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Jamaica, VT Rental Listings

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Avg / night: $271. 2nd-floor condo near Okemo Mtn with streaming, WiFi, partial AC, & full kitchen | Located in Cavendish, VT | 2.4 Stars | 3 Bed, 1 Bath | No Pets. No pets. Max 6 guests. Find tranquility and adventure at this second-floor condo located only four and a half miles from Okemo Mountain and right on the shuttle route! This home away from home is within a short walking distance of d... $271

3 Bedroom 1BA Condo Vacation Rental in Hidden Gem, Cavendish, VT

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Vacation Rentals Offered in Cavendish, VT. Avg / night: $271. 2nd-floor condo near Okemo Mtn with streaming, WiFi, partial AC, & full kitchen | Located in Cavendish, VT | 2.4 Stars | 3 Bed, 1 Bath | No Pets. No pets. Max 6 guests. Find tranquility and adventure at this second-floor condo located only four and a half miles from Okemo Mountain and right on the shuttle route! This home away from h...
Avg / night: $170. Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer | Located in Dover, VT | 4.32 Stars | 2 Bed, 2 Bath | No Pets. No pets. Max 7 guests. This third-floor condo makes a great home base for your snowy endeavors. Skiing enthusiasts will be happy to know a brisk walk is all that's needed to hit the slopes of Mt. Snow. Not only that, but you can enroll in class... $170

2 Bedroom 2BA Condo Vacation Rental in Skiing Haven, Dover, VT

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Vacation Rentals Offered in Dover, VT. Avg / night: $170. Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer | Located in Dover, VT | 4.32 Stars | 2 Bed, 2 Bath | No Pets. No pets. Max 7 guests. This third-floor condo makes a great home base for your snowy endeavors. Skiing enthusiasts will be happy to know a brisk walk is all that's needed to hit the slopes of Mt. Snow. Not...
Avg / night: $560. Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace | Located in Dover, VT | 3.79 Stars | 3 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Tucked into the trees close to Mount Snow Ski Resort, you ll find this inviting three-level condo boasting an ideal location for four seasons of fun. The winter is made for skiing, snowboarding, and downhill tubing... $560

3 Bedroom 3BA Condo Vacation Rental in Suntec Getaway, Dover, VT

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Vacation Rentals Offered in Dover, VT. Avg / night: $560. Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace | Located in Dover, VT | 3.79 Stars | 3 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Tucked into the trees close to Mount Snow Ski Resort, you ll find this inviting three-level condo boasting an ideal location for four seasons of fun. The winter is made for sk...
Avg / night: $129. Riverfront studio with river view, full kitchen, & free WiFi | Located in Proctorsville, VT | 3.88 Stars | 0 Bed, 1 Bath | No Pets. No pets. Max 3 guests. Enjoy a great location in the heart of the charming town of Proctorsville and within walking distance from Outer Limits Brewery, Singleton's General Store, and Crows Bakery. This well-appointed studio located on the banks o... $129

1BA House Vacation Rental in Vermont Farm Studio, Proctorsville, VT

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Vacation Rentals Offered in Proctorsville, VT. Avg / night: $129. Riverfront studio with river view, full kitchen, & free WiFi | Located in Proctorsville, VT | 3.88 Stars | 0 Bed, 1 Bath | No Pets. No pets. Max 3 guests. Enjoy a great location in the heart of the charming town of Proctorsville and within walking distance from Outer Limits Brewery, Singleton's General Store, and Crows Bakery. Th...
Avg / night: $316. Charming home with fireplace, game room, full kitchen, gas grill, & balcony | Located in Wilmington, VT | 4.0 Stars | 3 Bed, 2 Bath | No Pets. No pets. Max 8 guests. Escape to the hills and valleys of gorgeous Vermont any time of the year to have the vacation of your dreams. The area is tranquil, surrounded by trees, and near many fun attractions like The Ledges, Green Mounta... $316

3 Bedroom 2BA House Vacation Rental in Farmhouse on the Road, Wilmington, VT

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Vacation Rentals Offered in Wilmington, VT. Avg / night: $316. Charming home with fireplace, game room, full kitchen, gas grill, & balcony | Located in Wilmington, VT | 4.0 Stars | 3 Bed, 2 Bath | No Pets. No pets. Max 8 guests. Escape to the hills and valleys of gorgeous Vermont any time of the year to have the vacation of your dreams. The area is tranquil, surrounded by trees, and near many f...
Avg / night: $417. Dog-friendly riverfront home with washer/dryer, partial A/C, river views, & wifi | Located in Proctorsville, VT | 5.0 Stars | 4 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 7 guests. Located on the banks of the Black River, this two-story home has all the comforts and amenities for a flawless and memorable family vacation. Enjoy a great location in the heart of the charming ... $417

4 Bedroom 2 baths Dog-friendly 5.0 5 reviews What our guests are saying... AI-generated...

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Vacation Rentals Offered in Proctorsville, VT. Avg / night: $417. Dog-friendly riverfront home with washer/dryer, partial A/C, river views, & wifi | Located in Proctorsville, VT | 5.0 Stars | 4 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 7 guests. Located on the banks of the Black River, this two-story home has all the comforts and amenities for a flawless and memorable family vacation. Enjoy...
Avg / night: $272. Charming & spacious two-story townhome with balcony - close to Okemo | Located in Proctorsville, VT | 4.32 Stars | 3 Bed, 3.5 Bath | No Pets. No pets. Max 9 guests. This beautiful Cavendish townhome features updated furnishings and is located close to everything Okemo and Ludlow have to offer. This rental showcases a spacious kitchen with granite countertops and stainless ste... $272

3 Bedroom 3.5BA House Vacation Rental in Castle Hill Condos - L4, Proctorsville,...

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Vacation Rentals Offered in Proctorsville, VT. Avg / night: $272. Charming & spacious two-story townhome with balcony - close to Okemo | Located in Proctorsville, VT | 4.32 Stars | 3 Bed, 3.5 Bath | No Pets. No pets. Max 9 guests. This beautiful Cavendish townhome features updated furnishings and is located close to everything Okemo and Ludlow have to offer. This rental showcases a spacious kit...
Avg / night: $184. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities | Located in Dover, VT | 4.08 Stars | 1 Bed, 1 Bath | No Pets. No pets. Max 4 guests. The location can t be beat at this trailside condo, located in Seasons, the only ski-in/ski-out community at Mt. Snow! Strap on your skis and head for the slopes, or spend days snowshoeing, cross-country skiing, or... $184

1 Bedroom 1BA Condo Vacation Rental in All Season Mountain Retreat, Dover, VT

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Vacation Rentals Offered in Dover, VT. Avg / night: $184. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities | Located in Dover, VT | 4.08 Stars | 1 Bed, 1 Bath | No Pets. No pets. Max 4 guests. The location can t be beat at this trailside condo, located in Seasons, the only ski-in/ski-out community at Mt. Snow! Strap on your skis and head for the slopes, or spend day...
Avg / night: $320. Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing | Located in Andover, VT | 4.61 Stars | 3 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Located within a short drive between Okemo Mountain, Bromley Mountain, and Magic Mountain, this gorgeous secluded cabin is perfect for outdoor activities. During the winter, visit the mountains for skiing and sno... $320

3 Bedroom 3 baths No pets 4.61 23 reviews What our guests are saying... AI-generated...

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Vacation Rentals Offered in Andover, VT. Avg / night: $320. Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing | Located in Andover, VT | 4.61 Stars | 3 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Located within a short drive between Okemo Mountain, Bromley Mountain, and Magic Mountain, this gorgeous secluded cabin is perfect for outdoor activities. During the winte...
Avg / night: $564. Picturesque, Euro-style ski chalet with beautiful setting, deck & fireplace | Located in Peru, VT | 4 Bed, 2 Bath | No Pets. No pets. Max 8 guests. From the floor-to-ceiling windows to the distant view of Stratton Mountain across the treetops, this Peru home is the quintessential Vermont getaway. Between the classic, ski-inspired decor, the crackling fireplace, and the wondro... $564

4 Bedroom 2 baths No pets 0 reviews New Vacasa Listing Worry-free cancellation Get...

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Vacation Rentals Offered in Peru, VT. Avg / night: $564. Picturesque, Euro-style ski chalet with beautiful setting, deck & fireplace | Located in Peru, VT | 4 Bed, 2 Bath | No Pets. No pets. Max 8 guests. From the floor-to-ceiling windows to the distant view of Stratton Mountain across the treetops, this Peru home is the quintessential Vermont getaway. Between the classic, ski-inspired decor, t...
Avg / night: $572. Renovated Ski-in/Ski-Out Condo w/ Shared Pools, Hot Tub, Sauna & Great Location | Located in Dover, VT | 4.57 Stars | 3 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Bring the whole crew to enjoy a bevy of alpine activities at this Mount Snow getaway, a fully renovated and professionally decorated condo with ski-in/ski-out access, shared resort amenities, and a prime location... $572

3 Bedroom 3 baths No pets 4.57 42 reviews What our guests are saying... AI-generated...

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Vacation Rentals Offered in Dover, VT. Avg / night: $572. Renovated Ski-in/Ski-Out Condo w/ Shared Pools, Hot Tub, Sauna & Great Location | Located in Dover, VT | 4.57 Stars | 3 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Bring the whole crew to enjoy a bevy of alpine activities at this Mount Snow getaway, a fully renovated and professionally decorated condo with ski-in/ski-out access, shared...
Avg / night: $237. Cozy condo near skiing with fireplace & deck | Located in Proctorsville, VT | 5.0 Stars | 2 Bed, 1 Bath | No Pets. No pets. Max 5 guests. This cozy mountain getaway places you right in the heart of the Green Mountains, only minutes away from Okemo Mountain Resort, Ludlow's Main Street, Fox Run Golf Club, and scenic hiking trails throughout the Proctor-Piper State Forest. At-h... $237

2 Bedroom 1BA Condo Vacation Rental in Cozy Mountain Getaway, Proctorsville, VT

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Vacation Rentals Offered in Proctorsville, VT. Avg / night: $237. Cozy condo near skiing with fireplace & deck | Located in Proctorsville, VT | 5.0 Stars | 2 Bed, 1 Bath | No Pets. No pets. Max 5 guests. This cozy mountain getaway places you right in the heart of the Green Mountains, only minutes away from Okemo Mountain Resort, Ludlow's Main Street, Fox Run Golf Club, and scenic hiking trails ...
Avg / night: $424. Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes | Located in West Wardsboro, VT | 4.86 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 9 guests. Beautifully situated on the bank of Wardsboro Brook, this secluded, family-friendly home is a place to find ease, relaxation, and wonderful access to outdoor recreation in every season. Skiing at Mount Snow ... $424

4 Bedroom 3 baths No pets 4.86 28 reviews What our guests are saying... AI-generated...

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Vacation Rentals Offered in West Wardsboro, VT. Avg / night: $424. Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes | Located in West Wardsboro, VT | 4.86 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 9 guests. Beautifully situated on the bank of Wardsboro Brook, this secluded, family-friendly home is a place to find ease, relaxation, and wonderful access to outdoor r...
Avg / night: $503. Exquisite home with fireplace, balcony, fast WiFi, jetted tub & washer/dryer | Located in West Dover, VT | 2.71 Stars | 4 Bed, 2.5 Bath | No Pets. No pets. Max 8 guests. Escape to a beautiful retreat in the charming countryside of Vermont, away from the hustle and bustle of everyday life. A perfect retreat for a group or family, you'll love everything you can do and see here.... $503

4 Bedroom 2.5BA House Vacation Rental in Wooded Wonder, West Dover, VT

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Vacation Rentals Offered in Dover, VT. Avg / night: $503. Exquisite home with fireplace, balcony, fast WiFi, jetted tub & washer/dryer | Located in West Dover, VT | 2.71 Stars | 4 Bed, 2.5 Bath | No Pets. No pets. Max 8 guests. Escape to a beautiful retreat in the charming countryside of Vermont, away from the hustle and bustle of everyday life. A perfect retreat for a group or family, you'll l...
Avg / night: $454. Winhall Woodland House | Winhall Home w/ large deck - near Stratton & Bromley | Located in Winhall, VT | 4.5 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 7 guests. Escape to the beauty of Winhall with our charming house, complete with a large deck that invites you to unwind and soak up the tranquility of the surroundings. Located near the renowned Stratton and Bromley Mounta... $454

4 Bedroom 3BA House Vacation Rental in Winhall Woodland House (All Season Rental),...

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Vacation Rentals Offered in Peru, VT. Avg / night: $454. Winhall Woodland House | Winhall Home w/ large deck - near Stratton & Bromley | Located in Winhall, VT | 4.5 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 7 guests. Escape to the beauty of Winhall with our charming house, complete with a large deck that invites you to unwind and soak up the tranquility of the surroundings. Located near th...
Avg / night: $530. Dog-friendly chalet w/ wood stove, deck, & outdoor firepit - close to Mt. Snow | Located in West Dover, VT | 4.07 Stars | 4 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 8 guests. Only one mile from Mount Snow, this home is perfectly situated for your next vacation! Come home after a long day on the slopes to cozy up in front of the wood-burning stove with a favorite novel wh... $530

4 Bedroom 2BA Pet-Friendly House Vacation Rental in Mount Snow Chalet, West Dover,...

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Vacation Rentals Offered in Dover, VT. Avg / night: $530. Dog-friendly chalet w/ wood stove, deck, & outdoor firepit - close to Mt. Snow | Located in West Dover, VT | 4.07 Stars | 4 Bed, 2 Bath | Pet-friendly. Dog-friendly. Max 8 guests. Only one mile from Mount Snow, this home is perfectly situated for your next vacation! Come home after a long day on the slopes to cozy up in front of the wood...
Avg / night: $151. Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains | Located in West Wardsboro, VT | 4.58 Stars | 1 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Take your pick of some of Vermont's best slopes at this West Wardsboro home, a retreat with a private deck and firepit, and an ideal location near Mt. Snow and Stratton Mountain Resort! This home... $151

1 Bedroom 1BA Pet-Friendly Cabin Vacation Rental in Stratton Woods, West Wardsboro,...

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Vacation Rentals Offered in West Wardsboro, VT. Avg / night: $151. Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains | Located in West Wardsboro, VT | 4.58 Stars | 1 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Take your pick of some of Vermont's best slopes at this West Wardsboro home, a retreat with a private deck and firepit, and an ideal location near ...
Avg / night: $576. Inviting mountain view home with game room, balcony & W/D | Located in West Dover, VT | 4.62 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Escape the everyday and experience the extraordinary when you book this fantastic vacation home in the countryside of beautiful Vermont. Filled with natural light and oversized windows that showcase picturesque views, there's no ... $576

4 Bedroom 3 baths No pets 4.62 16 reviews What our guests are saying... AI-generated...

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Vacation Rentals Offered in Dover, VT. Avg / night: $576. Inviting mountain view home with game room, balcony & W/D | Located in West Dover, VT | 4.62 Stars | 4 Bed, 3 Bath | No Pets. No pets. Max 8 guests. Escape the everyday and experience the extraordinary when you book this fantastic vacation home in the countryside of beautiful Vermont. Filled with natural light and oversized windows that ...
Avg / night: $170. Beautiful retreat close to Okemo with free WiFi, private washer/dryer | Located in Proctorsville, VT | 5.0 Stars | 2 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Whether you're here for fun outdoor adventures or just a quiet place to spend some quality time with someone you love, this bright and spacious two-bedroom home is waiting to provide you with the vacation ... $170

2 Bedroom 1BA Pet-Friendly Retreat Vacation Rental in Proctorsville Paradise, Proctorsville,...

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Vacation Rentals Offered in Proctorsville, VT. Avg / night: $170. Beautiful retreat close to Okemo with free WiFi, private washer/dryer | Located in Proctorsville, VT | 5.0 Stars | 2 Bed, 1 Bath | Pet-friendly. Dog-friendly. Max 4 guests. Whether you're here for fun outdoor adventures or just a quiet place to spend some quality time with someone you love, this bright and spacious two-bedroom ho...
Avg / night: $289. Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck | Located in Newfane, VT | 3.12 Stars | 3 Bed, 2.5 Bath | Pet-friendly. Dog-friendly. Max 6 guests. This comfy home is the perfect getaway for a trip into the wilderness! You'll be close to a ton of beautiful parks, one such being Fort Dummer State Park, where you can take a lovely stroll along the... $289

3 Bedroom 2.5BA Pet-Friendly House Vacation Rental in Newfane Hill Retreat, Newfane,...

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Vacation Rentals Offered in Newfane, VT. Avg / night: $289. Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck | Located in Newfane, VT | 3.12 Stars | 3 Bed, 2.5 Bath | Pet-friendly. Dog-friendly. Max 6 guests. This comfy home is the perfect getaway for a trip into the wilderness! You'll be close to a ton of beautiful parks, one such being Fort Dummer State Park, whe...
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