
Family-friendly holiday rentals in Jackson
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Jackson
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Apartment in Historic Village Home
Our home was built in the 1830's, and the apartment added in the 1950's. The apartment has a throwback feel. We are an easy walk to restaurants, Flynn's funeral home, the school, and churches. We are minutes from the Washington County Fairgrounds. We are 1/2 an hour from the Saratoga race track, 45 minutes to Lake George, 10 minutes from Willard Mt, and an hour from great Vermont skiing! We have a full kitchen, guests say our beds are super comfy, and we have hi-speed cable and Internet!
4.94 out of 5 average rating, 143 reviews
Country Colonial Home with rolling fields & stream
This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.
4.99 out of 5 average rating, 135 reviews
Apartment on the Battenkill 30 minutes to Saratoga
Enjoy the natural beauty of the Battenkill River in our private, charming, guest apartment located on the outskirts of Greenwich, New York just 20 miles from Saratoga Race Course and a lovely scenic drive to Lake George and Vermont. Our cozy space includes 1 private bedroom with a queen size bed (linens included), a couch that can sleep an additional 2, TV, dining space and a complete kitchen. Lounge on the spacious deck, fish, take a dip in the river and enjoy comfort of our cozy space!
4.96 out of 5 average rating, 178 reviews
Warm Brook Farm | Farmhouse & Gardens | Hot Tub
Step into the timeless charm of Warm Brook Farm, a beautifully restored 18th-century farmhouse in Southern Vermont. Once a lively inn and stagecoach stop in the early 1800s, this elegant retreat combines historic character with modern luxury. Enjoy a genuine chef's kitchen, award-winning gardens, and upscale amenities throughout. We cover your Airbnb service fees — the price you see is what you pay. An inviting getaway to relax, explore, and create lasting memories with family and friends.
5.0 out of 5 average rating, 140 reviews
Edelweiss Cottage, Manchester VT
Welcome to Edelweiss, a beautiful guest cottage in Manchester Vermont. Our idyllic cottage is nestled into the hillside at the base of Mount Equinox. The two story cottage boasts a stunning stone fireplace and large windows overlooking the tiered landscape and Green Mountains in the distance. We are located minutes to Manchester viliage, shopping outlets, Equinox Resort, Hildene, and the Equinox Skyline drive. We are 20 minutes to Bromley and 35 minutes to Stratton and Magic Mountain.
4.99 out of 5 average rating, 110 reviews
Historic Farm Stay | Heated Pool + Hot Tub
Escape to your own private 18th-century farmhouse surrounded by our 100-acre farm in beautiful Upstate New York. Designed for families and groups to reconnect, the Farmhouse sleeps 12 and comes with a heated saltwater pool, year-round hot tub, fire pit, game room, farm animals and acres of countryside to explore. Spend summer days by the pool, fall evenings around the fire, snowy weekends soaking in the hot tub, or simply slow down with coffee in the sunroom overlooking the farm.
4.98 out of 5 average rating, 214 reviews
Airbnb @ Sweet & Savory Farmette
Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.
4.92 out of 5 average rating, 366 reviews
Cozy rustic cabin in the hamlet of Shushan. N.Y.
This cabin overlooks a nature preserve.lots of wildlife,with a peaceful and Serene atmosphere. animals are welcome. the battenkill river is closeby 30 min from Manchester v.t and Saratoga springs ny.cozy up to a fire with a good book,or head out for some designer shopping.hiking trails in Vermont and newyork and plenty of ski resorts ,and snowmobilng.within 30 min. we welcome all animals in the home. enjoy the quiet, and views of shushan NY.here..
4.86 out of 5 average rating, 296 reviews
The Vermont Farmhouse|Hiking|Dog Trails|Village
The Luxury of Slowing Down — Vermont Style. Leave the rush behind and feel rested, reconnected and renewed at our dog-friendly, beautifully restored 1860s farmhouse. Wide-plank floors, sun-filled rooms and modern comforts create a warm, impeccably clean retreat. Walk across the road into 280 acres of peaceful Mile Around Woods trails, or stroll into historic North Bennington for cafés and shops. It's all right at your doorstep.
5.0 out of 5 average rating, 138 reviews
Guest Cottage Battenkill BnB- A Peaceful Getaway
This newly renovated carriage house is nestled in the Battenkill River Valley alongside a picturesque spring fed Marsh . The post and beam structure is private and quiet as it is distanced from my family home . The kitchen is stocked with a bounty of delicious local and organic self serve breakfast choices plus a wide range of organic coffees and teas.Please feel free to let us know if you have any dietary restrictions.
4.99 out of 5 average rating, 122 reviews
Suite on Salem
Keep it simple at this peaceful and centrally-located place. Walking distance to Salem Central, Fort Salem Theater, the Historic Salem Courthouse, Jacko's, Salem Art Work, On a Limb Bakery, and less than an hour to vermont sking. Come stay in our secure 2-room suite plus bathroom with a separate entrance uniquely filled with local art and antiques. Includes cube-sized refrigerator, coffee maker, and microwave for use.
5.0 out of 5 average rating, 142 reviews
Guest House at Hummingbird Hill
Our small above-garage guesthouse on the NY/VT border is a retreat from busy life. The open floor plan, airy apartment has windows on all sides & overlooks woods & meadow. The guesthouse is ideal for those looking to get away from electronics and the internet (note: no Wifi). There are plenty of options nearby for hiking, rail trail biking, or paddling. Pets are welcome (we do charge a small fee for pets)!
4.97 out of 5 average rating, 148 reviewsPopular amenities for Jackson family-friendly rentals
Family-friendly home rentals with a hot tub

Cottage On The Farm
4.97 out of 5 average rating, 858 reviews
The Birchwood Cabin - Stunning Mountain Views
4.99 out of 5 average rating, 162 reviews
Saratoga Fall Escape | Hot Tub, Fire Pit & Game Rm
5.0 out of 5 average rating, 104 reviews
Out On a Limb • A Magical Treehouse Experience
4.99 out of 5 average rating, 138 reviews
The Hygge Loft- mid-mod cabin on 70 acres w/HotTub
4.99 out of 5 average rating, 335 reviews
Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
4.95 out of 5 average rating, 270 reviews
Town & Country Getaway: Pool Gardens Views 6 Acres
4.82 out of 5 average rating, 209 reviews
MOUNTAIN NEST, views, Manchester, hot tub,
4.97 out of 5 average rating, 284 reviewsFamily- and pet-friendly home rentals

Majestic Mountain Top Retreat
4.87 out of 5 average rating, 167 reviews
Runamuk Farm
4.93 out of 5 average rating, 236 reviews
Farm Stay! - 20 min from Lake George-30 Saratoga
4.96 out of 5 average rating, 414 reviews
The Chal-A-Frame Vermont
4.99 out of 5 average rating, 224 reviews
East Cabin
4.98 out of 5 average rating, 179 reviews
Quaint One-Story Vermont House with Mountain View
4.88 out of 5 average rating, 155 reviews
White Doe Farm •Lovingly restored antique farmhome
4.95 out of 5 average rating, 117 reviews
Moon Valley Country Retreat no clean fee pets yes
4.91 out of 5 average rating, 1025 reviewsFamily-friendly home rentals with a pool

Waterfront Saratoga Lake home!- Pool, dock, kayak
4.97 out of 5 average rating, 126 reviews
Cozy cottage with pool, walking distance to lake
4.95 out of 5 average rating, 171 reviews
Luxury Oasis: Heated Pool + Walk to Town/Track
4.99 out of 5 average rating, 103 reviews
Need a Getaway? Newly Relisted! Guest Favorite!
4.96 out of 5 average rating, 377 reviews
Spacious Retreat mins to Lake George pool&hot tub
4.96 out of 5 average rating, 100 reviews
Hideaway Lodge - Glen Lake, Lake George
4.93 out of 5 average rating, 122 reviews
Hollywood Bungalow in the Berkshires #C0191633410
4.9 out of 5 average rating, 241 reviews
Pool/Hot tub, king bed, between Lk George/Saratoga
4.97 out of 5 average rating, 298 reviewsDestinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Salem Holiday rentals
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Thacher State Park
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Killington Resort
- Rensselaer Polytechnic Institute
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Saratoga Spa State Park
- MVP Arena
- New York State Museum
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Trout Lake





