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Chestertown Holiday Homes

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    Travellers to Chestertown are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 57 Rentals in Chestertown
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    Atateka Point Lodge and Treehouse Guest Cottage1 / 34
    (13)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Black Bear Cabin1 / 15
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Loon Lake Retreat with Private Dock1 / 36
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The Treehouse at Atateka Point  Lodge1 / 23
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Grill
    • Wi-Fi
    • Central Heating
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 December 2019
    We were looking for a quiet, secluded, lake-front rental and hit the jackpot with this stay. The property was beautiful, had tons of amenities and gave us the comfortable and...
    Reviewed 11 August 2019
    We had a wonderful time at the lodge! My girls (age 16 and 20) want to make it an annual trip. The lake is beautiful, the house is cozy and there is nothing better than meals...
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    About this property
    The Treehouse is a two story guest house located on the shore of Friends Lake in the Adirondacks. One bedroom upstairs with ensuite bathroom and filtered lake views. The first floor includes a living room with full sized futon, a window seat, kitchenette with new electric range, apartment size...
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    Chestertown, New York 12817
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Friends Lake- Quaint and New1 / 22
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Housekeeping Included
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2019
    Really sweet country cabin, clean and spacious, 2 min walk to lake. Owner super nice and responsive.
    Reviewed 25 June 2018
    My friends and I spent all of our time either in the house or on the lake. We had a great time and the people there are very nice. James was very helpful and available...
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    About this property
    4.5 Stars on VRBO!. The property is totally updated with all new interior, including the kitchen and baths (1 1/2), windows and doors. The home also has a brand new furnace as well as fresh air provided through a heat recycling ventilation system. You will be able to enjoy this home in the summer...
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    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Green Mansions Vacation Condo1 / 25
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
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    • Internet Access
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    Beach was very close, just down the hill behind the condo. Condo was nicely decorated with Adirondack themes. Close to Lake George and to a grocery store. The farmer’s market...
    Reviewed 15 August 2017
    Clean and well maintained unit a few steps from Tripp lake beach. Only 15 minutes from Lake George village. It's our second stay and we would definitively rent again.
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    About this property
    Located in the Southern Adirondack Mountains between Lake George and Gore Mountain Ski Resort our Green Mansions Vacation Condo is the perfect year-round getaway for outdoor lovers, adventure seekers and romantics. Our 2-bedroom, 2-bath home is exceptionally decorated with Adirondack and rustic...
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    Chestertown, New York 12817
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Wi-Fi
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    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cottage on the Cove Relax on the coast of the Atlantic at this authentic oceanfront cottage in Wells! You'll love the multiple furnished sun porches, perfect for curling up with a novel on a beautiful Maine day. This charming vacation rental features a quaint interior decor that will truly make you...
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    Chestertown, New York 12817
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Terrace
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    • Balcony
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Laurel Valley Lounger Located in the beautiful PGA West Country Club, this second-floor condo boasts endless views of the Jack Nicklaus golf course and desert mountains. The City of La Quinta offers endless activities day and night for the perfect vacation or weekend getaway. Spend the day hanging...
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    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Redfish Village M2-424 Gorgeous and beautifully decorated, this inviting home is perfect for friends and family to relax and unwind. The fully equipped kitchen has stainless steel appliances, granite countertops, and plenty of workspaces, which make this kitchen every chef's dream! Gather around...
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    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amalfi Coast 425-D Make the best beach memories in this spacious and family-friendly condo located in Miramar Beach. This beachfront getaway has space for a family or friends to spread out and have privacy. The fully equipped kitchen offers everything you will need to prepare delicious meals and...
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    Location Information
    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Wi-Fi
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    • Hot Tub
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amalfi Coast D 326 Enjoy the perfect beach vacation in this spacious and family-friendly condo located in Miramar Beach. This getaway features a convenient and well-equipped kitchen that makes preparing delicious meals and beach snacks easy. The private balcony is perfect for sipping a morning cup...
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    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Air Conditioning
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amalfi Coast A204 Enjoy the best that the beach offers in this spacious and family-friendly condo located in Miramar Beach. Gorgeous beach decor and plenty of space for a family or friends to spread out and relax make Amalfi Coast A204 a dreamy getaway to create everlasting memories. The fully...
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    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Ocean Views
    • Hot Tub
    • Waterfront
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Edgewater - Windward 207 Enjoy spending time at the beach in this gorgeous beachfront condo. Plenty of space for friends and family to spend time together and make amazing beach memories make Edgewater 207 the perfect place to host your next getaway. The fully equipped kitchen will make preparing...
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    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Hot Tub
    • Patio
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    • Mountain Views
    • Washer
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Canyon Place Retreat Canyon Place Retreat is a lovely place to enjoy a family vacation, as this home has an open space with high ceilings that everyone will enjoy. Turn on the gas fireplace to warm up the living room while watching a movie on the flat-screen TV. Plus, you can have some time to...
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Ocean Views
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harvey's House Getaway in this spacious, bright, Eastsound home! With its picturesque wrap around deck, you can take in the beautiful garden and water views. You can cook for your whole family in the home's full kitchen with all of the tools you'll need. In the living room, you can stay warm by the...
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    Chestertown, New York 12817
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Patio
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Place in the Pines This vacation rental is a wonderful choice for your next stay in Bonita Springs. It offers great amenities and conveniences such as a shared pool private shuttle to the beach a few miles away! Here you can spend your evenings relaxing on the large wrap-around lanai, or if you...
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    Chestertown, New York 12817
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Grill
    • Mountain Views
    • Central Heating
    • Waterfront
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Loon Lake Serendipity This fantastic, direct lakefront house on the eastern shore of Loon Lake has it all! You'll have desirable eastern exposure and decks on both levels plus a bonus lakeside deck. It's an extremely comfortable home with an oversized sunken living room, full kitchen, and plenty of...
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Central Heating
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    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adirondack Great Camp This delightfully unique Loon Lakefront home is situated on the eastern shoreline, with fabulous views and a dock for your use. This incredible home is packed from top to bottom and side to side with Adirondack charm and ambiance! Enjoy summer breezes, warm sunshine, and all...
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
    5 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Central Heating
    • Washer
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adirondack Contemporary This is a fabulous oversized home proudly poised on the eastern shore of Friends Lake, decorated in a tasteful mix of antiques and contemporary style. It boasts a bright interior with a spacious great room specially designed for family get-togethers. Whether you want to...
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    Chestertown, New York 12817
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
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    • Terrace
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    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Loon Lookout Chalet This extremely popular lakefront chalet offers a spacious great room, lake rights on the eastern shore of Loon Lake, and a dog-friendly attitude so the whole family can come along. You'll have a breakfast bar, two sets of sliding patio doors that lead to the front deck, and a...
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    Adirondack Dreaming This spacious house is tucked lovingly in a hollow, directly on the eastern shoreline of the beautiful Friends Lake! While you're here, you'll enjoy the beautifully appointed house itself, as well as outdoor amenities that range from a campfire area and private dock to a sandy...
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    Chestertown, New York 12817
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    6 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Washer
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    Pet friendly
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    About this property
    The Historic Chester Inn Take a step back in time at this Greek Revival style home. This rental is meticulously detailed with each room decorated in period fashion, from hand-painted and imported wallpaper to handcrafted cherry cabinets. There are four porches, including one screened-in porch, to...
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    Chestertown, New York 12817
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Solitude at Lake's End This uncomplicated lakefront camp offers all the comforts of home, including a spacious eat-in kitchen and an island, a renovated bathroom on the first floor, a 16-foot dock, and a dog-friendly attitude. Whether you want to spend your time fishing on Friends Lake or...
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    LOON LAKE luxury Ski Gore,snowmobile,canoe,kayaks1 / 37
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    Pet friendly
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    Reviewed 14 August 2019
    Wow were we happy with this rental! Stumbled across it on this site rather by accident and it seemed too good to be true but I have to say, it was really amazing. Here are the...
    Reviewed 1 August 2019
    Loved it. Very thought out house. Excellent and close access to the lake. Downside was absence of the boat launch But were able to overcome that.
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    About this property
    Your summer paradise awaits. Enjoy the spectacular lake views and lifestyle. The semi private beach is just steps away with a dock for a boat (up to 18 ft). Swim, jet ski, kayak, paddle board or just sit on the beach and chill. Fish from the dock or your boat. Roast marshmallows over the bonfire on...
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 14
    Single-level, spacious house with kayaks, lake access nearby1 / 29
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pine's Way Camp Come visit this contemporary, one-level home with lake rights on the eastern shore of Friends Lake. It's perfect for a small group, offering Adirondack style, easy walking distance to the lake, and more. The open living area provides ample space for a board game or to enjoy a movie...
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Affordable Lake Rights This terrific chalet cottage has deeded lake rights and is just 100 steps to a shared sandy beach on Loon Lake! Space and simplicity make this home a wonderful place for vacationing, with a great room and the added living space of a fully screened porch. The interior is well...
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Irresistible Schroon River Front Log Cabin You'll be absolutely smitten by this delightful log home that is the perfect getaway in any season! Nestled in a beautiful Adirondack setting beneath the pines and overlooking the Schroon River, this adorable log home offers charm from the top to the...
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    Location Information
    Chestertown, New York 12885
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Single-level, spacious house with kayaks, lake access nearby1 / 29
    (7)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    A beautiful family camp/Lake House on Loon Lake in the Adirondacks in NYS1 / 30
    (5)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
    Lakefront cabin with beautiful loft, game room, views, private dock1 / 46
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    A beautiful lake view cabin on Friends Lake1 / 37
    (9)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    The Roost, a lakefront 4 season home in the Adirondack Mountains1 / 28
    (14)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Loon Lake Waterfront - Fish, Bike, Hike High Peaks, Leaf Peep and Ski the ADKs1 / 25
    (12)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Convenient to Gore Mountain.  Adjacent to skimobile trail and the' POKER RUN'.1 / 16
    (37)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    #6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront1 / 18
    (3)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 6
    Year round lake front LOG CABIN on over 2 acres on Loon Lake updated in 20181 / 47
    (10)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    THE STONE LODGE on Blythewood Island, Loon Lake, New York1 / 24
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Adirondack Getaway at Tripp Lake1 / 13
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Chestertown, New York 12817
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Large, Historic Adirondack Vacation House in ground pool wifi1 / 24
    (21)Very good
    6 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 20
    Adorable log home w/ a full kitchen - river frontage close by!1 / 25
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Chestertown, New York 12885
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Tripp Lake Beautiful  4 Season Adirondack Condo Close To Skiing And Lake George1 / 24
    (48)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Chestertown, New York 12817
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    LODGE * BIRCHWOOD COTTAGES AT LOON LAKE. Adirondack Family Friendly Waterfront1 / 50
    (8)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
    Beautiful family friendly lakefront house with dock, beach, multiple decks1 / 40
    (7)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 6
    Lake George Region ADK Camp on Friends Lake1 / 39
    (17)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    Adirondack Lake and Gore Ski House Loon Friends & Brant Schroon Lakes Region1 / 35
    (25)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Gorgeous Friends Lake Home1 / 19
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Tall Pines On Loon Lake1 / 20
    (10)Very good
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
    DO YOU LIKE TO SKI, SNOWSHOE, OR SNOWMOBILE?  RESERVE TRIPP LAKE RETREAT! ENJOY!1 / 49
    (27)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Comfortable year round Lake house on Loon Lake perfect for a getaway1 / 26
    (7)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Chestertown, New York 12817
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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