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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.

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Top guest favourite
A winter scene captures snow-covered trees and a peaceful landscape, framed by distant mountains. A row of townhomes sits blanketed in white, and parked cars are visible on the cleared driveway. The soft glow of sunset casts a warm hue against the snow.
Apartment in Burke
4.88 out of 5 average rating, 152 reviews

Burke Mt condo -gap view & ski and bike trails.

Recently Renovated 2 Bedroom condo on Burke Mountain on bike trail steps from resort hotel and day lodge. 1380 sq ft, well equipped late 80's vintage condo. Heated outdoor hottub and weight room ($5) available through hotel (at their discretion) Enjoy a spectacular view and sunset by the wood stove or on your private deck after a day out in nature. Enjoy early fresh powder runs or biking without driving! Now available Shared community Charging for your Ev. through the Epic charging app!

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, 142 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
Home in Westfield
4.77 out of 5 average rating, 13 reviews

Jay Peak Chalet: Family Friendly |Hot Tub|Ski|Hike

Nestled in a serene community just 9 minutes from Jay Peak Resort, Chalet Weiss is a newly updated mountain retreat that offers the perfect mix of peaceful seclusion and convenient access to the slopes, golf course course, and nearby restaurants. Walk the trails behind our chalet over picturesque streams. Hike the numerous trails the area has to offer. After a day of adventure, relax in the private hot tub or splash in the community pool (seasonal pool). The chalet is family and dog-friendly.

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, 274 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
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, 90 reviews

Beautiful 3 BR, 2 Bath, Sleeps 8, w/wading pool

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 three-story chalet is illuminated at night, showcasing warm light spilling from large windows. Snow blankets the ground, and an inviting front porch is adorned with railings. Pine trees surround the property, creating a cozy and serene winter atmosphere.
Chalet in Westfield
4.89 out of 5 average rating, 28 reviews

Chalet Jay

Escape to our cozy 3-bedroom, 2.5-bath chalet 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 and snowshoe trails, frisbee golf, playground, and park. Set in a peaceful setting with a backup generator for added peace of mind, it’s the perfect spot for relaxation or adventure.

Top guest favourite
A tranquil view of Lake Memphremagog is presented from the deck. The expansive water stretches toward the horizon, framed by a clear blue sky. A grassy area and a single tree are visible in the foreground, enhancing the serene lakeside setting.
Apartment in Newport
4.97 out of 5 average rating, 105 reviews

10% off week/ Cozy Lakeside Condo AND Heated Pool!

MINI BREAKS WELCOME! Welcome to our cozy two-bedroom condo featuring stunning views of Lake Memphremagog with a private balcony. Enjoy access to the lake and heated pool, open from Memorial Day through Labor Day. This first-floor (upper-level) condo offers two bedrooms and two bathrooms, along with a comfortable living space. The open-concept kitchen and dining area flow into a bright, inviting living room, complete with baseboard heating. PLEASE NOTE: There is NO AC in the summer.

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, 122 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.

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
4.91 out of 5 average rating, 98 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
Chalet in Westfield
5 out of 5 average rating, 26 reviews

Family Friendly l Peak + Pine l 10 min Jay Peak

Escape to this charming, recently renovated chalet nestled in the serene woods of Vermont’s Northeast Kingdom. Ideal for families or small groups, it features a cozy living area with vaulted ceilings, a fully equipped kitchen, and a private deck surrounded by nature. Just 10 minutes from Jay Peak, with skiing, hiking, golf, and fishing nearby. Guests also enjoy access to the community pool.

Top guest favourite
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, 53 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.

Popular amenities for Orleans County rentals with a pool