Holiday 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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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, 291 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!

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 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
4.88 out of 5 average rating, 17 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, 136 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, 255 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 wooden dock extends into the calm waters of Lake Memphremagog, leading into expansive views of the lake and surrounding greenery. Clear skies reflect on the water's surface, creating a serene and inviting scene.
Apartment in Newport
4.97 out of 5 average rating, 96 reviews

Cozy Lakeside Condo/ heated pool 10% off week stay

Welcome to our cozy two-bedroom condo featuring stunning views of Lake Memphremagog! Step out onto the private balcony to take in the scenery, or enjoy access to the 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 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 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.
Apartment in Jay
4.92 out of 5 average rating, 178 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, 97 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, 148 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.

Top guest favourite
Chalet in Westfield
5 out of 5 average rating, 25 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.

Popular amenities for Orleans County rentals with a pool