Vacation 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 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, 98 reviews

Cozy Chalet at Jay Peak

The house is meticulously clean & set up with everything to make your stay cozy, comfortable & fun. Gas Fireplace, 5 Bedrooms, 2.5 Bathrooms, 2 separate Living Room areas. Large Deck with Gas Grill overlooks small brook. Private wooded setting 1/4 mi off Rte 242 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 only in large upstairs bedroom (king bed) with desk.

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, 196 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

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, 25 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 favorite

Home in Lyndon

4.98 out of 5 average rating, 50 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 favorite

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

4.96 out of 5 average rating, 56 reviews

Lakeside Breeze Condo with a heated pool!

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!

Superhost

The exterior of the condo is showcased with a covered entrance and a small adjacent patio area. Green doors and two symmetrical storage closets are visible, while a grassy area surrounds the entrance, providing an inviting approach to the unit.

Condo in Burke

4.91 out of 5 average rating, 44 reviews

Cozy 1 Bedroom Condo Right On The Trails

Stay cozy and peaceful on Burke Mountain, directly next to Roly Grail, the bike park, and ski trails. This condo is a perfect stay for any couple, solo-adventurer, or a family with a young child. Utilize the full kitchen and bathroom. Enjoy Kingdom Trails in the summer and all the winter sports the Northeast Kingdom has to offer during the snowy months. The 360 degree views will impress anyone! Shared pool, hot tub, washer/dryer, and workout room closely located at the hotel up the hill.

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

4.91 out of 5 average rating, 161 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 favorite

A refreshing community pool is framed by vibrant flowers with pink blossoms swaying in the foreground. Surrounding the pool, white lounge chairs are arranged on a sunlit patio, inviting relaxation. Towering trees offer shade in the background, enhancing the serene outdoor atmosphere.

Chalet in Westfield

4.91 out of 5 average rating, 86 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 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, 141 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.

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

4.74 out of 5 average rating, 43 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.

Superhost

A cozy living room is presented, featuring a light gray sectional sofa and a black television mounted on the wall above a gas fireplace. A wooden coffee table sits center, surrounded by a patterned area rug. A plush chair is positioned nearby, and large windows with sheer curtains allow natural light.

Condo in Jay

4.9 out of 5 average rating, 52 reviews

True Ski-in Ski-out! Walk to hotel-waterpark-golf

This is the perfect mountain spot all-year-round! “The Shredquarters” is a true ski-in-ski out condo with a fully fitted kitchen, new furniture throughout, free Wi-Fi, in unit dryer and washer, a WFH desk setup, and more! Easy access to all, it’s a three minute walk to the hotel restaurants, spa, and pump house water park and ice rink, and a 7 min walk/2 min shuttle to the golf course. There is A/C for the summer and a cozy gas fireplace in the winter.

Guest favorite

A spacious living area features a high wooden ceiling and warm wood paneling. A stone fireplace adds a focal point, surrounded by comfortable seating. A staircase leads to the upper level, while a dining area is visible in the background, creating an inviting open layout.

Chalet in Westfield

4.97 out of 5 average rating, 33 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.