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Plymouth Family & Kid Friendly Rentals

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    49 Matching Rentals in the Plymouth AreaView all 51 rentals
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    Plymouth
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Plymouth
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Plymouth
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Central Heating
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    About this property
    Birch Landing #16 Take long walks amongst the lovely foliage of Vermont, or frolic around in the snow and try various winter sports. With lake access and a shared pool and tennis courts, the whole family will love this space! Near beautiful hiking and the famous Okemo Resort's ski slopes, this...
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    Plymouth, Vermont 05056
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Mountain Views
    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Amherst Lake Cozy Cottage Make your Vermont dreams a reality with a reservation in this cute cabin, where lake and mountain views surround you! There's something for every season here, from plenty of outdoor seating to a convenient, secluded location. This cabin is a great home base for a ski...
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Plymouth
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Easy Living Come experience the charming family-friendly atmosphere of this Plymouth home. Whether you're looking to hit the slopes at one of the local ski resorts, do a little bit of shopping, or play a few rounds of golf, this home puts it all at your fingertips. Located over 11 miles from...
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    Plymouth, Vermont 05056
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    About this property
    Cozy in Plymouth Admire beautiful forests, lakes, and streams as you drive down Route 100 to get to and from this cozy, family-friendly home in Plymouth! Whether you spend your days hiking, gazing at fall foliage, or skiing the world-class slopes of Killington, you'll come home to a comfortable...
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    • Waterfront
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    Pet friendly
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    Smoking allowed
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    Kurtz Lake Cottage The leafy views and all-seasons outdoor options are unbeatable at this three-bedroom, one-and-a-half-bathroom Ludlow cottage right on the water. Welcoming up to seven guests and two dogs, it's perfect for a Green Mountain getaway with friends or family! Located on picturesque...
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    Plymouth, Vermont 05149
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms1 / 39
    (2)Excellent
    Plymouth
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Wi-Fi
    • Grill
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    • Secure Parking
    • Mountain Views
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2019
    Found this cottage by accident- so happy I did! Sept 2018 & back July 2019! Alecia & John have thought of everything! Every detail- from fully stocked kitchens &amp...
    Reviewed January 8, 2019
    What a terrific house for a winter vacation! It was conveniently located between Killington and Okemo Ski Resort. The weather was perfect. The amenities inside the house were...
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    About this property
    The adventurous and spirited traveling family or group will enjoy a festivity of colors and furnishings in this quintessential 1930's era cottage with modern creature comforts. Occupy the entire cottage with lush lawns and lake-side seats, green or white, summer or winter. This spacious cottage...
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    Plymouth, Vermont 05056
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Plymouth
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Plymouth
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    • Skiing: Property Is In A Ski Resort
    • Balcony
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    Pet friendly
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    Plymouth, Vermont 05056
    Rental Home - 6 Bedrooms, 3 Bathrooms, Sleeps 10
    Plymouth
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Cable/satellite TV
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    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the luxurious Hawk Mountain Resort community, this 5-bedroom, 3-bathroom Plymouth vacation rental home is ideally situated between the Okemo and Killington resorts! This private home features comfortable accommodations for 12 guests, a private hot tub, a recreation room, wood-burning...
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    Plymouth, Vermont 05056
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Plymouth
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Mountain Views
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    • Outdoor Dining Area
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A light filled mountain retreat overlooking pond on 22 acres. Very comfortable for 2 couples or a family, can accommodate unto 6 people. Located in historic Plymouth, birthplace and resting place of President Calvin Coolidge. Enjoy skiing/sledding in Winter, listening to peepers in Spring, hiking...
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    Plymouth, Vermont 05096
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Lakeview: Comfortable Lakefront Cabin between Okemo & Killington1 / 25
    (21)Very good
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Smoking allowed
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    'BEAR DOWN' 'in this gorgous Vermont House !1 / 16
    (22)Excellent
    Plymouth
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
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    Plymouth, Vermont 05149
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    Private, All Season 10 Acre Retreat Close to the Slopes, Trails, and Swimming1 / 28
    (8)Excellent
    Plymouth
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Hot Tub
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    Pet friendly
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    Smoking allowed
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    Plymouth, Vermont 05149
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Cute family-friendly cabin w/ lake views and convenient proximity to skiing1 / 25
    (11)Excellent
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lakeview: Comfortable Lakefront Cabin between Okemo & Killington1 / 19
    (5)Excellent
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Gorgeous Mountaintop Hawk Townhome:Spectacular Views; Okemo/Killington/Echo Lake1 / 24
    (10)Excellent
    Plymouth
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Shared Indoor Pool
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    Pet friendly
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Ultimate Lakefront Chalet1 / 20
    (20)Excellent
    Plymouth
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Hot Tub
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    Pet friendly
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    Smoking allowed
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    Plymouth, Vermont 05056
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    New Construction 4 season Killington VT Ski House on Lake Amherst  okemo1 / 24
    (15)Very good
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Smoking allowed
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    Plymouth, Vermont 05149
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Plymouth
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Patio
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    Smoking allowed
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 9
    Located between Okemo and Killington with a hot tub1 / 30
    (4)Very good
    Plymouth
    9 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 9 Bedrooms, 3 Bathrooms, Sleeps 18
    NEW LISTING! Lovely home w/deck, firepit, pond & shared pool-near Killington1 / 49
    (14)Excellent
    Plymouth
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    Great Ski House/Summer House on pristine Echo Lake - Flexible Dates Available1 / 36
    (12)Excellent
    Plymouth
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Balcony
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    Plymouth, Vermont 05149
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Beautiful and spacious condo w/ shared pool, lake access - close to skiing1 / 40
    (20)Very good
    Plymouth
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Plymouth, Vermont 05056
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 11
    Luxury Home at Hawk Resort with Views of Okemo and Lakes1 / 20
    (21)Excellent
    Plymouth
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    Beautiful Echo Lake Vacation Home1 / 21
    (10)Excellent
    Plymouth
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Plymouth, Vermont 05149
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Available Holiday Weekends1 / 36
    (21)Very good
    Plymouth
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    New Lakeside Cottage near Okemo and Killington1 / 24
    (91)Excellent
    Plymouth
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Spacious Log Home, 5 bedrooms, sleeps 16!  Near Okemo, Killington, Woodstock!!!1 / 13
    (4)Average
    Plymouth
    5 Bedrooms, 2 Bathrooms, Sleeps 16 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 16
    Quaint family-friendly home between Killington & Okemo for great skiing!1 / 24
    (7)Excellent
    Plymouth
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Northern Woods Vacation Mountain Home1 / 20
    (6)Very good
    Plymouth
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Plymouth, Vermont 05056
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Mountain Getaway Minutes From Okemo And Killington Mountains1 / 23
    (19)Excellent
    Plymouth
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Plymouth, Vermont 05056
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Plymouth
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Central Heating
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the family along to this charming vacation rental in Vermont! Located in the heart of Vermont's ski country, this 3-bed, 2-bath townhouse was made for spring skiing, summer vacations, the winter holidays, and long weekends spent with loved ones. No matter the season, you'll love this central...
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    Plymouth, Vermont 05056
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Plymouth
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Washer
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage is such a relaxing, calming place. We have added many 'must-have' conveniences with high quality creature comforts because it needs to be 'that' special place. We love entertaining at the cottage because the set-up is so 'entertainment friendly' and there is plenty of room for many...
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    Plymouth, Vermont 05056
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    The following rentals are within 5 miles of Plymouth.
    Ski-in/ski-out Sunrise townhome w/ shared pool & hot tub for year-round retreats1 / 56
    (3)Excellent
    Sherburne
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Shared Indoor Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 26, 2017
    Good roomy Condo with 3 bedrooms. Had access to a very nice Sports Center with indoor and outdoors pool, hot tub and sauna.
    Reviewed April 24, 2017
    Great location! Right on the hill. The fireplace was fantastic. The only complaint I have is we didn't stay long enough. Enjoy your stay
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    About this property
    Sunrise: East Glade-D2 This lovely Killington townhouse features ski-in/ski-out access and gorgeous mountain views. Located on the Sunrise Mountain slopes, this bright and open vacation rental is mere steps from beginner-level Sundog Trail. Ski down the mountain to Sunrise Village Triple...
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    Sherburne, Vermont 05751
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Sherburne
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Sunrise: Timberline-G4 Feel the stress melt away as you enjoy a steam in your private sauna when you stay at this Killington escape. Located in the Sunrise community, guests have access to a shared hot tub as well as ski-in access via the green run Sunrise Trail, and the Sunrise Village Triple...
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    Sherburne, Vermont 05751
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Sherburne
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    Ledge End 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 movie room, wrap-around deck, and roomy private sauna. This home is perfect for anyone who wants a relaxing, fun, and memorable mountain...
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    Location Information
    Sherburne, Vermont 05751
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Sherburne
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Sunrise: Eastglade-C4 Enjoy ski-in/ski-out access to Sunrise Mountain when you stay at this three-bedroom condo, which offers lovely mountain vistas and access to a community indoor swimming pool, hot tubs, a gym, and a sauna. Perfectly situated less than 100 feet from the Sundog Trail, this...
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    Sherburne, Vermont 05751
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Sherburne
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Top Ridge: 34A This lovely ski-in/ski-out townhouse is a great spot for families or groups seeking easy access to all of what Killington has to offer. This three-story home is sleek and modern, with natural wood accents reminiscent of the classic ski lodge feel. Leading from the atrium is the...
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    Sherburne, Vermont 05751
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Gorgeous cabin with mountain views, near gondola & nature - walk to ski slopes!1 / 32
    (1)Average
    Sherburne
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    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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    Killington's Hideaway 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....
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    Sherburne, Vermont 05751
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Bridgewater Corners
    6 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • Mountain Views
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    About this property
    Ledges was built in 1988 and since has been totally renovated into a six bedroom with two loft cubbies. For extra sleeping. This, contemporary ski house provides full accommodations. It's perfect for a romantic getaway or a cozy overnight stay with the family or friends near Killington and Okemo in...
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    Bridgewater Corners, Vermont 05035
    Rental Home - 6 Bedrooms, 2 Bathrooms, Sleeps 13
    Sherburne
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise: West Glade-J2 This ski-in/ski-out townhome is the perfect place for your next mountain retreat. With its prime location and a private deck and sauna, you'll be living in style in this lovely accommodation. Natural beauty abounds with this rental, which is located at the beginning Sundog...
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    Sherburne, Vermont 05751
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Sherburne
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise: Timberline-L5 This cozy Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to six guests for an unforgettable stay in the Green Mountains! For ski slope access, it doesn't get any better than this ski-in/ski-out...
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    Sherburne, Vermont 05751
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sherburne
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sundog Retreat Find everything from snow-covered slopes to spectacular foliage at this Killington condo, a ski-in/ski-out property with direct access to the Sundog run, gorgeous mountain views from its two decks, and community amenities that include pools, a hot tub, a gym, and tennis courts!...
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    Sherburne, Vermont 05751
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Sherburne
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Roundabout Ridge Experience Killington in awe-inspiring style at this four-bedroom Vermont lodge, a hillside retreat with its very own sauna, a private deck and picnic area, and majestic views of the surrounding slopes in winter, spring, summer, and fall. This home sits among the trees on the...
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    Sherburne, Vermont 05751
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 6
    Ski-in/ski out from this cozy Vermont condo w/ shared pool, hot tub, & two decks1 / 43
    (1)Terrible
    Sherburne
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Terrace
    • Mountain Views
    • Central Heating
    • Balcony
    • Shared Indoor Pool
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise: Timberline-L8 The slopes of Sunrise Mountain are just outside your door at this ski-in/ski-out Killington townhome, a convenient and comfortable three-bedroom property that offers beautiful mountain vistas, and two private decks. This recently renovated home is perfectly located on the...
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    Sherburne, Vermont 05751
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Bridgewater Corners
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
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    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note the homeowner lives on site, in a completely separate unit, and may be present during your stay* Enjoy a picture-perfect getaway when you stay at 'Southgate Healing,' a 1-bed, 1-bath vacation rental apartment in Bridgewater Corners. A quintessential Vermont spot, this home stands out...
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    Location Information
    Bridgewater Corners, Vermont 05035
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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