The Best Hotels Closest to Tripp Pond in Chestertown for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Tripp Pond hotels

An aerial view of a lakeside property with a dock, a gazebo, and a large house with a porch.

A grand wooden staircase with a handrail, leading to a high ceiling with a chandelier.

A beach with rows of red chairs and a dock with boats.

A wooden deck with white railings leading to a lakeside view.

1. Depe Dene Lakeside Resort

16.8 km from Tripp Pond

Jessica

₩120,953

₩134,243 total

includes taxes & fees

Oct 4 - Oct 5

A log cabin-style building with a porch, windows, and a green roof.

A room with two beds, wooden walls, a window, a desk with a computer, and a lamp.

A room with a wooden dining table and chairs, a window with lace curtains, and a radiator.

A wooden cabin with a picnic table and a barbecue grill.

2. Super 8 by Wyndham Lake George/Warrensburg Area

12.6 km from Tripp Pond

Andrew

₩96,675

₩107,317 total

includes taxes & fees

Oct 5 - Oct 6

A lakeside patio with wooden chairs, a fire pit, and boats in the background.

A living room with a stone fireplace, leather furniture, and a chandelier.

A beach with white lounge chairs and a pier extending into the water.

A waterfront deck with lounge chairs, a sailboat, and a dock extending into calm water.

3. The Juliana Resort

15.1 km from Tripp Pond

Julia

₩134,045

₩148,790 total

includes taxes & fees

Oct 5 - Oct 6

An indoor swimming pool with a glass ceiling, clear pool water, and a few chairs along the side.

A cozy room with a large bed, a fireplace, a stone wall, and wooden beams on the ceiling.

A hotel room with two beds, a balcony, and a view of neighboring houses.

A compact hotel room with a kitchenette, a dining area, a bed, and a TV.

4. Adirondack Retreat Inn & Suites

19.6 km from Tripp Pond

Rowell

₩132,826

₩152,730 total

includes taxes & fees

Oct 5 - Oct 6

A lakeside view with docked boats, a gazebo, and a clear view of the lake and surrounding hills.

A hotel with outdoor seating and a view of a lake.

A two-story building with a balcony on the upper floor, a covered porch, and a picnic table in the front yard.

A two-story house with a balcony, a parked van, and a car in the driveway.

5. Tea Island Resort

19 km from Tripp Pond

Mary

₩144,769

₩160,705 total

includes taxes & fees

Oct 4 - Oct 5

A covered outdoor seating area with wooden benches and chairs, overlooking a residential neighborhood and a lake.

A front door with a blue door and a hanging flower basket.

A swimming pool with a view of a lake and a white fence.

A wooden bookcase filled with books, a blue door with a window, a lamp, and a light blue armchair.

6. Inn on the Hill

19.1 km from Tripp Pond

Helen

₩108,098

₩120,003 total

includes taxes & fees

Oct 4 - Oct 5

Two people dining at an outdoor table with a pizza and drinks, overlooking a lake with a boat and hills in the background.

A modern lounge area with a round table, chairs, a fireplace, and a television mounted on a textured wall.

A couple sitting on a green sofa in a hotel lobby with a tiled floor and wooden shelves in the background.

A bar area with wooden chairs, a counter with a glass display, and hanging lights.

7. Courtyard by Marriott Lake George

20 km from Tripp Pond

Natalie

₩188,693

₩209,449 total

includes taxes & fees

Oct 19 - Oct 20

A poolside area with lounge chairs and umbrellas, a bar, and a view of the sea and mountains at night.

A bar area with a view of a lake and hills, a chalkboard menu, and a variety of bottles and glasses.

A marina with docked boats, a covered seating area, and a view of a lake with mountains in the background.

A restaurant with tables and chairs, large windows with a view of a beach and mountains, and a carpeted floor.

8. The Georgian Lakeside Resort

19.8 km from Tripp Pond

cait

₩147,585

₩163,821 total

includes taxes & fees

Oct 4 - Oct 5

An indoor swimming pool with clear water, surrounded by stone walls and wooden windows.

A wooden cabin interior with a kitchen featuring a stainless steel refrigerator, wooden cabinets, and a bar area with stools.

A snow-covered lodge with cabins, a clear view of a lake, and mountains in the background.

A terrace with outdoor seating, a view of a lake, and a dock.

9. Lodges At Cresthaven

18.1 km from Tripp Pond

Robert

₩263,440

₩292,420 total

includes taxes & fees

Oct 19 - Oct 20

A wooden deck with Adirondack chairs facing a calm lake and distant mountains.

A beachside seating area with a fire pit surrounded by chairs and red umbrellas, overlooking a lake with mountains in the background.

A log cabin-style building with a metal roof, stone pillars, and a glass door entrance.

A lakeside beach with rows of beach chairs and a dock with boats.

10. Scotty's Lakeside Resort

19.5 km from Tripp Pond

Judy

₩120,505

₩133,761 total

includes taxes & fees

Oct 5 - Oct 6

A covered outdoor seating area with wooden furniture, a stone fireplace, and a view of a lake and mountains.

A wooden deck with Adirondack chairs, a stone fire pit, and a wooden structure with a staircase.

A hotel room with two beds, a chair, a desk, and a television.

A marina with boats docked, a wooden pier, and a row of blue lounge chairs.

11. The Lake Motel

19.8 km from Tripp Pond

Belinda

₩134,045

₩148,790 total

includes taxes & fees

Oct 4 - Oct 5

A castle-like structure with stone walls, a central courtyard, and a bridge leading to a larger building.

A spacious room with a large window, wooden furniture, and a fireplace.

A stone-walled room with a wooden ceiling, a large arched doorway, and a view of a forested area outside.

A stone building with a wooden door and a stone archway.

12. HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

11.1 km from Tripp Pond

Matthew

₩2,259,617

₩2,817,075 total

includes taxes & fees

Oct 7 - Oct 8

A beach with lounge chairs and umbrellas, a pier extending into the water, and a building in the background.

A pool area with white lounge chairs and a fenced deck, overlooking a body of water with hills in the background.

A small, single-story building with a white exterior, a covered porch, and a small front yard with a hedge and a tree.

A beach with lounge chairs and an American flag.

13. Marine Village Resort

20 km from Tripp Pond

Catherine E

₩165,160

₩201,677 total

includes taxes & fees

Oct 4 - Oct 5

A spacious balcony with a view of a lake, furnished with a table, chairs, and a TV mounted on the wall.

A kitchen with a large window overlooking a lake and a wooden building.

A formal dining room with tables set for a meal, large windows with curtains, and a view of a lake.

A row of wooden houses with green roofs, surrounded by lush greenery and a body of water in the background.

14. Sun Castle Resort

18.3 km from Tripp Pond

john

₩323,333

₩460,438 total

includes taxes & fees

Oct 4 - Oct 5

A patio area with a stone floor, green lawn, and outdoor furniture.

A backyard with a wooden swing set, picnic tables, and Adirondack chairs around a fire pit.

A compact kitchen with white cabinets, a stove, and a microwave. There's a dining area with a wooden table and chairs.

A building with a wooden deck, a covered porch, and a number '2' sign.

15. Adirondack Sunrise Motel and Cabins

18.7 km from Tripp Pond

Valerie

₩135,568

₩150,481 total

includes taxes & fees

Oct 6 - Oct 7

16. Friends Lake Inn

6.7 km from Tripp Pond

Michael

₩177,697

₩197,259 total

includes taxes & fees

Oct 27 - Oct 28

A flagpole with an American flag, a red Adirondack chair, and a building with a red awning in the background.

A room with two patterned armchairs, a small round table, and a painting on the wall.

A hotel room with a bed, a desk with a computer, a chair, a small table, and a window with curtains.

A swimming pool with white lounge chairs and a white picket fence.

17. Fran Cove Motel

18.6 km from Tripp Pond

Angela

₩97,487

₩111,447 total

includes taxes & fees

Oct 12 - Oct 13

A lakeside setting with a boat docked near the shore, surrounded by trees and a fire pit area with seating.

A large, multi-story log cabin with a prominent chimney, surrounded by dense forest and rocky terrain.

A pathway leading to a lake surrounded by dense forest and a wooden signpost.

A cozy room with a stone fireplace, a comfortable sofa, and a table with books and snacks.

18. The Fern Lodge

5.4 km from Tripp Pond

robert

₩542,883

₩602,602 total

includes taxes & fees

Oct 4 - Oct 5

A lake with a rainbow, boats, and umbrellas.

A beach with rows of sun loungers, a small dock, and a few kayaks.

A hotel room with two beds, a desk, a TV, and a balcony.

19. Surfside On The Lake

19.8 km from Tripp Pond

Renee

₩110,050

₩156,093 total

includes taxes & fees

Oct 20 - Oct 21

A rustic cabin with a wooden porch and a small stream in the background.

A modern kitchen with white cabinets, a black dining table, and a view of a garden through a glass door.

A cabin by a flowing stream surrounded by dense forest.

A cozy log cabin room with a large bed, a nightstand with a lamp, a framed picture, and a window with curtains.

20. Seven Dwarfs Motel and Cabins

19.3 km from Tripp Pond

Arnold

₩107,439

₩119,246 total

includes taxes & fees

Oct 4 - Oct 5

View all properties

Compare popular hotels close to Tripp Pond

Property	Property class	Guest rating
Depe Dene Lakeside Resort	9.0 Wonderful 543 reviews	View
Super 8 by Wyndham Lake George/Warrensburg Area	8.6 Excellent 1,007 reviews	View
The Juliana Resort	8.8 Excellent 214 reviews	View
Adirondack Retreat Inn & Suites	9.2 Wonderful 1,001 reviews	View
Tea Island Resort	9.4 Exceptional 243 reviews	View

Top Tripp Pond Hotel Reviews

Pine Tree Motel & Cabins

8/10 Good

"Charming old fashion Adirondack rustic style / decor individual small cabins (also has motel-styled rooms) - parking either in front of rooms or between cabins, a couple of minutes outside Chestertown, NY, 30 minutes from Schroon Lake, and 45 minutes from Ticonderoga (StarTrek Museum & Fort). Very nice, friendly, and accomidating owners / operators. Breakfast / coffee place "Two Sparrows" 5 minutes down the road. Driveway very well lite / marked at night, although wish those lights had either dimmed or turned off post midnight for a better / darker sleep . . . As it was a very wet / rainy, and cold night - heat worked very qickly / well and found extra pillows and blanket. Plenty of hot water in sink / shower, soap, shampoo, small college refrigerator and microwave provided, however no hairdryer for partner . . . Did not test WiFi as we only stayed for 8 hours total time. Would have wished to have had more time to explore grounds and Chestertown itself."

Friends Lake Inn

10/10 Excellent

"Just a great place to make home base during your time exploring the Adirondack"

The Fern Lodge

10/10 Excellent

"A beautiful place. Everything was wonderful!!!"

Other attractions near Tripp Pond

Loon Lake

8.8/10 (8 reviews)

Commune with nature and explore the great outdoors at Loon Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

See properties

Friends Lake

9.4/10 (14 reviews)

Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

See properties

Pack Demonstration Forest

Enjoy the mountain views and explore Pack Demonstration Forest, a lovely green space in Warrensburg. Wander the lakeside in this quaint area.

See properties

Pond Mountain

Commune with nature and explore the great outdoors at Pond Mountain during your travels in Warrensburg. Wander the riverfront or discover the area's mountain views.

See properties

Loon Lake Beach

8.4/10 (7 reviews)

If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.

See properties

Trout Lake

Commune with nature and explore the great outdoors at Trout Lake during your travels in Diamond Point. Wander the lakeside and beaches in the area.

See properties

The Sagamore Golf Club

Enjoy a round of golf in Bolton Landing at The Sagamore Golf Club. While you're in the area, stroll along the lakeside.

See properties

Frequently asked questions

What's the area like around Tripp Pond?

Tripp Pond is located in Chestertown. Travelers like the surrounding area for its lakeside setting. If you're looking for a convenient place to stay, check out the 16 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay near Tripp Pond?

The Fern Lodge is one of the top choices for your stay based on our traveler data, and this B&B offers free breakfast and free parking. It's located 3.3 mi (5.4 km) from Tripp Pond.

How many hotels can I expect to find near Tripp Pond?

Expedia has 16 hotels and other accommodations within a mile from Tripp Pond.

If I need to cancel the hotel reservation for my stay near Tripp Pond, will I receive a refund?

Yes, you'll find most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, you may still be able to cancel and be given a refund within a 24-hour period of your booking. Add your dates and click on "Search", then filter by "fully refundable" to get the best deals available near Tripp Pond.

Where can I learn more about changing or cancelling my trip in the area near Tripp Pond?

For more details about changing or cancelling your stay near Tripp Pond, click here.

Find hotels near Tripp Pond, Chestertown from ₩107,317

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Tripp Pond hotels

1. Depe Dene Lakeside Resort

2. Super 8 by Wyndham Lake George/Warrensburg Area

3. The Juliana Resort

4. Adirondack Retreat Inn & Suites

5. Tea Island Resort

6. Inn on the Hill

7. Courtyard by Marriott Lake George

8. The Georgian Lakeside Resort

9. Lodges At Cresthaven

10. Scotty's Lakeside Resort

11. The Lake Motel

12. HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

13. Marine Village Resort

14. Sun Castle Resort

15. Adirondack Sunrise Motel and Cabins

16. Friends Lake Inn

17. Fran Cove Motel

18. The Fern Lodge

19. Surfside On The Lake

20. Seven Dwarfs Motel and Cabins

Compare popular hotels close to Tripp Pond

Top Tripp Pond Hotel Reviews

Pine Tree Motel & Cabins

Friends Lake Inn

The Fern Lodge

Other attractions near Tripp Pond

Loon Lake

Friends Lake

Pack Demonstration Forest

Pond Mountain

Loon Lake Beach

Trout Lake

The Sagamore Golf Club

Frequently asked questions