Holiday houses in Jackson

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Top-rated holiday rentals in Jackson

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Top Guest favourite
Guesthouse in North Bennington
4.99 out of 5 average rating, 304 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Top Guest favourite
The colonial home features a classic white exterior with black shutters and a welcoming front porch. An American flag is displayed prominently, and soft outdoor lighting highlights the entrance. The well-maintained lawn includes neatly trimmed bushes, creating a warm first impression.
Home in Sandgate
4.99 out of 5 average rating, 123 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.

Top Guest favourite
A spacious family room features wooden walls and beams, with a comfortable couch and a coffee table in the foreground. A large TV is mounted on the wall, and a dining area is visible in the background, illuminated by natural light from windows framed by greenery.
Apartment in Greenwich
4.95 out of 5 average rating, 121 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!

Top Guest favourite
A spacious wooden deck is adorned with a rustic table set for a meal, surrounded by lush green trees. Below, the Battenkill River flows gently, reflecting the nearby foliage. A glimpse of the apartment's inviting interior is visible, featuring cozy bedding and a decorative table. Steps lead upward to the deck.
Guesthouse in Greenwich
4.96 out of 5 average rating, 167 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!

Top Guest favourite
A midcentury modern cabin is nestled among trees, its dark exterior contrasting with the fresh snow covering the ground. A spacious deck is visible, adorned with wooden railings, while large windows reflect the serene winter landscape.
Cabin in Shaftsbury
4.99 out of 5 average rating, 296 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Guest favourite
A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.
Apartment in Bennington
4.95 out of 5 average rating, 176 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Guest favourite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 725 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Guest favourite
A group of twelve alpacas stands in a lush outdoor setting, showcasing various colors including white, brown, black, and grey. A wooden structure is visible in the background, surrounded by greenery and fencing.
Farm stay in Hoosick
4.94 out of 5 average rating, 280 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.

Guest favourite
The cabin's A-frame structure is surrounded by trees, with warm light glowing from the large windows. A spacious deck is visible, featuring outdoor seating. The tranquil landscape offers a serene atmosphere, blending the home harmoniously with nature.
Cabin in Shushan
4.85 out of 5 average rating, 278 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..

Top Guest favourite
A wooden sign marked 'Battenkill Bed & Breakfast' stands prominently at the entrance, framed by lush green grass and flowering plants. Tall trees provide a natural backdrop, enhancing the serene setting.
Cottage in Cambridge
4.99 out of 5 average rating, 114 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.

Superhost
The living area features a cozy couch and a table with built-in seating for dining. A well-equipped kitchen is visible in the background, complemented by warm yellow walls. Soft lighting and a rug create a comfortable atmosphere.
Apartment in Gansevoort
4.78 out of 5 average rating, 142 reviews

Cozy, Pets, Coffee, B-Ball, Fire Pit, BBQ

⭐"Cozy, clean and affordable! Highly recommend." -Alison 🏡 Family Style Apartment 🛏️ Sleeps 3 🏀 Basketball Court 🔥 Fire Pit 💻High speed internet 🚽 Heated Bidet 🐶 Pets 🌲 Front yard 🔥 BBQ 🏠Patio with Sun Loungers 🚗 Convenient Parking 📍 15 min to Saratoga Springs, 20 min to Lake George 🍽️ Fully Equipped Kitchen ☕Coffee, Tea & Decaf Note: Potential for noise from upstairs guests

Guest favourite
A stationary white bus sits on a gravel path surrounded by green grass. In the background, sparse trees and expansive fields are visible. Two outdoor chairs and a small shed can be seen nearby, highlighting the serene, rural setting.
Bus in Granville
4.89 out of 5 average rating, 179 reviews

Serene Bus Getaway Among Rolling Farm Land

Tucked off a quiet dirt road, this stationary bus promises to provide you and yours an unforgettable accommodation for your next Upstate NY retreat. Come stay in the Sleepy Tire, and wake up to beautiful views of Vermont’s Green Mountains, an indoor bathroom with flushing toilet and hot shower, and WiFi so you can stay connected to those that matter.

Popular amenities for Jackson holiday rentals

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  4. Washington County
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