodge
Great experience, loved cross country skiing so conveniently located out the door.

The Green Mountain, Colchester, Vermont
Fantastic place to stay just north of Burlington! Colchester was beautiful and this condo is so close to the bike paths and causeway. Beautiful spot!
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- Sugarbush Resort
- Smugglers' Notch Resort
- Parc Safari
- Bolton Valley Resort
- Spruce Peak
- Cochran's Ski Area
- Fort Ticonderoga
- Autumn Mountain Winery
- Whiteface Mountain Ski Resort
- Country Club of Vermont
- Ethan Allen Homestead Museum
- Vermont National Country Club
- Leahy Center for Lake Champlain
- Lincoln Peak Vineyard
- Burlington Country Club