Holiday rentals in Orange County

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!

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

The Barnbrook House

Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

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.

Pine Cabin, Galusha Hill Farm, incredible view!

Gorgeous view from your super private and charming cabin on Galusha Hill. This spot is beyond special and has been described as breathtaking by guests and locals alike. Pine Cabin has a sweeping view of the White and Green Mts, located on 1000+ acres of conservation land. The cabin itself has a fully equipped kitchen, newly renovated bathroom, two bedrooms, and a cozy living room with fireplace. The Front Porch, looking out at the view,is the best place to be with a cup of coffee or cocktail.

The Guest House at Chandlery Farm

This classic Vermont farm estate has everything that description implies: end-of-the-road privacy with breathtaking views, where the only sound is the wind rustling through the leaves. The manicured gardens, stone walls and quaint but luxurious home seem plucked from classic American folklore. Guests can drink their morning coffee while soaking in views of rolling pastures and forested hills, and spend their days exploring the property's trails, and the beautiful towns and countryside nearby.

Fairytale cabin at The Wild Farm

Lay in bed and look out the huge picture window at the farm. You might see cats climbing trees, hummingbirds, snowflakes falling, lightning storms and many more beautiful moments. We have a Wolf, don't be alarmed she is as friendly as can be and will greet you and escort you to the cabin. If you like nature, animals, walking in the forest, cuddling up by the wood stove, then this is the place for you. The cabin is surrounded by gorgeous perennial gardens. We look forward to hosting you!

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.

The Green Mountain Chalet

Picture yourself at one of the Top Airbnbs in Vermont! Big discounts for week and month+ stays! The atmosphere is rejuvenating in this spacious and unique Chalet with beautiful pastoral views! Stylishly built with gorgeous, exposed post and beam cathedral ceilings and decor with a unique style to host you a peaceful getaway. The kitchen has recently been updated with stylish subway tiles & quartz countertops! Min to Lake Fairlee & Lake Morey.

Vermont Highland

Large private home built in 1890. Stained glass windows, pocket doors. 4 bedrooms, 9 beds ...two of the bedrooms have 1 queen and a daybed with trundle, third bedroom has 1 queen and fourth bedroom has a daybed with a trundle (this room is still awaiting some floor work but is function-able for sleeping) and a full size couch can be used as well in the TV room which has doors for privacy. Sleeps 12 people comfortably. Automatic thermostat

Scandinavian design Cabin hiking trail + hot tub

Welcome to our charming cabin nestled in the heart of the woods, where comfort meets tranquility. This 400 sq. ft retreat is bathed in natural light, boasting high-quality appliances, strong WiFi and thoughtfully curated design furniture to ensure a cozy and memorable stay. Relax in our private Goodland wood burning hot tub. Goodland wood burning hot tub is available 365 days a year. EV charger level 2 available.

Luna Cabin - Private brookside cabin on homestead

Step away from it all into the quiet mountains of old Vermont where you'll find our tiny cabin nestled on the banks of our brook. Sway in the hammock by the private fire pit or head inside to curl up on the couch and revel in a sublime, uninterrupted view of the forest. This space beckons you back to simplicity, where you can breath deeply and let your soul smile.