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A waterfront town with a pier, dock, and several buildings.

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Our top choices for Chestertown holiday homes

A view through a window of a deck area with outdoor furniture and a barbecue grill.

A person fishing by a lake with a boat in the background.

A living room with a television, sofa, armchair, coffee table, and a fireplace.

A bedroom with a large bed, two nightstands, a headboard, and wall-mounted animal decorations.

1. The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain

Chestertown

9.6 out of 10, Exceptional, (43 reviews)

9.6/10

Exceptional

(43 reviews)

"Perfect for what we needed as a family of 8,, the host was very easy to communicate with as well."

Sara Beth E.

The price is €408

€408

includes taxes & fees

20 Sept - 21 Sept

The Lily Pad at Loon Lake near Gore Mountain

A bedroom with a bed, a window with blinds, a wall-mounted air conditioner, and a framed picture above the bed.

A person fishing by a lake with a forested hill in the background.

A two-story wooden house with a front deck, a garage, and a well-maintained garden with various plants and flowers.

A staircase with wooden railings and a handrail, leading to an upper floor.

2. Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown

10.0 out of 10, Exceptional, (122 reviews)

10/10

Exceptional

(122 reviews)

"Great house. Great location"

David S.

Eagles Nest at Loon Lake near Gore Mountain

A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, a dishwasher, and a coffee maker.

A bathroom with a white sink, a toilet, a shower with a glass door, and a towel rack with towels.

A living room with a grey sofa, a red cushion, a wooden stool, a mounted TV, and a painting on the wall.

A living room with a grey sofa, red cushions, a wooden coffee table, a TV on a stand, and a window with blinds.

3. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

Gore MTN & Saratoga ADK Crash Pad! The Cocoon

Warrensburg

The price is €175

€175

includes taxes & fees

8 Sept - 9 Sept

Gore MTN & Saratoga ADK Crash Pad! The Cocoon

A compact living space with a wooden ceiling, a sofa, a dining table, and a TV mounted on the wall.

A room with a wooden floor, a dark wooden table, and a green patterned rug. There are two wooden doors, one with a sign above it, and a wall with a framed picture and a mounted bird.

A cozy living room with a wooden wall, a flat-screen TV, a bench, a coffee machine, and a microwave.

A room with wooden panel walls, a leather sofa, a dining table, and framed pictures.

4. The Office at North Creek All Season Rental

The Office at North Creek All Season Rental

North Creek

8.8 out of 10, Excellent, (13 reviews)

8.8/10

Excellent

(13 reviews)

"Fun property to stay at! We enjoyed our stay and hope to come back during ski season. "

Brandon A.

The price is €246

€246

includes taxes & fees

20 Sept - 21 Sept

The Office at North Creek All Season Rental

A white building with a red umbrella, a stone chimney, and a black fence in front.

A living room with a brown leather sofa, a black ottoman, a wooden coffee table, and a TV mounted on the wall.

A compact kitchen with wooden cabinets, a stove, a sink, and a trash bin.

A fireplace with a stone surround, a framed picture above it, and a set of four wall-mounted lights.

5. Adirondack Bungalow Getaway

Adirondack Bungalow Getaway

Warrensburg

9.8 out of 10, Exceptional, (84 reviews)

9.8/10

Exceptional

(84 reviews)

"Enjoyed our weekend stay here. Close to the main road and a short drive to Lake George. House was very clean and met all our needs. Will definitely stay here again if we visit the area."

Virginia (Ginger) S.

The price is €169

€169

includes taxes & fees

13 Sept - 14 Sept

Adirondack Bungalow Getaway

A single-story building with a red door and a garage door.

A covered porch with a red chair and table, a red door, and a view of the outside.

A red door with a geometric dog design and a doorbell.

A hotel room with a bed, a TV on a stand, a painting on the wall, and a bathroom visible through an open door.

6. Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

North Creek

9.4 out of 10, Exceptional, (15 reviews)

9.4/10

Exceptional

(15 reviews)

"The host was very responsive and helpful. The space was very cozy and had all the basics. Location was perfect for a ski weekend."

annie k.

The price is €282

€282

includes taxes & fees

18 Sept - 19 Sept

Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

A cozy living room with a sofa, a television, a fireplace, and a bookshelf.

A rustic kitchen with wooden cabinets, a dining table with a checkered tablecloth, and a stone fireplace.

A wooden cabin with a porch, wooden furniture, and a view of a forest.

A single bed with a metal frame in a room with a sloped ceiling and a window.

7. Lovely 3-bedroom house close to Gore Mountain for skiing.

Lovely 3-bedroom house close to Gore Mountain for skiing.

North Creek

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Very cute and cozy / responsive and helpful host"

Renee B.

Lovely 3-bedroom house close to Gore Mountain for skiing.

A yurt with an open door, surrounded by rocks and trees, under a sunset sky.

A forested area with a gravel path, trees, and a covered grill area.

A rustic wooden shed with a slanted roof and large doors, situated on a gravel path surrounded by trees.

A wooden room with a bed, a wall-mounted shelf, and a hanging plant.

8. Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

Minerva

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Absolutely fantastic! Hosts were very kind and responsive. Property was clean and cozy. "

Christine T.

The price is €234

€234

includes taxes & fees

6 Oct - 7 Oct

Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

A bedroom with a bed, a desk, a TV, and a bathroom visible through an open door.

A living room with a brown leather sofa, a TV mounted on the wall, and a kitchen visible through an open doorway.

A compact kitchen with a stove, refrigerator, and dining area with chairs and a table.

9. Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

North Creek

9.0 out of 10, Wonderful, (24 reviews)

9.0/10

Wonderful

(24 reviews)

"Proximity to downtown and nearby attractions."

joseph

The price is €225

€225

includes taxes & fees

5 Oct - 6 Oct

Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

A wooden room with two large circular windows, a blue floor, and a wooden bench.

A cozy cabin interior with a wooden interior, a kitchenette, a dining area, and a living room with a sofa and a coffee table.

A cozy cabin interior with a sofa, a coffee table, a wooden cabinet, and a bookshelf.

A cozy cabin interior with a wooden bench by a large window, shelves with various items, and a fireplace.

10. Sweet New Cabin With Amazing Views Of The Hudson River

Sweet New Cabin With Amazing Views Of The Hudson River

North River

9.8 out of 10, Exceptional, (51 reviews)

9.8/10

Exceptional

(51 reviews)

"The cabin has the most amazing views and the experience was truly incredible! Thanks to Leslie and her family for hosting us."

Gregory P.

The price is €240

€240

includes taxes & fees

18 Sept - 19 Sept

Sweet New Cabin With Amazing Views Of The Hudson River

A log cabin interior with a fireplace, leather seating, and a ceiling fan.

A rustic wooden interior with a staircase, a wooden desk, a lamp, and a coffee station.

A rustic dining area with a wooden table set for six, surrounded by chairs.

A red house with a covered porch, a gravel patio, and a stack of firewood.

11. Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.

Brant Lake

The price is €1,651

€1,651

includes taxes & fees

8 Sept - 9 Sept

Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.

A cabin with a deck, outdoor seating, and a staircase.

A triangular attic bedroom with two beds, a ceiling fan, and a window.

A cozy cabin interior with a high ceiling, wooden walls, a stone wall, and a large window overlooking a forest.

12. Gather in 5BR Lodge with Epic View, AC, Near Lakes

Gather in 5BR Lodge with Epic View, AC, Near Lakes

North Creek

10.0 out of 10, Exceptional, (35 reviews)

10/10

Exceptional

(35 reviews)

"We enjoyed our stay here! "

Jeremy H.

Gather in 5BR Lodge with Epic View, AC, Near Lakes

A hot tub in a room with wooden walls, two potted plants, and a clock on the wall.

A dining area with a long wooden table and chairs, a chandelier, and a view into the kitchen.

A wooden staircase with a geometric pattern, a desk with a lamp, and a chair in a room with a patterned carpet.

A large, two-story house with a wrap-around porch, surrounded by dense forest.

13. GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT

North Creek

10.0 out of 10, Exceptional, (31 reviews)

10/10

Exceptional

(31 reviews)

"Our 3rd time staying here and it's always wonderful!"

Blair G.

The price is €486

€486

includes taxes & fees

8 Sept - 9 Sept

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT

A porch with green railings and red rocking chairs.

A kitchen with a central island, white tiled floor, wooden cabinets, and a red fridge.

A dining area with a table and chairs, a sofa, a foosball table, and a staircase.

A dining area with a wooden table, four chairs, a chandelier, and a view of the outdoors through a window with floral curtains.

14. 7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10

7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10

Johnsburg

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Nice place and area, nice and quiet"

thomas c.

The price is €555

€555

includes taxes & fees

5 Oct - 6 Oct

7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10

A covered porch with a red door, two rocking chairs, and a view of the street.

A living room with a flat-screen TV, a fireplace, a leather sofa, and a lamp.

15. 6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12

6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12

North Creek

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"This is a wonderful location. We thoroughly enjoyed the town of North Creek!"

Jane H W.

The price is €410

€410

includes taxes & fees

29 Sept - 30 Sept

6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12

A wooden deck with outdoor furniture, a grill, and a view of a forested area.

A spacious kitchen with a large island, wooden cabinets, and a stone accent wall.

A cozy living room with a stone fireplace, blue sofas, and a glass coffee table.

A cozy cabin interior with large windows, wooden furniture, and a patterned rug.

16. Sagamore Golf House|Wine Cellar|Movie Theater|15 beds|Hot Tub|Pet Friendly|

Bolton Landing

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"The Sagamore Golf house was everything advertised and more! James was a great host and the home was perfect. I recommend this house to anyone looking to visit lake George for a golf trip or just to relax and unwind."

Nicholas F.

A spacious living area with a wooden ceiling, a sofa set, a coffee table, and a fireplace.

A spacious kitchen with wooden cabinets, a large island, and a dining area with a long table and benches.

A kitchen with wooden cabinets, a wooden countertop, a sink, and a trash can. There is a dining table with chairs and a window with a view of the outdoors.

A spacious kitchen with wooden cabinets, a central island, and a ceiling fan.

17. Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces

Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces

Lake Luzerene

9.8 out of 10, Exceptional, (17 reviews)

9.8/10

Exceptional

(17 reviews)

"Great stay. Barn is fun for hanging out with a group. Would recommend bringing your own camp chairs. Hottub was great. House was awesome for cooking and hanging out"

Ryen H.

The price is €480

€480

includes taxes & fees

27 Sept - 28 Sept

Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces

A multi-story house with a dock and boats, surrounded by dense trees.

A lakeside deck with outdoor seating and a dock extending into the water.

A bathroom with a glass shower door, marble tiles, and a brass towel rack.

A kitchen with granite countertops, wooden cabinets, a central island with chairs, a microwave, an oven, and a refrigerator.

18. Private Sandy Beach with 125 feet of lake frontage

Private Sandy Beach with 125 feet of lake frontage

Paradox

9.8 out of 10, Exceptional, (28 reviews)

9.8/10

Exceptional

(28 reviews)

"Great place, great location on the lake with a very short flat walk to the water! Would stay at this house again."

Brandon Y.

The price is €767

€767

includes taxes & fees

10 Sept - 11 Sept

Private Sandy Beach with 125 feet of lake frontage

A fire pit with Adirondack chairs in a forested area with a lake view.

A kitchen with wooden cabinets, a central island, a stove, a refrigerator, and a chandelier.

A rustic cabin with a metal roof, surrounded by dense forest and a lake.

A log cabin-style bedroom with a bed, dresser, and framed pictures on the wall.

19. Copeland Cabin - Charming Lake House in the Adirondacks

Copeland Cabin - Charming Lake House in the Adirondacks

Fort Ann

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Extremely charming house! Perfect for a quiet get away!"

Halley S.

The price is €736

€736

includes taxes & fees

28 Sept - 29 Sept

Copeland Cabin - Charming Lake House in the Adirondacks

A modern living room with a flat-screen TV, a black entertainment unit, and a 'Welcome to our home' sign.

A dining area with a table, chairs, and a decorative table runner. There is a ceiling fan above and a door with a window in the background.

A residential house with a front porch, a small table and chairs, and a garden area.

A residential driveway leading to a house with a garage.

20. Cozy 3 bedroom house

Cozy 3 bedroom house

South Glens Falls

8.4 out of 10, Very good, (23 reviews)

8.4/10

Very good

(23 reviews)

"Nice place with comfortable beds"

Anonymous traveller

The price is €289

€289

includes taxes & fees

8 Sept - 9 Sept

Cozy 3 bedroom house

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Chestertown Hotel Reviews

Great Escape Lodge & Indoor Waterpark

10/10 Excellent

"The room was clean and spacious. The Waterpark was fun"

Christine 2-night trip

Posted 2 hours ago

Great Escape Lodge & Indoor Waterpark

Adirondack Retreat Inn & Suites

8/10 Good

"Clean motel, decent bed, hot ower, and quiet. A little bit of a walk from the festival commons but it's doable. Didn't get to try the pool but I'll definitely stay there again when I come back to Lake George."

Christopher 1-night trip

Posted 4 hours ago

Adirondack Retreat Inn & Suites

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"“The staff was very friendly and helpful. “The room was spotless and the breakfast was very good with a lot of options”"

Sarbjit 2-night trip

Posted 4 hours ago

La Quinta Inn & Suites by Wyndham Lake George

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent

"Great resort. Very clean and staff were great. Outdoor areas great for families."

Sharon 2-night trip

Posted 4 hours ago

Holiday Inn Resort Lake George - Adirondack Area by IHG

Pine Tree Motel & Cabins

10/10 Excellent

"What a great little place. So friendly. We will go back again."

Barbara 2-night trip

Posted 5 hours ago

Pine Tree Motel & Cabins

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent

"Walking distance to Great Escape. Lovely staff, very helpful. Nice pools both indoor and outdoor. Clean room with separate living room and bedroom area in the 1 bedroom suite."

Kristina 2-night trip

Posted 9 hours ago

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

The Georgian Lakeside Resort

10/10 Excellent

"Had a great time in the resort. Staff was friendly, place was clean. Highly recommend"

Dennys 2-night trip

Posted 9 hours ago

The Georgian Lakeside Resort

Lakefront Terrace Resort

10/10 Excellent

"Na"

Jean 2-night trip

Posted 11 hours ago

Lakefront Terrace Resort

Comfort Inn & Suites Lake George

8/10 Good

"Clean rooms, friendly staff and breakfast is included. Can’t go wrong. Close to the beach."

Jen 1-night trip

Posted 12 hours ago

Comfort Inn & Suites Lake George

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews	481
Accommodation	537 Holiday Homes
Lowest Price	€169
Highest Price	€1,651

Holiday Homes in Chestertown

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown holiday homes

1. The Lily Pad at Loon Lake near Gore Mountain

2. Eagles Nest at Loon Lake near Gore Mountain

3. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

4. The Office at North Creek All Season Rental

5. Adirondack Bungalow Getaway

6. Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

7. Lovely 3-bedroom house close to Gore Mountain for skiing.

8. Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

9. Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

10. Sweet New Cabin With Amazing Views Of The Hudson River

11. Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.

12. Gather in 5BR Lodge with Epic View, AC, Near Lakes

13. GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT

14. 7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10

15. 6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12

16. Sagamore Golf House|Wine Cellar|Movie Theater|15 beds|Hot Tub|Pet Friendly|

17. Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces

18. Private Sandy Beach with 125 feet of lake frontage

19. Copeland Cabin - Charming Lake House in the Adirondacks

20. Cozy 3 bedroom house

Find holiday rentals that suit your style

Top Chestertown Hotel Reviews

Great Escape Lodge & Indoor Waterpark

Find out more about Chestertown

Chestertown Holiday Homes information