Chestertown offers - Accommodations - Explore the USA: unique stays, iconic cities and unforgettable trips

Chestertown

Eagles Nest at Loon Lake near Gore Mountain

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Chestertown USA Picture a journey across the USA where every stay opens a new chapter. Wake near Manhattan’s bright avenues, wander through San Francisco, relax on Florida beaches or explore the vast landscapes of Yosemite and the Grand Canyon. Choose a welcoming hotel, apartment or guesthouse close to the places you want to see. From mountain trails and peaceful lakes to legendary landmarks and lively neighborhoods, America offers many ways to travel. Find your ideal base and make every day a story worth remembering.

Offers count: 24

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Friends Lake Inn

Chestertown

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8.3/10

2026-10-18->2026-10-19

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Chestertown - 963 Friends Lake rd

Elegant AccommodationsFriends Lake Inn in Chestertown offers 5-star comfort with air-conditioning, private bathrooms, and modern amenities. Guests enjoy garden views, balconies, and terraces, complemented by free WiFi in public areas.Exceptional FacilitiesThe inn features a sauna, sun terrace, and outdoor fireplace. Additional amenities include a lounge, games room, and bicycle parking. Free toiletries, bathrobes, and a spa bath enhance the relaxing atmosphere.Dining ExperienceA family-friendly restaurant serves American and Italian cuisines with vegetarian, vegan, gluten-free, and dairy-free options. ...

Additional information about the offer USA - Chestertown - Friends Lake Inn, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1883130

The Lodge at Loon Lake

Chestertown

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9.3/10

2026-10-18->2026-10-19

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Chestertown - 5381 State Route 8

Featuring a private beach area, The Lodge at Loon Lake is located in Chestertown. Free WiFi access is available.A TV and a balcony with lake views are included with each guest room.BBQ facilities are available for guests’ use at the Chestertown The Lodge at Loon Lake. The property has free parking.The property is 5 minutes’ drive off Interstate 87. Loon Lake Marina is 2.5 km away.The hotel day starts from hour 16:00 and ends at 11:00.Guests are required to show a photo identification and credit card upon check-in. Please note thatSpecial Requests are subject to availability and additional charges ...

Additional information about the offer USA - Chestertown - The Lodge at Loon Lake, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1661027

4 Mi to Beach & Lake: Spacious Home in Chestertown

Chestertown

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10.0/10

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Chestertown - 189 Stock Farm Rd

Spacious Accommodation4 Mi to Beach & Lake: Spacious Home in Chestertown offers a spacious holiday home in Chestertown, United States. The property features four bedrooms and three bathrooms, ensuring ample space forguests.Modern AmenitiesGuests enjoy free WiFi, air-conditioning, a washing machine, and a fully equipped kitchen with a dishwasher, microwave, and coffee machine. Additional amenities include a fireplace, barbecue, hairdryer, and free toiletries.Convenient LocationLocated 26 km from Fort William Henry and Lake George, the property is also close to attractions such as Deadwood Mountain ...

Additional information about the offer USA - Chestertown - 4 Mi to Beach & Lake: Spacious Home in Chestertown, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1168776

Adirondack Oasis, 15 Mi to Lake George Village!

Chestertown

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10.0/10

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Chestertown - 105 Balsam Crest Rd

Spacious AccommodationAdirondack Oasis in Chestertown offers a spacious holiday home with three bedrooms and two bathrooms. The living room provides ample space for relaxation.Modern AmenitiesGuests enjoy free WiFi, air-conditioning, a washing machine, and a fully equipped kitchen. Additional amenities include a sauna, fireplace, and barbecue.Leisure FacilitiesThe property features a games room with a variety of games, ensuring entertainment forages.Local AttractionsLocated 24 km from Fort William Henry and Lake George, 32 km from Six Flags Great Escape And Splashwater Kingdom, and 105 km from ...

Additional information about the offer USA - Chestertown - Adirondack Oasis, 15 Mi to Lake George Village!, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1207613

All-Season Family Retreat w Dock on Loon Lake!

Chestertown

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Chestertown - 13 Marina Rd

Comfortable AccommodationAll-Season Family Retreat w Dock on Loon Lake! in Chestertown offers three bedrooms and two bathrooms. The holiday home features a terrace, free WiFi, and free on-site private parking.Modern AmenitiesGuests enjoy air-conditioning, a washing machine, patio, fully equipped kitchen, fireplace, barbecue, lake views, and free toiletries. Additional amenities include a dishwasher, microwave, and TV.Local AttractionsNatural Stone Bridge & Caves is 13 km away, Seagle Music Colony 23 km, and Albany International Airport 117 km from the property. Fort William Henry and Lake George ...

Additional information about the offer USA - Chestertown - All-Season Family Retreat w Dock on Loon Lake!, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1958259

Basic Adirondack Camp

Chestertown

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9.0/10

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Chestertown

Comfortable AccommodationBasic Adirondack Camp in Chestertown offers a holiday home with three bedrooms and one bathroom. The ground-floor unit features a private entrance and stunning lake and mountain views.Modern AmenitiesThe property includes a fully equipped kitchen with a refrigerator, oven, stovetop, toaster, microwave, and coffee machine. Guests can enjoy a dining area, work desk, and free toiletries.Outdoor SpacesAn outdoor fireplace, seating area, and picnic area provide relaxing spaces. The outdoor dining area features furniture and a barbecue for alfresco meals.Local AttractionsNearby ...

Additional information about the offer USA - Chestertown - Basic Adirondack Camp, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.234891

Cozy Adirondack JEM Your Four Season Getaway

Chestertown

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Chestertown - 3 High Pines Terrace E

Spacious AccommodationCozy Adirondack JEM Your Four Season Getaway in Chestertown offers a spacious apartment with two bedrooms and two bathrooms. The living room features a sofa bed and a work desk, ensuring comfort and convenience.Modern AmenitiesGuests enjoy free WiFi, air-conditioning, and a fully equipped kitchen with a refrigerator, microwave, dishwasher, oven, and stovetop. Additional amenities include a balcony with garden views, a tea and coffee maker, and a bidet.Outdoor SpacesA beautiful garden provides a relaxing outdoor area, while free on-site private parking is available for guests ...

Additional information about the offer USA - Chestertown - Cozy Adirondack JEM Your Four Season Getaway, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.874334

Eagles Nest at Loon Lake near Gore Mountain

Chestertown

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10.0/10

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Chestertown - 7129 U.S. 9

Spacious Holiday Home in ChestertownEagles Nest at Loon Lake near Gore Mountain offers a spacious setting with seven bedrooms and four bathrooms. The property features a private entrance and a fully equipped kitchen with modern appliances.Outdoor Amenities and ComfortGuests can enjoy a garden and an outdoor seating area. The holiday home includes air-conditioning, a balcony, and a fireplace. Additional amenities include a washing machine, patio, and free WiFi in public areas.Nearby AttractionsLocated 11 km from Natural Stone Bridge & Caves and 38 km from Fort William Henry and Lake George, the ...

Additional information about the offer USA - Chestertown - Eagles Nest at Loon Lake near Gore Mountain, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.935246

Forest Lake Haven Main House

Chestertown

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Chestertown - 123 Forest Lake Rd

Spacious AccommodationForest Lake Haven Main House in Chestertown offers three bedrooms and three bathrooms. The holiday home features a garden, terrace, and free WiFi.Outdoor AmenitiesGuests can enjoy an outdoor fireplace, indoor play area, outdoor seating, and picnic area. The property includes free on-site private parking.Comfortable LivingThe home offers air-conditioning, a fully equipped kitchen, washing machine, and family rooms. Additional amenities include a dining area, sofa bed, and parquet floors.Local AttractionsLocated 101 km from Albany International Airport, the property is near ...

Additional information about the offer USA - Chestertown - Forest Lake Haven Main House, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1121190

Hideaway Chalet

Chestertown

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10.0/10

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Chestertown

Spacious AccommodationHideaway Chalet in Chestertown offers a spacious holiday home with three bedrooms and two bathrooms. The property features a fully equipped kitchen, dining area, and comfortable living spaces.Amenities and FacilitiesGuests can enjoy an outdoor seating area, picnic area, and games room. The chalet includes air-conditioning, a terrace, balcony, washing machine, and a cosy fireplace. Additional amenities include a barbecue, tea and coffee maker, and a work desk.Local AttractionsLocated 24 km from Fort William Henry and Lake George, the property is also close to Six Flags Great ...

Additional information about the offer USA - Chestertown - Hideaway Chalet, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.257753

Hudson Riverside Cottage

Chestertown

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Chestertown - 47 East Hudson River Dr

Comfortable AccommodationHudson Riverside Cottage in Chestertown offers two bedrooms and a bathroom. The property features a fully equipped kitchen, dining area, and a cosy sofa. Guests can enjoy river views from the outdoor seating and picnic areas.Convenient FacilitiesThe holiday home includes a restaurant, barbecue, and a work desk. Additional amenities include a kitchenette, tea and coffee maker, and free toiletries. The private entrance ensures privacy and comfort.Local AttractionsNearby, and cycling are available nearby. Points of interest include Natural Stone Bridge & Caves (16 km), Seagle ...

Additional information about the offer USA - Chestertown - Hudson Riverside Cottage, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.271991

Lakefront Townhome Chestertown "Lakeside Escape"

Chestertown

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Chestertown - 16 Evergreen Way

Spacious AccommodationLakefront Townhome Chestertown "Lakeside Escape" in Chestertown offers a spacious holiday home with three bedrooms and two bathrooms. Guests enjoy a terrace and a patio, perfect for relaxation.Modern AmenitiesThe property features a fully equipped kitchen with a refrigerator, microwave, dishwasher, oven, stovetop, toaster, and electric kettle. Additional amenities include a washing machine, barbecue, tea and coffee maker, and free toiletries.Convenient LocationLocated 23 km from Fort William Henry and Lake George, 24 km from Million Dollar Beach, and 31 km from Six Flags Great ...

Additional information about the offer USA - Chestertown - Lakefront Townhome Chestertown "Lakeside Escape", opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1657319

Lily Pad North at Loon Lake near Gore Mountain

Chestertown

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9.5/10

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Chestertown - North 7131 U.S. 9

Spacious AccommodationLily Pad North at Loon Lake near Gore Mountain in Chestertown offers a spacious apartment with two bedrooms and one bathroom. The property includes a fully equipped kitchen, air-conditioning, and a private entrance.Modern AmenitiesGuests enjoy free WiFi in public areas, a washing machine, and a barbecue. Additional amenities include a TV, microwave, and free toiletries. The apartment features a garden and a private balcony for relaxation.Local AttractionsLocated 11 km from Natural Stone Bridge & Caves and 38 km from Fort William Henry and Lake George, the property provides ...

Additional information about the offer USA - Chestertown - Lily Pad North at Loon Lake near Gore Mountain, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1234326

Lily Pad South at Loon Lake near Gore Mountain

Chestertown

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9.0/10

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Chestertown - South U.S. 9

Spacious AccommodationLily Pad South at Loon Lake near Gore Mountain in Chestertown offers a spacious apartment with two bedrooms and one bathroom. The property includes a fully equipped kitchen, air-conditioning, and a private entrance.Modern AmenitiesGuests enjoy free WiFi in public areas, a washing machine, and a barbecue. Additional amenities include a TV, microwave, and free toiletries. The apartment features a garden and a private balcony for relaxation.Local AttractionsNearby attractions include Natural Stone Bridge & Caves (11 km), Seagle Music Colony (20 km), and Gore Mountain Garnet Mine ...

Additional information about the offer USA - Chestertown - Lily Pad South at Loon Lake near Gore Mountain, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.2106651

Pine Tree Cove on Friends Lake

Chestertown

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Chestertown - 948 Friends Lake Road

Spacious AccommodationPine Tree Cove on Friends Lake in Chestertown offers a spacious holiday home with four bedrooms and four bathrooms. The property includes a living room and family rooms, ensuring comfort forguests.Modern AmenitiesGuests enjoy free WiFi, air-conditioning, a balcony with lake views, and a fully equipped kitchen. Additional amenities include a washing machine, fireplace, TV, and free on-site private parking.Local AttractionsLocated 31 km from Fort William Henry and Lake George, the property is also close to Natural Stone Bridge & Caves (17 km) and Highliner Charter Fishing (30 ...

Additional information about the offer USA - Chestertown - Pine Tree Cove on Friends Lake, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.2007063

Private Contemporary

Chestertown

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Chestertown

Beachfront and DiningPrivate Contemporary in Chestertown offers direct beachfront access and a restaurant. Guests can relax on the terrace or balcony with stunning lake and mountain views.Spacious AccommodationThe holiday home features four bedrooms and two bathrooms, ensuring ample space forvisitors. Amenities include a fully equipped kitchen, washing machine, and free toiletries.Outdoor SpacesAn outdoor fireplace, seating area, and picnic spot provide ideal settings for leisure. Additional facilities include a barbecue and outdoor dining area.Activities and AttractionsGuests can enjoy skiing, ...

Additional information about the offer USA - Chestertown - Private Contemporary, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1573366

Private Dock & Beach! Lakefront, Fire Pit, Boats

Chestertown

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Chestertown - 206 Hill Park Rd

Beachfront LivingPrivate Dock & Beach! Lakefront, Fire Pit, Boats in Chestertown offers direct beachfront access and stunning sea views. Guests can relax on the private beach or enjoy the lake views from the outdoor dining area.Modern AmenitiesThe holiday home features free WiFi, air-conditioning, and a fully equipped kitchen with a coffee machine, refrigerator, oven, stovetop, toaster, microwave, and dishwasher. Additional amenities include a barbecue, dining table, work desk, and TV.Local AttractionsNearby attractions include Natural Stone Bridge & Caves (19 km), Deadwood Mountain Trading Company ...

Additional information about the offer USA - Chestertown - Private Dock & Beach! Lakefront, Fire Pit, Boats, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.1862360

River Road Retreat

Chestertown

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Chestertown - 2849 Schroon River Road

Comfortable AccommodationRiver Road Retreat in Chestertown offers a holiday home with three bedrooms and a living room. The ground-floor unit features a private entrance and garden views.Modern AmenitiesThe property includes a fully equipped kitchen, fireplace, and streaming services. Additional amenities include a dining area, work desk, and outdoor seating.Outdoor SpacesGuests can enjoy an outdoor fireplace, picnic area, and childrens playground. The outdoor dining area provides a relaxing space for all.Local AttractionsNearby attractions include Natural Stone Bridge & Caves (15 km) and Lake ...

Additional information about the offer USA - Chestertown - River Road Retreat, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.389133

Riverside Bliss

Chestertown

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9.7/10

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Chestertown - 41 East Hudson River Drive

Spacious AccommodationRiverside Bliss in Chestertown offers a spacious holiday home with three bedrooms and two bathrooms. The property features a fully equipped kitchen, dining area, and comfortable living spaces.Outdoor AmenitiesGuests can enjoy an outdoor fireplace, hot tub, and outdoor seating area. The property includes a picnic area, perfect for relaxing by the river.Local AttractionsNearby attractions include Natural Stone Bridge & Caves (16 km), Seagle Music Colony (25 km), and Gore Mountain Garnet Mine (26 km). Albany International Airport is 124 km away.The hotel day starts from hour ...

Additional information about the offer USA - Chestertown - Riverside Bliss, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.271938

Rustic Adirondacks Home w Hot Tub & Lake Access!

Chestertown

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9.7/10

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Chestertown - 7133 U.S. 9

Spacious AccommodationRustic Adirondacks Home w Hot Tub & Lake Access! in Chestertown offers three bedrooms and two bathrooms. The property includes a fully equipped kitchen, washing machine, and free WiFi.Relaxing AmenitiesGuests can enjoy a hot tub, fireplace, and outdoor dining area. Additional features include air-conditioning, a work desk, and free toiletries.Local AttractionsNatural Stone Bridge & Caves is 11 km away, while Lake George and Fort William Henry are both 38 km from the property. Adirondack Regional Airport is 123 km distant.The hotel day starts from hour 16:00 and ends at 10:00.Guests ...

Additional information about the offer USA - Chestertown - Rustic Adirondacks Home w Hot Tub & Lake Access!, opinions of holidaymakers as well as available dates can be found on the website our partner.

BG.272017