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Wilmington Holiday Rentals

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    Travellers to Wilmington are booking November dates now. Secure your holiday rental today, and have the perfect trip.
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    Condo on Haystack/Hermitage Ski Mountain1 / 28
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Mount Snow Area Home with 5 Bedrooms1 / 13
    (1)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Family vacation destination - farm cottage w/ onsite activities1 / 14
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 BR/2 Bath Post and Beam - Next to Haystack Golf Course.1 / 17
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This well-furnished home sleeps 12 with 3 bedrooms and 3 full baths. Great for families, this home with its open floor plan has a cozy, carpeted living room with vaulted ceilings and open style fireplace; a fully equipped kitchen, loft, bunk beds, fully finished basement serving as family/game...
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lakefront Log Cabin, Perfect Vacation Spot for Winter season fun.1 / 24
    (4)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Parking
    • Grill
    • Patio
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    Pet friendly
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    Smoking allowed
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Quintessential Vermont Chalet1 / 23
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Central Heating
    • Patio
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have fun and recharge in this newly remodeled home in Chimney Hill. Perfect for 2 or more families. Newer furniture, new floors. Our home offers 2 family rooms, each with a beautiful wood burning fireplace, LCD cable TV with wifi enabled blue ray players(Amazon, nextflix). There are 5 comfortable...
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    CH #488  488-011 / 10
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Grill
    • Mountain Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    OMG Where do I even start. This house is AMAZING, big and beautiful. With many rooms, people can retire to get some privacy and with 2 huge living area, family can come together...
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    This house includes Clubhouse and Amenity Privileges.
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Satellite TV
    • Parking
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This completely renovated townhouse features three bedrooms + a separate loft with Queen Sleeper and two full bathrooms. Brand new Gas stove. Open floor plan. Large deck with open mountain views and grill. 20 ft ceilings, large brand new windows. Large Washer Dryer. Full open kitchen, completely...
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Central Heating
    • Mountain Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a peaceful getaway at this lovely Wilmington, Vermont cabin. With 2 bedrooms, 1 bathroom and room to sleep 6 guests, families will feel right at home. You'll love the deck overlooking the stream, a big, open yard, and a great location near recreation, dining, and more! THE PROPERTY From the...
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    Wilmington, Vermont 05363
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a lovely Vermont chalet - style home with 3 bedrooms, 2 full baths, a fireplace, deck, cable TV with DVD player and an X-Box. This home has all the modern conveniences to make your stay as comfortable as your own home. It also comes with WiFi so you can stay connected.This house...
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a wonderful vacation home located across from the clubhouse. It has access to the snowmobile trails. This home has a wood fireplace and gameroom. This house includes Clubhouse and Amenity Privileges.
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Parking
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is comfortable and cozy. Accepts pets. Has WiFi and surround sound.This house includes Clubhouse and Amenity Privileges.
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    Location Information
    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Parking
    • Satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom, 2 bathroom home is a custom built log home. It has an interior that is tastefully decorated. It has a loft area and a fireplace to enhance the Vermont country essence. It also has internet available for those who need to stay connected. 4 Wheel Drive - RECOMMENDEDThis house...
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Parking
    • Satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to 37 Three Streams way! Gary and Romer purchased the lot from Gary's brother back in the '80's. When it came time to build in 1988, our contractor offered 4 popular models. One of the models was called 'The Norwich' - and since we lived in Norwich, CT, that is the model we selected....
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Air Conditioning
    • Porch
    • Internet Access
    • Waterfront
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This new lakefront log cabin is available the rental season! Minutes away from Mount Snow and Stratton, winter activities include: skiing, ice skating and ice fishing. Also 2 miles from the center of Wilmington. The property has 160 ft of water frontage on Spruce Lake. Fish for brook trout in...
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Hermitage Club Member's Ski Chalet 4 bed plus loft - 3 full baths1 / 24
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Terrace
    • Patio
    • Central Heating
    • Internet Access
    • Grill
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Beautiful, New Custom Built Timber Frame Home, Sleeps 121 / 22
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Washer
    • Central Heating
    • Grill
    • Patio
    • Satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Mountain Log Cabin Getaway1 / 24
    (8)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Satellite TV
    • Shared Indoor Pool
    • Patio
    • Hot Tub
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Grill
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful Country Getaway near Downtown Wilmington!1 / 24
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Washer
    • Grill
    • Patio
    • Hot Tub
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    • Central Heating
    • Satellite TV
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    Pet friendly
    Kid friendly
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 16
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    Gorgeous Renovated, 6BR/5BA  -  Available for 2018 Seasonal Rental - VAST Access1 / 21
    (2)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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    Beautiful Mountainside 2 Bedroom 2 Bath Condominium1 / 13
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Wilmington, Vermont 05363
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mountain Top, Family Friendly Home In Vacation Neighborhood1 / 22
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Sauna
    • Central Heating
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    Pet friendly
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    Perfect Year Round Home with 5 Bedrooms1 / 15
    (4)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    Wilmington, Vermont 05363
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    Rustic home with modern amenities1 / 23
    (23)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    PLAY IN THE SNOW, EAT, DRINK&NO NEED TO DRIVE, YOU'RE IN THE MIDDLE OF TOWN!1 / 23
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Warm Cozy Cabin In The Beautiful Green Mountains In Vermont1 / 19
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Quiet location, beautiful views Hottub & Sauna Sleigh riding on property1 / 23
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • DVD Player
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    Pet friendly
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1st Class -  Brand New Custom Barn Apartment1 / 23
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    4BR - Mount Snow Ski Home in Chimney Hill - HOT TUB and Clubhouse Included1 / 23
    (15)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful  Vermont Vacation Home- Mount Snow!!1 / 22
    (9)Very good
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    1,200 Square foot chalet. 15 minutes to Mt. Snow.  WIFI1 / 17
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    Beautiful Golf/Ski Home * The Hermitage Club - Available Green Fee's/Lift Tix1 / 24
    (36)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Beautiful 4 Bedroom + Loft with Hot Tub near Town, Mt Snow and lake! - Sleeps 101 / 23
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Beautiful Mountain Home minutes to Mt. Snow, shops, restaurants, golfing, & more1 / 24
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Central Heating
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    Spectacular 4 Season Home On Spruce Lake Near Mt. Snow1 / 24
    (19)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    Perfect Wilmington/Mt. Snow Getaway! Central To Village, Adam's Farm & Mt. Snow!1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Winter Special, New 5Br, CAC, 2 Mstr Suites, Sled Hill, 5 Acres, Stream, Private1 / 24
    (6)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Location Information
    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Spacious 5 Bdrm A-Frame: Walk to Lake Raponda. Wooded Setting. Ski Mount Snow!1 / 21
    (6)Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    New Lakefront Log Home1 / 23
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    15min. to Mt.Snow. 5 bedrooms, 3.5 baths, whirlpool in master bath, steam shower, open kitchen-greatroom floor plan with stone fireplace. Large screen porch with chaise for sleeping and hammock. Large open deck overlooking Lake Raponda. Canoe and kayak available. Very family friendly and charming....
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    Wilmington, Vermont 05363
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Mountain Views
    • DVD Player
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    • Skiing: Property Is In A Ski Resort
    • Hot Tub
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Set hilltop, just above the Chimney Hill Community Center (Clubhouse). Enjoy all that So. Vermont has to offer. Enjoy area activities and festivals, or, relax and recharge. Wilmington/Dover has what you are looking for. Ski, hike, snowmobile, bike, take in a good book or watch the big game....
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    Wilmington, Vermont 05363
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 13
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