Holiday rentals in Gaysville, Stockbridge

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Top-rated holiday rentals in Gaysville, Stockbridge

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Top guest favourite
Aerial view of a serene landscape in Vermont, displaying rolling hills adorned with vibrant autumn foliage. A white yurt is nestled within the lush greenery, set against a backdrop of trees and open fields. A winding road leads through the natural beauty.
Yurt in Randolph
4.93 out of 5 average rating, 221 reviews

Peaceful Woodland Yurt with Pond View

Enjoy the natural beauty of Vermont in this amazing, fully loaded, 14' guest yurt! It comes with a toasty propane fireplace, queen bed, two burner cooktop, fridge, great wi-fi, an incredibly charming and immaculate bathhouse, magnificent views, and privacy! This is the perfect getaway for those seeking peace and natural beauty without sacrificing comfort or amenities! Explore our remote hiking trails and beautiful pond. And be sure to enjoy off-grid meditation yurt when available in season.

Top guest favourite
A rustic sugarhouse cabin is surrounded by lush greenery, with trees lining the background. The building features a metal roof and several windows that reflect natural light. A picnic table is placed on the covered porch, offering a comfortable space for relaxation.
Cabin in Royalton
4.99 out of 5 average rating, 239 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Top guest favourite
Guest suite in Stockbridge
5 out of 5 average rating, 105 reviews

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

Guest favourite
An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.
Chalet in Stockbridge
4.84 out of 5 average rating, 174 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Guest favourite
A charming farmhouse exterior is shown at night, with warm light glowing from multiple windows. The snowy landscape surrounding the house is accentuated by tall trees under a dark blue sky. The roof displays a gentle slope covered in a blanket of snow.
Home in Stockbridge
4.87 out of 5 average rating, 148 reviews

Escape to Vermont

Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

Guest favourite
A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.
Cabin in Stockbridge
4.94 out of 5 average rating, 120 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Top guest favourite
A view from a wooden balcony, showcasing a serene pond surrounded by lush greenery and colorful foliage. The water reflects the cloudy sky and trees, creating a peaceful natural scene. A gravel path and nearby fences add to the rustic charm.
Guest suite in Bethel
4.98 out of 5 average rating, 191 reviews

Two bedroom. Separate entrance.

Please be advised that during winter months you may need to walk up Winterberry lane and our driveway if you do not have an AWD vehicle with good snow tires. Two bedroom apartment in the heart of Vermont. Snowmobile trail located off lane. Snowshoe, hike, or mountain bike from the door. Quiet private location with separate entrance and parking onsite. Ramp to access apartment, with stair free access. Pond, views and located in the center of the state, a great place to start!

Top guest favourite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 136 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling perfect for any admirer of a beloved wizarding world, or anyone who just truly appreciates a isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled among the branches of several maple trees, providing a magical and secluded escape from the hustle and bustle of everyday life.

Guest favourite
A newly built tiny cabin is nestled among lush green trees, accessed by a wooden deck leading to a cozy seating area. Natural stones and grass surround the cabin, enhancing its peaceful woodland setting, while warm lights add a welcoming touch.
Cabin in Pittsfield
4.98 out of 5 average rating, 173 reviews

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

Guest favourite
A large house with a gray exterior features a welcoming front porch and a gabled roof. Surrounding greenery includes trees and flower bushes, creating a peaceful outdoor environment. The driveway is visible, leading to the house amid a spacious lawn.
Home in Bethel
4.87 out of 5 average rating, 171 reviews

Affordable, private, surrounded by flower gardens

Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

Top guest favourite
A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.
Chalet in Stockbridge
4.97 out of 5 average rating, 143 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

Top guest favourite
A spacious living area features a light grey sectional sofa with cozy throw pillows. Natural light floods in through large glass doors that open to the yard, while a modern ceiling fan hangs above. A rug defines the seating arrangement, and simple decor adds warmth.
Cabin in Rochester
4.95 out of 5 average rating, 487 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Popular amenities for Gaysville, Stockbridge holiday rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Stockbridge
  6. Gaysville