Holiday houses 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

Apartment in Fairlee

4.98 out of 5 average rating, 146 reviews

Kismet Cottage, Perfect for longer stays

Welcome to your home away from home! This charming, fully-furnished 1-bedroom apartment sits right on the lake, offering serene views and a peaceful retreat after a long shift. With four major hospitals located within a 30-minute commute, this is the ideal spot for traveling nurses looking for comfort and convenience. Everything you need is here from a cozy queen bed to a fully equipped kitchen and comfortable living space including a laundry room so you can stay fresh and ready for your shifts.

Top Guest favourite

Home in Orford

4.98 out of 5 average rating, 119 reviews

Romantic Mountain Getaway

Come enjoy the peacefulness that only living in the mountains can give you, without letting go of every day luxuries. Our place is ideal for romantic getaways with its beautiful and private setting! Lots of things to do in the area as well. The serene Indian Pond is located just down the road and it is ideal for swimming & kayaking in the summer and snowshoeing in the winter. Hike Mt. Moosilauke and enjoy stunning views, or hike Mt. Cube or Smarts Mountain for smaller fun family adventures.

Superhost

Treehouse in Stockbridge

4.94 out of 5 average rating, 118 reviews

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

Superhost

Chalet in Stockbridge

4.86 out of 5 average rating, 155 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Top Guest favourite

Cabin in Williamstown

5 out of 5 average rating, 22 reviews

Cabin @ Top of Hill

Cabin @ Top of Hill ~ Cathedral ceilings, unique woodworking, granite countertops, and an open kitchen/living floor plan ~ truly an original place to spend your next adventure! Located in the heart of central Vermont, we are within an hour drive to Sugarbush, Mad River, and Bolton ski resorts, and only a 15-minute drive to snowshoeing, cross country skiing, and ice skating venues. Enjoy a walk to a local eatery, take a granite quarry tour, or simply enjoy a movie at home on the big screen TV!

Top Guest favourite

Farm stay in Roxbury

4.96 out of 5 average rating, 194 reviews

Moonlight Mountain Farm Vermont Studio w Hot Tub

Welcome, this is a Farmhouse. Our idyllic Farmstay offers a private, spacious, modern studio within a beautiful 1840's farmhouse in rural Roxbury, Vermont. Including a dedicated, private sunroom with in floor Hot Tub. Roam our ambling 20 acre property offering a swimming pond, woodland paths, open pastures, and small farm. Explore the headwaters of the Dog River. Revel in Vermont's finest skiing, hiking, biking, beer, and food just up and down the road. Outdoor sauna available for added fee.

Top Guest favourite

Cabin in Stockbridge

4.95 out of 5 average rating, 107 reviews

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Guest favourite

Loft in Fairlee

4.96 out of 5 average rating, 330 reviews

The Massive Loft at The Fairlee Inn

The Fairlee Inn is a historic duplex Victorian built in 1800 tastefully updated and standing proud in the charming town of Fairlee Vermont. Conveniently off the i91 highway on Route 5N. Very close to Lake Morey Resort & Golf Course, The Drive in Movie Theater, Beaches & Fairlee Marine Boat rentals. 20min from Dartmouth college, hospital & skiway! Fully stocked kitchen & Perfect location for outdoor activities & centrally located. By Wings Market, Broken Heart Burger & Samurai Soul Food

Guest favourite

Apartment in Williamstown

4.91 out of 5 average rating, 122 reviews

Cozy/Private, close to hospital, i-89

Relax in Central Vermont. Easy access to hike/ski/tour Private apartment, sleeps up to 5, peaceful area, beautiful views, close to VAST trails 5 minutes from I-89, 15 minutes to Norwich University, 50 minutes to burlington, 45 minutes to ski areas, 5 minutes to Rock of Ages, 10 min to Central VT Hosp. Private entrance/bath/living space, deck overlooking trees/mtns/sliding, microwave, mini fridge, grill, washer dryer, hot plate. Moments to restaurants. 1 queen, twin over full bunk.

Superhost

Cabin in Barnard

4.8 out of 5 average rating, 15 reviews

Private post & beam log cabin on Macintosh Pond.

Post and beam log cabin is completely private on a dead end road. Large flat lawn to enjoy. On the VAST trail system. Short trail leads to the abutting MacIntosh Pond. Located close to the VT Law School, skiing & swimming. Open concept kitchen/dining and living room makes cooking and entertaining easy. Lower level in-law offers 2 BRs and its own living area. Wi-Fi is ECFiber which is fast. Cell service can be spotty, check with your carrier.

Superhost

Home in Stockbridge

4.9 out of 5 average rating, 10 reviews

Tranquil Mountain Retreat, Ideal for Adventure!

Unwind at this charming A-Frame Chalet in Stockbridge, VT, with stunning Green Mountain views. Minutes from Pico and Killington skiing, Green Mountain National golf, and Woodstock, adventure awaits. Enjoy nearby mountain biking, river tubing, hiking, and Warren Falls. Relax on your private deck after a day of excitement. This chalet is the perfect blend of comfort and adventure – book your stay today and create unforgettable memories!

Guest favourite

Cabin in Fairlee

4.95 out of 5 average rating, 139 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 :)