Holiday houses in Weybridge

4.93 out of 5 average rating, 310 reviews

Yurt in Bristol

Bristol Cozy Yurt near Hiking/Swimming|MapleFarm

Our cozy yurt is located within minutes of amazing, hiking, biking, skiing, breweries and much more! Relax around the fire while listening to our resident owls or stare up at the stars through the dome. We're centrally located to some of the best hiking and swimming skiing in Central Vermont. Mt Abe and Bartlett's Falls are the closest options. We're also close to civilization with several towns close by to explore for food, drink, art, and shopping. Or travel a bit further to Burlington..

4.99 out of 5 average rating, 196 reviews

Apartment in New Haven

Gracious two bedroom just minutes to Middlebury!

This 2 bedroom unit was built in 2021 with modern amenities... large gourmet kitchen with granite countertops and full sized stainless steel appliances. Enjoy the spacious great room with a 65" smart TV, a cozy sitting area, and dining tables and chairs for 6. Both bedrooms are furnished with brand new queen beds, dressers and bedside tables. Super fast free WiFi. Drive to Middlebury in minutes. Clean and comfortable. This spacious, well appointed apartment will make you want to stay forever!

4.95 out of 5 average rating, 123 reviews

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.

4.93 out of 5 average rating, 231 reviews

Farm stay in Cornwall

Cozy country guest house

Our guesthouse is nestled in the Lemon Faire River Valley. This 1 bedroom with kitchen, bathroom, and extra sleeping loft gives you a quiet experience of the Vermont countryside. The outside entry deck overlooks over a 1000 acres of open field and farmland. Middlebury is only 3 miles away and offers museums, restaurants, and shopping. This is an active farm: horses, dogs, geese, a duck, and chickens. Please read the house manual as it has lots more information about the house and property.

4.87 out of 5 average rating, 913 reviews

Cottage in Lincoln

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

4.99 out of 5 average rating, 175 reviews

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.

4.92 out of 5 average rating, 285 reviews

Yurt in New Haven

Song Bird Sangha Yurt

Songbird Sangha was thoughtfully created to provide a peaceful retreat from the world. It is nestled into a beautiful forest with privacy in mind. You will fall in love with the sky dome over your queen sized bed for the most comfortable star gazing ever! Your stay would not be complete without a complimentary campfire & marshmallow and if you would like more magic sign up for our Airbnb Experience The Healing Nature of Horses, a life enhancing encounter . Certified Wildlife Habitat.

4.98 out of 5 average rating, 130 reviews

Mountain View Retreat

This clean, quiet, ground-level apartment enjoys an out-of-town feel and expansive mountain views while being conveniently located to the town of Middlebury, Middlebury College, the Green Mountain National Forest, the Middlebury College Snow Bowl and the Rikert Nordic Center, and more. This 1 bedroom/1 bath apartment features an open living concept and a fully equipped kitchen and is just 1.5 miles from restaurants and grocery stores and 2 miles from the college.

4.97 out of 5 average rating, 118 reviews

Guesthouse 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.

4.99 out of 5 average rating, 157 reviews

Guest suite in Cornwall

Home Suite Home in Cornwall, Minutes from Midd!

Looking for a home away from home on your travels in the Champlain Valley? Whether you're searching for a place to lay your head while visiting your Middlebury College student, a home base while exploring the gorgeous Green Mountain State, or a secluded, peaceful retreat in which to write the next chapter of your book, we've got just the spot! Our home, with the private guest suite and deck, is situated perfectly for your Vermont holiday.

4.86 out of 5 average rating, 155 reviews

Apartment in Bristol

Overlook at the Office

Fall in love with Bristol. This sweet one-bedroom efficiency right in the Gateway to the Green Mountains has everything you need, whether you are looking for a short weekend getaway or longer seasonal stay. Opening up this listing with all new small-kitchen appliances, queen bed, and new bathroom. Central to the town park and stores, and only miles away from ski areas, hiking trails, and water activities.

4.93 out of 5 average rating, 152 reviews

Cabin in Bridport

Champlain Valley Alpacas

Located in central Vermont, our honeymoon cottage is the ideal private getaway, adjacent to in-ground pool (pool available in Vermont season: late June, July- August) ) when you stay with us. You might just be lucky enough to wake up with the alpacas munching outside your window or hear the roosters crowing nearby! Please plan to slip off your shoes at the door.

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Other great holiday rentals in Weybridge

4.96 out of 5 average rating, 24 reviews

Chipman Hill Apartment.

AustinRating, 5 stars2 weeks ago

Wonderful loft, with gorgeous woodwork, just a few feet from the trailhead of chipman hill, while also being conveniently close to downtown and the college. Gem!

4.77 out of 5 average rating, 66 reviews

Home in Weybridge

Quintessential Vermont Renovated Farmhouse

LizRating, 5 stars5 days ago

Beautiful, cozy home in a peaceful setting. Easy access to downtown area if that’s your vibe. Kitchen had everything we needed for an easy weekend stay. The house slept 6 adults very comfortably, with plenty of clean blankets, sheets, and towels. Perfect setting for a relaxing escape!

5 out of 5 average rating, 75 reviews

Guesthouse in Bristol

Studio Retreat

MaryRating, 5 stars2 weeks ago

Absolutely beautiful and peaceful studio! It was such a great location to access Bristol, Middlebury, and plenty of nearby hiking. We would happily stay here again!

5 out of 5 average rating, 10 reviews

Apartment in Bristol

Scandinavian inspired studio

MichaelRating, 5 stars3 days ago

David and Hannah have created a perfect Vermont getaway. The studio is stylish, spotless, and full of thoughtful touches. Bristol is a charming location with easy access to everything Vermont offers. The hosts are kind, responsive, and truly care about the guest experience. From the comfy bed to the well-appointed kitchen, everything was just right. We'll absolutely be back!

Home in Weybridge

5 out of 5 average rating, 4 reviews

Updated farmhouse minutes from Middlebury

DianeRating, 5 stars1 week ago

Hands down one of the best Air B and Bs I’ve been to, and I’ve been to a lot! Mary and Luis, our hosts, were so welcoming that we instantly felt like family. Their communication was great. We had an incredible stay at their charming, beautifully updated farmhouse in Vermont! The home is full of character, with thoughtfully curated antique decor that gives it a warm, welcoming feel. Every detail has been considered, from cozy linens and a fully stocked kitchen to extra touches that made our stay especially comfortable. The views from the property are stunning, with rolling hills and peaceful scenery in every direction. We loved being able to walk to downtown Middlebury—just a short stroll away—for great shops, restaurants, and a true New England village vibe. This place is the perfect blend of rustic charm and modern comfort. Whether you're relaxing indoors or enjoying the scenery outside, you’ll feel right at home. I highly recommend and would return in a heartbeat!

5 out of 5 average rating, 143 reviews

Bluebird Studio- Light filled and airy

AbbyRating, 5 stars2 weeks ago

Dutton’s place was perfect. We came for Middlebury’s commencement with our 6 year old and the location was excellent and quiet. Our son loved how cozy it was. The kitchen was really great to have on such a busy weekend. Dutton was super flexible and helpful too, letting us stay a few extra hours so our grad could finishing packing up her room. The bed was firm, just good to know. We all slept well. Absolutely recommend.

5 out of 5 average rating, 83 reviews

Treehouse in Moretown

4-Season Treehouse @ Bliss Ridge; Best Views in VT

EmilyRating, 5 stars2 weeks ago

We absolutely loved staying at Jordan and Dan’s treehouse at Bliss Ridge. It was such a unique experience and our family made memories there that will last a lifetime. The treehouse is stunning- whimsical and charming -and the perfect spot to unplug and connect with nature. Jordan and Dan were responsive and kind, and we are so appreciative they created this magical place to share with others. Highly recommend!