Vacation rentals in Orange County

4.88 out of 5 average rating, 186 reviews

A serene landscape captures rolling hills blanketed in morning mist. The soft pastel colors of dawn create a gentle gradient across the sky, with lush greenery framing the view. An expansive field stretches in the foreground, inviting a sense of calm and tranquility.

Guest suite in Fairlee

Cloud 9 Private Suite Retreat

This space is perfect for a short weekend getaway or a traveling nurse/other traveling professional for a long term stay. Only 27 miles from DHMC! We are within walking distance of hiking, ATV and snowmobile trails! This cozy and charming in-law apt is located inside our large home with its own private entrance, parking, kitchen, living room, bathroom and electric fireplace! You will also fall in love with our beautiful mountainous views this place will leave you feeling like you’re on cloud 9!!

4.95 out of 5 average rating, 432 reviews

An inviting entrance is framed by wooden gates adorned with colorful glass pieces, leading into a lush garden. Greenery surrounds the area, with rolling hills visible in the background, partially shrouded in mist, creating a serene and vibrant landscape.

Yurt in Randolph

Lower Yurt Stay on VT Homestead

We are located in the hills of central VT, close to hiking, skiing and swimming. Disconnect to reconnect! Our homestead is based on permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. We have an ideal environment for digital detox. This is one of three listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay on VT homestead and Tiny house on VT homestead

4.95 out of 5 average rating, 164 reviews

A serene pond is surrounded by lush green grass and dense trees, reflecting the clear blue sky and nearby foliage in its still waters. The natural setting offers a peaceful atmosphere, inviting guests to explore the outdoor environment.

Cabin in Randolph

Remote, pond view log home, fully loaded, sleeps 6

Enjoy our remote, easily accessible, immaculate, pond-side cabin, set in nature on 109 acres: pond, woods, fields, and trails; with high-speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker, and many other amenities. Screened in porch. Views from every room! In the heart of the Vermont ski corridor. Explore the trails, and our meditation yurt when available!

4.96 out of 5 average rating, 183 reviews

A friendly donkey stands near a fallen tree in a grassy area, surrounded by a natural landscape of trees and open space. The donkey's features are soft and approachable, with prominent ears and a gentle expression.

Cabin in Washington

Back to Nature Romantic Getaway Cabin

This charming, cozy 2 bedroom cabin w small kitchen and living area is situated on a beautiful pond in a truly idealistic setting. Come unwind and unplug!! Propane fridge, lighting and stove and also an outdoor grill. No electric. No running water but water is provided and available. There is an OUTHOUSE. Hiking, mountain biking, relax....experience VT. Nestled in the mountains with a beautiful pond right outside your door. We reside on the property yet a fair distance from the cabin.

4.98 out of 5 average rating, 118 reviews

A serene landscape is showcased with soft rolling hills and a distant mountain illuminated by the rising sun. Wisps of fog hover over a green field, while a single tree is framed by a wooden fence in the foreground, adding to the tranquil setting.

Townhouse in Barre

A Sunrise in Vermont - 1 Bedroom Suite

A tastefully decorated suite with private second story entrance, king bed, large bath, coffee bar, & office space. While the suite does not offer a full kitchen, a coffee bar with mini fridge, microwave, and toaster is all yours to enjoy! 12 minutes from Montpelier & I-89. A few minute walk from the suite will give you access to beautiful hiking and biking trails. Including the Millstone trails. Contactless check in & checkout. We are glad to have you stay & experience a sunrise in Vermont!

5 out of 5 average rating, 129 reviews

Yurt in Randolph

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Apartment in Williamstown

A porch area features two wooden rocking chairs and a small side table, situated along a gray deck. Green foliage is visible in the background, enhancing the peaceful outdoor setting.

4.96 out of 5 average rating, 165 reviews

Garden Getaway

Second floor, 2 bedroom apt above a garage located in Williamstown VT, four miles from I-89. We live right on sight to address any and all needs. 6 miles from Millstone Trails 8 miles from Barre the Granite capital of the world. 9 miles from Norwich University 13 miles from Braggs Farm Sugar House and Gifts & Morse Farm Maple Sugarworks. 18 miles from Vermont State University Randolph Located less than hour from Killington and 24 miles to Sugarbush, and 34 miles from Bolton.

4.98 out of 5 average rating, 122 reviews

A charming kitchen space is visible, featuring a deep farmhouse sink beneath three windows. Crafted wooden countertops complement two-tone cabinetry in mint green and dark wood. Pendant lighting hangs above, and various kitchen items, including a vintage red container, are neatly arranged on the countertop.

Barn in Corinth

Scenic Barn Loft on Private Vermont Estate

Scenic, private, and beautifully crafted, this 1,200 sq ft barn loft sits atop our 140-acre Vermont farm estate with stunning views, artisan finishes, and total comfort. Two bedrooms, two baths, a chef’s kitchen, and a cozy gas stove and A/C make it perfect for couples or families year-round. Wander rolling pastures, hike forest trails, sled in winter, or stargaze in silence—this is a countryside retreat designed to restore and inspire.

5 out of 5 average rating, 235 reviews

A log cabin features a welcoming wooden porch with hanging flower baskets, complemented by a set of red chairs. Surrounded by lush greenery, the cabin maintains a natural aesthetic with steps leading up to the entrance and stone accents along the landscaping.

Cabin in Vershire

Comfortable cozy cabin in the hills of Vermont!

Lovely cabin situated in a small clearing in the woods of Vermont. Brand new 2019. All appliances, WiFi, washer and dryer. No TV, but strong WiFi for streaming on your own device. We have approximately 20 private acres of hiking rails, ponds, streams, and woods. 15 miles from Lake Fairlee, 26 miles from Dartmouth College, 44 miles from Woodstock VT. Golf course at nearby Lake Morey. Not suitable for children or pets, sorry.

4.99 out of 5 average rating, 207 reviews

A historic red barn structure is depicted, showcasing a metal roof and multiple windows reflecting the evening light. The surrounding landscape includes gentle hills, complemented by a sunset casting warm hues across the sky. The dirt path leads to additional outbuildings.

Apartment in Randolph

Historic Wayside Farm - a working dairy farm

Located on a historic Vermont farm. The apartment is located on the first and second floor of our large home. This is an ideal place if you want to explore everything Vermont has to offer. We are centrally located, just a short drive away from area ski resorts, hiking trails, mountain bike networks, breweries and more. We are a certified organic dairy farm. The cows can be found grazing the surrounding hillsides.

4.93 out of 5 average rating, 113 reviews

The Treehut emerges from a lush green forest, elevated among trees with an outdoor deck extending from its entrance. The fire pit area, equipped with chairs, is visible nearby, set within a serene natural landscape. Surrounding ferns contribute to the tranquil ambience.

Treehouse in Braintree

Treehut - Secluded Treehouse in the Forest

Discover the Treehut, a cozy off-grid escape nestled among four trees that we built by hand. This unique retreat features a tiny wood stove inside, an invigorating outdoor shower (with hot water), and a serene fire pit under the stars. Ideal for nature enthusiasts seeking peace and quiet, yet only 10 minutes from Randolph. Unplug and unwind in this magical hideaway.

4.89 out of 5 average rating, 133 reviews

A tranquil scene features a pond reflecting vibrant sunset colors against a backdrop of rolling hills. Trees are silhouetted in the distance, and the grassy landscape shows scattered fallen leaves, enhancing the serene environment.

Tiny home in Chelsea

Windswept Acres Sugarhouse

Looking for a Rustic adventure? ...the Sugar House is your stop. Well water comes via a hand pump and there is an outhouse in the back. A favorite of many of our "regulars" with a great view of the sunrise. You are on 55 acres with two ponds for swimming, fishing, and paddling, plenty of hilltops to hike to and soak in panoramic views... and plenty of privacy.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Orange County vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Orange County

4.99 out of 5 average rating, 241 reviews

A private balcony features two padded rocking chairs positioned around a small table. Warm string lights hang along the railing, illuminating the serene view of the expansive green field and pond below, bordered by lush trees, creating a tranquil outdoor setting.

Cabin in Corinth

Skip's Place

ChristineRating, 5 stars4 weeks ago

A wonderful place to stay. As a host Matthew goes the extra mile. We stay here every year and this year my 7 year old niece visited and is now making plans for next year. Family memories in the making. Thank you for sharing this special place. It's always a joy to go and stay.

4.98 out of 5 average rating, 120 reviews

Home in Orford

Romantic Mountain Getaway

MarkRating, 5 stars2 weeks ago

My business associate were in town for work and Bianca's place was perfect for relaxing after working all day. The space was exquisite and just as described. Hoping to return with my wife for a vacation stay in the future.

4.85 out of 5 average rating, 144 reviews

A bathroom area presents a full-size washer and dryer stacked against one wall. A patterned shower curtain adds color, while a light blue mat complements the decor. The space is well-lit by natural light streaming through the window next to the toilet.

Apartment in Barre

Lovely Two Bedroom Apt in Barre Vermont!

ToddRating, 5 stars2 weeks ago

We have stayed in 2 of the units in this building. It’s quiet. Its clean. It comes as advertised. Fair price. Whenever we are in town this is the first place we try to book. Kristen is very responsive to messages. And goes out of her way to help. One time we had an issue with the washer. Not her fault. And she assisted us in using another unit in the building to do our wash. As our unit advertised a washer and dryer. If thats not top notch service i dont know what is. Looking forward to our next visit Thank you Kristen

4.94 out of 5 average rating, 163 reviews

Apartment in Barre

Relax in Recreation Paradise!

JenniferRating, 5 stars3 months ago

Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!

4.97 out of 5 average rating, 144 reviews

A spacious farmhouse is nestled in a vibrant meadow, surrounded by autumn-colored trees and mountains. The structure features large windows that capture the natural landscape, while a covered porch extends along one side, creating a seamless connection with the outdoors.

Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

BrandonRating, 5 stars1 month ago

We had a quiet stay at the Farmhouse. Very peaceful and quiet location. Lots of space for our dog to roam. The house is very nice and clean. We enjoyed having coffee and looking out across the fields, reading, and cooking. It’s near the small village of Rochester with a few restaurants and otherwise we explored neighboring towns like Middlebury, Waitsfield, Stowe, and Montpelier.

4.8 out of 5 average rating, 15 reviews

A log cabin with a red metal roof is set against a green landscape. It features a covered porch and large windows, offering a view of the surrounding lawn. A small tree and several bushes are visible in the yard, contributing to the serene environment.

Cabin in Barnard

Private post & beam log cabin on Macintosh Pond.

NinaRating, 5 stars5 months ago

It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!

4.84 out of 5 average rating, 158 reviews

A hallway is visible, featuring warm wooden flooring and a decorative rug. Light enters from a partially open door at the end of the corridor. A small seating area is seen beyond the hallway, creating a cozy and inviting entrance to the open space.

Chalet in Stockbridge

Vermont Chalet

JugoRating, 5 stars2 weeks ago

Great little cabin. My wife and I had an amazing time. We really enjoyed both decks and the fire pit by the pond. We will be back for sure. It’s located in between some great Vermont towns.