Holiday rentals in Weybridge

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Top-rated holiday rentals in Weybridge

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Top guest favourite

Cottage in Middlebury

The Cottage Apartment in downtown Middlebury.

This charming, 1st floor two-bdr. cottage apartment is steps from Main Street, downtown Middlebury, & walking distance to shops, restaurants, and the College. An historic college town, Middlebury is replete with great restaurants, shops and cultural events to enjoy, all within walking distance. The comforts of this home include private parking, gardens, separate entrance, full kitchen and bath, and sleeps four. It is only a half hour from The Middlebury College Snow Bowl, and Lake Champlain.

4.92 out of 5 average rating, 168 reviews

Top guest favourite

A spacious living area features a queen size bed with a blue quilt, adjacent to a cozy fireplace. Green armchairs and a small round table provide additional seating. Tall curtains frame windows, and a bookshelf adds a touch of color to the wall.

Flat in Middlebury

Bluebird Studio- Light filled and airy

This studio apartment attached to the main house has a style all its own. Contemporary design with high ceilings, clerestory windows and a skylight. Spaces include a large Living Room/Bedroom, Kitchen/Dining area, bathroom with a step-in shower and an adjoining Dressing Room with vanity and sink. There is also an outdoor covered space to enjoy. Furniture includes a Queen size bed, 3 comfy chairs, small round table and 4 chairs. Location is a bit more than one mile from downtown Middlebury.

4.99 out of 5 average rating, 188 reviews

Top guest favourite

The entrance of the cottage features a small wooden porch with a smooth surface. A decorative bench is adorned with flower pots filled with colorful blooms, creating an inviting and cheerful entryway. The door is painted a calming blue, complemented by matching shutters.

Home in Middlebury

The Middlebury Cottage

A family, visiting professionals, vacationing couples, and recreation enthusiasts will all enjoy their stay at this Middlebury Cottage. You will be close to everything you want and need - the cottage is just a short bus ride from the Middlebury Amtrak Station, within walking distance of Middlebury College, downtown Middlebury, the Middlebury Food Coop, and the 19-mile Trail Around Middlebury. Just a short drive brings you to Rikert Nordic Center, Middlebury Snow Bowl, the Long Trail, and more!

4.92 out of 5 average rating, 116 reviews

Top guest favourite

A private balcony is presented with a small round table and two white ornate chairs. A vase of colorful flowers adds a touch of nature, while a cup is placed beside it. The view beyond showcases the sparkling waters of Lake Champlain surrounded by trees.

Flat in Vergennes

Lake Champlain charming apartment amazing views

Charming, bright apartment attached to a 2007 custom Vermont country french home located on the shores of Lake Champlain. Breath taking westerly Adirondack views offer dramatic sunsets and lake views of Button Bay. The property consists of 12 acres of fields, woods, stone walls and gardens with the home situated privately looking over the lake shore. The apartment has a private entrance. We are 12 minutes to Vergennes restaurants and shops, 25 minutes to Middlebury and 45 minutes to Burlington

4.99 out of 5 average rating, 329 reviews

Top guest favourite

An open living area features a grey sectional sofa beside a light wood coffee table. The kitchen, equipped with modern appliances, can be seen in the background. A dining table with dark chairs is positioned adjacent, with natural light illuminating the space through the windows.

Home in New Haven

SunnyVale | Tiny Home Charm Near Middlebury

Welcome to SunnyVale, where vintage charm meets Vermont tranquility. Tiny? Yes. Ordinary? Not even close. This lovingly restored vintage mobile home has been thoughtfully reimagined into a cozy retreat on 35 peaceful acres, blending timeless character with modern comforts. Just 10 minutes from Middlebury College and 45 minutes from Burlington Airport, SunnyVale is the perfect place to explore Vermont, chase fall colors, reconnect with nature, unwind under the stars, and make yourself at home.

4.98 out of 5 average rating, 65 reviews

Top guest favourite

A spacious grassy yard is framed by trees, leading to distant views of mountains under a partly cloudy sky. A set of wooden chairs is positioned on the lawn, offering a peaceful spot to relax. The corner of a building with stairs is visible in the foreground.

Farm stay in Cornwall

Orchard Guesthouse - 1 mile to Middlebury

Orchard Guesthouse on our apple orchard is a delightfully unique place to stay. A former pickers cottage, we offer dorm style bedrooms and bathrooms with a rustic yet cozy interior. Includes full use of the house and adjacent yard. We are conveniently located 2 miles from Middlebury and 1 mile from Middlebury College campus. Come enjoy a full range of outdoor activities, adventure is on your doorstep! Perfect set up for groups - cycling, hiking, skiing (nordic/alpine) or college events.

4.95 out of 5 average rating, 155 reviews

Top guest favourite

Cottage in New Haven

Hilltop Cottage With a View

Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

5.0 out of 5 average rating, 200 reviews

Top guest favourite

Home in New Haven

Beautiful timber frame just minutes to Middlebury!

This large, gracious home was custom built in 1987 and was fully renovated in 2019. Gorgeous post and beam construction with endless windows and mountain views! Enjoy the large kitchen surrounded by a great room & solarium. 6 bedrooms with 3.5 baths can accommodate a crowd. Mudroom with custom lockers. Enormous fire ring with Adirondack chairs. Central heating/AC, super fast WiFi . 5 mins to Middlebury. Home is on 25 acres, providing privacy and peace. Making memories is easy here!

5.0 out of 5 average rating, 154 reviews

Top guest favourite

The exterior of the guesthouse is shown, featuring a white wooden facade with multiple windows. A prominent cupola tops the structure, reflecting sunlight under a clear blue sky. Lush green trees and shrubs surround the building, enhancing the serene ambiance of the area.

Guest house in Vergennes

Private Guesthouse in the heart of Vergennes

Completed in 2013, the Guesthouse perfectly complements the 1871 Victorian home to which it is attached. Located on Main Street in historic Vergennes, Vermont, our home is one of several fine examples of the architecture of the 19th Century that grace our City. Our thriving downtown is a short walk away, boasting exceptional dining and shopping opportunities. Vergennes is a 20-minute drive away from Middlebury College, and 45 minutes from Burlington.

4.98 out of 5 average rating, 145 reviews

Top guest favourite

An open-concept kitchen and dining area is furnished with modern appliances and sleek cabinetry. A central island provides additional counter space, while a dining table with four chairs is positioned nearby. Natural light filters through windows, enhancing the space's bright and airy feel.

Home in Weybridge

Close to college-cheerful, quiet, 2 bedroom home

This recently renovated home is conveniently located 1.5 miles from Middlebury College campus and all that Middlebury has to offer! The back deck and spacious yard are perfect for relaxing outdoors. The open floor plan is cozy for one and accommodates families well. The master bedroom is furnished with a queen bed and the second bedroom has two twin beds. Pack 'n Play and highchairs are available for young children upon request.

4.99 out of 5 average rating, 131 reviews

Top guest favourite

Home in Middlebury

Weybridge Cottage |Steps from Middlebury College

Welcome to Weybridge Cottage, a newly renovated 2-bedroom, 1.5-bathroom home just a few minutes walk from Middlebury College and downtown Middlebury. Conveniently located just two blocks from campus, Otter Creek Bakery, and downtown, the location is perfect for Middlebury College visits. The house comfortably accommodates 4 people with a daybed for an extra guest and is fully equipped with modern comforts.

5.0 out of 5 average rating, 18 reviews

Top guest favourite

A flowing waterfall cascades over rocky terrain, surrounded by lush greenery. Sunlight filters through the trees, creating a serene atmosphere. The water splashes against large stones, while vibrant foliage frames the scene.

Flat in New Haven

Dog Team Falls Apartment - Minutes from Middlebury

Beautiful 1-bedroom apartment overlooking the scenic New Haven River and Dog Team Falls. Just minutes away from Middlebury College and centrally located to major ski areas and hiking in the Green Mountains. Not Suitable for young children. In the interest of price transparancy, please note that the amount you pay includes the 15.5% Airbnb service fees and the 12% local occupancy tax.

5.0 out of 5 average rating, 274 reviews