Holiday houses in Orwell

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Top-rated holiday rentals in Orwell

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

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Top Guest favourite
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, 26 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 favourite
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
4.96 out of 5 average rating, 50 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 Internet. Bedrooms have window A/Cs.

Guest favourite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 255 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Top Guest favourite
Apartment in Ticonderoga
4.99 out of 5 average rating, 101 reviews

Cabin at Lake's George/Champlain

Guests will enjoy a private one bedroom apartment that is attached to our log cabin in Ticonderoga. Our central location between the lakes provides quests easy access to everything the Adirondacks have to offer. We are 1 mile from the boat launch in Lake George and 3 miles from the boat launch on Lake Champlain and historic Fort Ticonderoga. The town beach on Lake George is within 3 miles. Hiking in both NY and VT. Main street Ticonderoga is just 1/2 mile away. 18 hole golf is within 3 miles.

Top Guest favourite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 175 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Top Guest favourite
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, 209 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.

Top Guest favourite
A serene lakeside scene captures a cozy cabin nestled among lush trees, illuminated by warm light. A dock extends into the water, featuring seating for relaxation. A canoe glides gently across the lake, adding to the tranquil atmosphere of this picturesque setting.
Cabin in Poultney
4.93 out of 5 average rating, 398 reviews

Waterfront Vermont Lake House w/ Panoramic Sauna

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from the decks or sauna. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Top Guest favourite
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, 100 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. Recent updates include new washer and dryer, new oven, Roku smart tv.

Top Guest favourite
A tranquil lake scene is depicted, featuring a clear blue sky reflecting on still waters. Lush greenery surrounds the shore, and the vibrant foliage can be observed on the hillside. A cozy red cottage is subtly mirrored in the lake's surface, enhancing the serene ambiance.
Cottage in Adirondack
5 out of 5 average rating, 276 reviews

Water's Edge at Beaver Pond

Like being on a boathouse, this unique custom cottage/camp embraces the spirit of Adirondack lakehouse living... with a breathtaking view from every room! Perched on the shore of private Beaver Pond, this pristine lake offers great recreational activities (canoe/ kayak/ paddleboard/ swimming/ fishing). Inside the cottage, this home is designed with every detail carefully selected, and all modern amenities included! Cozy, comfortable and well-appointed... a perfect vacation location!

Top Guest favourite
A welcoming farm sign displays 'Des Marais Farm' alongside an illustration of a red barn and fields. Colorful flowerbeds filled with red and pink blooms enhance the entrance, framed by lush greenery and a clear blue sky.
Farm stay in Brandon
4.95 out of 5 average rating, 109 reviews

The Swallows Nest in a wildlife preserve

NEW THIS YEAR: High speed internet, Heat pumps for heat and AC throughout the house, and a new refrigerator/ freezer Secluded and beautiful, at the end of a gravel dead end road, the Swallow’s Nest is part of our organic farm and wildlife refuge. You’ll find serenity here with huge open vistas. We are two miles from the town of Brandon. Brandon has restaurants, shops, art galleries and music venues. Check out what’s happening in Brandon at the Brandon area chamber of commerce.

Top Guest favourite
Tiny home in Ludlow
4.96 out of 5 average rating, 101 reviews

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Guest favourite
A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.
Cabin in Goshen
4.97 out of 5 average rating, 141 reviews

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

Popular amenities for Orwell holiday rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Addison County
  5. Orwell