Vacation rentals in Orwell

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Top-rated vacation rentals in Orwell

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming guest house is depicted, characterized by its red siding and gabled roof. An American flag is displayed at the entrance, while a covered porch features seating options. Lush green grass and trees frame the property, adding to the serene landscape.

Guesthouse in Leicester

5 out of 5 average rating, 10 reviews

Peace of the Farm Guest House

Forget your worries in this spacious and serene space. Located on 57 acres of pastures, hayfields and woods, our guest house sits central on Foxcroft Farm and is situated about 800' from the main road, down the driveway past our house, barns and gardens. The farm is about 5 miles from Brandon, 3 miles to Lake Dunmore, 12 miles to Middlebury, 45 minutes to Killington or Lake Champlain ferries/ bridge to NY State. Biking, hiking, kayaking, boating, fishing, skiing, local wineries, beers, arts...

Top guest favorite

A charming one-bedroom cabin is nestled among tall trees in a forested area. The wooden exterior is complemented by a porch with a railing and flower pots, creating a rustic appeal. Natural light filters through the windows, enhancing the cabin's tranquil setting.

Tiny home in Castleton

4.99 out of 5 average rating, 109 reviews

Cabin-by-the-falls

One-bedroom cabin, one double bed, for those who want tranquility. Parking at the main house and then a short walk downhill, then a level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

Guest favorite

A spacious family room showcases an extensive vinyl record collection against a backdrop of yellow walls. A wall of photographs adds interest, while a relaxed seating area is present. Natural light floods in from large windows, enhancing the inviting atmosphere of this multipurpose space.

Guest suite in Lake Bomoseen

4.97 out of 5 average rating, 201 reviews

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Top guest favorite

A wide expanse of green pasture is visible under a golden sunset, casting long shadows across the field. Round bales of hay dot the landscape, adding texture to the serene setting. The sky is adorned with scattered clouds, reflecting the warm tones of dusk.

Home in Orwell

4.97 out of 5 average rating, 35 reviews

Heron Bluff on East Creek

A modern, private retreat overlooking East Creek situated on 114 acres of fenced pasture and woodlands. 35 minutes from Middlebury, Heron Bluff abuts East Creek, a haven for wildlife -- and an ideal getaway for paddlers, anglers, cyclists, birders, hikers... families, couples, artists looking for tranquility and inspiration. Guests may kayak on the East Creek from a private dock, hike nearby Mount Independence Park, bird watch, and be at peace. Starlink supports remote work and streaming.

Top guest favorite

Two llamas are observed resting on a bed of straw, surrounded by hay scattered across the floor. Sunlight filters in through nearby windows, softly illuminating their fur and creating a serene atmosphere in their cozy space.

Cottage in Leicester

4.97 out of 5 average rating, 278 reviews

Banjo's Cottage near Middlebury & Recreation Areas

Private getaway on our 200 acre organic farm with sunroom, wood stove, fully equipped kitchen & wifi. Level 2 EV charger. Walk to Fern Lake, hike/ski/bike our woods trails, explore Moosalamoo Recreation Area by foot, bike or kayak. Canoe Lake Dunmore, swim Silver Lake. 15 minutes to the Rikert Nordic Center, Blueberry Hill, and Middlebury Snow Bowl; an hour to Killington, Sugarbush & Mad River ski areas. Easy access to Middlebury College, golf courses, local breweries & top tier restaurants.

Top guest favorite

An aerial view reveals a farmhouse surrounded by lush green fields and blooming apple trees. The landscaped driveway curves gently toward the entrance, showcasing the expansive property with vibrant greenery and organized garden areas, creating a serene rural setting.

Apartment in Whiting

4.95 out of 5 average rating, 198 reviews

360° mountain views near Middlebury

Very cozy, large private loft apartment with a kitchenette and bathroom 10 miles from Middlebury College Vermont. Lake Champlain, ski resorts, and other outdoor activities within 20 miles. Burlington, Albany, Montreal, Boston, New York are only 1 - 4 hours away. ——— FOLLOWING THE RECOMMENDATIONS OF THE VERMONT STATE'S DEPARTMENT OF HEALTH, OUR RENTAL PROPERTY IS ONLY AVAILABLE FOR FULLY COVID-19 VACCINATED GUESTS. PROOF OF VACCINATION RECORD REQUIRED. This is for the well-being of us all.

Superhost

A spacious bedroom features a wooden bed frame with a light gray quilt and a decorative pillow. Nearby, a nightstand holds a lamp, and a large window allows natural light to fill the room. A rug adds warmth to the wooden floor.

Apartment in Shoreham

4.84 out of 5 average rating, 37 reviews

Stay at Trade Winds Farm

Newly upgraded space of a beloved family farm house. Spacious room with light filled windows perfect for a cozy read. Comfortable bed with sitting area, a great rest stop after a busy day. Just 12 min drive from Middlebury & doorstep away from the farm’s hiking & X-country ski trails. Autumn brings magnificent foliage views & summer days smell of fresh hay. Enjoy a slice of life in a Vermont rural setting. J1772 EV charger (10KW) on site. VT Meals and Rooms Tax ID number is MRT-10126712.

Top guest favorite

The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.

Farm stay in Salisbury

4.95 out of 5 average rating, 363 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Guest favorite

The cabin interior is shown with rich wooden walls, featuring a wood stove for warmth. A dartboard is mounted on the wall, and a red swing chair hangs from the ceiling. Outside, brightly colored adirondack chairs surround a gravel area, enhancing the rustic outdoor space.

Tiny home in Orwell

4.93 out of 5 average rating, 41 reviews

Off-Grid Cabin Camping

Our off grid rustic cabin is nestled in the woods on the edge of a meadow on our 250 acre Organic Dairy Farm. Come to relax and unplug. Our cabin was built for memories to be made. The bunkroom is full of beds. The cabin is full of boardgames, cards to be played at the 8’ table and a dart board! There is a small kitchen with a farmhouse sink (water via handpump) full size propane stove and fridge. There is even a quintessential Vermont Outhouse. We have everything you will need!

Guest favorite

A modern wooden house is surrounded by lush greenery, featuring a small pool on a wooden deck. Views of distant mountains and a serene lake are visible in the background, creating a tranquil outdoor setting.

Tiny home in Warren

4.99 out of 5 average rating, 244 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Top guest favorite

The exterior of the guest house is showcased, featuring dark wood siding and a welcoming porch with a railing. An American flag hangs from the side, while colorful flowers and neatly trimmed shrubs add to the charm of the front yard.

Home in Shoreham

5 out of 5 average rating, 78 reviews

Vantage Point Guest House Mountain Views

Charming 2-bedroom home located on 27 acres is a perfect retreat! Vantage Point is surrounded by apple orchards, fields and woods. Whether you stay for two nights or a month, our home has all the amenities to make your stay comfortable and relaxing! Close to Middlebury & Middlebury College (20 min) and Vergennes (30 min). Ferry to Ticonderoga, NY is just 2 miles down the road as is a boat ramp to Lake Champlain.

Guest favorite

A kitchen space is visible, featuring modern appliances and a light-colored countertop. Natural light enters through a window overlooking a wooden deck. A small table and two stools are positioned near the window, while a stylish fridge is situated adjacent to the countertop.

Guesthouse in Hubbardton

4.95 out of 5 average rating, 58 reviews

Flatlanders Outpost on Lake Beebe

Are you looking for a quiet getaway? We are located at the end of the road right on Lake Beebe, a small lake north of Lake Bomoseen. The apartment is above the garage (stairs inside the garage), which is separate from the house. It is a really peaceful, out of the way location. The studio apartment has a full kitchen and a private porch overlooking the lake.