Holiday 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.

%{current} / %{total}1 / 1
Top guest favourite
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
4.86 out of 5 average rating, 290 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 favourite
The living room features a cozy gas fireplace framed by light-colored wood. Large windows allow natural light to fill the space, highlighting a green sofa set and a rustic rocking chair. A wooden coffee table and two log-style stools complete the inviting atmosphere.
Flat in Jay
4.86 out of 5 average rating, 14 reviews

Ski in/ski out Jay Peak condo with view of slopes

Ski-in/ski-out spacious 2 bed/2 bath condo at Jay Peak. Beautifully appointed with gas fireplace, view of mountain from living room and sunrise from bedrooms. Family friendly. Private entrance with boot room. Access Racoon Run & Village Double. Centrally located at Tramside base and restaurants, Ice Haus, waterpark, Nordic Trails (all 2-5 minute walk). 1/2 mile from golf course. All Slopeside advantages, with a nicer condo! Access to pool, hot tub, and fitness center for fee through resort.

Top guest favourite
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, 129 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 favourite
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, 51 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 favourite
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.
Flat in Newport
4.99 out of 5 average rating, 243 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 favourite
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, 42 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 favourite
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, 82 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.

Top guest favourite
A bright living room features large windows overlooking the lake, allowing natural light to fill the space. A comfortable seating area includes a cream-colored sofa and an armchair. A round coffee table sits in the center, while a warm, inviting fireplace adds a cozy touch.
Apartment in Newport
4.97 out of 5 average rating, 89 reviews

SKI Jay's Peak only 30 minutes Cozy Lakeside Condo

Welcome to our cozy two bedroom condo with the gorgeous views of Lake Memphremagog! The SNOW is FANTASTIC at the moment! Are you ready for some winter fun? The reindeer farm is close by and sleigh rides in the North East Kingdom are on our doorstep! Skiing in the area, ONLY 30 minutes from Jay's Peak! 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.

Top guest favourite
The exterior of the condominium features a blend of grey and green siding, accented by vibrant red doors. A well-maintained landscape includes shrubs and ornamental plants surrounding the entrance. The pitched roof and decorative gables create an inviting architectural design against a backdrop of lush trees.
Townhouse in Jay
4.93 out of 5 average rating, 118 reviews

Ski In Ski Out in style on Village Chair

This condo lies in the heart of the original Jay Village, offering flexible living space for a larger family or group and the best of Jay's ski-on ski-off locations. With a well stocked kitchen and central great living area as well as 5 bedrooms and a den, everyone can have the space that they need. Private entrance with a mud room and ski locker. Free parking. Access to the Jay Peak Resort facilities, including pool, water park and skating rink are available for a fee to the resort.

Top guest favourite
Chalet in Westfield
5 out of 5 average rating, 20 reviews

Peak + Pine Chalet 10 minutes to Jay Peak

Escape to this charming , recently renovated, chalet nestled in the serene woods the Northeast Kingdom of Vermont. Perfect for families or small groups, it boasts a cozy living area with vaulted ceilings, a fully equipped kitchen, and a private deck overlooking nature. Enjoy year-round activities with Jay Peak Resort just 10 minutes away, offering skiing in winter and hiking in summer. Relax in the peaceful surroundings and make lasting memories in this inviting mountain retreat.

Guest favourite
The chalet is framed by lush greenery, showcasing a large deck and unique architecture. A fire pit is positioned in the foreground, surrounded by rocks, while two drinks are placed on a log, inviting guests to relax in the natural setting.
Chalet in Westfield
4.9 out of 5 average rating, 94 reviews

The Shangri-la House

The Shangri-la House is an amazing 3 bedroom, 2 full bathroom chalet located in the Alpine Haven resort community in Northern Vermont. Guests of the house have access to the community pool, tennis court, volley ball court and hiking trails. The chalet is fully furnished, has high speed wi-fi, is dog friendly and is just 5 miles from The Jay Peak Ski, Golf and Indoor Water Park Resort. The chalet is also close to many restaurants the closest of which is .5 miles down the road.

Top guest favourite
The chalet's inviting exterior features beautiful wooden walls and a warm red roof, harmonizing with the surrounding snowy landscape. A spacious deck wraps around the front, providing views of the trees and hillside, while a wooden stack is neatly arranged beneath it.
Guest house in Westfield
4.99 out of 5 average rating, 146 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.

Popular amenities for Orleans County rentals with a pool