Vacation rentals in Rupert

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Top-rated vacation rentals in Rupert

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Top guest favorite

A wooden guesthouse with a pitched roof is set against a lush green backdrop. Wildflowers and vegetables are visible in a garden area in the foreground. A vehicle is parked by the garage, and the natural environment surrounds the property, enhancing its serene atmosphere.

Guesthouse in Salem

4.97 out of 5 average rating, 109 reviews

Guest House at Hummingbird Hill

Our small above-garage guesthouse on the New York-Vermont border is a retreat from busy life. The open floor plan, airy apartment has windows on all sides & overlooks woods, meadow & animal pastures. The guesthouse is ideal for those looking to get away from electronics and the internet, and hike and bike the area’s trails, and/or paddle the Battenkill River and area lakes. Or just sit on the deck with a book and cup of tea or glass of wine. Pets are welcome (we do charge a small fee for pets)!

Guest favorite

A rustic wooden staircase leads up to the entrance of the treehouse, surrounded by trees. The staircase features uneven treads and a handrail formed from a natural branch, integrating seamlessly with the organic design of the structure.

Treehouse in West Pawlet

4.96 out of 5 average rating, 119 reviews

Treehouse compound, no cleaning fee

The rental includes both treehouses (toilet in each), cooking/eating pavilion (outhouse nearby), outside shower (cold), firepit. The price is $200 per night for 2 people (my price before commission and fees). Additional guests above the 2 are $30 per person per night up to a maximum of 11 guests during the warmer months and 5 guests total during the cooler ends of the season (June and mid Sept to mid Oct). Beds: 3 doubles, 5 singles. No pets allowed. Not ideal for people with mobility issues.

Top guest favorite

The exterior of a rustic building is shown, featuring weathered wood siding and a metal roof. A welcoming wreath adorns the front door, which is set against a backdrop of fallen leaves and colorful potted flowers. Sunlight filters through the trees, casting gentle shadows.

Home in Sandgate

4.99 out of 5 average rating, 112 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 favorite

Apartment in Dorset

4.99 out of 5 average rating, 188 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 4 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Top guest favorite

The exterior of a historic guesthouse is shown, featuring white siding and classic black shutters. The structure is located amidst lush green grass and trees, with a red barn visible in the background. A gentle sunset casts a warm glow over the scene.

Guesthouse in Wallingford

4.98 out of 5 average rating, 700 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Top guest favorite

A front porch features two rocking chairs and a swing, surrounded by wooden logs. A decorative blanket drapes over a barrel, adding color. The natural wooded landscape is visible in the background, highlighting the tranquility of the cabin’s setting.

Cabin in Granville

4.98 out of 5 average rating, 183 reviews

Quaint log cabin nestled in the woods

Enjoy a break from the daily grind at this lovely tiny log cabin nestled among beech and ash trees. This tiny cabin provides peace and quiet on nearly 4 wooded acres just minutes from the town of Granville, NY. A full kitchen, living room, one bathroom and a loft bedroom complete with stackable washer/dryer provide a place to relax and soak in nature. The spacious front porch grants a protected outdoor space to watch the wildlife and enjoy the fresh air with your family and pup.

Guest favorite

A serene winter scene is captured, featuring a snow-covered pathway leading through a landscape of white. Historic buildings, including a red structure and a stone wall, are visible amid trees blanketed in snow, set against a backdrop of a clear blue sky.

Cottage in Pawlet

4.92 out of 5 average rating, 191 reviews

The Smithy Cottage at Consider Bardwell Farm

The historic “Smithy" at Consider Bardwell Farm is the original building used for blacksmithing by Consider Bardwell, himself, in the 1800s. Complete with brand-new, architect-designed kitchen and bathroom, wood-burning fireplace, and stone patio for outdoor grilling and dining, the Smithy is beautiful inside and out. Enjoy meeting our goats and all the local goodies and products that we can stock in your cottage.

Guest favorite

The historic two-story house features a blue exterior complemented by a white porch adorned with hanging flower baskets. A pathway lined with greenery leads to the entrance, enhancing the inviting appearance of the home surrounded by mature trees.

Guest suite in Dorset

4.9 out of 5 average rating, 181 reviews

Guest Suite in historic 1804 tavern, w/ Breakfast.

You'll have the whole 3rd floor to yourself with a new private bath, large bedroom with a/c, and a separate sitting room/library. Stay in an historic gem, listed on the National Register of Historic Places. Historically sensitive restoration has been done. You'll have a continental breakfast in the house's original dining room. We're a four a minute drive from the center of historic Dorset village.

Top guest favorite

A vintage-style mailbox painted in a metallic turquoise color is mounted on a white post. The mailbox features the name 'Shadow Hills' and the address '1546 Mahaffy' displayed prominently in gold lettering, set against a naturally rustic background.

Cabin in Fort Edward

4.97 out of 5 average rating, 110 reviews

Sasquatch Theme! - Local to Lake George & Saratoga

A 10-acre farm with a cozy 10x20 cabin, one queen-sized bed and one futon. • Proximity to Lake George, West Mountain, Gore Mountain, and Saratoga Springs • Amenities, including WIFI, TV, fire pit, BBQ grill, fridge, microwave, coffee maker, heat, and AC. • Camp has an outdoor handwashing station with running water provided by a hose, an outdoor heated shower, and a porta-potty for bathroom needs.

Guest favorite

A bright sunroom features large windows and a vaulted ceiling, allowing natural light to fill the space. A comfortable white sofa is paired with decorative pillows, while a wooden coffee table sits at the center, complementing the warm wood flooring.

Farm stay in Rupert

4.94 out of 5 average rating, 101 reviews

White Doe Farm•Lovingly restored Antique Farm Home

Built circa 1860, our Rupert, VT farmhouse has been fully renovated for modern comfort while still retaining original rustic touches like original hardwood floors, a Rumford fireplace, and an antique wood-burning stove. We'd love to host your next family gathering, romantic getaway, or solo retreat! Minutes to Dorset, and Manchester. Micro-Wedding inquiries welcome!

Superhost

A window view offers a serene panorama of rolling green fields and distant hills. Soft colors of the sky reflect the time of day, while a wooden countertop supports two black chairs, inviting a moment of relaxation while enjoying the scenic landscape.

Bus in Granville

4.88 out of 5 average rating, 144 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.

Top guest favorite

A serene view of rolling hills is captured at dawn, with soft pink and blue hues painted across the sky. Low-lying mist blankets the landscape, merging with greenery and trees visible in the foreground. A gravel area and flower pots frame the scene.

Guest suite in Salem

4.99 out of 5 average rating, 113 reviews

Hilltop Country Views Studio Apartment

Enjoy a relaxing stay in the country. Easy access to Vermont & Saratoga. Eat local produce. Fresh eggs, bread and butter or oatmeal for your first breakfast, coffee and tea provided. Go shop, ski, hike or stay put & enjoy a good book! (After you're confirmed, please let us know if you're vegan, and or glucose or lactose intolerant.)