Family-friendly vacation rentals in Jackson

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Jackson family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.
Apartment in Townshend
4.93 out of 5 average rating, 240 reviews

Private Apt. on Farm, Hot Tub with views!

MathildeRating, 5 stars3 weeks ago
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!
Guest favorite
A captivating sunset paints the sky with hues of orange, pink, and purple, with rolling hills silhouetted in the foreground. The distant mountains create a serene backdrop, accentuating the natural beauty of the secluded setting.
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars3 months ago
Nice place thanks Mike
Top guest favorite
A charming red farmhouse is set against a backdrop of rolling hills and blue skies. The property includes a separate red building nearby, surrounded by lush green grass and a landscaped stone garden featuring colorful flowers and greenery.
Home in Colrain
4.94 out of 5 average rating, 179 reviews

Secluded Farmhouse Retreat - stunning views

ColinRating, 5 stars2 weeks ago
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.
Top guest favorite
The spacious A-frame home is set against a backdrop of vibrant trees and lush greenery. A well-manicured hill leads to the house, which features large windows allowing natural light to fill the interior. The bright blue sky complements the tranquil outdoor scenery.
Chalet in Dover
4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

CaterinaRating, 5 stars3 months ago
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.
Superhost
A rustic living space features wooden beams and warm, ambient lighting. An antique stove serves as a focal point, surrounded by comfortable seating and a wooden table. Shelves filled with various items add character to the cozy atmosphere.
Cabin in Londonderry
4.81 out of 5 average rating, 477 reviews

Stunning Rustic Apple Barn - hot tub & sauna

ChristianRating, 5 stars1 week ago
We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.
Top guest favorite
An open-concept kitchen features a central island with bar seating for two, surrounded by wooden cabinetry and ample natural light from large windows. A dining area with a table for six is visible, complemented by wooden chairs and a cozy living space in the background, showcasing a comfortable setting.
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars3 months ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.
Guest favorite
The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.
Apartment in Londonderry
4.96 out of 5 average rating, 582 reviews

Vermont Getaway Apartment

AshleyRating, 5 stars1 week ago
The getaway apartment was just as described. Peaceful, private, and with ample space and amenities for a family of three. We enjoyed our weekend!
Guest favorite
A modern kitchen features gray cabinets and stainless steel appliances. A large island with bar stools provides casual seating. Natural light enters through the window above the sink and the sliding door, which leads to an outdoor space. Neutral colors create a fresh and inviting environment.
Home in Saratoga Springs
4.98 out of 5 average rating, 124 reviews

Updated Colonial Close to Town Available All Year

NickRating, 5 stars1 day ago
Recently wrapped up a stay & could not have had a better experience! Everything was in well order, Charles was a responsive & active host, and I greatly enjoyed the space as well as Saratoga! The location is super close to everything from downtown, to Saratoga Lake, to the racetrack, & the casino! Really appreciated the warm reception, clear instructions, and professionalism! When working with Charles, you're working with a true pro! Thanks again!

Family- and pet-friendly home rentals

Top guest favorite
A serene pond reflects the cloudy sky, surrounded by lush greenery and tall grasses. The still water enhances the tranquil atmosphere of the landscape, with distant buildings nestled among the trees, completing the rural setting.
Guesthouse in Stephentown
5 out of 5 average rating, 416 reviews

Dog Friendly Studio

LilyRating, 5 stars3 weeks ago
We absolutely loved Maple Hill Farms. It's a wonderful place and a perfect choice for a trip to the Berkshires if you're an animal lover. The best part of our weekend was bonding with Philip's sweet and friendly donkeys! The studio is well laid out with everything you need, the farm is beautiful and peaceful (except for the roosters, haha!), and the location is great for visiting local sights like Mass MoCA and The Mount. We hope to be back!
Guest favorite
A charming exterior is visible with a well-maintained pathway leading to a covered porch. The porch features colorful seating options, and greenery surrounds the area, including shrubs and small trees. A flag hangs proudly from the porch, while a mailbox is positioned near the driveway.
Loft in Wilmington
4.91 out of 5 average rating, 202 reviews

Walk to Village/Lake Whitingham

JuliannRating, 5 stars4 weeks ago
Great little studio apartment attached to Emily’s house, very peaceful yet walkable to downtown Wilmington!!! Easy to get to the Hoot and Toot trail, and about a mile from the boat launch/picnic grove at the lake!! Absolutely would recommend and stay again!!
Guest favorite
A horse is seen galloping on a training track during sunrise, with a rider positioned securely on its back. The sky is filled with soft hues of pink and orange, providing a serene backdrop to the scene. The track is composed of a sandy surface, and gentle greenery is visible in the distance.
Home in Saratoga Springs
4.8 out of 5 average rating, 167 reviews

Entire HOUSE Walk to ALL Dogs OK Track/Spac

CarleyRating, 5 stars1 day ago
Nancy’s place was clean and in a great location. We enjoyed walking downtown for meals and events. She was incredibly communicative and kept us in the loop for all current events, check in/check out instructions and more. Thanks for having us Nancy!
Guest favorite
Chalet in Dover
4.92 out of 5 average rating, 307 reviews

A charming VT chalet

carolynRating, 5 stars2 weeks ago
Mary was a super good hostess and she even left us a welcome basket full of goodies including Bogle red wine (cabernet), coffee, and other treats plus homebred brownies in the fridge! We loved the chalet and the beauty of it inside and out with the greenery of the forest and the brook which our dog, Beau, got right into it and loved it! We all enjoyed the area and the cozy home with the room to spread out and hear the rain as we were snug inside. The bed we chose to sleep in was comfy and warm and I (Carolyn) loved having coffee on the deck of a morning with Beau. We enjoyed our long walks down the road and the town of Dover was fun to visit as well as the beautiful wedding we attended over Wilmington not far away. It was a wonderful stay and we certainly love Vermont! This was our 4th stay in Vermont between the years of 2004 - now. Our first "Dog Vacation" took us to Brattleboro, Middlebury, Willoughvale with Lake Willoughby, and last summer to White River Junction and Barre. Fun!
Top guest favorite
A quaint colonial home is surrounded by lush greenery, with a vibrant rainbow arcing across the sky in the background. The well-maintained garden features blooming daffodils, and the soft grass invites relaxation and exploration.
Apartment in Newfane
4.97 out of 5 average rating, 455 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars2 weeks ago
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.
Superhost
A scenic farmstead is presented, featuring grazing sheep across a grassy field. The structure includes an historic barn surrounded by trees and a fenced garden area. A birdbath stands in the foreground, offering a tranquil farm setting.
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Top guest favorite
A cozy living area features a navy blue sofa and armchair surrounding a coffee table. Light wood walls complement the wooden ceiling beams, while a television is positioned on a white console. A large window is dressed with patterned curtains, providing natural light.
Home in Saratoga Springs
4.98 out of 5 average rating, 131 reviews

Charming lake front home with dock near racetrack.

SamanthaRating, 5 stars6 days ago
We had a fantastic stay at this beautiful 3-bedroom, 2-bath home on Saratoga Lake! The house was comfortable, clean, and had everything we needed for a relaxing getaway. One of the highlights was definitely the dock—it made fishing right from the property incredibly easy and fun. Vicki and John were wonderful hosts—super responsive and available for any questions we had throughout our stay. Their hospitality really made us feel at home. We’re already looking forward to coming back and making more great memories. Highly recommend this place to anyone looking for a peaceful lakefront escape in the Saratoga area.
Superhost
The charming exterior of a yellow house is surrounded by lush greenery and tall trees. A well-maintained lawn features flowering bushes and a small seating area. The rustic allure of the home is complemented by a gravel pathway leading to the front door.
Home in Jamaica
4.86 out of 5 average rating, 295 reviews

Yellow Sweetie at the Base of Stratton

NatalieRating, 5 stars2 months ago
We have enjoyed Erin's cute cottage very much. It has everything you might need, plus the location is great. Would definitely return and recommend)

Family-friendly home rentals with a pool

Guest favorite
An outdoor heated pool is surrounded by a stone patio, furnished with lounge chairs and umbrellas. Lush green grass and neatly trimmed shrubs outline the pool area, complemented by trees and well-maintained landscaping in the background.
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

NikkiRating, 5 stars4 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Guest favorite
A clear blue pool is surrounded by a sunbathing area featuring white lounge chairs. Lush greenery and trees are visible in the background, providing a natural setting. A fenced area with tall trees enhances the outdoor space for relaxation.
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favorite
A clear blue pool is surrounded by a paved area, featuring built-in steps for easy access. Lounge chairs are positioned nearby, providing a comfortable space for relaxation. A wooden fence encloses the area, ensuring privacy, while greenery adds a natural touch to the setting.
Home in Saratoga Springs
4.86 out of 5 average rating, 111 reviews

Saratoga Springs convenient tranquil location.

MelissaRating, 5 stars1 month ago
Really just a great weekend! The house was spacious and perfectly accommodated our family. Also perfect distance from town where there is tons to do. Julie was available for questions and was so easy to communicate with. We were in the area to celebrate our son’s college graduation and really could not have selected a more perfect spot!
Superhost
The inground pool, surrounded by a concrete deck, glistens under sunlight in a serene outdoor setting. Lounge chairs and shaded tables are positioned nearby, providing space for relaxation. Tall trees and a wooden fence create a private atmosphere.
Cabin in Johnsburg
4.83 out of 5 average rating, 239 reviews

Adirondack 2 Bedroom Cabin 1st to the right. #1

StevenRating, 5 stars3 months ago
Our second stay here and the place was just as great as the first time.
Guest favorite
An indoor pool area is highlighted by a spacious swimming pool. Natural light enters through large windows, offering views of the outdoor patio. Seating areas with chairs are arranged along the walls, complemented by warm-toned curtains.
Condo in Ludlow
4.93 out of 5 average rating, 110 reviews

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars2 months ago
Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.
Guest favorite
A heated swimming pool is set within a fenced area, featuring a vibrant blue surface reflecting the sky. Several loungers are positioned beside the pool. Flags representing the United States, Puerto Rico, Ireland, and Italy are displayed along the perimeter, adding a festive touch.
Apartment in Rexford
4.96 out of 5 average rating, 360 reviews

Need a Getaway??

AbbeyRating, 5 stars6 months ago
Great hosts that make you feel right at home. We were greeted with some extra special touches that we were not expecting during our stay, that was very thoughtful. The space is exactly as pictured and very comfortable. We would definitely come back
Superhost
An outdoor pool area is showcased with a well-maintained pool surrounded by a paved deck. Sun loungers are placed at various points, accompanied by red umbrellas for shade. The backdrop features a multi-story building, enhancing the serene atmosphere of the space.
Condo in Killington
4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars4 weeks ago
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!
Top guest favorite
Home in Ballston Spa
4.94 out of 5 average rating, 109 reviews

Time to Relax, close to Saratoga.

SiddharthRating, 5 stars9 months ago
The house was beautiful and Rhonda was great, she was very responsive and helpful. We felt right at home and enjoyed the place more than Lake George :) , the hot tub and pool were great and i would recommend anyone coming to this area to definitely book the place if they get the chance.

Quick stats about vacation rentals that are family-friendly in Jackson

  • Total rentals

    20 properties

  • Nightly prices starting at

    R1,961 ZAR before taxes and fees

  • Total number of reviews

    990 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

Destinations to explore