Vacation rentals in Woodford

Guest suite in Shaftsbury

A white picket fence lines a stone pathway, leading through a vibrant display of autumn foliage. Warm hues of orange and yellow leaves create a picturesque backdrop, where a slight curve in the path invites exploration amid the natural beauty.

4.99 out of 5 average rating, 166 reviews

Peaceful Get Away at Birds of a Feather Farm

Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. Spa services are available. For Booking & Fees contact host.

Guest favorite

4.92 out of 5 average rating, 184 reviews

Escape the City- Vermont Studio

Our studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Grn. Mtn. National Forest. It's on the second floor of our home (above the garage) through a private entrance with a personal deck and outdoor seating. Take an afternoon stroll to the Mile Around Woods, or day hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Guest favorite

A charming log cabin is set on a lush green hillside, surrounded by trees. The exterior is accented with a large half-moon window and a welcoming deck that features a patio umbrella. Nature creates a serene backdrop.

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.

Guesthouse in North Bennington

4.99 out of 5 average rating, 255 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 animal

4.95 out of 5 average rating, 113 reviews

Cabin in Woodford

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.

4.99 out of 5 average rating, 269 reviews

An airy living space showcases vaulted ceilings with exposed wooden beams. A wood-burning fireplace features a dark surround, with a light area rug beneath a round coffee table. Bright natural light streams through strategically placed windows, illuminating the modern kitchen and dining area.

Cabin in Shaftsbury

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!

4.98 out of 5 average rating, 177 reviews

A wooden horse silhouette is displayed on the wall above, showcasing a trotting design in dark green and natural wood tones. Exposed wooden beams add a rustic charm to the space, contributing to the overall tranquil atmosphere.

Farm stay in Bennington

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 .

4.98 out of 5 average rating, 693 reviews

The historic schoolhouse stands under a star-filled sky, illuminated by moonlight. The surrounding landscape features snow-covered ground and trees, enhancing the serene atmosphere. The wooden decks glow softly from exterior lighting, creating a welcoming contrast against the night sky.

Cottage in Shaftsbury

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 350 acre property.

Guest favorite

A cozy corner features a tan leather chair with a fluffy white throw draped over its back. A small round table holds a stack of books beside a modern lamp. A potted plant adds a touch of greenery, while a woven basket stores assorted magazines.

4.95 out of 5 average rating, 165 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.

4.85 out of 5 average rating, 369 reviews

A winter landscape features a dramatic sunset with vibrant hues of orange and pink in the sky. The foreground shows a snow-covered area with a black dog walking, while a gravel road extends into the distance, bordered by trees and mountains.

Cabin in Woodford

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.

4.94 out of 5 average rating, 199 reviews

A modern bathroom features a walk-in shower with a glass enclosure and sleek gray tiles. Adjacent to the shower, neatly folded towels are stacked on a shelf, with a decorative towel hanging on a rack. A contemporary sink completes the clean design.

Apartment in Pownal

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

4.97 out of 5 average rating, 565 reviews

A circular structure is set in a wooded area, partially surrounded by snow-covered ground. Warm light spills from the open doorway, contrasting with the cool tones of twilight. Trees with bare branches frame the scene, creating a serene winter ambiance.

Apartment in North Adams

Steps to MoCA: 2bd + SAUNA!

A large and private 2 bedroom apt at the Small Mansion of Chase Hill, 3 mins by walk to Mass MoCA. 10 mins drive to Williams College, Clark. 5 mins walk to downtown’s restaurants. Whimsically restored (yes, fast Wi-Fi & great water pressure). Part of @chasehillartistretreat YOUR STAY HERE ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

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Other great vacation rentals in Woodford

A metal bucket is mounted to the side of a tree, featuring a flat lid resting on top. The background consists of a wooded area with bare branches and fallen leaves, indicating a natural and serene environment.

4.97 out of 5 average rating, 91 reviews

Suite Sunset 311 Rice Lane Bennington VT

EllenRating, 5 stars1 month ago

George went about and beyond! We arrived to find a beautiful basket of fruits and bagels and cream cheese in the refrigerator. We were only there for one night but I wish we could have stayed longer to have had a chance to relax in such a spacious accommodation. Looking forward to returning.

4.79 out of 5 average rating, 66 reviews

A two-story white building is surrounded by vibrant autumn foliage, showcasing yellow and orange leaves. A spacious patio area is visible alongside the entrance. The ground is dotted with fallen leaves, creating a serene outdoor setting. A grassy area complements the natural surroundings.

Loft in Bennington

1 bedroom guest house on dead-end rd

Pk Rating, 5 stars3 weeks ago

Thanks for another great stay! Perfect location, nice people, etc ;)

Tiny home in Eagle Bridge

A charming cabin is situated in a snowy landscape, surrounded by tall trees. Large windows provide a glimpse of warm light from inside, while a covered porch with seating is partially visible in the foreground, enhancing the inviting atmosphere of this winter retreat.

4.77 out of 5 average rating, 26 reviews

Hoosick Hideaway

KevinRating, 5 stars2 weeks ago

Great Private atmosphere off main road. Saw wildlife. Nice Stream on the property. A/C worked well. Sleeping Loft was cozy. Kitchen was what we needed. All I will say is READ Zachary’s ARRIVAL INSTRUCTIONS especially about LOCATION. We ended up about 1000 yards past the driveway bc GPS DIRECTIONS took us around the corner from driveway( literally through the trees to the cabin). I spoke to Zachary and he talked me into the driveway. Great Host. His Arrival Instructions gave great instructions I just didn’t realize it and relied on the gps on my IPhone. We Definitely would stay there again. We used it as a base camp while we attended The Cambridge Balloon Festival. Until next year Little Cabin K&E

A modern kitchen with a sleek black countertop and stainless steel appliances is visible, including a stovetop and a knife block. A cozy living area is seen in the background, featuring a navy couch and a warm lamp, adding a welcoming touch to the space.

4.99 out of 5 average rating, 72 reviews

Modern Rustic Hideaway in Town

NanRating, 5 stars1 week ago

I was looking for a birthday get-away, and Claire's place was just right. Nice, clean apartment on the second floor of an older house, with all amenities plus a full kitchen, which we always appreciate. The bedroom has a really comfy bed and lots of storage with two beautiful dressers and a closet. Kitchen had everything we needed, and she even left homemade jam and local honey for us. We loved walking into town, just a few blocks away, and we discovered lots of hiking trails nearby. It was a lovely stay!

5 out of 5 average rating, 9 reviews

A rustic stone fire pit sits in a grassy area, with flames flickering inside. Surrounding trees create a natural backdrop, and the soft glow from the fire contrasts with the green of the grass and foliage. This outdoor setting invites relaxation and warmth.

Home in Stamford

Peaceful Retreat near Unique Animal Encounter

JenRating, 5 stars4 weeks ago

Daniel's place was the perfect home base for our Berkshires getaway. We visited Mass MoCA and loved coming back to this quiet, peaceful retreat. The backyard was especially serene, I enjoyed my morning coffee outside and relaxing by the fire at night. One of my favorite parts was cracking the window open and falling asleep to the soothing sound of the brook out back, pure magic. Daniel was a gracious host, friendly, responsive, and thoughtful. The local charm added so much to the experience, including camels and other farm animals across the street, Farmer Dave is a gem. We'd happily stay here again!

5 out of 5 average rating, 66 reviews

The exterior entrance of the house features steps leading to a white door framed by large windows. Decorative potted plants add greenery to the space, while neatly trimmed hedges line the pathway. The house is painted in a serene blue, complementing the surrounding landscape.

Home in Bennington

1865 Farm House with mountain and meadow views.

AliaRating, 5 stars1 week ago

Our stay was fantastic! The house is so charming, better than the photos, and so clean. The surroundings are idyllic, and the hosts were kind and responsive. Would love to come back!

4.92 out of 5 average rating, 76 reviews

The cabin exterior features warm wooden siding and a covered front porch with a sturdy railing. Two sets of stairs lead up to the main entrance, surrounded by autumn foliage that adds natural color to the setting. A picnic table is seen to the side.

Cabin in Readsboro

The Hidden Gem

DylanRating, 5 stars3 months ago

Jody’s place was perfect for our weekend trip to Mount Snow. The place was clean and as advertised.