Vacation rentals with a pool in Orleans County

Find and book unique homes with a pool on Airbnb

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, 275 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 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

The exterior of a white two-story house is shown, framed by a well-maintained yard with lush green grass and a row of yellow flowers. A fenced area includes a chlorinated above-ground pool, set against a backdrop of trees and gentle hills.

Home in Lyndon

4.99 out of 5 average rating, 69 reviews

Newly Refreshed 3 BR, 2 Bath, Sleeps 8

1835 newly refreshed home. Located on 5 acres along the Passumpsic River. Minutes from Kingdom Trails and Burke Mountain. Well appointed kitchen. All bedrooms on the 2nd floor. Bed 1 - king Bed 2 - queen. Bed 3 - queen and full. Bonus area on main floor includes a daybed and a pull out ottoman. Keypad entry for self check in. High speed WIFI, Cable TV, games, fire pit, (chlorinated above ground pool in summer). Owner on site in private unit, offering full privacy but quick response.

Superhost

A chalet-style home is nestled among snow-covered trees, offering a serene winter landscape. The house features a spacious front porch and large windows that reflect the surrounding natural beauty. Majestic mountains are visible in the background, enhancing the peaceful atmosphere.

Home in Westfield

5 out of 5 average rating, 5 reviews

SnowDream Chalet

Private, beautiful chalet-style 3 Bedroom/2 Bath home 7 min drive to Jay Peak Resort. Minutes from he Long Trail. Located in a peaceful community at the foot of Jay Peak with private hiking trails, an outdoor pool, kids park, tennis court, disc golf & volleyball. Private driveway fits 3-4 cars. Surrounded by forest, a small brook, and mountain views. Enjoy the best of Northern VT! • Managed by Vermont Mountain Experience. Backcountry & resort guiding available - 15% discount for guests!

Top guest favorite

Condo in Newport

4.97 out of 5 average rating, 71 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, 169 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

The three-story chalet is surrounded by lush green trees, presenting a welcoming facade. Balconies adorned with railings overlook the serene natural landscape. A gravel path leads to the entrance, providing easy access to the home and its tranquil outdoor 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

4.97 out of 5 average rating, 39 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.