Vacation rentals in Woodford

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Top-rated vacation rentals in Woodford

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Top guest favorite

The entrance to the guest house displays a dark wood-paneled exterior with a black door featuring a grid window. A small window is positioned beside the door. Recessed lighting illuminates the covered porch area above.

Guesthouse in North Bennington

4.99 out of 5 average rating, 293 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

Guest favorite

A log-sided cabin is surrounded by lush greenery under a clear blue sky. The structure features a distinctive half-moon window and a green metal roof. A spacious deck with outdoor seating and an umbrella is visible, inviting relaxation in a natural setting.

Cabin in Woodford

4.91 out of 5 average rating, 151 reviews

Lakeview Cabin in the Mountains - beautiful

Lovely log sided cabin situated across from Woodford lake with view. Large Great room cathedral ceiling, halfmoon window, pine ceiling & floors, dining table,woodstove, corner gas fireplace, full kitchen. Beautiful ambiance, rustic yet elegant. 2 bedrooms, full bath with clawfoot tub, romantic sleeping loft w sitting area. Basement play area heated with 2 beds for children. Central heat, washer/dryer TV/Roku, ceiling fans. Great getaway for nature lovers, skiers, snowmobilers, hikers. Wifi.

Top guest favorite

The exterior showcases a blue wooden cabin with large windows reflecting its natural surroundings. A spacious deck is visible in the foreground, providing a welcoming access point. Autumn foliage surrounds the property, indicating a peaceful, rural setting.

Cabin in Wilmington

4.96 out of 5 average rating, 104 reviews

Peaceful Cabin Perfect for All Seasons

A little blue gem hidden in hills of Southern Vermont. This 4-bedroom, 1.75-bath cabin places you just 7.4 miles from Mount Snow, 2.5 miles from the Haystack Mountain Trail, and 2 miles from the Wilmington Village Historic District. Whether you're discovering an assortment of hiking trails, enjoying a historic walk in Bennington, soaking up the summer sun on the Harriman Reservoir, hitting the winter slopes, or admiring the beauty of a vibrant New England autumn, you will love your stay here!

Top guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 308 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Guest favorite

A cozy living area features a gray sofa and a matching chair beside a wooden coffee table. A stone fireplace is centered on the wall, with a television mounted above. Shelves display books and decorative items, while plants add a touch of greenery.

Cabin in Woodford

4.95 out of 5 average rating, 122 reviews

Charming Cabin with 2 baths in the Green Mountains

A cozy cabin nestled high up in the green mountains. A perfect getaway on a quiet street. This home is located in between the towns of Bennington and Wilmington. Across the street from Prospect Mountain (cross-country skiing and snow shoeing) and about 25-30 minutes to Mount Snow (downhill skiing). Vast snowmobile trail in our backyard. Visit the quaint general store nearby or go hiking in Woodford National State Park. At 2,000 ft elevation, the stars are on stage when it's a clear night.

Top guest favorite

A spacious living area features high vaulted ceilings with exposed wooden beams and large skylights. Natural light illuminates the modern decor, including a comfortable couch, sleek bar stools, and a central coffee table. A fireplace is positioned beside expansive windows that offer views of the surrounding forest.

Cabin in Shaftsbury

4.99 out of 5 average rating, 290 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!

Top guest favorite

A charming cottage is set in a green, open yard, surrounded by tall trees. A white fence encloses the property, with a small flowerbed in front. A rustic red barn is visible in the background, complementing the tranquil rural setting.

Farm stay in Bennington

4.98 out of 5 average rating, 211 reviews

The Farm cottage

Take a break and unwind at this little peaceful oasis. A little bit of the country is right beside you with the neighing of horses and the clucking of chickens who roam our property. We are close to Bennington College and great restaurants and Robert Frost house. We are 35 minutes from Manchester that has some great restaurants and shopping. Bromley ski resort is just beyond Manchester in Peru Vermont . It is a year around resort with water slides in summer and skiing in winter .

Guest favorite

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, 717 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated 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 favorite

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, 174 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 favorite

A spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.

Guest suite in Wilmington

4.92 out of 5 average rating, 797 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Top guest favorite

The historic Gate House is framed by lush greenery and a manicured lawn, set against a vibrant sunset sky. Its stone façade and charming architecture are accentuated by soft lighting that bathes the exterior in warmth, inviting guests to explore the expansive outdoor space.

Home in Bennington

4.98 out of 5 average rating, 146 reviews

The Gate House--Experience Vermont!

The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

Guest favorite

Cabin in Woodford

4.84 out of 5 average rating, 380 reviews

400+ Airbnb Visits: Incredible Mountain Cabin

Our cabin is off the grid, NO running water (read this twice) or indoor bathroom, but it’s comfortable and has been enjoyed by 100’s of Airbnb travelers. There is electricity, but this cabin takes an adventurer in the winter months. Winter Stays take work! Don’t be surprised of shoveling and bringing in your gear! Our reviews speak for how great rental is for people, thank you for considering a stay at our cabin.