The Best Hotels Closest to Overlook Mountain Trailhead in Woodstock - 2026 Updated Prices

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Our top choices for Overlook Mountain Trailhead hotels

A buffet with labeled food stations including omelets and cheese.

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

An outdoor patio with round tables and chairs, string lights, and a glass partition.

A hotel with a modern facade, a covered entrance, and a landscaped area with potted plants.

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

14.5 km from Overlook Mountain Trailhead

Mark

3.499.544 ₫

3.919.487 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

A wooden deck with outdoor seating, a wooden deck with a view of the interior, and a wooden deck with a view of the exterior.

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

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

2. Woodstock Way Hotel

3.4 km from Overlook Mountain Trailhead

Jennifer

7.875.541 ₫

9.839.131 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

A bedroom with a large window offering a view of a forested mountain.

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

3. Hunter Lodge, a Bluebird by Lark

15.8 km from Overlook Mountain Trailhead

sarah

3.307.591 ₫

4.136.305 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

An indoor swimming pool with clear water, a 5 feet deep sign, and a tiled floor.

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

4. Hampton Inn Kingston

15.7 km from Overlook Mountain Trailhead

stephen

3.493.798 ₫

3.913.054 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

A modern hotel lobby with a wooden floor, a reception desk, two patterned armchairs, a chandelier, and a view of the outdoors through a glass door.

5. Hotel Mountain Brook

14 km from Overlook Mountain Trailhead

Qiang

4.674.764 ₫

5.048.745 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

A Courtyard by Marriott hotel with a modern facade, large windows, and a well-maintained entrance area.

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

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

6. Courtyard by Marriott Kingston

15.9 km from Overlook Mountain Trailhead

Thuy

3.085.605 ₫

3.455.877 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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

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.

An outdoor patio with a fire pit, wicker furniture, and a red building in the background.

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

7. Residence Inn by Marriott Kingston

16.1 km from Overlook Mountain Trailhead

Ali

3.525.660 ₫

3.948.738 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

A wooden deck with outdoor seating and a house in the background.

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

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

8. Twin Gables of Woodstock

3.4 km from Overlook Mountain Trailhead

Coleen

5.197.084 ₫

6.236.501 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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 large garage and a vintage camper parked in the driveway.

A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.

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

9. AutoCamp Catskills

8.9 km from Overlook Mountain Trailhead

Thomas

3.751.563 ₫

5.225.496 ₫ total

includes taxes & fees

17 Sept - 18 Sept

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

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

10. Overlook Hotel

13 km from Overlook Mountain Trailhead

Tim

4.570.263 ₫

5.118.696 ₫ total

includes taxes & fees

25 Aug - 26 Aug

A modern house with a wooden deck, a fire pit, and a covered outdoor seating area.

A wooden sign with the text "Mitchell Manor" hanging from a building.

A two-story house with a porch, a sign for 'The Herwood Inn', and a well-maintained lawn.

A modern kitchen with a wooden island, black cabinets, and a built-in refrigerator. There are hanging plants, a coffee machine, and shelves with dishes and utensils.

11. The Herwood Inn

3.4 km from Overlook Mountain Trailhead

John

5.731.156 ₫

6.418.894 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.

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

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

12. The Graham & Co.

16.2 km from Overlook Mountain Trailhead

Laura

4.202.848 ₫

4.707.409 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

13. Phoenicia Lodge

17 km from Overlook Mountain Trailhead

Kathy

4.518.590 ₫

5.060.758 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

14. Diamond Mills Resort

14.2 km from Overlook Mountain Trailhead

6.941.110 ₫

8.426.849 ₫ total

includes taxes & fees

25 Aug - 26 Aug

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

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

A cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.

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

15. Kaatskill Mountain Club & Condos by Vail Resorts

16.7 km from Overlook Mountain Trailhead

jason

4.798.075 ₫

5.713.643 ₫ total

includes taxes & fees

26 Aug - 27 Aug

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.

16. The Leeway

13.4 km from Overlook Mountain Trailhead

Shih-Chun

6.276.981 ₫

7.030.218 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A serene garden with a stone pathway, a small bridge, and a bench.

A hallway with a framed portrait on the wall, a door to the right, and a window on the left.

A room with a large tapestry, two wicker chairs, a small table, and a globe lamp.

A dining area with a wooden table, chairs, a chandelier, and a view of the outdoors through large windows.

17. Morning Glory B n B Woodstock NY

3.4 km from Overlook Mountain Trailhead

Lucian

5.458.244 ₫

6.113.233 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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

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

A cozy living room with a fireplace, comfortable seating, and a dining area with a table set for four.

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

18. The Woodstock Inn on the Millstream

3.8 km from Overlook Mountain Trailhead

Robert

5.980.564 ₫

6.698.232 ₫ total

includes taxes & fees

25 Aug - 26 Aug

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

A large tree in a grassy area with a small white building in the background.

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

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

19. SunView Motel

13.9 km from Overlook Mountain Trailhead

Arnold

3.448.618 ₫

3.724.403 ₫ total

includes taxes & fees

1 Sept - 2 Sept

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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 1,005 reviews	View
Woodstock Way Hotel	9.6 Exceptional 306 reviews	View
Hunter Lodge, a Bluebird by Lark	9.2 Wonderful 1,013 reviews	View
Hampton Inn Kingston	9.0 Wonderful 1,005 reviews	View
Hotel Mountain Brook	9.8 Exceptional 592 reviews	View

Top Overlook Mountain Trailhead Hotel Reviews

Woodstock Way Hotel

10/10 Excellent

"Best place I’ve stayed in a long time- gorgeous setting in the trees yet just up the street from everything!! Easy in and out- felt private, clean and serene!"

The Herwood Inn

10/10 Excellent

"Absolutely loved staying in the king suite! I didn’t want to leave! Will definitely return!"

Twin Gables of Woodstock

10/10 Excellent

"We loved our cute, artsy stay at Twin Gables! Everything was a pure perfection!! :)"

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 226 hotels and other accommodations within a few miles for a convenient home base.

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

Expedia has 226 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 Colony, Bearsville Theater 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.

Search Hotels Near Overlook Mountain Trailhead, Woodstock

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Overlook Mountain Trailhead hotels

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

2. Woodstock Way Hotel

3. Hunter Lodge, a Bluebird by Lark

4. Hampton Inn Kingston

5. Hotel Mountain Brook

6. Courtyard by Marriott Kingston

7. Residence Inn by Marriott Kingston

8. Twin Gables of Woodstock

9. AutoCamp Catskills

10. Overlook Hotel

11. The Herwood Inn

12. The Graham & Co.

13. Phoenicia Lodge

14. Diamond Mills Resort

15. Kaatskill Mountain Club & Condos by Vail Resorts

16. The Leeway

17. Morning Glory B n B Woodstock NY

18. The Woodstock Inn on the Millstream

19. SunView Motel

Compare popular hotels close to Overlook Mountain Trailhead

Top Overlook Mountain Trailhead Hotel Reviews

Woodstock Way Hotel

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