Family-friendly vacation rentals in Chesterfield

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chesterfield family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A wooden dining table is surrounded by upholstered chairs, with an antler chandelier overhead. A vibrant artwork featuring a buffalo hangs on the wall, adding color to the white-paneled room. Natural light enters from an adjoining living area, enhancing the space's inviting feel.
Cabin in Stowe
4.93 out of 5 average rating, 353 reviews

The Rabbit Hole - Luxury Cabin in heart of Stowe

KaleyRating, 5 stars4 weeks ago
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!
Guest favorite
A modern kitchen features wood cabinetry complemented by quartz countertops. Stainless steel appliances, including a refrigerator, stove, and dishwasher, are prominently displayed. A small window above the sink allows natural light, while recessed lighting illuminates the space effectively.
Cabin in Jay
4.91 out of 5 average rating, 185 reviews

Camp Serenity

BrookeRating, 5 stars2 months ago
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!
Superhost
The exterior of a spacious home is set against a bright blue sky with fluffy clouds. Flowering plants and grass surround the entrance, creating a welcoming outdoor space. The architecture features various slopes and shapes, highlighting the unique design of the residence.
Guest suite in Jericho
4.74 out of 5 average rating, 288 reviews

Apartment, comfy and cozy with kitchen/gas fire

ZachRating, 5 stars1 month ago
Rebecca’s air bnb is awesome in a great location and she truly goes the extra mile for her visitors.
Top guest favorite
The exterior of a two-story home is shown, featuring dark wood siding with red accents. Snow covers the ground in front, while a wooden balcony extends from the upper level. Ski equipment leans against the house, and a few evergreen trees are visible in the background.
Home in Wilmington
4.96 out of 5 average rating, 233 reviews

The Brookside @ Wilmington, NY

LaurenRating, 5 stars2 months ago
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!
Guest favorite
A spacious outdoor area is surrounded by lush greenery, featuring a well-maintained lawn. Various structures, including the cabin and a garage, are visible, with a tree providing shade. A paved driveway leads into the property, enhancing accessibility to the outdoor space.
Cabin in Saranac Lake
4.77 out of 5 average rating, 452 reviews

Canary Cabin

BrynnaRating, 5 stars1 week ago
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!
Guest favorite
A well-lit outdoor Jacuzzi features soothing water jets, creating a relaxing ambiance. The water is illuminated with soft lights, enhancing the tranquil setting. Visible edges and seating areas allow for comfortable relaxation. Surrounding space remains dark, emphasizing the warm glow of the Jacuzzi.
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars1 month ago
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
Guest favorite
A comfortable living area features a light-colored sectional sofa, two armchairs, and a wooden coffee table. Natural light fills the space through large windows with wooden blinds. Artwork and framed photos decorate the walls, while a piano is positioned near the window.
Home in Waterbury Center
4.96 out of 5 average rating, 131 reviews

Peaceful setting with Mountain Views

HallieRating, 5 stars2 months ago
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 :)
Top guest favorite
A hot tub is positioned on a covered porch, with steam rising over the water. Colorful chairs are visible in the snow-covered landscape, framed by tall pine trees and distant mountains under a partly cloudy sky.
Cabin in Ripton
5 out of 5 average rating, 106 reviews

#7 - Hemlock Hideaway Cabin

ChrisRating, 5 stars2 months ago
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

Top guest favorite
A charming two-story house with a sloped roof is surrounded by greenery. A welcoming wooden porch features Adirondack chairs, inviting relaxation. The front yard is spacious and well-maintained, enhancing the overall appeal of the home.
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.
Superhost
A living area features a plush leather sofa with decorative pillows, a wooden coffee table, and a TV console. Warm wood flooring complements the cozy atmosphere. Natural light filters through the front windows, and a welcoming entrance can be seen in the background.
Home in Lake Placid
4.82 out of 5 average rating, 173 reviews

Fox Hollow on Sentinel

JohnRating, 5 stars3 months ago
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
Guest favorite
A custom home nestled among lush greenery features a detailed wooden exterior with blue accents. Spacious windows allow natural light to enhance the inviting façade, surrounded by an array of plants and trees that create a tranquil setting.
Home in Lake Placid
4.96 out of 5 average rating, 148 reviews

Placid Point-Walk Downtown

BruceRating, 5 stars1 month ago
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!
Guest favorite
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!
Superhost
The image captures a view of the shoreline of a scenic lake, where the water appears choppy under a cloudy sky. Trees line the edge of the shoreline, with some areas illuminated by sunlight, revealing the textures of land and foliage.
Cabin in Burlington
4.83 out of 5 average rating, 506 reviews

The Sunrise Cabin

AbbyRating, 5 stars6 months ago
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.
Guest favorite
A welcoming porch is presented with a rocking chair and small side table. Hanging planters add greenery, while a flower basket enhances the inviting atmosphere. The wooden flooring is complemented by a small welcome mat, creating a cozy outdoor space for relaxation.
Apartment in Montpelier
4.87 out of 5 average rating, 696 reviews

Entire 2nd Floor Walk to Montpelier

IanRating, 5 stars1 week ago
Felt right at home. A nice spacious place for us to stay on our way to Montreal.
Top guest favorite
A scenic view showcases a distant mountain against a clear blue sky, with vibrant red and orange trees in the foreground. A white fence lines a grassy area, and sports fields can be seen in the background, enhancing the natural landscape.
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.
Superhost
A bright living area features a dark sectional sofa adorned with patterned pillows. Sunlight pours in through skylights and windows, illuminating the cozy space. A wooden coffee table and a floor lamp enhance the inviting environment, while the walls display a neutral hue.
Home in Burlington
4.84 out of 5 average rating, 477 reviews

The Sanctuary: 3 Bedrooms, Easy Walking, +Parking!

KyleRating, 5 stars2 weeks ago
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

Superhost
A cozy living area features a dark leather sofa, a plush area rug, and a comfortable armchair. French doors lead to an outdoor view, while a dining table for four is positioned nearby. Wall decor complements the warm tones of the space.
Condo in Stowe
4.79 out of 5 average rating, 137 reviews

Luxury 1 Bedroom at Topnotch Resort!

ChrisRating, 5 stars2 months ago
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!
Top guest favorite
A clear blue pool is surrounded by a stone patio and lush green landscaping. Two lounge chairs are positioned nearby. A flagpole is visible in the background, and a hanging planter adds a touch of color.
Guesthouse in Ticonderoga
5 out of 5 average rating, 210 reviews

Chilson Brook Alpacas

DavidRating, 5 stars6 months ago
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
Superhost
A clean bathroom features a light-colored countertop and a sink, accompanied by a towel neatly folded beside it. A colorful shower curtain with intricate patterns enhances the space, while a full-length mirror reflects the room's details. Light-colored tiles cover the floor.
Condo in Stowe
4.81 out of 5 average rating, 284 reviews

Spacious Stowe condo Amzing views w/shared hot tub

JeffRating, 5 stars4 weeks ago
great place close to Stowe.
Top guest favorite
A breathtaking view showcases the sun rising above the horizon, casting warm orange and yellow hues across the sky. The silhouette of Camel's Hump is visible in the distance, framed by softly illuminated clouds. The scene evokes a sense of tranquility and natural beauty.
Apartment in Barre
4.94 out of 5 average rating, 163 reviews

Relax in Recreation Paradise!

JenniferRating, 5 stars1 month ago
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!
Guest favorite
Home in Stowe
4.88 out of 5 average rating, 257 reviews

Lodge At Spruce Peak Alpine Studio Pool / Mt Views

SevastiRating, 5 stars2 months ago
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!
Top guest favorite
A children's playground is set among trees, featuring various climbing structures and slides. In the foreground, a gas grill is positioned on a grassy area, offering a convenient cooking option. Sunlight filters through the leaves, creating a pleasant outdoor environment.
Condo in Warren
4.97 out of 5 average rating, 128 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

PedroRating, 5 stars1 month 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
Guest favorite
A balcony features two canvas chairs positioned on a wooden deck. A view of vibrant autumn foliage is visible, with trees displaying shades of orange and yellow against a clear blue sky and scattered clouds.
Condo in Jay
4.92 out of 5 average rating, 160 reviews

Ski in Ski out - fantastic location on the trail

PatrickRating, 5 stars1 week ago
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!
Superhost
A well-lit bathroom features a clean white sink with modern fixtures. A large mirror reflects the space, while striped curtains add a touch of color. Neatly arranged towels hang from a towel ring, and toiletries are placed nearby, enhancing the functional design.
Apartment in Stowe
4.75 out of 5 average rating, 117 reviews

Theatre in the Woods - Stowe, VT

KatieRating, 5 stars1 month ago
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!

Destinations to explore