Holiday rentals in Orange County

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Top-rated holiday rentals in Orange County

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

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Top guest favourite
Tiny home in Fairlee
5 out of 5 average rating, 172 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
A bright and inviting interior features natural wood paneling and blue accents. A cozy couch, dining table, and wood stove are arranged to create a comfortable gathering space. Large windows allow natural light to illuminate the room and offer views of the surrounding greenery.
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
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, 119 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, 160 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 fire pit with logs burning brightly is situated near a tranquil pond. Behind the fire, a stack of firewood is neatly arranged, and a hammock hangs between trees. Lush greenery surrounds the area, creating a peaceful outdoor setting.
Cabin in Vershire
5 out of 5 average rating, 270 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 cozy living area features warm wood paneling, with a light-colored sofa and two rattan chairs, one adorned with colorful cushions. A vintage record player sits atop a small table, beside a glass-top coffee table. Natural light streams in through large windows, illuminating the space.
Cabin in Roxbury
4.99 out of 5 average rating, 202 reviews

Cozy cabin retreat

Escape to a cozy, romantic cottage tucked beside a gently flowing stream—where you’ll fall asleep to the sound of water just outside your window and wake to quiet Vermont mornings. Set in a secluded valley in central Vermont, the cottage offers a peaceful, nature-immersed stay with access to open land, trails, and dark, star-filled skies. Whether you're here to unplug, explore, or simply slow down, this is a place that invites you to settle in.

Top guest favourite
A log cabin is positioned within a lush green landscape. The exterior features a red metal roof and a welcoming front porch with wooden chairs. Surrounding trees provide a sense of privacy, while flowers in planters add color to the entrance.
Cabin in Fairlee
4.96 out of 5 average rating, 160 reviews

Fairlee Log Cabin

Cozy Log cabin 0.2 miles from Lake Fairlee! This year-round cabin is a cozy getaway from the hustle and bustle of life. Just two hours north of Boston, and 30 minutes from Dartmouth, Lebanon, and the White River Junction. Additional amenities: -Clawfoot tub -Outdoor firepit -40 acres of land for hiking, mountain biking, snowshoeing, etc. -dog only friendly for a $40 additional fee -**as of 2/1/23 new oven and dishwasher :)

Top guest favourite
An expansive view of the farm house reveals a charming structure surrounded by lush grass and autumn foliage. The building features a varied roofline with dormer windows, nestled against a backdrop of hills, showcasing vibrant fall colors under a clear blue sky.
Guest suite in Royalton
4.96 out of 5 average rating, 297 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
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.

Guest favourite
Tiny home in Fairlee
4.91 out of 5 average rating, 175 reviews

Private Tiny House Retreat

The Hemlock Tiny House provides a cozy place to stay in wooded Vermont. You have the Tiny House to yourself, along with a private patio. Must be able to climb ladder to access lofted bed. No kitchen. Well-behaved animals allowed 1 Queen-sized lofted bed 1 Fold-down sofa bed (good for someone who can sleep anywhere or child)

Top guest favourite
The open living space features wooden walls and a cozy decor. A queen bed is paired with a single camp bed, while a comfortable seating area includes two leather chairs. A kitchenette and bookshelves line the wall, enhancing the cabin's inviting atmosphere.
Guest house in Fairlee
4.96 out of 5 average rating, 256 reviews

Sunshade

Sunshade cabin is a step back in time recalling the golden age of family lake camps in Vermont. Able to accommodate 3. It features one queen bed and one single camp bed. Steps away from Lake Morey and hiking trails. Relax, refresh, recharge and make new memories at a wonderful location in rural Vermont.

Popular amenities for Orange County holiday rentals

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  2. United States
  3. Vermont
  4. Orange County