Vacation rentals with a pool in Orleans County

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Top-rated rentals with a pool in Orleans County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite
A serene view of rolling mountains is captured during sunset, with soft hues of orange and purple filling the sky. Lush treetops in the foreground provide a natural frame, highlighting the beauty of the landscape and creating a peaceful atmosphere.
Guest suite in Hyde Park
4.85 out of 5 average rating, 279 reviews

Hill Top Apartment With Amazing View Near Stowe

Charming one-bedroom suite high on a hill with one of the best views in the county. Very private setting on a country road. You will have the whole top floor to yourself including a bedroom, open kitchen/dining/living space, a wardrobe room, bathroom complete with 2-person jet tub and an enclosed porch. Ramble around our large property, or use as your base of operations for your Vermont Adventure. We're right in the heart of northern Vermont, a modest drive from best things to see in the area!

Guest favorite
The living room features tall windows that provide ample natural light and overlook the surrounding wooded area. A stone fireplace is flanked by a television and cozy seating options, including a leather sofa and lounge chairs. A patterned rug adds texture to the wooden floor.
Chalet in Westfield
4.96 out of 5 average rating, 112 reviews

Cozy Chalet at Jay Peak

The house is set up with everything to make your stay cozy, comfortable & fun. Gas Fireplace, 5br, 2.5 Bath, 2 separate Living Room areas. Large Deck with Gas Grill overlooks small brook. Private wooded setting with panoramic mountain views once leaves have fallen. Seasonal Pool, Disc Golf, Volleyball, Playground & Hiking Trails a short walk from the house. 3 mi to Jay Peak. Air Conditioning is in three bedrooms which are installed by the 2nd Sunday of June then removed the last Sunday of Sep.

Guest favorite
A cozy living area features a sectional sofa with dark leather cushions and a tufted ottoman on a decorative rug. A colorful piece of wall art adds visual interest, while a kitchen counter with bar seating is visible in the background, equipped with modern appliances.
Condo in Burke
4.87 out of 5 average rating, 15 reviews

Cozy Mountainside Condo

Welcome to the beautiful NEK! This charming one-bedroom, one-bath condo on Burke Mountain is centered in of one of the finest four-season recreational areas in the world. It’s a two-minute walk to the Mid-Burke Express chairlift and the Burke Mountain resort hotel, restaurants, pool, hot tub, and gym. Just downhill from the patio (with a view) is the Roly Grail mountain bike trail, which is part of the world-renowned Kingdom Trails network. A perfect base camp for your mountain activities.

Guest favorite
A newly renovated swimming pool is surrounded by a wooden deck, with lush green grass and trees in vibrant autumn colors in the background. The sky is clear with a few scattered clouds, creating a serene outdoor space.
Villa in Hyde Park
4.98 out of 5 average rating, 50 reviews

Private Mountain Villa with Pool & 12 Acre Forest

Enjoy a private villa with 12 acres of forested land & heated swimming pool all to yourselves. Just 15 mins from Stowe, 40 mins from Jay Peak & 1 hr from Sugarbush. In fall, enjoy the explosions of yellow, amber and red from the copious maples, birches and oaks on the property, then take a scenic drive in the surrounding mountains. In summer you can hike through the woods, or climb the nearby mountains, and come home for a dip in the pool. Or just chill and watch the wildlife from the patio!

Top guest favorite
A wooden bench with a decorative wrought iron back is positioned in front of a sign reading 'The House of the Setting Sun.' Lush greenery surrounds the bench, and a small rabbit is situated nearby, creating a peaceful outdoor scene.
Apartment in Newport
4.99 out of 5 average rating, 220 reviews

The House of the Setting Sun, Private Apartment

The House of the Setting Sun is a great place to rest, relax & re-energize. Located in a family friendly neighborhood, while still within walking distance to restaurants & close to downtown Newport. The apt has its own dedicated WiFi, easy for working remotely. Downstairs is a room with a ping pong/pool table. You will have your own deck, where you can sit & enjoy a cup of coffee to begin your day or unwind with a glass of wine as the sun sets. Hosts on site and ready to assist if needed.

Top guest favorite
A spacious living area features a stone fireplace as its focal point, flanked by large windows offering views of the surrounding nature. Comfortable seating, including a red chair and a sectional sofa, invites relaxation. A rustic coffee table sits atop a decorative rug, enhancing the cozy atmosphere.
Chalet in Montgomery
5 out of 5 average rating, 35 reviews

The Chalet Getaway, 3 Baths, 5 Bedrooms, 12 Beds

Relax with the family or friends at our peaceful Chalet Getaway. Located just 4 miles from Jay Peak Ski Resort & Golf Course. Enjoy our beautiful well maintained Vacation home that has 5 bedrooms, 3 baths and a large open social area. There is a separate game room with TV & foosball for the kids. In the summer there is a pool, disc golf course, a park and a tennis/pickle ball court in our plan for your use. The Jay Peak/Montgomery Center, area has incredible restaurants & something for All.

Top guest favorite
Condo in Newport
4.97 out of 5 average rating, 72 reviews

Lakeside Cozy Condo! Fall Peeping Ready!

Welcome to our cozy condo with the gorgeous views from Lake Memphremagog! This upstairs 1st floor condo features two bedrooms and two bathrooms, offering a living area with an open kitchen/dining area and a bright living room that includes base board heating. The primary bedroom has an en-suite with a full bath, and there's a second bedroom with an additional ¾ bath with laundry facilities. The views and breezes from deck provides stunning lake views and the property has lake access!

Guest favorite
A balcony features two canvas chairs positioned on a wooden deck. A view of vibrant autumn foliage is visible, with trees displaying shades of orange and yellow against a clear blue sky and scattered clouds.
Condo in Jay
4.92 out of 5 average rating, 170 reviews

Ski in Ski out - fantastic location on the trail

This condo lies in the heart of the original Jay Village, offering flexible living space for a family or group of friends. With 2 bedrooms and 2 bathrooms, everyone can have the space that they need. Access via private entrance with a mud room for leaving all the outdoor gear, in summer and in winter. Enjoy free parking, outside space and a balcony with a serene view into the woods. Make the most of the resort activities (Water park, pool, golf, ice rink) for a fee to the resort.

Top guest favorite
A charming guest house with wooden walls and a red metal roof is surrounded by vibrant fall foliage. The porch features a decorative railing, and large windows allow natural light to fill the interior. The entrance is set back from a cobblestone path lined with grass.
Guesthouse in Westfield
4.99 out of 5 average rating, 142 reviews

Beautiful Chalet minutes to Jay Peak Resort

Our guest house "Le Petit Chalet" is only a few years old, has very beautiful wooden walls and floors, and is both elegant and warm. We love all dogs and your well behaved pet is welcome The house is very comfortable, with all utilities big and small including coffee machine, nespresso machine, food processor, etc Jay Peak is the best ski resort of the East, guaranteed the best snow no matter the conditions. Great for skiing and snowboarding, on the slopes and in the glades.

Guest favorite
A three-story chalet is nestled among trees, with a snow-covered exterior. A large front deck features white railings, providing a cozy entry point. Snow blankets the ground, highlighting the peaceful winter setting.
Chalet in Westfield
4.81 out of 5 average rating, 16 reviews

Chalet Jay

Our cozy 3-bedroom, 2.5-bath chalet is just 7 minutes from Jay Peak Ski & Golf Resort. Enjoy a fully stocked kitchen, gas fireplace, Bluetooth stereo, smart TVs, premium mattresses, luxurious linens, and large picture windows. Outdoor amenities include a gas grill, seasonal pool, tennis courts, hiking/snowshoe trails, Frisbee golf, playground, and park. With a backup generator and peaceful surroundings, it’s the perfect spot for relaxation or adventure. Book your stay today!

Superhost
A modern kitchen is presented with wooden cabinetry and a dark countertop. A gas stove and sink are positioned next to a window, allowing natural light. A dining table with stool seating provides additional functionality, with a view of the outdoors visible through sliding glass doors.
Condo in Burke
4.77 out of 5 average rating, 47 reviews

Trail Side Mtn Bike + Ski Condo w Amenities Access

Beautiful renovated ground level walk-out condo. Features 1 bedroom with 1 King OR 2 twin beds plus pull out couch, 2 baths, full mini kitchen (new pots and pans April 2025), located slope-side at Burke Mtn & on Kingdom Trails. Direct walking access to MidBurke Express Chairlift & Burke Hotel. Close to Burke Mountain Academy. There are magnificent views west to Willoughby Gap. Access to separate, heated, secure storage cage and barn with tuning bench for all gear.

Guest favorite
The interior features a warm wood-paneled layout complemented by natural light. A staircase leads to an upper level, while a seating area showcases a cozy sofa near a stone fireplace. A dining space can be seen in the background, with ample seating available.
Chalet in Westfield
4.98 out of 5 average rating, 40 reviews

Edelweiss! Ski Chalet: 5 Bed, 5 Mins to Jay Peak!

Welcome to Edelweiss our charming mountain ski chalet near Jay Peak Resort, Vermont! Nestled in the heart of the picturesque mountain landscape, this spacious and luxurious retreat is the perfect destination for your next family vacation or group getaway. Perfectly situated between Jay Peak Resort and Montgomery Center, enjoy all that this area has to offer.

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