⭐ Top 10 Hotels Near Overlook Mountain Trailhead for 2026

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Our top choices for Overlook Mountain Trailhead hotels

A hotel room with two beds, a desk, and a large window.

An outdoor patio with a round table and orange chairs, a black metal fence, and string lights.

A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

A modern building with multiple windows and a landscaped area with decorative pumpkins and a tree.

1. Holiday Inn Express & Suites Kingston-Ulster by IHG

14.5 km from Overlook Mountain Trailhead

Timothy

S$176

includes taxes & fees

15 Nov - 16 Nov

A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.

A spacious living area with a sofa, armchairs, and a coffee table. There is a dining area with chairs and a table, and a stone fireplace.

A candy store with shelves of various treats and a sign that reads "TREATS".

A Hampton Inn hotel with a modern facade, multiple entry points, and a well-lit entrance.

2. Hampton Inn Kingston

15.7 km from Overlook Mountain Trailhead

Jennifer

S$180

includes taxes & fees

15 Nov - 16 Nov

A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.

A modern house with a sloped roof, large windows, and a well-maintained lawn.

A modern house with a large garage and a vintage camper parked in the driveway.

A modern interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.

3. AutoCamp Catskills

8.9 km from Overlook Mountain Trailhead

Raquel

S$257

includes taxes & fees

12 Nov - 13 Nov

A living room with a fireplace, green sofa, and a leopard print armchair.

A modern bedroom with a large bed, a bedside table with a lamp, a view of greenery outside, and a checkered rug.

A white house with a green door, black trim, and a porch with a lantern.

A hallway with a patterned floor, a potted plant, a chandelier, and a door with a decorative mirror.

4. Twin Gables of Woodstock

3.4 km from Overlook Mountain Trailhead

Coleen

S$222

includes taxes & fees

9 Nov - 10 Nov

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.

A modern living room with a large window, a blue sofa, a wooden coffee table, and a rustic wooden wall.

A cozy lounge area with a sofa, armchairs, a coffee table, and a bookshelf.

5. Hunter Lodge, a Bluebird by Lark

15.8 km from Overlook Mountain Trailhead

Marina

S$203

includes taxes & fees

12 Nov - 13 Nov

An outdoor patio with a fire pit, seating, and a building in the background.

A modern hotel room with a grey sofa, an orange armchair, a small wooden table, and a large window with sheer curtains.

A modern cafe with a wooden counter, bar stools, and a menu board above the counter.

A hotel room with two beds, a desk, a chair, and a large window with curtains.

6. Courtyard by Marriott Kingston

15.9 km from Overlook Mountain Trailhead

Ana

S$182

includes taxes & fees

25 Oct - 26 Oct

A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

A well-maintained garden with a red bridge, a welcome sign, and a building with a gabled roof.

A couple standing on a wooden deck overlooking a landscaped garden with a river view.

A hallway with intricate carvings on the walls and a large vase in the center.

7. Emerson Resort & Spa

13.9 km from Overlook Mountain Trailhead

Ashley

S$236

includes taxes & fees

8 Nov - 9 Nov

A spacious lobby with a fireplace, comfortable seating, and large windows.

A multi-story hotel with a well-lit entrance, a flag, and a sign indicating it is a Marriott Residence Inn.

An indoor swimming pool with lounge chairs and a view of the outside.

A breakfast buffet setup with a variety of food items, including bread, cereal, and fruits, in a modern hotel dining area with striped chairs and a large window.

8. Residence Inn by Marriott Kingston

16.1 km from Overlook Mountain Trailhead

Lamisa

S$187

includes taxes & fees

15 Nov - 16 Nov

A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

A corridor with white walls, wooden slats, and a concrete floor.

A pool area with a wooden deck, benches, and umbrellas.

A campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.

9. The Graham & Co.

16.2 km from Overlook Mountain Trailhead

Daniel

S$224

includes taxes & fees

11 Nov - 12 Nov

A modern two-story house with a dark exterior, a front porch, and a small outdoor seating area.

A room with a wooden desk, a chair, a coffee maker, a framed picture, a vase with flowers, and a bed.

A modern bathroom with a marble floor, a large mirror, and a towel rack.

A modern building with a large driveway, a covered outdoor seating area, and a large tree in the background.

10. Overlook Hotel

13 km from Overlook Mountain Trailhead

Leonardo

S$248

includes taxes & fees

27 Oct - 28 Oct

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

A modern lobby with a reception desk, seating area, and a dining section.

A modern breakfast area with a coffee machine, cereal, and bakery options.

A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

11. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

12.4 km from Overlook Mountain Trailhead

Linda

S$177

includes taxes & fees

15 Nov - 16 Nov

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

A bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.

A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

A wooden-paneled bedroom with a bed, bedside tables, and a hanging light fixture.

12. Hotel Mountain Brook

14 km from Overlook Mountain Trailhead

Kristen

S$325

includes taxes & fees

8 Nov - 9 Nov

A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.

A historic hotel with a prominent tower and a brick facade.

A dining area with a brick fireplace, wooden beams, and a chandelier.

13. Diamond Mills Resort

14.2 km from Overlook Mountain Trailhead

luping

S$414

includes taxes & fees

19 Oct - 20 Oct

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

A park with picnic tables and chairs, a tall cylindrical structure, and autumn-colored trees.

A conference room with multiple tables and chairs, a large blackboard, and a chandelier.

A bathroom with three sinks, a trash can, and a chair.

14. SunView Motel

13.9 km from Overlook Mountain Trailhead

Furquan

S$183

includes taxes & fees

25 Oct - 26 Oct

An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.

A restaurant with a bar area, wooden booths, and a coffee machine.

A hotel room with two beds, a TV, a dresser, and a door leading to another room.

15. Howard Johnson by Wyndham Saugerties

12.4 km from Overlook Mountain Trailhead

Shirley

S$155

includes taxes & fees

15 Nov - 16 Nov

A multi-story building with outdoor seating and a stone-paved patio.

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

16. Kaatskill Mountain Club & Condos by Vail Resorts

16.7 km from Overlook Mountain Trailhead

Ryan

S$269

includes taxes & fees

15 Nov - 16 Nov

A wooden cabin with large windows overlooking a forested area with a waterfall.

A modern bedroom with a wooden bed, a desk, and large windows.

A two-story wooden house with a stone retaining wall, a stone pathway, and a small garden with various plants.

A modern living room with a grey sofa, a small round table, and a hanging light fixture.

17. Woodstock Way Hotel

3.4 km from Overlook Mountain Trailhead

Vannetta

S$496

includes taxes & fees

20 Oct - 21 Oct

A white house with a porch, surrounded by lush greenery and two green Adirondack chairs.

A picnic setup with a table, food, drinks, and binoculars by a stream.

A spacious living room with a fireplace, two sofas, a coffee table, and a TV mounted above the fireplace.

A bedroom with a large bed, a fireplace, a TV, and a painting on the wall.

18. The Woodstock Inn on the Millstream

3.8 km from Overlook Mountain Trailhead

Carolyn

S$328

includes taxes & fees

26 Oct - 27 Oct

A dining area with a stone fireplace, wooden beams, and large windows.

A spacious living room with a stone fireplace, wooden beams, and large windows.

A row of red buildings with a gravel driveway and a bench outside.

A hammock between trees, a red cabin, and a blue chair in a wooded area.

19. Phoenicia Lodge

17 km from Overlook Mountain Trailhead

Thomas

S$248

includes taxes & fees

19 Oct - 20 Oct

A cozy room with wooden walls, a dining table with chairs, a fireplace, and a staircase.

A wooden deck with two Adirondack chairs and a red-framed window.

A cozy living room with a sofa, a dining table, and a fireplace.

A rustic interior with wooden walls, a dining table with a bench, a sofa, and a hanging light fixture.

20. The Leeway

13.4 km from Overlook Mountain Trailhead

Shih-Chun

S$328

includes taxes & fees

2 Nov - 3 Nov

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Compare popular hotels close to Overlook Mountain Trailhead

Property	Property class	Guest rating
Holiday Inn Express & Suites Kingston-Ulster by IHG	9.4 Exceptional 1,000 reviews	View
Hampton Inn Kingston	9.0 Wonderful 1,002 reviews	View
AutoCamp Catskills	9.0 Wonderful 586 reviews	View
Twin Gables of Woodstock	9.8 Exceptional 229 reviews	View
Hunter Lodge, a Bluebird by Lark	9.2 Wonderful 1,008 reviews	View

Top Overlook Mountain Trailhead Hotel Reviews

The Herwood Inn

10/10 Excellent

"Very intimate (4 rooms) and wonderfully appointed place down the road from downtown Woodstock. Will definitely stay here again in the future!"

Twin Gables of Woodstock

10/10 Excellent

"Loved our stay at Twin Gables! It's a very bright, well-kept property within walking distance of lots of dining, shopping & a park with a nice hiking loop. I was surprised at how quiet it was, despite it being full the last 2 nights of our 4 night stay. Our room faced the street but that end of the street was quiet so there was no issue. The clothes rack and shelves in the room and the bench shelf in the bathroom were helpful for having a place to put things. Good shower pressure and hot water. The included breakfast was simple but convenient and helped us get out the door to our adventures. I would definitely stay here again."

Other attractions near Overlook Mountain Trailhead

Woodstock Music Shop

9.6/10 (18 reviews)

You can search for that perfect souvenir at Woodstock Music Shop during your visit to Woodstock. Discover the mountain views while you're in the area.

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Karma Triyana Dharmachakra Monastery

10.0/10 (12 reviews)

After visiting Karma Triyana Dharmachakra Monastery, make a plan to see the other sights and activities in Woodstock. Discover the mountain views while you're in the area.

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Byrdcliffe Barn

Byrdcliffe Barn is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's forests or experience its art scene.

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Levon Helm Studios

You can get tickets for a performance at Levon Helm Studios during your stay in Woodstock. Amble around this relaxing area's forests or experience its art scene.

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Colony

You can get tickets for a performance at Colony on your trip to Woodstock. Amble around this relaxing area's forests or experience its art scene.

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Woodstock Public Library

8.8/10 (25 reviews)

Woodstock Public Library is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Discover the mountain views while you're in the area.

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Woodstock Artists Association and Museum

You can spend time exploring the galleries in Woodstock Artists Association and Museum in Woodstock. Amble around this relaxing area's forests or experience its art scene.

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SweetHeart Gallery

9.4/10 (3 reviews)

You can spend an afternoon studying the exhibits at SweetHeart Gallery in Woodstock. Discover the mountain views while you're in the area.

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Frequently asked questions

What's the area like around Overlook Mountain Trailhead?

Overlook Mountain Trailhead is located in a welcoming area of Woodstock known for its magnificent mountain views. You'll find 229 hotels and other accommodations within a few miles for a convenient home base.

What's the best place to stay close to Overlook Mountain Trailhead?

Woodstock Way Hotel is one of the top choices for your stay based on our traveller data, and this hotel offers free parking and private balconies. It's located 2.1 mi (3.4 km) from Overlook Mountain Trailhead. Other good options within a few miles include Twin Gables of Woodstock and The Herwood Inn.

How many hotels should I expect to find near Overlook Mountain Trailhead?

Expedia has 229 hotels and other accommodation options a few miles from Overlook Mountain Trailhead.

If I need to cancel the hotel reservation for my stay near Overlook Mountain Trailhead, will I receive a refund?

Yes! Most hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Add dates, click "Search", then you can use the "fully refundable" filter to review the best deals available near Overlook Mountain Trailhead.

What can I see and do near Overlook Mountain Trailhead?

You can catch a show at Bearsville Theater, Colony and Levon Helm Studios. Get outside and spend some time strolling around Opus 40, The Comeau Property and Woodstock Dog Park. Explore nature at Platte Clove Preserve - Catskill Center and Thorn Preserve - Catskill Center.

Hotels near Overlook Mountain Trailhead

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Treat yourself

Be picky

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Our top choices for Overlook Mountain Trailhead hotels

1. Holiday Inn Express & Suites Kingston-Ulster by IHG

2. Hampton Inn Kingston

3. AutoCamp Catskills

4. Twin Gables of Woodstock

5. Hunter Lodge, a Bluebird by Lark

6. Courtyard by Marriott Kingston

7. Emerson Resort & Spa

8. Residence Inn by Marriott Kingston

9. The Graham & Co.

10. Overlook Hotel

11. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

12. Hotel Mountain Brook

13. Diamond Mills Resort

14. SunView Motel

15. Howard Johnson by Wyndham Saugerties

16. Kaatskill Mountain Club & Condos by Vail Resorts

17. Woodstock Way Hotel

18. The Woodstock Inn on the Millstream

19. Phoenicia Lodge

20. The Leeway

Compare popular hotels close to Overlook Mountain Trailhead

Top Overlook Mountain Trailhead Hotel Reviews

The Herwood Inn

Twin Gables of Woodstock

Other attractions near Overlook Mountain Trailhead

Woodstock Music Shop

Karma Triyana Dharmachakra Monastery

Byrdcliffe Barn

Levon Helm Studios

Colony

Woodstock Public Library

Woodstock Artists Association and Museum

SweetHeart Gallery

Frequently asked questions