Vacation Home Rentals By Owner In Chestertown, NY

$557.88

4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.

Chestertown, New York, United States

Property DescriptionbrEscape to the heart of the Adirondacks at this charming 19th-century farmhouse, perfectly positioned on the pristine shores of Loon Lake. Whether you’re looking for a peaceful morning coffee overlooking the water or an action-packed family reunion, this property offers the rare combination of historic character and expansive outdoor space.brbrThe Waterfront & OutdoorsbrStep out your back door to 173 feet of private lake frontage. Our property features a private dock, perfect for swimming, fishing, or launching a kayak into the crystal-clear waters of Loon Lake. The nearly one-acre lot provides plenty of room for kids to play and for evening bonfires under the stars.brbrThe FarmhousebrThis bright and spacious 1,768 sq. ft. home maintains its Modern Farmhouse soul while offering all the comforts of home.brbrBedrooms: 4 comfortable bedrooms designed for a restful night's sleep.brbrBathrooms: 2 full bathrooms (conveniently located on both levels).brbrLiving Space: Inviting layout, cozy living room, a fully stocked kitchen, separate laundry area, and high-speed internet for those who need to stay connected.brbrThe Bonus Building: The Gathering Hall (used to be an ice house for the farmhouse)brUnique to this property is the separate secondary building, specifically designed for larger family gatherings. This flexible space is perfect for rainy-day games, celebratory dinners, or simply giving the teenagers a space of their own while the adults relax in the main house.brbrKey Features & AmenitiesbrLoon Lake Access: Private dock and 173' of direct water frontage.brSpacious Accommodations: 4 Bedrooms / 2 Bathrooms.brGathering Space: Separate building on-site for large family gatherings.brPrime Location: Only 2 miles from the heart of Chestertown; 20 minutes to Gore Mountain or Lake George.brModern Comforts: Fully furnished, high-speed Wi-Fi, and window AC units.brKayaks and lifejackets included.brbrThe NeighborhoodbrLocated in Chestertown, NY, you are minutes away from local favorites like the Main Street ice cream parlor and unique Adirondack boutiques. Outdoor enthusiasts will love the proximity to the North Warren Snowmobile Trails and the Natural Stone Bridge and Caves.

Bed

Bath

Sleeps

$592.0

/ Nightly

Private Vacation Home

Large Cozy House in the Woods .Few minutes from Lake George and Gore mountain

Chestertown, New York, United States

3 bedroom house in the woods, private house but caretaker lives in another building on the property.brTwo bedrooms upstairs each with a queen and full size bed, one bedroom also has a twin and the other a futon. Full bath upstairs. Master bedroom has a queen size bed & has a full bath.brHouse is about 20 minutes from Gore mountain and Lake George village.brHottubbrSnowmobile /boat trailer parking if neededbrPets welcome on a case by case basis.

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Bath

Sleeps

$366.7

/ Nightly

Private Vacation Home

TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!

Chestertown, New York, United States

Tripp Lake Retreat is nestled in the woods overlooking Tripp Lake in Chestertown, NY. This peaceful get-away is easily accessed just minutes from the Adirondack Northway (Rt. 87), yet is located in a secluded setting. Since our home is in a secluded setting we have installed two security cameras. Both are outside. One is mounted on a tree near the wood box and faces the driveway and the front door. The other is mounted on the house and faces the stairs to the back door off the kitchen. brOur fully furnished 3 bedroom home has 2 full bathrooms and sleeps 7. Bedroom #1 has a King bed. Bedroom #2 has a Queen and a Twin. Bedroom #3 has a Queen bed. Queen and Twin bed linens are NOT provided. You'll have to bring those with you. King bed linens ARE provided. Bathroom and Kitchen hand towels are provided. Bath towels are NOT provided. This cuts down on the amount of laundry that must be done by my very busy housekeeper. Both bathrooms have shower/tub combinations. The kitchen with breakfast bar is fully equipped with 2 coffee makers (not Keurig coffee maker), toaster, microwave, blender, etc. The dining table in the Family Room seats up to 10 guests. Our spacious Living Room has a gas fireplace and ample seating. This living area including the Family Room is surrounded by windows that offer beautiful views of the lake and all outdoors! Enter Tripp Lake Retreat through the Mud Room, a great place to leave coats, shoes, toys, and wet beach towels. On the same level is a Laundry Room with washer and dryer. All the comforts of home are available to you while you experience Adirondack adventures during the months of July, August, and September.. We have an automatic generator so you will never have to worry about losing power! brSwim, fish, kayak, canoe, skate, on the lake or just sit on the deck and enjoy the view. If you like to hike, bike, shop, ride horses or roller coasters, have bon-fires by the lake, or sit inside by the cozy fire, Tripp Lake Retreat is an ideal vacation spot for you and your friends and family.

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Bath

Sleeps

$487.33

/ Nightly

Private Vacation Home

Newly Renovated 3 BRD, 2 BA chalet on 50 acres. Easy access to Loon Lake/Gore

Chestertown, New York, United States

Disconnect, leave the bustle and lights of the city behind and escape to Pine Notch, our newly renovated 1900 s/f chalet nestled on 50 acres. Fully upgraded in 2025, thoughtful, modern amenities anchor all new furnishings throughout the wood beamed living room, gourmet kitchen, cozy bonus room, a large bedroom downstairs with two rustic queen beds, two master bedrooms with decks and vaulted ceilings upstairs and two full bathrooms. Four decks allow you to enjoy the woods and night skies with coffee or wine in hand. Or talk a walk outside in your personal Adirondack Park with trails throughout the pines and maples out back. brbrWhile you are completely secluded via a private road and winding driveway (AWD/4WD suggested in winter), you are still less than 5 minutes from stores (Tops Market, Walgreens, Mountain Hardware) in downtown Chestertown, restaurants (casual dining, pizza and an icecream shop), the Loon Lake (Chester) public beach and boat entry, and snowmobile and ATV trails. Gore Mountain is only 13 miles (20 min), Schroon Lake is 15 miles (22 minutes) and Lake George is 21 miles (30 min). Starlink internet keeps modern life accessible. brbrAs unique as the house is - our land is a feature that stands alone. Each season brings its own unique beauty to the “Pine Notch” property. Be sure to explore our 50 private acres where the only sounds are birds and the wind through the trees. There are established trails amidst our pines and maples with plenty of “sitting” stumps and rocks to sit and disconnect. At night, pull out the firepit and stargaze in a dark that is rarely experienced these days. brbrAdditional amenities include: Starlink wireless, keyless entry, AC Minisplits in each bedroom and the living areas, ceiling fans, standing fans, 3 TVs, nightstand and wall chargers, 100% cotton linens with a light blanket, top sheet in summer, comforter in winter, throw blankets, luxury towels, shampoo and shower gel, dishwashing detergent, laundry detergent, trash bags, toilet paper, paper towels, dishes, glasses, cutlery, bowls, baking sheets, pyrex baking dishes, crock pot, toaster, microwave, spice rack, placemats, gas grill, charcoal grill, firepitbrbrWhen you arrive and emerge from the driveway, the first thing you will see is our expansive parking area for 8-10 cars. Perfect for boat, motorcycle and ATV trailers. There is also a covered carport. Follow the walkway down to the front door and enter on the beautiful main floor level with the kitchen, living room, bonus room, laundry room, full bathroom and our double queen bed room. The gourmet kitchen is fully equipped with stainless steel appliances and all the necessities you will need to prepare your meals - even a spice rack. There is a coffee station conveniently located by the sliding door to the massive back deck with both a drip and Keurig coffeemaker. The large island with 3 barstools has ample space for food and dining and a separate table is perfect for additional seating or just checking emails. Just across from the kitchen is the laundry with multiple pantry shelves and floor space for food and coolers as well as a full sized washer and dryer.brbrRelax after dinner in the living room with woodland views out of every window and wooden beams and ceilings that echo a chalet in Europe. The comfortable chairs and couches surround the SmartTV which is ready for your logins. Or, get drawn outwards to the massive covered back deck with its comfortable ADK chairs to sit with your morning coffee or favorite beverage.brbrCompleting our main floor is the “Turkey” bedroom with two queen beds, a large closet and benches. Across the hall is a full bathroom with a walk in shower with a relaxing rainfall showerhead and our cozy “library” bonus room with its wooden ceiling, a chaise couch and TV. There are cables for a gaming console, board games and books. The space is perfect for reading or for that quiet space to do some work.brbrHead upstairs to a soaring beamed landing which has a café table and access to the second floor deck. To the right is “Bear” with a King bed, TV and access to a covered private deck with chairs and ceiling fan. To the left is “Moose” with a King bed and access to a deck level with the driveway. Both rooms have ceiling fans, multiple closets and bureaus. In between the rooms is the expansive second full bathroom with a tiled tub, shower and double vanity. The vaulted windows framing the trees provides ample light and makes it feel like you are outside.brbrWith nature at our door, we have also made several areas gear friendly to accommodate our guests. There is a large closet by the front door with trays for boots, hooks and cubbies. In the Moose bedroom, there is an area with a bench, trays and mats, hooks and an open closet for those coming in through the deck sliding doors. Under the carport is a ski rack.brbrIf you are looking for a unique place to disconnect, rest and recharge in nature while remaining completely comfortable and connected, Pine Notch will not disappoint!

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Sleeps

$270.73

/ Nightly

Private Vacation Home

Big single-level house with firepit & spacious yard - lake access nearby

Chestertown, New York, United States

Pine's Way CampbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrCome 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 and easy walking distance to the lake. The open living area provides ample space for a game night. Sink into the plush seating and enjoy a movie on the flatscreen TV. Offering stainless steel appliances and ample meal prep space, the open layout kitchen is the perfect spot for conversation and great cooking. Custom blinds and wood beam ceilings give you a sense of coziness throughout the home. As the day winds down, enjoy your private firepit for evening campfires right outside your back door. Let the kids play catch in the large backyard, or take a walk to the beach and watch the loons. Walk down to the shared sandy beach with a swim raft and amazing sunset views.brbrThings to KnowbrThis is a quiet lake. Neighbors are particularly sensitive to loud noises. Many will immediately call the state police if guests are loud or intrusive. Please respect these neighbors.brPlease note that there is no public boat launch on Friend's Lake and no boat launch at this location. You are not allowed to bring your own boats to this lake. This includes kayaks, canoes, and other small personal watercraft.brTrash service is not available at this property. This property is located in an area administered by the Adirondack Park Commission. As with many remote homes in the Adirondack Park, this is a carry-in, carry-out location. Please take trash to the Chestertown Landfill/Transfer Station . We recommend calling early in your stay to find out fees and open days.brThis property is managed by Vacasa New York LLC.brVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 3 vehicles.brThis rental is located on floor 1.brbrDock details: brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

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Sleeps

$411.03

/ Nightly

Private Vacation Home

Adirondack Oasis, 15 Mi to Lake George Village!

Chestertown, New York, United States

Escape to the Adirondack Mountains when you book this 3-bedroom, 2-bathroom home! This charming vacation rental features a projector to watch your favorite movies and shows, a private balcony to enjoy the fresh air, and a fire pit to relax around after a long day of adventure. Take a drive to sample wine at Adirondack Winery Lake George Tasting Room, explore Six Flags Great Escape, or soak up the sun at Tripp Lake. Retreat back to the property to watch the sunset!brbr-- THE PROPERTY --brbrSunroom | Fire Pit | Gas Grill | Private Access to Tripp Lake (Free Kayak & Canoe Rentals in Summer) | Private Access to Green Mansions Tennis CourtsbrbrBedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: Full Bed | Lower Living Room: Queen Sleeper Sofa | Sunroom: Full FutonbrbrOUTDOOR AMENITIES: Private balcony, private deck, patio furniture, outdoor dining table, sauna, outdoor TV, game roombrINDOOR AMENITIES: 4 flat-screen TVs, dining table, projector, sofa seating, fireplacebrKITCHEN: Stove/oven, refrigerator, microwave, dishwasher, Keurig coffee maker, knife set, tea kettle, cooking basics, trash bags/paper towelsbrGENERAL: Free WiFi, linens/towels, washer/dryer, seasonal window A/C units (living room, basement, & all bedrooms), heatingbrFAQ: Steps required to access, open staircase to loft (may not be suitable for young children), 2 exterior security cameras (facing out)brPARKING: Side of carport (1 vehicle), driveway (3 vehicles)brbr-- THE LOCATION --brbrGET OUTSIDE: Green Mansion Golf Course (2 miles), Cronin's Golf Resort (9 miles), Hudson River Recreation Area (9 miles), Lake George (14 miles), Shepard Park Beach (14 miles), Million Dollar Beach (15 miles), Crane Mountain Trailhead (21 miles), Gore Mountain Ski Resort (23 miles), Saratoga Race Track (41 miles), Lake Placid (69 miles)brTHEME PARKS: Lake George Expedition Park (17 miles), Six Flags Great Escape (20 miles)brATTRACTIONS: Adirondack Extreme Adventure Course (14 miles), Adventure Family Fun Center (21 miles), Saratoga Performing Art Center (44 miles)brWINE & BEER: Adirondack Winery Lake George Tasting Room (14 miles), Adirondack Pub & Brewery (15 miles), Bolton Landing Brewing Company (19 miles)brAIRPORT: Albany International Airport (67 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires stairs to accessbr- NOTE: This property may not be suitable for children due to the open staircase leading to the loftbr- NOTE: The window A/C units are available seasonally from June 1st-September 30th. The window A/C unit in bedroom 1 is available year-roundbr- NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is a Ring doorbell facing the entrance and camera 2 faces the driveway. The cameras are outward facing and do not look into interior spaces. Both cameras record video and sound when activated by motion

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$371.49

/ Nightly

Private Vacation Home

Chalet house w/ access to Friends Lake, sandy beach, kayak, fireplace, deck

Chestertown, New York, United States

Hillcrest Acres RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrbrbrWelcome to your serene Adirondack retreat on beautiful Friends Lake! This charming 3-bedroom, 2-bathroom house offers full guest access to the private Hillcrest HOA beach and Friends Lake area, making it the perfect getaway for families and friends seeking tranquility and adventure. With a sandy beach and a boat dock (for launching kayaks only) just a short walk away, you can enjoy swimming, kayaking, or simply relaxing by the water's edge.brbrThe main floor features a cozy bedroom and a full bath, while the second floor boasts two additional bedrooms and another full bath, providing ample space for everyone. The home is designed for comfort and relaxation, with a screened-in porch and a large wrap-around deck where you can soak in the stunning natural surroundings. Gather around the wood-burning fireplace on cooler evenings or enjoy outdoor dining with patio furniture and a gas grill.brbrThis retreat is not just about relaxation; it’s also a hub for outdoor activities. Explore nearby attractions like the Green Mansions Golf Club, Gore Mountain, and Loon Lake Marina, all within a short drive. Whether you're into hiking, skiing, or simply enjoying the beauty of nature, this location has something for everyone throughout the four seasons.brbrEquipped with modern amenities including WiFi, a fully stocked kitchen, and laundry facilities, your stay will be both comfortable and convenient. With plenty of space for family gatherings and a variety of activities at your fingertips, this Adirondack retreat is the ideal destination for your next vacation. Book your stay today and create unforgettable memories at Friends Lake!brbrVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brThis unit does not have air conditioning.brbrParking notes: There is free parking available for 4 vehicles.brThis rental is located on floor 1.brbrDock details: Shared dock just a short walk awaybrbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$285.04

/ Nightly

Private Vacation Home

Secluded and Cozy Townhome at Tripp Lake

Chestertown, New York, United States

You will find a great stay during any season at this townhome located in the Southern Adirondacks. We are central to many outdoor activities including Summer features include a short 15 minute drive to Lake George, 5-20 minutes from white water rafting, tubing, hiking, cruise boats, powerboat rentals and the Great Escape. Winter activities include downhill skiing with a short 20 minute drive to Gore Mountain. Other things to do include hiking, historical attractions, nature trails and shopping.brbrWe are available if you need us but will give you your space to enjoy your stay.brbrWe are a small townhome community that has 7 buildings and 28 units spread throughout the property.brbrWe have a smart lock for entrancebrbrOur unit has the living room, kitchen and dining along with a half bath on the main floor. Our gas fireplace is a popular feature. On the second floor we have all 3 bedrooms and 2 full bathrooms.brbrWalking, biking and driving to the lake and beach are a short distance away. You can also walk, bike or drive to the tennis and pickleball courts.

Bed

Bath

Sleeps

$288.62

/ Nightly

Private Vacation Home

Dog-friendly cabin with lakefront location, 20' dock, smart TV

Chestertown, New York, United States

Basic Adirondack CampbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis rustic dog-friendly house is a basic Adirondack camp-style cabin nestled under the pines just yards from the water's edge on Loon Lake! Look out over the lake while sitting at the kitchen table, or cozy up in the evenings in front of the smart TV with Netflix streaming. This property has a total of 105 feet of direct frontage on the eastern shore of Loon Lake, and it also offers a 20-foot dock with space to park your boat. Swim or fish from the dock, spend your days out on the water, and start a campfire back at the shore in the evenings. Come and check out what the excitement on Loon Lake is all about!brbrThings to know:brFree WiFibrFull kitchen (no dishwasher)brDogs welcome for an additional nightly pet feebrbr*Water in this house is non-potable, as it is pulled directly from the lake. We recommend bringing bottled water for cooking and drinking.br**Trash service is not available at this property. This property is located in an area administered by the Adirondack Park Commission. As with many remote homes in the Adirondack Park, this is a carry-in, carry-out location. Please take trash to the Chestertown Landfill/Transfer Station. We recommend calling early in your stay to find out fees and open days.brbrThis property is managed by Vacasa New York LLC.brSusan E. Scanlon - Principal Real Estate BrokerbrVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brThis rental is located on floor 1.brbrDock details: 20 footbrbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$639.57

/ Nightly

Private Vacation Home

Lakefront cabin with beautiful loft, game room, views, private dock

Chestertown, New York, United States

Loon LodgebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience the captivating views from this log chalet directly on the western shore of Loon Lake! It offers three floors of unforgettable Adirondack class, featuring a great room, a well-stocked game area downstairs, and a private dock. Handmade railing leads you up to the loft, which is perfect for reading or relaxing, though in the summer you may prefer to spend time outside in the yard. There's a campfire area, outdoor seating, and a sandy beach on the lake. You're welcome to borrow the rowboat on-site, or bring your own and paddle out onto the lake for some fishing. This direct lakefront location allows easy access to the water, whether you prefer swimming, boating, fishing, or simply sunbathing on the shore.brbrThings to know:brFree WiFibrFull kitchenbrbr**Trash service is not available at this property. This property is located in an area administered by the Adirondack Park Commission. As with many remote homes in the Adirondack Park, this is a carry-in, carry-out location. Please take trash to the Chestertown Landfill/Transfer Station. We recommend calling early in your stay to find out fees and open days.brbrThis property is managed by Vacasa New York LLC.brSusan E. Scanlon - Principal Real Estate BrokerbrVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 4 vehicles.brbrDock details: NOT AVAILABLE AFTER OCTOBER 1brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$269.62

/ Nightly

Private Vacation Home

Lakefront Cottage with Screened Gazebo, Dock, and Two Acres of Space

Chestertown, New York, United States

The Lakeside White HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to the quiet beauty of Loon Lake at this classic Adirondack waterfront retreat, set on two private acres with direct lake access, a dock, screened gazebo, lakeside fire pit, and room for unforgettable family vacations.brSpend your mornings sipping coffee by the water, afternoons swimming, fishing, kayaking, or relaxing on the dock, and evenings gathered around the fire pit under Adirondack stars. With a spacious lawn, private shoreline, and peaceful wooded setting, this home offers the kind of timeless lake experience families return to year after year.brbrInside, you’ll find the charm of a traditional Adirondack camp paired with comfortable gathering spaces ideal for reconnecting after a day on the lake. The screened gazebo creates the perfect spot for outdoor dining, card games, or enjoying summer evenings without the bugs.brbrGuests also enjoy a tennis court, a playset for children, and plenty of open outdoor space for lawn games and exploring. Whether you're planning a summer lake vacation, a fall foliage getaway, or a peaceful retreat from city life, this Loon Lake escape delivers privacy, relaxation, and authentic Adirondack charm.brHighlights:brbr• Direct lakefront location on Loon Lakebr• Private dockbr• Firepit and outdoor seatingbr• Screened Gazebobr• Play structure and swingsbr• Tennis courtbr• Free WiFi and full kitchenbrbrThings to Know:brbr• Seasonal Adirondack cottage best suited for late spring through fall staysbr• No pets allowedbr• Parking available for up to 4 vehiclesbr• Must be 21+ to rentbrbrPlease note: As part of the protected Adirondack Park region, this is a carry-in/carry-out property. Guests can dispose of trash at the nearby Chestertown transfer station during operating hours.brbrbrbrPlease note that the property does not have heat. Please bring appropriate clothing depending on the weather. This property is managed by Vacasa New York LLC.brbrSusan E. Scanlon - Principal Real Estate BrokerbrVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 4 vehicles.brbrDock details: This is a new dock, but it is designed for small craft such as rowboats and canoes. The water here is shallow. A boat with a 1 1/2 to 2 foot draft may get scratched on the rocks.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$229.74

/ Nightly

Private Vacation Home

Lakefront cabin with beautiful views, lake and beach access

Chestertown, New York, United States

Edgewater CabinbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThe Sagevick Cabin is a nostalgic rental right on the shores of Loon Lake, offering a rustic atmosphere with everything you'll need for a comfortable getaway. Inside, you'll have a full kitchen, a cozy living area, and inviting spaces for everyone to sleep at night. Outside, find a sandy beach and a dock. Note that the adjacent cottage is also available to rent for larger groups - look for the Hunerburg White House. Fish, swim in the lake, play on the sandy beach, or head out to explore the nearby area - the choice is yours!brbrThings to know: brFree WiFi brFull kitchen brNo heatbr*Trash service is not available at this property. This property is located in an area administered by the Adirondack Park Commission. As with many remote homes in the Adirondack Park, this is a carry-in, carry-out location. Please take trash to the Chestertown Landfill/Transfer Station. We recommend calling early in your stay to find out fees and open days.brbrThis property is managed by Vacasa New York LLC.brSusan E. Scanlon - Principal Real Estate BrokerbrVacasa is a registered New York State sales tax vendor. And if Vacasa is the merchant of record will collect sales tax and applicable unit fees on all sales of short-term rental unit occupancy within New York State that it facilitates.brbrParking notes: There is free parking available for 2 vehicles.brbrDock details: NOT AVAILABLE AFTER OCTOBER 1brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Bed

Bath

Sleeps

$279.69

/ Nightly

Private Vacation Home

Fireside Cabin, Pool & AC, Wonderful Cozy Adirondack Cabin steps from Loon Lake.

Chestertown, New York, United States

Nestled in the breathtaking Adirondack Park, Twin Pine Lodge is a hidden gem waiting for you! Our 26-acre family resort offers the perfect blend of relaxation and adventure, just steps from the serene Loon Lake, a sandy beach, and beautiful waterfalls.brEnjoy easy access to Lake George Village and Gore Mountain Ski Area, both just 15 minutes away! Explore the charming Village of Chestertown, only 2 miles from your doorstep, featuring delightful restaurants, a grocery store, pharmacy, and a beloved ice cream shop. brChoose from a variety of non-smoking, self-catering cabins, each equipped with a picnic table, grill, and screened-in porch for your comfort.brDive into fun with our on-site amenities! Take a dip in the outdoor pool, explore the lake with our rowboat, kayaks, and canoe, or challenge friends to volleyball, basketball, and horseshoes. Kids will love the playground and game room, while everyone can unwind around the fire pit or take in the beauty of our pond and hiking trails.brEscape the hustle and bustle and create unforgettable memories with family and friends at Twin Pine Lodge. Book your stay today and experience the magic of the Adirondacks!

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$316.35

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Private Vacation Home

Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake

Chestertown, New York, United States

Nestled in the breathtaking Adirondack Park, Twin Pine Lodge is a hidden gem waiting for you! Our 26-acre family resort offers the perfect blend of relaxation and adventure, just steps from the serene Loon Lake, a sandy beach, and beautiful waterfalls.brEnjoy easy access to Lake George Village and Gore Mountain Ski Area, both just 15 minutes away! Explore the charming Village of Chestertown, only 2 miles from your doorstep, featuring delightful restaurants, a grocery store, pharmacy, and a beloved ice cream shop. brChoose from a variety of non-smoking, self-catering cabins, each equipped with a picnic table, grill, and screened-in porch for your comfort.brDive into fun with our on-site amenities! Take a dip in the outdoor pool, explore the lake with our rowboat, kayaks, and canoe, or challenge friends to volleyball, basketball, and horseshoes. Kids will love the playground and game room, while everyone can unwind around the fire pit or take in the beauty of our pond and hiking trails.brEscape the hustle and bustle and create unforgettable memories with family and friends at Twin Pine Lodge. Book your stay today and experience the magic of the Adirondacks!

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Sleeps

$1114.77

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Private Vacation Home

Mimi’s by the lake

Chestertown, New York, United States

Take it easy at this unique and tranquil getaway. Enjoy this once upon a time bed and breakfast located lakefront on one of the Adirondacks most peaceful private lakes. This home offers 3 separate apartments each consisting of 2 bedrooms, a bathroom, and a kitchen. And a main common room also with a kitchen. This is the perfect get away for large families or multiple families who wish to stay together. A truly amazing place to enjoy all seasons in the Adirondacks.

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$320.13

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Private Vacation Home

Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.

Chestertown, New York, United States

Welcome to Loon Run Lodge that is located in the Adirondack mountains of upstate New York, ready to be your place to relax and enjoy skiing, snowshoeing, cross country skiing, snowmobiling, hiking, horseback riding, kayaking, boating, and swimming.brThis property only 15 min from Gore Mountain ski resort, few minutes to Adirondack Snowmobile Tour, loon lake beach, Loon Lake Marina, local restaurants and stores. Only 20 min to Lake George, Bolton Landing and 25 min to Lake George Village.brbrThis newly furnished 2 floors 1,350 Sq ft house on 1.2 acres has 2 bedrooms and 2 full bathrooms, fully equipped kitchen, deck, bbq gas grill, washer/dryer, 2 fireplaces inside and 1 fire pit outside. 4 persons Hot Tub. Sleeps up to 6 adults and 2 kids comfortably. Radiant heat tile floors throughout the house. Smart front door lock, free WiFi. Plenty of parking available for cars, boat, jet ski and snowmobile.brbrMaster bedroom: located on second floor and has king size bed and a double twin daybed with Sierra memory foam mattresses , 450 thread bedding sheets, duvet cover hypoallergenic comforters, fireplace, and ceilings fans. 45in HD Smart TV, just sigh in to your favorite channels. brbr Second bedroom: located on second floor and has queen size bed with Casper memory foam mattress, 450 thread bedding sheets, duvet cover, hypoallergenic comforter, twin sleeper sofa.brbrJack and Jill bathroom: located on second floor with jacuzzi bathtub & double sink vanity.brbrLiving room: located on first floor and has queen sofa bed with memory foam mattress.brTwo accent chairs and coffee tables.br4 sitting live edge bar with 4 barstools.br55in HD Smart TV. Gas fireplace. Dry guy boots and gloves drier. Full bathroom with washer and dryer.brbrKitchen: fully equipped, basics kitchen essentials, drip, Keurig and Nespresso coffee maker, milk frother, complementary coffee and tea, blender, toaster, tea kettle, 6 sitting dining table.brbrGeneral: free WiFi, radian heat, linens & towels, washer/drier, boots/gloves drier, hair dryer, toiletries, laundry detergent, garbage bags, paper towels, dishwasher tablets, dish soap, iron.brbrBackyard: deck/ gas Grill, fire pit, fire wood, 4 Adirondack chairs, picnic table.brbrHouse rules brGas Grill: We request our guest to shut off the gas valve and clean cooking grates with scraper after grill use.brDishes/utensils Please load all used dishes and utensils in the dishwasher and run full wash cycle.brFurnitures : If you moved any of the indoor/outdoor furniture, please put that back in its original spot.br-Leave use towels on the floor.br-Turn off all lights and lock all doors br-Discard trash and recycling to the garbage cans outsidebr-Must be at least 25 years old to book.br-No smoking br-No parties brFireplaces: turn on fans/blower while using fireplaces.brbrHot Tub Rules br-Please shower with soap before you enter.br-Do not bring glass in or near hot tub.br-Please do not sit or lay on Hot Tub cover.br-Turn off the high jets, replace Spa cover and latch after use.br-Children must be supportive by an adult.br-Please no jumping, horseplay, or toys.br-Do not enter if the temperature is above 104fbr-Please do not use soaps or oils in Hot Tub.brbrPlease note that the house is located in the woods of the Adirondacks. Despite our cleaning and Maintenance efforts, you may encounter insects and/or wildlife in the house. For this reason it is very important that you keep all screens to windows as well as doors closed all the time to avoid entry of insects/wildlife into the house. Even the best prevention efforts aren't guaranteed.

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$370.34

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Private Vacation Home

Private Waterfront House on Loon Lake w Amazing Views- 20 Min Lake George & Gore

Chestertown, New York, United States

Key Features:br- Private lakefront with magnificent views of the lake and mountainsbr- Secluded location at the end of a private road for full privacybr- Spacious deck with outdoor seating, picnic table, and grillbr- Large private dock with access to a rowboat, 2 kayaks, swim up island for water activitiesbr- High-speed Wi-Fi, perfect for working remotely in a tranquil settingbr- Only minutes from local stores and restaurants and 20 min from Lake George and Gore Mountain for year-round activitiesbrbrThe Space: brStep inside to an open and inviting main floor featuring a large family and dining area with floor-to-ceiling windows that showcase great lake views. Cozy up in the living room with a wood-burning fireplace, big-screen smart TV, and a variety of board games for family fun.brbrThe spacious dining room seats 8, and the fully-equipped newly renovated kitchen has everything you need, from dishwasher, microwave and toaster to a coffee bar with both a regular coffee machine and Keurig—bring your favorite K-cups!brbrSleeping ArrangementsbrbrMain Floor:br- Bedroom 1: Queen bed with a large closet brbr- Bedroom 2: Two twin beds with a large closet and dresserbrbr- 1.5 bathroomsbrbrLoft Level: br- 4 twin beds and dresser, perfect for kids or extra guestsbrbrAll bedrooms and the loft are equipped with AC window units for your comfort in the summer. Fresh linen and towels are provided (please bring extra towels for lake activities).brbrOutdoor Living: brStep through the glass doors onto a spacious deck, fully furnished with a sectional, perfect for lounging, as well as a picnic table and grill for outdoor dining. A short path leads to your private lakefront, complete with a fire pit, dock, rowboat, and kayaks for endless water fun. Outdoor shower (cold water only) for a refreshing rinse after lake activities. The Loon Lake Marina on the lake offers boat rentals. brbrYear-Round Activities:br- Summer: Swim, kayak, boat, or fish from your private dock, or explore local hiking trails.brbr- Winter: Enjoy ice fishing, skating on the lake, or head to Gore Mountain for skiing, just 20 minutes away.brbrAdditional Amenities:br- Ample parking for up to 3 carsbr- Professional cleaning service after every rental to ensure a spotless staybrbrBook your stay today for a memorable vacation with all the beauty and activities the Adirondacks have to offer—right outside your door!

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$368.82

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Private Vacation Home

Year-Round Loon Lake Retreat: Ski, Hike, Explore!

Chestertown, New York, United States

Walk to Loon Lake | 2 Living Areas | 14 Mi to Skiing | Wooded PropertybrbrEvery season is worth the trip here! Hit the slopes at Gore, explore Loon Lake, or unwind under the pines — this Chestertown vacation rental serves up Adirondack adventure all year long. With 3 bedrooms and 3 baths, this home has space to spread out and enjoy the quiet moments between outings. Fire up the grill, sink into the swing, and let the mountains take it from there. Make this escape the first of many — book today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 2 twin bedsbr- Sleeping Nook: 1 twin bunk bedbrbrOUTDOOR LIVINGbr- Spacious deckbr- Picnic tablebr- 2 ski-lift chair swingsbr- Propane grill, fire pitbrbrINDOOR LIVINGbr- Smart TVs, dartsbr- Gas stovebr- Family dining tablebr- Washer & dryerbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Drip coffee makerbr- Toaster, microwavebr- Cooking basics, dishware & flatwarebr- Spices, cooking oil & condimentsbrbrGENERALbr- Free WiFibr- Central A/C & heating (heat pump)br- Laundry detergentbr- Linens & towelsbrbrFAQbr- 1 exterior security camera (facing out)brbrACCESSIBILITYbr- 2-story home, 12 steps to enterbr- 3 bedrooms & 2 bathrooms on main floorbrbrPARKINGbr- Driveway (5 vehicles)brbr-- THE LOCATION --brbr- Easy access to Loon Lake: public beach, hiking, boating & fishing (5-minute drive)br- 5 miles to Loon Lake Marina: boat rentalsbr- 14 miles to Gore Mountain (20-minute drive)br- 7 miles to Natural Stone Bridge and Cavesbr- 4 miles to Chestertown Main Street: old-fashioned ice cream parlor, antique shops & Carol Theatrebr- 13 miles to Schroon Lake, 25 miles to Lake George Villagebr- 76 miles to Albany Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 21 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story home requires 12 steps to enter. There are 3 bedrooms and 3 bathrooms on the main floorbr- Your safety matters. This property features 1 exterior security camera located on the outside front door, facing outward toward the entrance. It does not look into any interior spaces. The camera records video and sound when activated by motion

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$286.96

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Private Vacation Home

Rustic Adirondack Retreat on Tripp Lake

Chestertown, New York, United States

Beautiful 3 bedroom townhouse located in the Green Mansions resort community on the private Lake Tripp, just 20 minutes from Lake George. Enjoy the tranquility of a private lake, yet easy access to all the Lake George region has to offer. This cozy townhouse is tastefully decorated with all the Adirondack touches and perfect for a comfortable and relaxing rustic retreat! There are plenty of year-round activities right on property like lake-side beach and swimming, free access to canoes, kayaks, row boats, and paddle boats. Great bass, pan-fish and pike fishing right on Lake Tripp. Tennis courts, basketball courts, and a 9 hole golf course. Hiking trails that end in the High Peaks of Lake Placid. Gore Mountain and Whiteface are close by for a terrific skiing adventure. Relax and enjoy toasting s'mores with the outdoor fire pit or in the winter enjoy hot chocolate fireplace-side.

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Sleeps

$888.0

/ Nightly

Private Vacation Home

WaterFront Adirondack Home-located between Gore and Lake George

Chestertown, New York, United States

Newly renovated 4 bedroom 2.5 bathroom. This Adirondack home is nestled on a beautiful property with a private beach and salt water pool. Enjoy your coffee under the covered porch while keeping an eye out for Adirondack wildlife. Our pet friendly home is the perfect spot for a family or group looking to get some R&R. Located just 15 minutes North of Lake George and minutes from Gore Mountain. Lots of local attractions including:Gore Mountain 13 miles,Lake George 20 miles, Loon Lake beach 1 mile, Saratoga Race Track/Casino 50 miles, Lake Placid 60 miles , Schroon Lake 12 miles, Brant Lake 7 miles, Dynamite Hill Skiing 2 miles, Six Flags Great Escape 25 miles. This properties location will fit all your families needs with a short distance to local hiking trails, snowmobile trails, fishing spots, horseback riding, boating and more. Lots of amazing local restaurants, distilleries, and breweries to try out. With the relaxing atmosphere and stunning mountain views we look forward to hosting your perfect get away. br

4

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2

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14

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Vacation Home Rentals By Owner In Chestertown, NY

$557.88

$592.0

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$229.74

$279.69

$316.35

$1114.77

$320.13

$370.34

$368.82

$286.96

$888.0

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