Holiday rentals in Orange County

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Top-rated holiday rentals in Orange County

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Top guest favourite
A cozy living area showcases a comfortable sofa adorned with patterned cushions and a soft throw. A rustic coffee table sits in front, complemented by stylish armchairs. Natural light filters through large windows, illuminating the modern kitchen with dark cabinetry in the background.
Tiny home in Fairlee
5 out of 5 average rating, 170 reviews

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

Top guest favourite
The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.
Home in Fairlee
4.96 out of 5 average rating, 561 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Top guest favourite
A charming wooden cabin is surrounded by lush greenery, with a sloped roof covered in red metal. Large windows provide ample natural light, while a gravel path leads to the entrance, inviting guests to explore the serene rural setting.
Tiny home in West Fairlee
4.96 out of 5 average rating, 191 reviews

Off Grid Tiny House

This sweet little house is great for those who want to get away from it all. It's like camping but with many more creature comforts. The house has hot and cold water in the summer but is off for the season now, end of October. The house does not come with sheets and towels but if you need that, please let me know and I’ll make that happen for a small fee ($15)! Great for kids! Mountain biking and hiking locally and right out your door. 10% veteran discount. Spectacular and cozy in the winter.

Guest favourite
A cozy corner features a daybed dressed in a black and white checkered blanket, adorned with various pillows. A wall art piece with floral designs is displayed above, while a small table sits nearby. Natural light enters through a window covered by light gray curtains.
Flat in Barre
4.93 out of 5 average rating, 119 reviews

Cute and Functional One Bedroom in Barre VT!

Enjoy a stay at this stylish experience at this centrally-located place! Three separate rooms. Large Bathroom and Kitchen and Bedroom/Living Room. The full size bed has a trundle underneath to pull out a twin size bed. The shades and curtains in the bedroom are blockout shades to keep out the lights of the night. Lots of off street parking and separate private entrance. You will be on the first floor apartment. There is an apt above the studio that is also rented to Air B and B travelers!

Top guest favourite
A vibrant garden features an array of yellow daffodils and blooming flowers, extending towards the grassy area. In the background, a charming cottage with a brown roof is nestled among lush trees under a clear blue sky, creating a serene country setting.
Cottage in Tunbridge
4.97 out of 5 average rating, 118 reviews

Vermont Hillside Garden Cottage

Cozy converted artists’ studio, tucked in the hills at the end of a country road. Open the French door to views of a sprawling garden and rolling fields, alight with fireflies in the spring and bursting with color in the fall. Warm yourself by the wood burning stove after winter fun or unwind with a local microbrew by the fire pit, listening to the Whippoorwills on a summer evening. Beautiful in all seasons, this modern, comfy cottage is the perfect place to get away from it all.

Top guest favourite
A charming cottage is set among lush greenery, featuring a dark wooden exterior. A spacious deck with seating options invites outdoor relaxation, while large windows provide natural light. A small pathway leads to the entrance, enhancing accessibility to the tranquil surroundings.
Cottage in Piermont
4.98 out of 5 average rating, 159 reviews

Fully Updated, Quiet & Cozy 1-Bedroom Cabin

Escape To Tuckaway Cottage - This perfect-for-two entire cottage is freshly remodeled, clean, comfortable and centrally located for your New Hampshire and Vermont adventures! All new furnishings and fixtures, a fabulous outdoor fire pit, and a wonderful enclosed porch with patio are just a few highlights. A short drive in any direction offers 4-season outdoor recreation with nearby mountains, lakes and rivers, plus dining, culture, and entertainment options abound.

Top guest favourite
A cozy living area is highlighted by warm wood paneling and large windows allowing natural light. A stylish record player is placed on a small table near a comfortable seating arrangement featuring a light sofa and wicker chairs. A decorative rug and a small stove add to the inviting ambiance.
Cabin in Roxbury
4.99 out of 5 average rating, 202 reviews

Cozy cabin retreat

This is the cozy, romantic cottage you've been dreaming of! Fall asleep to the sound of the stream outside the window. Enjoy sledding, snowshoeing, or XC skiing around the meadow, or use this as a convenient base for all your Vermont adventures. Nestled in a hidden valley in the center of Vermont, the cottage is conveniently located a short drive from many ski areas, award-winning Montpelier and Randolph restaurants, the bustle of the Mad River Valley and I-89.

Top guest favourite
The cabin features a wooden deck with steps leading to the front door, surrounded by lush green grass and a variety of colorful foliage in the background. Potted plants are positioned near the entrance, enhancing the natural setting.
Cabin in Vershire
5 out of 5 average rating, 269 reviews

Comfortable cozy cabin in the hills of Vermont!

Lovely cabin situated in a small clearing in the hills of Vermont. All appliances, fully equipped kitchen, washer and dryer. No TV, but strong WiFi for streaming on your own device. We have approximately 20 private acres of hiking trails, ponds, streams, and woods. 15 miles from Lake Fairlee, 26 miles from Dartmouth College, 44 miles from Woodstock VT. Our home is next door, about 40 yards away through a grove of trees. Not suitable for children or pets, sorry.

Top guest favourite
A spacious living area features a light grey sectional sofa with cozy throw pillows. Natural light floods in through large glass doors that open to the yard, while a modern ceiling fan hangs above. A rug defines the seating arrangement, and simple decor adds warmth.
Cabin in Rochester
4.95 out of 5 average rating, 504 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Top guest favourite
A renovated barn with a dark exterior is set against a backdrop of mountains. The structure features wooden decks and large windows, allowing for views of the surrounding landscape filled with trees, and open fields.
Barn in Fairlee
4.91 out of 5 average rating, 547 reviews

Private Barn On a Hilltop in Fairlee, Vermont

This carefully renovated barn is located in the hills of Fairlee, five minutes from I-91. A stand-alone private space with two spacious living areas and decks overlooking ponds and the mountains. You're welcome to bring your dog; please note there is a $75 pet fee for the length of your stay. With direct access to extensive hiking trails and minutes from Lake Morey and the Lake Morey Country Club there's lots of fun things to do.

Top guest favourite
Guest suite in Royalton
4.96 out of 5 average rating, 296 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Top guest favourite
A bright living area displays a red couch facing large windows that provide natural light. A small table with two metal chairs is set nearby, accompanied by a vase of colorful flowers. Wooden floors create a warm and inviting feel.
Loft in Corinth
4.96 out of 5 average rating, 203 reviews

Garden Retreat

Located in Central Vermont our studio apartment for two is surrounded by gardens with its own patio. Due to Covid precautions, we are only accepting FULLY VACCINATED guests, at this time. We are located north of Dartmouth College, near Barre/ Montpelier and close enough for day trips to the White Mountains, major ski areas and fly fishing.

Popular amenities for Orange County holiday rentals

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