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Vacation Rentals in Pittsfield, VT and nearby

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    The following rentals are within 15 kilometres of Pittsfield, Vermont.

    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    3 of 5 stars (1) Average
    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    3.5 of 5 stars (3) Average
    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    These neat and tidy 3BR/2BA accommodations have everything you'd need in a ski vacation property, featuring a gas fireplace. But it's all about location, location, location. Not only are you a stone's throw from the mountain, you're right in the middle of the action for Killington's famous... View all property information
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    Killington, Vermont 05751
    1 / 16
    5 of 5 stars (1) Excellent
    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
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    • DVD Player
    • Balcony
    • Washer
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    • x
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    • x
    About this property
    Three Bedroom Slopeside (sleeps 8) Beautifully Decorated Condo at Pico Ski Resort! Ski home right to your back door! Spend a great family vacation in the Killington Valley away from the crowds of big mountain skiing & riding. Enjoy the laid back, quiet atmosphere of Pico Mountain featuring 50... View all property information
    Location Information
    Killington, Vermont 05751
    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • Shared Indoor Pool
    • Sauna
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • Secure Parking
    • Satellite TV
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    • x
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    About this property
    This Very cozy and convenient ski condo is just minutes from the Killington ski slopes and night life! Recently updated condo in Building 1 with flat screen TV's in the living room and bedroom, stereo, wood burning fireplace, and classic mountain views! The perfect romantic getaway for any season!... View all property information
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    Killington, Vermont 05751
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    Killington
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Hot Tub
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    • x
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    • x
    About this property
    When you stay in this spacious Killington rental, you can admire the area's natural beauty, be close to the slopes, and enjoy luxurious amenities like a game room, wrap-around deck, and roomy private sauna. This home is perfect for anyone who wants a relaxing, fun, and memorable mountain vacation!... View all property information
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    Killington, Vermont 05751
    1 / 26
    Mendon
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Enjoy spectacular views and a location close to skiing when you stay in this spacious home. Perfect for both warm-weather and cold-weather travelers, this rental provides a convenient home away home while you explore the beautiful Vermont scenery, shop and see the sights, or just relax and... View all property information
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    Mendon, Vermont 05701
    1 / 35
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This ski-in/ski-out townhome puts you right on the slopes and offers a private balcony, along with access to shared amenities like a pool, sauna, and hot tub. Offering a resort experience, this three-level townhome is situated on peaceful Pico Mountain in Killington. You'll have access to outdoor... View all property information
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    Killington, Vermont 05751
    1 / 33
    Killington
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Picturesque views of lush woodlands are just waiting for you outside of this Killington vacation rental. Nestled in Vermont's Green Mountains, this ski-themed townhome includes hot tub, pool, and fitness center access. This condo is conveniently placed just four and a half miles north of Killington... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Pristine snow in the wintertime, shining sun in the summer, and evergreen trees and mountain slopes along the horizon - Killington offers some of the most beautiful sights in Vermont. You can experience it all from the comfort of this amazing vacation townhome, alongside resort amenities like a... View all property information
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    Killington, Vermont 05751
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    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    This ski-in condo offers the perfect combination of amenities and shuttle access for an unforgettable mountain vacation in Vermont. The Edgemont condo complex is just south of Killington, with the Diamond Express Shuttle (free until 5 p.m.) stopping right outside your door! When you're ready to... View all property information
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    Killington, Vermont 05751
    1 / 37
    Killington
    5 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    This recently updated lodge-style home offers room for eight, mountain views, and easy access to the slopes and nearby hiking trails. Regardless of when you choose to stay, you and your large group will be well situated for your next well-deserved mountain retreat. This 3,000-square-foot home is... View all property information
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    Killington, Vermont 05751
    1 / 25
    Killington
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    You'll be mere steps from the lifts in this ski-in/ski-out condo with gorgeous mountain views from your private balcony and access to the rec center with lots of amenities! Located right on the slopes at Sunrise Mountain, one of Killington's six peaks, you have direct access to beginner-level... View all property information
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    Killington, Vermont 05751
    1 / 30
    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Visit Vermont and stay in this lovely ski-in/ski-out condo on Pico Mountain. All year long, guests at Pico Mountain have access to Pico Sports Center, including the 75-foot pool, saunas, classes, and a fitness center for an additional fee. Just 11 miles from downtown Rutland in the heart of... View all property information
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    Killington, Vermont 05751
    1 / 26
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This cozy mountain condo has it all: comfy furnishings, easy access to the slopes, and resort amenities at the Pinnacle Spa and Lounge. Located right on the mountainside, up to six lucky guests at a time can enjoy the beauty of Killington up close and personal, with access to Vermont's slopes that... View all property information
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    Killington, Vermont 05751
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    Killington
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A retreat to this charming Killington townhome will provide you with a nice balance of relaxation and fun, thanks to access to two mountain resorts, your own private sauna, and some shared amenities! This vacation home is located in the Woods Resort & Spa and includes access to an indoor pool, hot... View all property information
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    Killington, Vermont 05751
    1 / 37
    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • Smoking allowed
    • x
    About this property
    Luxuriate in all the perks that come with this ski-in/ski-out Killington townhome, like the ski lift right outside your door, gorgeous mountain views from your private deck, and your in-house, private sauna. Access to the Falls Brook Common Health Spa also gives you shared access to amenities like... View all property information
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    Killington, Vermont 05751
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    Killington
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    You won't be far from the action in this dog-friendly mountain townhome, no matter the season! With both the slopes and some excellent golf courses nearby, you'll find plenty of ways to fill your days with fun and activity. As an added bonus, this vacation rental includes access to some shared... View all property information
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    Killington, Vermont 05751
    1 / 25
    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Ski-in/ski-out from this cozy Pico Mountain condo with immediate access to chairlifts, multiple-level slopes, and the Pico Sports Center, which offers guests a pool, saunas, and more (additional fees apply). Located in Pico Mountain Resort in the heart of Vermont's Green Mountains, this condo... View all property information
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    Killington, Vermont 05751
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    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Seasonal resort amenities, quick shuttle access to Killington's incredible slopes, and cozy home comforts - what more could you ask for in a quaint mountain retreat? Part of Pinnacle Condos, this single-level home is less than a mile from the base of Killington Ski Area, and closer to Killington... View all property information
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    Killington, Vermont 05751
    1 / 28
    Killington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... View all property information
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    Killington, Vermont 05751
    1 / 34
    Killington
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    Located near the Woods Resort and Spa's private pools, tennis courts, and gym, this beautiful townhome is the top choice for those wanting to experience the best of Central Vermont. Located on Killington Peak, this multilevel getaway is conveniently located near some of the best terrain parks and... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    This lovely Killington townhouse features ski-in/ski-out access, gorgeous mountain views, and shared amenities like a gym, steam room, pool, and hot tub. Located on the Sunrise Mountain slopes, this bright and open vacation rental is mere steps from beginner-level Sundog Trail. Ski down the... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This ski-in/ski-out townhome is the perfect place for your next mountain retreat. With its prime location, private deck, and sauna, as well as the shared indoor pool, hot tub, steam room, and fitness center, you'll be living in style in this lovely accommodation. Natural beauty abounds with this... View all property information
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    Killington, Vermont 05751
    1 / 29
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    Conveniently situated close to Pico Mountain and the six peaks of Killington, this condo is the ideal spot for a summer or winter vacation. It comes complete with an outdoor deck and great community amenities, like an indoor pool, hot tub, sauna, gym, and seasonal tennis courts. You're just a few... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Take in the gorgeous mountain views at this convenient ski-in/ski-out Killington townhouse, which has plenty of room for up to eight guests. Enjoy the slopes of Sunrise Mountain right outside, sit back and relax on one of the two private decks, and make the most of the community indoor pool, hot... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Experience all that Vermont has to offer when you stay in this spacious condo at Pico Mountain! With room for six lucky guests, all of the comforts of home, and convenient access to nearby attractions year-round, this rental is the perfect choice for your next vacation. Located near the base of... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Between the nearby slopes, shared hot tub, pool, and tennis courts, up to eight guests can enjoy an amazing mountain getaway at this cozy Woods Resort condo in Killington, VT. Located in a quiet area near the summertime hikes of Gifford Woods State Forest Park, you're just a four-mile drive from... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    As one of the rare ski-on/ski-off complexes in the Sunrise Mountain Village community, this vacation townhouse is perfect for your ultimate ski getaway. A convenient location, private sauna, and community amenities like a shared pool and hot tub are always a plus, too! This home has immediate... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This chic, renovated Vermont home is an amazing opportunity for a group or family of six to get away from it all and enjoy skiing, swimming, and more. This multi-level townhome is conveniently located in the heart of the Woods Resort & Spa, with access to an indoor pool, hot tub, fitness center,... View all property information
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    Killington, Vermont 05751
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    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    This recently renovated Vermont home offers a cozy place to stay as you and your family enjoy a host of natural attractions and modern comforts. The multi-level townhouse is located in the Woods Resort & Spa, with access to amenities like an indoor pool, hot tub, fitness center, steam room, and... View all property information
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    Killington, Vermont 05751
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    Mendon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Walk, ski, or snowboard to Pico Mountain's lifts from this ski-in/ski-out condo, the perfect home base for your next winter getaway to Mendon and Killington. Conveniently and scenically situated at the bottom of the Little Pico Triple Chair Lift, this three-bedroom condo will provide families and... View all property information
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    Mendon, Vermont 05751
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    Killington
    6 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • ?
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    • x
    About this property
    Enjoy three levels of pure decadence at this gorgeous Killington vacation rental. Soak in the hot tub or recline in any of the three living rooms. With six bedrooms and two sleeping lofts, up to 16 people can get that much-needed shut eye! The slopes at Killington are just three miles away and... View all property information
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    Killington, Vermont 05751
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    Killington
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    Book this pet-friendly two-bedroom, two-and-a-bathroom Killington vacation rental and you'll experience ultimate relaxation at The Woods Resort & Spa, which features luxe amenities like clay tennis courts, a large pool and hot tub, a full spa, and a fitness center! A picturesque getaway near... View all property information
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    Killington, Vermont 05751
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    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Just three miles to the slopes, this cozy and charming Killington vacation rental is the perfect base for a family ski weekend in Vermont. Part of the Woods Resort and Spa at Killington, this condo development sits on 100 acres and offers a wealth of amenities, from an indoor pool to a sauna and... View all property information
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    Killington, Vermont 05751
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    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    With a private balcony and mountain views, this ski-in/ski-out retreat has everything you'll need for a memorable Vermont vacation! Situated on Pico Mountain, this rental offers immediate access to the slopes. There's a rope tow to Pico's steepest trail, Giant Killer, and the Bonanza Learning area... View all property information
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    Killington, Vermont 05751
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    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • ?
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    • x
    About this property
    Charming doesn't begin to describe this Killington home. When you stay in this house you can look forward to amazing amenities, from a wood-burning fireplace to a communal spa to a jetted tub in the master bath. This home is in The Woods Resort and Spa, which is just four miles from Killington... View all property information
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    Killington, Vermont 05751
    1 / 34
    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Guests looking to relax, explore, or just get away alike will love this charming Vermont townhouse at The Woods Resort & Spa with easy access to amenities like an indoor pool, hot tub, fitness center, steam room, and sauna. Courtesy of the Diamond Express shuttle, ski slopes at Killington and Pico... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 26
    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
    • Hot Tub
    • Grill
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    For a Vermont vacation you'll never forget, this chic, ski in/ski-out condo is just what you're looking for. This Pico Mountain condo provides easy access to 57 trails, with the Pico Sports Center nearby offering a 75-foot heated indoor pool, hot tubs, and a sauna. If one mountain isn't enough,... View all property information
    Location Information
    Killington, Vermont 05751
    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Terrace
    • Satellite TV
    • Balcony
    • Wi-Fi
    • Skiing: Property Is...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    1 Bedroom Whiffletree Condo (sleeps 4) - Whiffletree Condominiums are centrally located in the heart of Killington's main basin area. In winter, a free shuttle goes to Snowshed base lodge, only 1/2 mile away and enjoy "ski home" access provided there is natural snow. This property has everything... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 5
    5 of 5 stars (2) Excellent
    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Right at the site of Killington's basin is where Whiffletree condominiums shall be. This three bedroom, two bathroom Killington vacation rental has everything you need, featuring a gas fireplace, wireless internet, cable tv, and a full kitchen and dining area. Bedroom one includes a king bed,... View all property information
    Location Information
    Killington, Vermont 05751
    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Balcony
    • Satellite TV
    • Parking
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Washer
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy this completely renovated Whiffletree 3 Bedroom, 2 Full Bath Unit in the heart of Killington Resort (one level). Brand New Flat Screen TV's in All Bedrooms and Living Room Area! Whiffletree Condominiums are centrally located in the heart of Killington's main basin area. In winter, a free... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 12
    5 of 5 stars (1) Excellent
    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Balcony
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Moose Lodge is the perfect Ski house. Moose Lodge has three bedrooms plus loft with two full bathrooms. Let the kids hang out in the lower level with the ping pong table while the adults relax in the living room. Summer months enjoy being walking distance to Green Mountain National Golf course.... View all property information
    Location Information
    Killington, Vermont 05751
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Wi-Fi
    • Shared Indoor Pool
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    With 468 acres of skiable terrain and close to 20 miles of trails to choose from, exploration awaits. Things To Do in Winter: Ski or Board at Pico or Killington Mountains, Beast Roller Coaster, Fat Bike Rental, Snow Tubing Park, SkyRide, Snowshoeing Tours, Sleigh Rides, Snowmobile Tours,... View all property information
    Location Information
    Killington, Vermont 05701
    1 / 8
    5 of 5 stars (3) Excellent
    Killington
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Internet Access
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Accommodations and amenities are the key to a successful vacation when it comes to Whiffletree condominiums. This four bedroom, two bathroom Killington vacation rental has all you need with a fireplace, wireless internet, cable tv, and a full kitchen and living area. Bedroom one has a king bed with... View all property information
    Location Information
    Killington, Vermont 05751
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Skiing: Property Is...
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Shared Indoor Pool
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy a condo which offers the best of everything. Mountain Green Resort is close to the ski slopes, just a short walk to Snowshed Base Lodge. The Killington Tubing park is a stones throw away. Enjoy such conveniences like the health spa, indoor pool, jacuzzi's, racquetball court, onsite... View all property information
    Location Information
    Killington, Vermont 05751
    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Studio Slopeside Condo at Pico Mountain Ski Resort! This condo features spacious, bright, cheerful and contemporary styling and is walking distance to the health club and the base lodge. Catheral ceilings with bright open living room area with sky lights and large windows with beautiful views of... View all property information
    Location Information
    Killington, Vermont 05701
    Killington
    1 Bedroom, 3 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • Hot Tub
    • Balcony
    • Terrace
    • Mountain Views
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    1 bedroom condo situated at the base of Killington, VT ski resort .Fully furnished, and with all cooking utensils supplied, BBQ, fireplace, deck, spa, gym, indoor and outdoor pool. Walking distance to Killington Mountain, for skiing, hiking and mountain biking. 18 hole golf course nextdoor and... View all property information
    Location Information
    Killington, Vermont 05751
    Killington
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Balcony
    • DVD Player
    • Mountain Views
    • Terrace
    • Wi-Fi
    • Parking
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    1 Bedroom Whiffletree Condo (sleeps 4) - Whiffletree Condominiums are centrally located in the heart of Killington's main basin area. In winter, a free shuttle goes to Snowshed base lodge, only 1/2 mile away and enjoy "ski home" access provided there is natural snow. This property has everything... View all property information
    Location Information
    Killington, Vermont 05751