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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Guest favorite

Chalet in Westfield

4.96 out of 5 average rating, 81 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.

Guest favorite

Townhouse in Burke

4.78 out of 5 average rating, 9 reviews

Beautiful vacation Town Home at Burke Mt, Vermont

Mt Bike, ski, ride, hike from your front door depending on the season. Pet friendly, ski in/ski out, beautiful, spacious, fabulous views, 5 bedroom, 3 bathroom, full kitchen. 3 floors, heated 1 car garage with new EV charging station Trailside location for easy skiing, boarding and mountain biking with exciting trails throughout Burke Mt and Kingdom Trails. Enjoy skiing, riding, hiking, biking, lots of attractions, eateries and local bars and pubs. Hot tub gym and pool at the Burke Mt hotel.

Guest favorite

Condo in Newport

4.97 out of 5 average rating, 29 reviews

Cozy Lake Front Condo 20 minutes Jay's Peak Ski

Welcome to the gorgeous views from Lake Memphremagog! It is an upstairs condo located in Newport Center, 3 miles from Newport, VT. This 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 an additional ¾ bath with laundry facilities. There is a deck that provides stunning lake views and the property has lake access!

Guest favorite

Villa in Hyde Park

4.97 out of 5 average rating, 38 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!

Guest favorite

Rental unit in Newport

4.99 out of 5 average rating, 166 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.

Guest favorite

Home in Westfield

4.98 out of 5 average rating, 42 reviews

Cheerful 3 bedroom mountain chalet

Spacious 3-bedroom home minutes from Jay Peak. Open living & dining room with wrap-around deck. Full kitchen with everything you need! Large basement with bar and extra space for sleeping. Access to community pool & tennis courts. Jay Peak Resort offers year-round fun: skiing, snowshoeing, indoor water park and surfing, golf course, indoor rock climbing, disc golf, hiking trails, and mountain biking. Two hours to Montreal. Come enjoy this space for skiing, summer fun, and fall leaf-peeping.

Guest favorite

Chalet in Montgomery

5 out of 5 average rating, 10 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.

Guest favorite

Home in Westfield

4.74 out of 5 average rating, 54 reviews

The Blue Mountain Lodge, 6 bedroom, 4 bathrooms...

The Blue Mountain lodge is a fantastic almost 6,000 square foot house with 6 bedrooms, 4 bathrooms, 2 living rooms, a game room, a backup generator and lots, lots more. In the summer the swimming pond is just off the deck and guests have access to the community pool, tennis court, sand volley ball court, disc golf course and hiking trails. In the winter those same hiking trails are perfect for snow shoeing and the Jay Peak Ski, Golf and Indoor Water Park are just a couple miles away.

Guest favorite

Condo in Jay

4.91 out of 5 average rating, 152 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

Guesthouse in Westfield

4.99 out of 5 average rating, 132 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.

Guest favorite

Condo in Burke

4.87 out of 5 average rating, 138 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!

Guest favorite

Chalet in Westfield

5 out of 5 average rating, 23 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.