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Pet Friendly Holiday Rentals in Pittsfield, VT and nearby

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    1 / 26
    1 of 5 bubbles (1) Terrible
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 20 | Quick View
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    1 / 30
    Pittsfield
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    1 / 24
    Pittsfield
    3 Bedrooms, 2 Bathrooms, Sleeps 20 | Quick View
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    1 / 24
    Pittsfield
    4 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • x
    About this property
    Your home away from home! Whether you are looking for peace and relaxation or convenience and accessibility, the Blue Diamond House is the perfect mountain retreat. Tastefully appointed, warm and inviting, you will love stepping into this charming home. Three beautiful bedrooms plus a loft... View all property information
    Location Information
    Pittsfield, Vermont 05762

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

    1 / 37
    5 of 5 bubbles (2) Excellent
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Our contemporary Killington trailside condo is perfect for a family or couples getaway! Conveniently located just steps from the Sundog trail and closer than many units in Sunrise. Ski home for lunch and avoid the shuttles, base lodges and parking. Larger than most Sunrise 2 bedrooms, offering a... View all property information
    Location Information
    Killington, Vermont 05751
    5 of 5 bubbles Reviewed 9 January 2017
    The condo is clean, has everything we need ( kitchen, cable TV, especially Wi-Fi since it is a must for our kids). Location is very convenience, we just step out of the door and...
    5 of 5 bubbles Reviewed 30 November 2016
    Four ladies who love golf had a wonderful stay at this very comfortable condo in Sunrise Village at Killington. The location is perfect, beautiful mountain views and close to...
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    1 / 26
    4 of 5 bubbles (1) Very good
    Killington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • DVD Player
    • Mountain Views
    • Wi-Fi
    • Secure Parking
    • Terrace
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Winter, spring, summer and fall, there is always something to do and something to fall in love with at this cozy Vermont vacation home. Kids will love the rustic sturdy bunk beds and folks just love to relax in front of the fire, cozying up to a good book. There are many downhill and cross country... View all property information
    Location Information
    Killington, Vermont 05035
    4 of 5 bubbles Reviewed 26 August 2014
    WE chose this rental house because of its 5 minute walk to the Long Trail Brewery. Hubby and I and another couple and their 2 pre-teen daughters went to the 25th Anniversary...
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    1 / 32
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Washer
    • Satellite TV
    • DVD Player
    • Shared Indoor Pool
    • Hot Tub
    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Getaway and enjoy yourself at this Green Mountain Vermont Chalet located in Stockbridge, VT near Killington Ski Resort. The views are breath taking at our secluded home. Cedar Rock has a large stone fireplace and a new outdoor Hot Tub to enjoy with friends and family. Our home is at the end of the... View all property information
    Location Information
    Stockbridge, Vermont 05746
    1 / 26
    5 of 5 bubbles (1) Excellent
    Killington
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    • Satellite TV
    • Central Heating
    • Wi-Fi
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Skiing: Property Is...
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Tanglewood Vista is a three-floor, five bedroom, three bathroom home that is located just off the main access road in Killington, Vermont. This puts you close to all the excitement of the shops, restaurant and bars and less than 2 miles to the resort. Our home is perfect for families or groups... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 30
    Killington
    8 Bedrooms, 4 Bathrooms, Sleeps 24 | Quick View
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    • DVD Player
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Washer
    • Skiing: Property Is...
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Cabin at Killington is the perfect place to spend your Killington vacation. Located just off the main access road in Killington, VT (close to the Killington Market), the house is less than 2 miles to the mountain and close to all the stores, bars and restaurants. It's the perfect vacation spot... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 27
    5 of 5 bubbles (1) Excellent
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Satellite TV
    • Washer
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Shared Indoor Pool
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A fantastic skiers dream getaway at Killington's Sunrise Village! Come stay in this cozy single level 2 bedroom trail side condo with access to Bear Mountain and Killington. Comfortably sleeps 4-6 people and is the perfect place for a romantic ski getaway or small family trip. Download our... View all property information
    Location Information
    Killington, Vermont 05751
    5 of 5 bubbles Reviewed 31 January 2015
    This is really ski on ski off. We were not disappointed. The space was clean, well stocked kitchen and nice linens.
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    1 / 18
    Killington
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Washer
    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Skiing: Property Is...
    • Satellite TV
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Cabin at Killington is the perfect place to spend your Killington vacation. Located just off the main access road in Killington, VT (close to the Killington Market), the house is less than 2 miles to the mountain and close to all the stores, bars and restaurants. It's the perfect vacation spot... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 11
    5 of 5 bubbles (5) Excellent
    Killington
    7 Bedrooms, 4 Bathrooms, Sleeps 28 | Quick View
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    • Hot Tub
    • Washer
    • Satellite TV
    • Central Heating
    • Mountain Views
    • Skiing: Property Is...
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Killington Mountain Retreat is a vacation home located just off the main access road in Killington, Vermont. This three-floor, 7 bedroom home is fully equipped and furnished. In addition to the bedrooms, there is a large kitchen, living room, game room, media room, mud room and large outdoor... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 9
    3.5 of 5 bubbles (3) Average
    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
    • Mountain Views
    • Satellite TV
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Bucolic in nature, the Killington Country Estate is where you can imagine yourself spending your Killington winter vacation. As beautifully white as the snow, this three-bedroom, and three-bathroom Vermont vacation home is the epitome of country living. This is one of the largest Killington ski... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 24
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Balcony
    • Grill
    • Washer
    • Internet Access
    • Parking
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Getaway and enjoy yourself at this Green Mountain Vermont Chalet located in Stockbridge, VT near Killington Ski Resort. The views are breath taking at our secluded home. Cedar Rock has a large stone fireplace and a new outdoor Hot Tub to enjoy with friends and family. Our home is at the end of... View all property information
    Location Information
    Stockbridge, Vermont 05772
    1 / 24
    Killington
    Studio, 2 Bathrooms, Sleeps 7 | Quick View
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    • Patio
    • Hot Tub
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Killington, Vermont 05751
    1 / 22
    Mendon
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Air Conditioning
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Want to get away from it all! This cozy three bedroom, one bath, private home with wrap around deck sits on a corner lot with a one car garage. Tucked away in the woods of historic Mendon Town, your minutes from all the activities Killington ski area has to offer.  Visit nearby Chittendon Town... View all property information
    Location Information
    Mendon, Vermont 05701
    1 / 24
    Killington
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Hot Tub
    • Washer
    • Sauna
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A fantastic skiers dream getaway at Killington's Sunrise Village! Come stay in this cozy single level 2 bedroom trail side condo with access to Bear Mountain and Killington. Comfortably sleeps 4-6 people and is the perfect place for a romantic ski getaway or small family trip. Download our... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 22
    Mendon
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Mountain Views
    • Balcony
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Want to get away from it all!This cozy three bedroom, one bath, private home with wrap around deck sits on a corner lot with a one car garage. Tucked away in the woods of historic Mendon Town, your minutes from all the activitiesKillington ski area has to offer. Visit nearby Chittendon Town where... View all property information
    Location Information
    Mendon, Vermont 05701
    1 / 26
    Killington
    Studio, 4 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
    • Shared Outdoor Pool...
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    • Grill
    • Hot Tub
    • Patio
    Suitability
    • 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
    Location Information
    Killington, Vermont 05751
    1 / 16
    Killington
    4 Bedrooms, 3 Bathrooms, Sleeps 19 | Quick View
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    • Washer
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Grill
    • Balcony
    • Sauna
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Killington, Vermont 05751
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    1 / 41
    Killington
    Studio, 3 Bathrooms, Sleeps 16 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Killington, Vermont 05751
    1 / 10
    5 of 5 bubbles (11) Excellent
    Killington
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Mountain Views
    • DVD Player
    • Central Heating
    • Hot Tub
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    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    The Dew Drop Inn, Winter Ski House is Charming & Cozy. It is in the valley surrounded by Scenic Mountain Views. <BR>There is an Outdoor Hot Tub in the back of the house. <BR><BR>It is 1 mile from Killington's worlds famous high speed "Skyeship Base Lodge GONDOLA" <BR>(8 passenger- hi speed Gondola... View all property information
    Location Information
    Killington, Vermont 05035
    5 of 5 bubbles Reviewed 9 March 2016
    What a beautiful and centrally located place for the price! The owners are such a pleasure to deal with, very prompt reply and Ronnie is so sweet she makes you feel like you're...
    4 of 5 bubbles Reviewed 1 March 2016
    I loved that the house was so close to the sky chair, which no one seems to know is there, that we could drive back and forth for lunch! The house needs some love: The...
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    1 / 33
    Killington
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • Hot Tub
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Killington, Vermont 05751
    1 / 16
    Rochester
    5 Bedrooms, 3 Bathrooms, Sleeps 22 | Quick View
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    • Grill
    • Porch
    • Satellite TV
    • Central Heating
    • Internet Access
    • Washer
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    **CALL FOR PRICE QUOTE AND DISCOUNT FOR SHORT NOTICE BOOKING** This is a home where a large group or family will enjoy the simple joys of being together in the middle of the beautiful green mountains of Vermont! Situated on 10 beautiful acres with a swimming pond, a brook with a water hole,... View all property information
    Location Information
    Rochester, Vermont 05767
    1 / 65
    2 of 5 bubbles (1) Poor
    Killington
    7 Bedrooms, 5 Bathrooms, Sleeps 25 | Quick View
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    • Satellite TV
    • Mountain Views
    • Hot Tub
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    For your next family reunion or company outing, consider the Sunburst Chalet as the place to stay, play, and enjoy Killington Vermont! As one of the largest premiere rental house properties in Killington, this house is able to accommodate a maximum capacity of 24 guests. With both indoor and... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 13
    Killington
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Quietly secluded, Hemlock Ridge is conveniently located near the the heart of Killington's fast-paced scenery. With its mountain-town decor and room for up to 10 people, this three bedroom, two bathroom Killington vacation rental has all the amenities you need! Have a home-cooked meal after a long... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 30
    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Balcony
    • Sauna
    • Terrace
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • 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... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 13
    Killington
    2 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
    • Sauna
    • Hot Tub
    • Internet Access
    • Private Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Want a vacation rental that has everything you need and then some? Well, it's The Woods Resort & Spa of course! This two bedroom, two bathroom Killington vacation rental will have you and your guests fully equipped for you vacation. Each unit features a whirlpool tub, fireplace, sauna, fully... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 24
    Killington
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • Terrace
    • Balcony
    • Sauna
    • Hot Tub
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 17
    4.5 of 5 bubbles (4) Very good
    Killington
    4 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Satellite TV
    • Internet Access
    • Mountain Views
    • Sauna
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The Trailside Retreat is where you will have a true Killington experience. This big rental house is situated in a secluded and woodsy setting near the Skyeship Gondola. This Killington vacation house has four bedrooms, two bathrooms, and everything you could wish for in a ski-on and ski-off rental... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 14
    5 of 5 bubbles (1) Excellent
    Killington
    7 Bedrooms, 3 Bathrooms, Sleeps 25 | Quick View
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    • Washer
    • Sauna
    • Satellite TV
    • Housekeeping...
    • Wi-Fi
    • DVD Player
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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. outside hot tub, pool table, 42" flat screen TV, in addition to new beds, bedspreads, and drapes. The fully equiped kitchen has... View all property information
    Location Information
    Killington, Vermont 05751
    5 of 5 bubbles Reviewed 21 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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    1 / 16
    Killington
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Sauna
    • Wi-Fi
    • Patio
    • Satellite TV
    • DVD Player
    • Washer
    • Hot Tub
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Meadows - 4 Bedroom Private Home (sleeps 12). Large Indoor Hot Tub room with Sauna. Game room great for both adults and children. Perfect vacation home for families. Main Level Living room w/ 24' TV with DVD player, Wood Burning Fireplace - Brand new living room furniture WiFi Dining area -... View all property information
    Location Information
    Killington, Vermont 05751
    1 / 24
    Killington
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Shared Outdoor Pool...
    • Grill
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Killington, Vermont 05751