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Killington Luxury Vacation Rentals

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    Travellers to Killington are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    33 Matching Rentals in KillingtonView all 221 rentals
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    About this property
    A beautiful custom built home on 18 acres in the heart of Killington. This unique property was built for those who truly enjoy life, family and entertaining. Significant thought and care went into every detail of this 6, 000 square foot home. Features include, gourmet kitchen, open floor plan,...
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    Killington, Vermont 05751
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    The '76' house is truly a special slopeside property. It is located in Killington’s Trailside Village, along the Great Eastern ski trail, which is Killington’s number one slopeside address! Designed by a famous architect, this home has lines in are beyond creative! The Trailside Village 76 House...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 14
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    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    About this property
    We are proud to introduce the newest member of our family here in Killington, a spectacular 5,500 sq. ft. property known as The Top Star House. (227 Dean Hill Road, Killington, VT 05751) This special property is brand new and located in the heart of Killington, providing a unique opportunity to...
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    Killington, Vermont 05751
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    The Vistas at Sunrise provides a home of comfort and timeless beauty. The Architecture reflects the elegant simplicity of nature, and the tranquility of its surroundings. From the breathtaking front entrance, to the private balconies and baths, which adjoin each of the four bedroom suites, the...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    • Private Indoor Pool
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    Pet friendly
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    Smoking allowed
    About this property
    The Matterhorn House offers a one-of-a-kind Vermont ski vacation experience, arguably boasting some of the most incredible mountain views of any property in all of the resort! The private slopeside setting on the Great Eastern ski trail (service by the Killington Skyeship Gondola) has inspired an...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Private Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a rare opportunity to experience one of the areas finest residences. Topridge is ideally located for ski on, ski off convenience, and offers panoramic views of Bear Mountain here at Killington. This elegantly furnished, serene retreat features double height vaulted ceilings in the living...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Hot Tub
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    • Private Indoor Pool
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a rare opportunity to experience one of the areas finest residences. Topridge is ideally located for ski on, ski off convenience, and offers panoramic views of Bear Mountain here at Killington. This elegantly furnished, serene retreat features double height vaulted ceilings in the living...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    8 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • DVD Player
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    • Central Heating
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    • Housekeeping Included
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hideaway Chalet is large ski house comfortably accommodating 24 people with ample amount of bathrooms, and privacy. Hideaway Chalet is located right on access road to ski slopes 3-4min by car or free bus. Walk in to restaurants and bars. Be in center of it all close to ski slopes, yet secluded in...
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    Killington, Vermont 05751
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 24
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    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
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    Pet friendly
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    About this property
    Become part of the legend! Before you book ask about our FREE extended checkout option! Beautiful 3000+ square foot home located less than five minutes from the lifts in the heart of the Killington Access Road. Second to none amenities to include indoor regulation racquetball court, 7-person...
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    Killington, Vermont 05751
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Queens Croft Home: Pamper yourself in this newly built, deluxe vacation home. From the living room with stone fireplace, to the hot tub on the deck, to the two master suites each with their own bath and walk-in closet, you will find attention to detail and comfort galore. Whether preparing a meal...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for more room to roam, while maintaining the ultimate in slopeside convenience and amenities, then treat your group to the Trailside Village Three Bedroom Townhouse Condo. These units have a wood burning fireplace and we supply all the wood you can burn, including fire starters!...
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    Killington, Vermont 05751
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • DVD Player
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    • Cable/satellite TV
    • Mountain Views
    • Hot Tub
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for more room to roam, while maintaining the ultimate in slopeside convenience and amenities, then treat your group to the Trailside Village Three Bedroom Townhouse Condo. These units have a wood burning fireplace and we supply all the wood you can burn, including fire starters!...
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    Killington, Vermont 05751
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Hot Tub
    • Mountain Views
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy luxury at the top of Killington's Sunrise Village, with one of the best Killington vacation townhomes for rent you'll find! 5 large bedrooms and 3 high-end finely detailed bathrooms will make you feel like you're staying in a palace with a modern Vermont Mountain style ambiance. This...
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    Killington, Vermont 05751
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Shared Indoor Pool
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    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I only accept payment through the FLIPKEY System. Upscale spacious 3 bedroom Townhouse Condo with family room. Sunrise Mountain Village - 2300 ft elevation. Ski-in/ski-out. All of the comforts of home. The location and accommodations are excellent. This three bedroom town house condo (three levels)...
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    Killington, Vermont 05751
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Grill
    • Balcony
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Slopeside Estate Apartment space is separate from the house, which represents an additional apartment above the detached garage on the property. That space can be rented to compliment your housing needs. The Slopeside Estate Apartment features one bedroom (king size bed) and a sleeping loft...
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    Killington, Vermont 05751
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Indoor Pool
    • Internet Access
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Sauna
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit property is ski off. You cannot ski on, but you can ski home. You may walk to the lifts, but if you have children you may consider driving up there (3min drive). You may walk 0.3 mile to the Sundog Ski Trail which will take you down Sunrise Village Triple Chair Lift. *** This unit...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    3 Bedroom plus Loft Private Home (sleeps 10). A Great Escape! Large Outdoor Hot Tub. Ski down 250 feet to Great Eastern, walk home 700 feet from Home Stretch trail. Perfect vacation home for 2 couples with children. Wi Fi, Wood Burning Fireplace and Foosball! Main Level Living room w 48'...
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    Killington, Vermont 05751
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    LUXURY, hot tub, private, 6 BR, 3 BA1 / 34
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
    • Patio
    • Central Heating
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    • Cable/satellite TV
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 7, 2017
    If you are looking for the perfect Vermont home experience, look no further! You've find it with CEDARWALK at Killington. Our family of 9 stayed Memorial Day weekend 2017 for a...
    Reviewed June 1, 2016
    The owner, Susan, was a pleasure to work with – personable, helpful and responsive – she made arrangements a breeze and offered suggestions for local activities, dining and...
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    About this property
    Welcome to CEDARWALK! In the heart of Killington you will find our beautiful private home (6 BD, 3 BA, sleeps 16) close to shops, restaurants and just two minutes drive to the Mountain for mountain biking and the Killington Summer Adventure Center. From our home you can explore all that Vermont has...
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    Killington, Vermont 05751
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    Killington Mountain Slopeside Home1 / 18
    (8)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Shared Indoor Pool
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    • Sauna
    • Mountain Views
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 2015
    Great location (ski in, and almost ski out). Nicely furnished especially kitchen. Spacious, surprisingly so from outside appearance. Well maintained. Owner easy to work with.
    Reviewed February 19, 2014
    I found a perfect house to stay in for my family and friends for our Christmas holiday break. Was exactly what I was looking for: cozy and warm and close to the trails which was...
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    About this property
    This house on Killington has it all. With scenic mountain views in all directions, this contemporary 14-room home is located on Sunrise Mountain, one of Killington's six peaks. It's just a 50-yard walk to the ski trail that provides direct access to Killington's 200 slopes and trails. The home is...
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    Killington, Vermont 05751
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Central Heating
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    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy our 6 bedroom, 3 bath- private home. Right in the heart of the best skiing and snowboarding in Vermont! World class hiking. Spectacular landscapes/sightseeing. Across the street from Pico Mountain and 5 minutes to the Killington access road. Minutes to delicious local restaurants, night...
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    Killington, Vermont 05751
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 20
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Sauna
    • Cable/satellite TV
    • Mountain Views
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    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you looking for the ultimate, romantic get away or the ultra affordable family ski vacation? These one bedroom units are located on the Great Eastern Ski Trail and are serviced by the Killington Skyeship Gondola (high speed, eight person, and HEATED)! Each deck has a private outdoor hot tub...
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    Killington, Vermont 05751
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Hot Tub
    • Washer
    • Internet Access
    • Sauna
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Are you looking for the ultimate, romantic get away or the ultra affordable family ski vacation? These one bedroom units are located on the Great Eastern Ski Trail and are serviced by the Killington Skyeship Gondola (high speed, eight person, and HEATED)! Each deck has a private outdoor hot tub...
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    Killington, Vermont 05751
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Secure Parking
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    • Private Garden
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    About this property
    8 Miles from Killington Slopes and close to Pico ski resort. Access to the Vast Trails for snow mobiles right across from our home. You can ride your snow mobiles from our garage to the trails. Summers are wonderful as you can hike the Long Trail, take the lift up to the top of Killington with...
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    Killington, Vermont 05751
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    Deer Leap Home: Large 6 bedroom 4 bath home with private hot tub in the heart of Killington. Just finished a 6 week renovation. New cherry kitchen with granite counter tops, stainless steel appliances. Large living room with cathedral ceilings. Living room features a 55' smart TV and a wood...
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    Killington, Vermont 05751
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    About this property
    Heavenly in Killington The house can be used as two separate fully equipped units (by floor) or together. This listing is for entire house and both units. Enjoy this brand new modern luxury home offering an unparalleled experience. This stunning retreat comfortably sleeps sixteen and is located...
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    Killington, Vermont 05751
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Moose Log Cabin: Unique authentic mountain Log-Cabin facing the Green Mountain National Golf Course. If you're looking for that special place look no further. The circular driveway leads up to the 'Killington Moose Log-Cabin' a special comfortable home that gives you the rustics and modern demands...
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    Killington, Vermont 05751
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    About this property
    This premium extra large two level is like your home away from home! The two downstairs bedrooms come equipped with a television, and the kitchen features a full-size fridge, stove, and dishwasher - as well as a full complement of utensils, cooking aids and appliances. A 50-inch flat screen HDTV...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
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    Smoking allowed
    About this property
    Perfection on the mountain! Charming and updated ski on/ski off condominium literally steps from the Sundog trail on Sunrise Mountain in Killington, Vt. Perfect for families. Ski down to the Sunrise chair lift to connect to Bear Mountain and the rest of Killington's 73 miles of terrain, or...
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    Killington, Vermont 05751
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    Gorgeous cabin with mountain views, near gondola & nature - walk to ski slopes!1 / 28
    (1)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 4, 2018
    Good location, close to a good pizza place and grocery store. The unit itself was very dated and rooms were not very comfortable, too much furniture in some, a pool table...
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    About this property
    Look no further for the ultimate ski retreat, where you can watch the gondolas go by from the living area and spacious deck of this four-bedroom Killington home. Mountain views and a short walk to great slopes mean you can't go wrong with this lovely vacation rental. Snow-capped trees surround the...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    The White House - Seven Bedroom Private Vermont Country Home with Outdoor Hot1 / 24
    (1)Excellent
    7 Bedrooms, 3 Bathrooms, Sleeps 24 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2016
    On arrival the house is huge, although it sleeps 20 we would not have put lots into the big room however for our group of 8 it was fun. The Jacuzzi and the Pool Room a huge...
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    About this property
    This very spacious two level house, with plenty of country farmhouse charm, is conveniently located to restaurants and the night life as well as the Killington Ski Area. Large outside hot tub, pool table, 42' flat screen TV, in addition to new beds, bedspreads, and drapes. The fully equipped...
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    Killington, Vermont 05751
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 24
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