Holiday rentals with a pool in Orleans County

4.85 out of 5 average rating, 269 reviews

Guest suite in Hyde Park

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!

4.95 out of 5 average rating, 105 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.

4.98 out of 5 average rating, 49 reviews

Villa in Hyde Park

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!

4.99 out of 5 average rating, 207 reviews

Flat in Newport

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.

5 out of 5 average rating, 31 reviews

Chalet in Montgomery

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.

4.98 out of 5 average rating, 59 reviews

Home in Lyndon

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.

4.74 out of 5 average rating, 298 reviews

Peak & Quiet | Dog-Friendly w/ Pool, Park & Views

This private house is four miles from Jay Peak Resort, boasting forest views and a brook running along the lower yard. This well-loved chalet has proudly provided a respite for mountain enthusiasts since 1969, with the last four decades under our family's care and the last eleven years as an Airbnb. Residing in the forest community of Alpine Haven, enjoy access to an eight-acre park, including scenic mountain views, nature trails, a summer pool, disc golf, sand volleyball, and more.

4.91 out of 5 average rating, 164 reviews

Apartment in Jay

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.

4.91 out of 5 average rating, 87 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.

4.99 out of 5 average rating, 142 reviews

Guest house in Westfield

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.