
Holiday rentals in Jackson
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Top-rated holiday rentals in Jackson
Guests agree: these stays are highly rated for location, cleanliness and more.

Where the Wild Things Are Author's Private Retreat
Previously owned by Maurice Sendak (author/artist "Where the Wild Things Are"). Dramatic views of the Green Mountains of Vermont. Natural, wild, full of character and charm. 2 mile private walking path, covered pickleball court, herb garden with gas grill & wood fired pizza oven, fire pit overlooking mountains and pond. 200 mi to NYC, Boston, Montreal. 25 mi to Saratoga Springs & Manchester VT. Farm-grown produce offered during growing season. Central Air & Heat, fireplace, sunroom with stove.
LocationFamilyCleanliness
5.0 out of 5 average rating, 54 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.
LocationFamilyBack garden
4.99 out of 5 average rating, 135 reviews
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!
FamilyValueAccuracy
4.94 out of 5 average rating, 143 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!
FamilyLocationOutdoor spaces
4.96 out of 5 average rating, 178 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.
LocationValueAmenities
4.99 out of 5 average rating, 110 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.
LocationValueTV
5.0 out of 5 average rating, 140 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.
FamilyLocationRiver
4.98 out of 5 average rating, 214 reviews
Meadow Cottage
Sitting in 13 acres of meadow, and bordering the hills of Battenkill State Forest, this cottage is the perfect place for a relaxing break or an outdoor adventure. You can hike the trail by the house, explore the beautiful farmland and the surrounding villages, or relax on the deck and watch the birds. We are a short walk from the Battenkill River, where you can fish, kayak, tube or relax. We are pet friendly with a large lawn for games and a fire pit for evening stories.
ValueFamilyCheck-in
4.93 out of 5 average rating, 67 reviews
The Cabin on Pine Hill
Relax with the whole family at this peaceful cabin getaway. Sitting on 55 acres, theres plenty of space for everyone. The hiking trail goes past the swimming pond and weaves its way to the top of the hill where there's wide open spaces thru the oak and pines. Listen to birds, watch deer and turkeys roam thru the yard while you sit on the front porch and enjoy the peace and quiet. 2 miles to town, close to the Battenkill River and other nearby attractions.
FamilyLocationIndoor spaces
4.94 out of 5 average rating, 48 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..
ValueLocationLayout
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.
ValueLocationAmenities
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.
ValueLocationKitchen
4.99 out of 5 average rating, 122 reviewsPopular amenities for Jackson holiday rentals
Other great holiday rentals in Jackson

Coleman’s Cabin
FamilyLocationCheck-in
4.84 out of 5 average rating, 19 reviews
Million dollar VIEWS | Hot Tub | Near Hedges Lake
ValueLocationCondition
5.0 out of 5 average rating, 17 reviews
Camden Creek Farm
ValueFamilyDecor
4.99 out of 5 average rating, 74 reviews
Slice of Heaven Cottage on Hedges Lake w/ Boat!
FamilyLocationKitchen
5.0 out of 5 average rating, 13 reviews
SunStache River Camp on the Battenkill
FamilyLocationBathroom
5.0 out of 5 average rating, 64 reviews
The Long Lodge - a secluded year round getaway
LocationValueWalkability
4.93 out of 5 average rating, 90 reviews
Little House on the River
FamilyLocationSleep quality
4.89 out of 5 average rating, 44 reviews
Cabins with breathtaking views
ValueLocationAir conditioning
4.92 out of 5 average rating, 12 reviewsDestinations to explore
- New York Holiday rentals
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- 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





