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Killington Luxury Holiday Rentals

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    Travellers to Killington are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    37 Matching Rentals in KillingtonView all 247 rentals
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    7 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    About this property
    The Slopeside Estate features Five Bedrooms and Four Full Size Custom Bathrooms, covering four floors of elegant living space. The master bedroom suite features a king size bed with an en suite custom bathroom featuring a steam shower, heated towel bars, jetted tub and a Toto NeoRest electronic...
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    Killington, Vermont 05751
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    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, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    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
    Condo/Apartment - 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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    Pet friendly
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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    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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    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    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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    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Navillus House has the distinction of sitting right on Killington’s number one novice ski trail, the Great Eastern, and is serviced by the Killington Skyeship Gondola (eight person, high speed and HEATED)! This home was completely rebuilt two years ago with no expense spared. The interior...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Mountain Views
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    Pet friendly
    Kid friendly
    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
    • Internet Access
    • Grill
    • Mountain Views
    • Hot Tub
    • Cable/satellite TV
    • DVD Player
    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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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Grill
    • Private Indoor Pool
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • DVD Player
    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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    Killington Mountain Slopeside Home1 / 18
    (8)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Shared Indoor Pool
    • Washer
    • Internet Access
    • Sauna
    • Mountain Views
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 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 19 February 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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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    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- 48' HD/TV/DVD...
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    Killington, Vermont 05751
    Holiday Rental House - 3 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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    • Mountain Views
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 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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    LUXURY, hot tub, private, 6 BR, 3 BA1 / 35
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 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 1 June 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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    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
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    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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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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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    Moose Log Cabin - Three Bedroom Private Country log cabin with hot tub1 / 24
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 26 August 2018
    Pictures looked great, few shortcomings: front and back porch overgrown with weeds/ broken chairs and snow sleds, bird poop on back porch. Electricity in the bathrooms was...
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    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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    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 4 January 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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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
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    • Cable/satellite TV
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    • Skiing: Property Is In A Ski Resort
    • Grill
    • Mountain Views
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy our 4 bedroom, 2 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 - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bear Run Home: This three level spacious home is located off of East Mountain Road between Bear Mountain and the Snowshed Base Lodge. The entrance level has two bedrooms, a full bathroom and large family room with widescreen TV, fireplace and Foosball table. The second level is sunny and...
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    Killington, Vermont 05751
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    • Balcony
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you love the Vermont outdoors, this home is for you! Riverview is a 4-bedroom private home in the heart of Killington. Winter fun is minutes away with the Skyship gondola just 5 minutes from the home and 10 minutes to the main basin for all the night life Killington has to offer. Located on the...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Winterberry Townhouse #4 is a premium, distinctive, spacious and sunny 4-level, 4 bedroom townhouse with WiFi throughout. This home offers a very high standard of accommodation and is located in a beautiful area set within close proximity of both the Killington and Pico ski areas both of which...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Winterberry Townhouse #1: This premium, distinctive and spacious 4-level, 4 bedroom townhouse is located between Killington and Pico ski areas. Upon entering this home you will be able to drop your skis and gear into a large walk-in closet in your mud room. The main floor features a living room...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Dean Hill Chalet: This spacious five bedroom chalet located smack in the Center of the Killington Basin area. Just minutes away from Killington Road, Snowshed, Ramshead and Killington Base Lodges. In between you find all the ski shops, Restaurants, bars and night life Killington has to offer....
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    Killington, Vermont 05751
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Alpine House: Extremely spacious well maintained home on Alpine Drive on Pico Mountain. Walk out your door and across the street is one of Pico's Trails to start skiing and riding. Enjoy the large living room with it's great mountain views and the huge fieldstone fireplace. The kitchen offers all...
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    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    3 Bedroom Plus Loft Private Home in Killington! Walk to the 'Home Stretch' trail from this nicely furnished sunny and spacious private home. This home has 3 levels and sleeps 10 persons comfortably. Just minutes from the Bear Mountain and the Skyeship base lodges. This home features a large wrap...
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    Location Information
    Killington, Vermont 05751
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Amenities & Details
    • Parking
    • DVD Player
    • Grill
    • 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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    Location Information
    Killington, Vermont 05751
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This quaint 4 bedroom home is located right in the heart of Killington Mountain. Yes, you can ski on and ski off right from your front door to the Home Stretch Trail and in the summer, if biking is your thing, you are close to some of the best mountain biking trails Killington has to offer. This...
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    Location Information
    Killington, Vermont 05751
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Sauna
    • Grill
    • Hot Tub
    • Mountain Views
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Exclusive three bedroom is true ski on, ski off, just 20 yards from the Great Eastern Trail. To make it even more special and relax after a day of skiing and riding in your own private hot tub out on the deck. This trail is serviced by the Sky Ship Gondola, a high speed heated 8 person...
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    Location Information
    Killington, Vermont 05751
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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