
Family-friendly vacation 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
Family-friendly home rentals with a hot tub

The Rabbit Hole - Luxury Cabin in heart of Stowe
Absolutely perfect house for the bachelorette party of 10 girls!! It was clean, cozy, spacious, and close to all Stowe has to offer! It slept all 10 adults very comfortably, the fireplace in the living room was lovely, the front porch was so comfortable and a great spot to gather on while some were in the hot tub! Massive driveway, plenty of parking, house was fully stocked with towels and kitchen appliances. We got a ton of snow while we were there and Ryan shoveled our porch and plowed the driveway! The decor and lights throughout the space were beautiful, so welcoming and inviting. We had the best weekend and can’t wait to come back!

Camp Serenity
We loved this cabin! Everything was updated but felt cozy and has an authentic Adirondack feel. The hot tub was a hit after long ski days and the beds were very comfortable. Stacy is a great host and this is an awesome home!

Apartment, comfy and cozy with kitchen/gas fire
Rebecca’s air bnb is awesome in a great location and she truly goes the extra mile for her visitors.

The Brookside @ Wilmington, NY
An incredibly beautiful home! It was spacious, clean and had everything we needed. Doug is a fantastic host. We asked if we could get some firewood and within ten minutes he brought some to the house for us. He even installed a baby gate at the top of the stairs so our little guy was safe. This is by far one of our favorite rentals in Wilmington. We are looking forward to coming back soon!

Canary Cabin
Our stay at Canary Cabin was truly wonderful! It’s a perfect private location that is close to town and anything you may need! The place was clean and so many details made it cozy and comfortable. The kitchenette was perfect for a small breakfast and dinner. The hot tub was the best way to end the day. Thank you Amy for your hospitality! We will be back!

Killington ski house winter MTbike -new jacuzzi
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend

Peaceful setting with Mountain Views
Home away from home! Susan was a fantastic host. She was very responsive and communicated quickly. This home was perfect for our group of 6 and it was extremely cozy! This was our first time in Vermont and it definitely exceeded all of our expectations. If you looking for a pleasant place to stay with amazing views, look no further than this adorable Airbnb! We skied in Stowe, toured the Ben and Jerry’s ice cream factory down the road and enjoyed some live music at the ZenBarn. I would highly recommend this property! We hope to visit again soon :)

#7 - Hemlock Hideaway Cabin
Home now after a couple days at the cabin. Feeling fully rested and can’t express enough how much we needed this getaway. Ago and Marty go above and beyond to make you feel comfortable and provide you with everything you could need to relax and have a great time. We will be coming back here. Hopefully soon.
Family- and pet-friendly home 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.

Fox Hollow on Sentinel
Our second stay at Fox Hollow. Great location next to town. Beds and baths worked well for us. Access to trails and sledding out the back of the property was great. The front porch puts you in a special place and mood. J

Placid Point-Walk Downtown
Had a great week at Chad’s property. Felt right at home and had all of the amenities we needed for our family and dog. Close to downtown, plenty of space, clean and he was very easy to communicate with and fast to respond. Appreciate it!

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!

The Sunrise Cabin
Ian’s place was a dream. Such a beautiful spot and cozy cabin. I mean, you couldn’t ask for a more beautiful view. We even saw an otter out on the shore! Quiet, peaceful, beautiful. Any nature lover’s dream plus close enough to the city to go see and do. I would 100% stay here again.

Entire 2nd Floor Walk to Montpelier
Felt right at home. A nice spacious place for us to stay on our way to Montreal.

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.

The Sanctuary: 3 Bedrooms, Easy Walking, +Parking!
Erinn was very polite and helpful. The place was clean and was exactly as advertised. Great location, walking distance from bars, restaurants, and the city plaza. Overall a great experience from the quality of the apartment to communication with host, as well as a great location in the city. Would definitely stay again if I was going back!
Family-friendly home rentals with a pool

Luxury 1 Bedroom at Topnotch Resort!
Our family had a great time at the Topnotch Resorts. The unit was cozy and clean with everything we needed. It was great to have access to a washer and dryer to throw in the ski clothes from the day. The indoor pool and hot tub facility was beautiful with fresh towels available and and a family changing area. The outdoor pool and hot tub were also awesome with a view of the mountains in the background. Kelly at the front desk was a complete pleasure to work with. She answered all of our questions promptly and went above and beyond to help us and made sure our stay was amazing. We will be back!

Chilson Brook Alpacas
I keep coming back as it is a great place, everything is top notch and the hosts are such good people. Highly recommend it if you want a perfect get away

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

Relax in Recreation Paradise!
Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!

Lodge At Spruce Peak Alpine Studio Pool / Mt Views
PERFECT winter getaway! The location was amazing…our room had a wonderful view of the mountain, pool and hot tub. The resort itself was beautiful-great staff! Nice shops, excellent dining and bars! And, of course-snowboarding! Will definitely return! Can’t say enough about Stowe Mountain Resort! AWESOME!

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

Ski in Ski out - fantastic location on the trail
Just awesome. Slopeside access, close to Tram Side and right on Grammy Jay which was easy for the littles to get the day started on the way to the double. When it was cold (once) we used the fireplace and the condo warms up quickly. Plenty of hot water. A near perfect stay. Fantastic!

Theatre in the Woods - Stowe, VT
We love our stay. Kitchen was well stocked which made cooking easy. Bathrooms were spotless. Kids loved the games. TVs were huge and we enjoyed watching movies after a long day skiing. Very convenient to ski Stowe. The pool, hot tub and sauna at the community center were great!
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