
Kid-friendly holiday rentals in Chesterfield
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Top-rated family-friendly rentals in Chesterfield
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Kid-friendly house rentals

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4.99 out of 5 average rating, 296 reviewsCozy home Lake Placid Village
We stayed at Andy’s place for 3 nights during the Empire State Winter Games and had a great experience! The location was close to the Olympic Center/main street and the house was exactly as described- the 3 full bedrooms were a huge plus. Andy also stocked coffee, snacks, and condiments in his kitchen which was a great help during some early mornings! He was very responsive before and during our stay and was flexible with checkin/checkout which we really appreciated- his asks for checkout were also minimal and reasonable. Thanks again to Andy for this great listing, from 3 very grateful figure skaters!

Home
4.95 out of 5 average rating, 101 reviewsLake Dunmore Home close to skiing & Middlebury
This is our second time staying here and, as always, it's a beautiful place with a wonderful host. The house is always clean, comfortable and well thought out. Our go to place for our yearly trip!

Home
4.91 out of 5 average rating, 112 reviewsWalk to town-Greenwood Cottage in Lake Placid
Great location! Love the walks to town and easy ride to Whiteface Mountain. Great host.

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4.86 out of 5 average rating, 155 reviewsGorgeous 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.

Home
4.95 out of 5 average rating, 192 reviewsThe McKinley House
Great stay! Cozy with spacious kitchen. Hosts were responsive and generous. 30 minutes to Killington! Would book again!

Home
4.98 out of 5 average rating, 157 reviewsHardy Rd Adventure House-50acres & private trails!
Loved the large space, beautiful property and how close it was to the ski hill. Kitchen had everything you need for a large group. So many fun games. Lots of spots for sleeping with a group of 7 adults. Overall, we loved our time there.

Home
4.98 out of 5 average rating, 313 reviewsBear Cub Lodge- An Adirondack Mountain Retreat
This is our second stay and we would absolutely stay again if we return to the area. The house is very clean, comfortable and well-equipped. Liz is a friendly and responsive host, and we appreciated her flexibility with our check-out time. There are snowshoe/ski trails right out the back door and Mount VanHovenburg and Lake Placid are only minutes away. It's a great place, we hope to be back. Thanks Liz!

Home
4.85 out of 5 average rating, 134 reviewsThe Paddle Inn
The Host ability to be there for the people staying at their locations! If there is any accolade above super host they are the ones that should have it!! Lovely stay, quick response if help is needed, willing to accommodate if any challenges arise
Family-friendly apartment rentals

Flat
4.95 out of 5 average rating, 144 reviewsPrivate apartment
Peggy’s place is the best!!!! This is our 5th year & we already booked for 2/26!!!!! Very centrally located, & only 20 minutes to Whiteface!!!!! Peggy is a true local who has great suggestions & is also very responsive!!!! Stayed there in summer as well as winter though winter is my favorite! Lake Placid + Peggy’s house = a great time!!!!!

Flat
4.93 out of 5 average rating, 197 reviewsCentral Lair
I've been to Burlington many times to visit my son and Lori's place is my favorite! So cute and comfy, clean and inviting! The charms of an old house but updated for modern convenience. Her attention to detail is quite evident making our experience even better, things like yummy snacks, chocolate on the bed, water filter in the fridge, great towels. I loved the Zebra kitchen so much! It's in a great location, close to downtown. The stairs to access the apartment are quite steep as she shares in her description, something to keep in mind, but we managed fine. Thank you Lori! We will be back!

Flat
4.96 out of 5 average rating, 134 reviewsQuaint NNE Apartment
Kent’s place was perfect for our 2 days in Burlington. It had everything we needed and Kent even included some eggs, English muffins, cereal, coffee, and milk for our breakfast. He really went above and beyond to make guests feel at home. Would definitely recommend and would love to come back!

Flat
4.97 out of 5 average rating, 218 reviewsLake 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.

Flat
4.84 out of 5 average rating, 341 reviewsFunky apartment near Lake Champlain
Comfortable for a short stay, walking distance to downtown

Flat
4.96 out of 5 average rating, 225 reviewsOlympic Village 2 Bedroom Apartment
Great place to stay, the place was cozy and clean and it was a quick easy to walk to anywhere on Main Street.

Flat
4.93 out of 5 average rating, 230 reviewsWalk Downtown | Private Balcony | Parking |Netflix
Lea was a phenomenal host! She provided clear instructions for how to enter her gorgeous home, proactively reached out to make sure we were able to get in, and thoughtfully reminded us about check-out timing and instructions. The place is exactly as pictured, in a lovely neighborhood with a private parking spot in a driveway, just a stone’s throw from a park if you’ve got a pup, and a slew of amazing restaurants. It was the perfect spot to stay in and I hope to repeat it the next time we’re in Burlington!

Flat
4.85 out of 5 average rating, 113 reviewsQuiet & Cozy 2bdrm walk anywhere pet friendly
Review for Our Wonderful Stay in Winooski, Vermont ⭐️⭐️⭐️⭐️⭐️ We recently had the pleasure of staying at Errin’s charming Airbnb in Winooski, Vermont, and I can confidently say it exceeded all our expectations! From the moment we arrived, we were greeted by a warm and inviting atmosphere that made us feel right at home. The space was impeccably clean and very comfortable, providing us with everything we needed for a relaxing family getaway. We loved the quiet surroundings, which allowed us to unwind and enjoy some quality time together without the hustle and bustle of everyday life. Our hostess was fantastic—super responsive and provided us with all the information we needed to make our stay enjoyable. Her recommendations for local attractions and dining were spot on! We had a great time exploring Winooski and the surrounding areas, and we can't wait to return. We would absolutely rebook & highly recommend.
Family-friendly apartment rentals

Apartment
4.87 out of 5 average rating, 141 reviews2 bed, 2Bath, fireplace, amazing location!
Perfect ski trip with my 23 yr old son at Danielle’s lovely place. Fireplace was perfect after long days skiing at Stowe. 2 bedrooms and 2 baths gave us our own space which was great. Walked to nice local restaurants and coffee shop/ bakery. This place and its location is what I love about visiting Vermont. Danielle was an excellent host and there were zero negative issues with this very nice condo. It was clean and in a great location. Beds comfortable. Definitely hope to be back soon. Thanks Danielle!

Apartment
4.97 out of 5 average rating, 124 reviewsTWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO
My two sons (26 and 28) and I had a fantastic 3 night stay over Super Bowl weekend. The condo was recently renovated, spotless, and exceeded expectations. The clear view of Mt Lincoln was an unexpected surprise. Communication with the Host was great, and check-in/check-out process was painless. I would highly recommend this condo.

Apartment
4.96 out of 5 average rating, 105 reviewsRenovated 4-bedroom House: Outdoor Space & Hot Tub
The place was really nice! Recently renovated, big comfy couch, and a hot tub. We packed 12 people in nice and comfortably. Josh was really responsive when we had trouble with the oven too. Great space, great host, great time!

Apartment
4.93 out of 5 average rating, 30 reviewsFamily condo ski in/ski out Bolton main lodge!
My family of six stayed for a week at this AirBnB. When we walked in we were surprised at how spacious it was. There was plenty of cookware as well which made cooking meals easy! The host was very communicative and kind. It was so nice to allow our children the freedom of just going to the mountain with easy access. The space was very comfortable my only “issue” was the beds weren’t the most comfortable (they are spring mattresses) which was an easy fix with putting another blanket down on the bed. I would 10/10 stay here again!

Apartment
4.82 out of 5 average rating, 22 reviewsRenovated Condo(unit #10) 3 Miles from Mtn
Great location. Minutes from the mountain. Great to deal with. Would stay again.

Apartment
4.92 out of 5 average rating, 109 reviewsFamily Friendly Large Condo at Smuggler Notch
Hosts were communicative and provided very clear instructions for everything. The sauna on the top floor was great. It's a short walk to the Morse lifts

Apartment
4.82 out of 5 average rating, 257 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
We had a great stay, everything was as described! Jonathan was great, always got back to us immediately when we had questions and was really accommodating and helpful.

Apartment
4.93 out of 5 average rating, 436 reviewsPico Ski in out 1 bedroom 1 nite Ok free shuttle
Gabe's place was great for our ski weekend at Killington and Pico. A spacious place for our family of four and the kitchen had everything we needed. Super convenient ski location for Pico and a short drive to Killington. Would definitely look to stay again!
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