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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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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.
Condo 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
4.97 out of 5 average rating, 143 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.

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.
Apartment in Newport
4.99 out of 5 average rating, 276 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 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 | 7 Min to Jay Peak | Sleeps 8

Escape to our cozy 3-bedroom, 2.5-bath chalet just 7 minutes from Jay Peak Resort and Waterpark. 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.
Condo 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.

Top guest favourite
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, 179 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.

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, 99 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 entrance of a condo is visible, framed by a vibrant red door under a snow-covered roof. Flurries are falling gently, creating a serene winter scene. A snowboard stands beside the door, and a small snow-covered shrub is present to the left.
Condo in Jay
5 out of 5 average rating, 46 reviews

Cozy Ski-in/Ski-out Jay Peak Mountain Condo

Discover the charm of our Jay Peak Slopeside condo, arguably the best on the mountain. Right by ski lifts, trails, dining, and the Pump House water park, it's perfect for both excitement and relaxation. Inside, enjoy a warm living room, a welcoming dining area for special meals, and a renovated, well-stocked kitchen ready for your culinary adventures. Every corner is crafted for your comfort, making it the ideal spot for creating lasting memories with those you cherish.

Top guest favourite
Chalet in Westfield
5 out of 5 average rating, 27 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.

Top guest favourite
Directional signs are positioned on a pole against a vibrant sunset backdrop. The signs indicate various nearby locations, with a gradient of warm colors filling the sky, creating a serene transition from day to night.
Condo in Jay
4.99 out of 5 average rating, 156 reviews

Jay Peak Ski in Ski out Condo

Bright and spacious 2 Bedroom ski in ski out condo located just off Grammy Jay. Our location offers lovely views of the surrounding valley and of the summit of Jay. The condo is kid-friendly and cozy a great place to retreat to after a day of skiing.

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