The Best Hotels Closest to Tripp Pond in Chestertown - 2026 Updated Prices

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

A reception area with a wooden counter, a welcome sign, and a ship's wheel decoration.

A poolside area with a blue sofa, white wicker chairs, and a small table with a basket.

A white building with a yellow awning, a porch with flowers, and American flags.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

1. Admiral Motel

19.8 km from Tripp Pond

Grayson

Rp1.387.554

Rp1.540.185 total

includes taxes & fees

3 Sept - 4 Sept

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

A wooden building with a balcony, a clock, and a lifebuoy.

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.

2. The Juliana Resort

15.1 km from Tripp Pond

Jozefina

Rp1.807.542

Rp2.006.372 total

includes taxes & fees

22 Sept - 23 Sept

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

A modern living room with a sofa, coffee table, and artwork on the walls.

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

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

3. Depe Dene Lakeside Resort

16.8 km from Tripp Pond

Melissa

Rp1.738.626

Rp1.929.680 total

includes taxes & fees

17 Sept - 18 Sept

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

A building with a covered porch, white doors, and a row of white plastic chairs.

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

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

4. Adirondack Retreat Inn & Suites

19.6 km from Tripp Pond

Beth ann

Rp1.738.430

Rp1.999.196 total

includes taxes & fees

31 Aug - 1 Sept

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

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

A lakeside lodge with a wooden exterior, a deck, and a row of beach chairs under umbrellas.

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

5. Lodges At Cresthaven

18.1 km from Tripp Pond

Jenn Hou

Rp4.814.574

Rp5.344.178 total

includes taxes & fees

7 Sept - 8 Sept

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

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

A hotel room with two beds, each with a wooden headboard, a bedside table with a lamp, and a red blanket on one bed.

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

6. Tea Island Resort

19 km from Tripp Pond

Anthony

Rp1.894.729

Rp2.103.305 total

includes taxes & fees

20 Sept - 21 Sept

A white building with a covered porch and a gazebo with flower baskets.

A building with a sign reading "The Heritage of La".

A covered outdoor seating area with two green lounge chairs, a tree with pink flowers, and a parking area in the background.

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

7. Heritage of Lake George

19.7 km from Tripp Pond

Elizabeth

Rp1.467.299

Rp1.628.702 total

includes taxes & fees

24 Sept - 25 Sept

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 table with a meal, a drink, and a view of the sea.

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

Denise

Rp1.931.589

Rp2.144.063 total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

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

9. The Lake Motel

19.8 km from Tripp Pond

Jeff

Rp1.754.379

Rp1.947.361 total

includes taxes & fees

8 Sept - 9 Sept

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

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

A hotel with a pool, beach chairs, umbrellas, and a view of the lake.

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

10. Scotty's Lakeside Resort

19.5 km from Tripp Pond

Leanne

Rp1.754.379

Rp1.947.361 total

includes taxes & fees

8 Sept - 9 Sept

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

A room with a wooden bench, a table, and chairs. There is a map on the wall and a window with a curtain.

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

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

11. Super 8 by Wyndham Lake George/Warrensburg Area

12.6 km from Tripp Pond

eric

Rp1.249.795

Rp1.387.270 total

includes taxes & fees

8 Sept - 9 Sept

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

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

A room with a light blue bench, a lamp, and a framed painting on the wall.

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

12. Inn on the Hill

19.1 km from Tripp Pond

Ryan

Rp1.270.916

Rp1.410.751 total

includes taxes & fees

30 Aug - 31 Aug

A fire pit surrounded by Adirondack chairs on a patio overlooking a lake and forested hills.

A bar area with wooden walls and a long counter. There are several wooden chairs with blue cushions.

A room with a large window overlooking a lake and hills, a table with a remote control, and a hanging lamp.

A balcony with potted plants and a view of a building with a red roof and white walls.

13. Nordick's Inn

19.4 km from Tripp Pond

Jack

Rp1.589.786

Rp1.764.662 total

includes taxes & fees

8 Sept - 9 Sept

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

A hotel room with two beds, a desk, and a mirror.

A beach with lounge chairs and an American flag.

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

14. Marine Village Resort

20 km from Tripp Pond

Lauren

Rp2.066.800

Rp2.523.825 total

includes taxes & fees

8 Sept - 9 Sept

A lakeside deck with chairs and a dock with boats.

Two single beds with wooden headboards, white bedding, and a patterned carpet.

A room with a closed door, a 'WELCOME NOW HIRING VACANCY' sign, a wicker sofa with patterned cushions, and a wooden cabinet.

A swimming pool with lounge chairs and umbrellas, surrounded by buildings with a view of a forested hill.

15. Park Lane Motel

19.9 km from Tripp Pond

Teresa

Rp1.738.626

Rp1.929.680 total

includes taxes & fees

13 Sept - 14 Sept

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

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

A covered outdoor deck with wooden furniture and a hanging planter.

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

16. Adirondack Sunrise Motel and Cabins

18.7 km from Tripp Pond

Virginia

Rp1.973.677

Rp2.190.781 total

includes taxes & fees

8 Sept - 9 Sept

17. Lakefront Terrace Resort

19.1 km from Tripp Pond

SIEF A

Rp1.709.084

Rp1.897.082 total

includes taxes & fees

13 Sept - 14 Sept

A row of cabins with a central building featuring a triangular roof, surrounded by trees with autumn foliage.

A swimming pool with a slide, surrounded by lounge chairs and a small building.

A wooden cabin room with two beds, a small table, and two windows with curtains.

A cabin with a triangular roof, a front porch with chairs, and a fire extinguisher mounted on the wall.

18. Amber Lantern Lake George Motel and Cottage Rentals

16.2 km from Tripp Pond

Arnaud

Rp1.772.100

Rp1.967.031 total

includes taxes & fees

30 Aug - 31 Aug

A row of white cabins with green trim, a small bridge, and a rushing stream in the foreground.

A playground with a slide, a small house, and a play structure.

A bridge over a flowing river with a building on the right.

A motel sign with a rainbow, 26 rooms, 10 cabins, and a pool.

19. Brookside Motel

19 km from Tripp Pond

Richard

Rp1.311.354

Rp1.455.603 total

includes taxes & fees

14 Sept - 15 Sept

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

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

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

A cabin by a lake with a view of the water and hills.

20. Sun Castle Resort

18.3 km from Tripp Pond

"The cabin was clean and the view was amazing. I would just caution anyone with mobility issues that the walk down to the cabin (#9) is steep and then there's stairs to get into the cabin. Then uphill to go back to the car. My husband needs a knee replacement and he was struggling. I called and asked if we could park down closer to the cabin & was told yes, if we had a handicap placard, which we do not do that was the only downside to our stay."

Cheryl

Rp4.231.775

Rp6.026.203 total

includes taxes & fees

21 Sept - 22 Sept

View all properties

Compare popular hotels close to Tripp Pond

Property	Property class	Guest rating
Admiral Motel	9.4 Exceptional 793 reviews	View
The Juliana Resort	8.8 Excellent 206 reviews	View
Depe Dene Lakeside Resort	9.0 Wonderful 514 reviews	View
Adirondack Retreat Inn & Suites	9.4 Exceptional 1,001 reviews	View
Lodges At Cresthaven	9.4 Exceptional 629 reviews	View

Top Tripp Pond Hotel Reviews

Pine Tree Motel & Cabins

10/10 Excellent

"Really clean. Very quaint. Lovely owners. Close to “town” and close to lake. Perfect for our purposes."

Friends Lake Inn

8/10 Good

"The staff was amazing and the restaurant was fantastic the little bit we got to try it. Unfortunately, the restaurant was closed two of the three days we were there however the nightly price increased each day. The grounds are in need of some TLC however the room was clean and comfortable. I think the nightly rate needs some adjusting."

The Fern Lodge

10/10 Excellent

"The Fern is a beautiful B&B on the Lake. We stayed in the Oak room and the view was spectacular. I highly recommend the Fern if you are looking for a quiet romantic getaway."

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 holiday is part of your travel plans, Loon Lake Beach might be the perfect place to visit 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. Travellers like the surrounding area for its lakeside setting. If you're looking for a convenient place to stay, take a look at the 16 hotels and other accommodation options 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 traveller 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 are there near Tripp Pond?

Expedia has 16 hotels and other accommodation options 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! Most room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and get a refund within 24 hours of your booking. Add dates, click "Search", then you can filter by "fully refundable" to view the best options available near Tripp Pond.

Search Hotels Near Tripp Pond, Chestertown

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. Admiral Motel

2. The Juliana Resort

3. Depe Dene Lakeside Resort

4. Adirondack Retreat Inn & Suites

5. Lodges At Cresthaven

6. Tea Island Resort

7. Heritage of Lake George

8. The Georgian Lakeside Resort

9. The Lake Motel

10. Scotty's Lakeside Resort

11. Super 8 by Wyndham Lake George/Warrensburg Area

12. Inn on the Hill

13. Nordick's Inn

14. Marine Village Resort

15. Park Lane Motel

16. Adirondack Sunrise Motel and Cabins

17. Lakefront Terrace Resort

18. Amber Lantern Lake George Motel and Cottage Rentals

19. Brookside Motel

20. Sun Castle Resort

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