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

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.

A stone building with multiple windows and a door, situated on a street corner.

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

9 mi from Overlook Mountain Trailhead

Cindy

£117

includes taxes & fees

25 Oct - 26 Oct

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

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

2. AutoCamp Catskills

5.5 mi from Overlook Mountain Trailhead

Raquel

£151

includes taxes & fees

29 Oct - 30 Oct

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 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.

3. Hunter Lodge, a Bluebird by Lark

9.8 mi from Overlook Mountain Trailhead

Shubhangi

£136

includes taxes & fees

26 Oct - 27 Oct

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

4. Courtyard by Marriott Kingston

9.9 mi from Overlook Mountain Trailhead

Ana

£107

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

5. Hotel Mountain Brook

8.7 mi from Overlook Mountain Trailhead

Kristen

£215

includes taxes & fees

20 Oct - 21 Oct

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

A bar with a patterned floor, bar stools, and a bar counter with taps.

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

6. Diamond Mills Resort

8.8 mi from Overlook Mountain Trailhead

£243

includes taxes & fees

5 Oct - 6 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 large tree in a grassy area with a small white building in the background.

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

7. SunView Motel

8.6 mi from Overlook Mountain Trailhead

Victoria

£85

includes taxes & fees

1 Oct - 2 Oct

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

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

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.

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

8. Hampton Inn Kingston

9.7 mi from Overlook Mountain Trailhead

stephen

£118

includes taxes & fees

26 Oct - 27 Oct

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

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.

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.

9. Woodstock Way Hotel

2.1 mi from Overlook Mountain Trailhead

Vannetta

£320

includes taxes & fees

20 Oct - 21 Oct

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

10. Twin Gables of Woodstock

2.1 mi from Overlook Mountain Trailhead

Coleen

£212

includes taxes & fees

28 Oct - 29 Oct

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

A modern bedroom with a bed, a small desk, and a kitchenette area.

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

2.1 mi from Overlook Mountain Trailhead

Diana

£212

includes taxes & fees

30 Sept - 1 Oct

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

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

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

12. Residence Inn by Marriott Kingston

10 mi from Overlook Mountain Trailhead

Harold

£121

includes taxes & fees

4 Oct - 5 Oct

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 bedroom with a bed, desk, chair, and a window with curtains.

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

13. Overlook Hotel

8 mi from Overlook Mountain Trailhead

Leonardo

£146

includes taxes & fees

5 Oct - 6 Oct

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

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.

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

14. The Graham & Co.

10.1 mi from Overlook Mountain Trailhead

Daniel

£144

includes taxes & fees

30 Sept - 1 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 spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

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

15. Emerson Resort & Spa

8.7 mi from Overlook Mountain Trailhead

Ashley

£175

includes taxes & fees

30 Sept - 1 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 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.

16. The Woodstock Inn on the Millstream

2.3 mi from Overlook Mountain Trailhead

Carolyn

£194

includes taxes & fees

30 Sept - 1 Oct

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

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.

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

17. Kaatskill Mountain Club & Condos by Vail Resorts

10.4 mi from Overlook Mountain Trailhead

Ryan

£177

includes taxes & fees

28 Oct - 29 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 Howard Johnson Inn with a beige facade, red trim, and a clear blue sky with clouds.

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

18. Howard Johnson by Wyndham Saugerties

7.7 mi from Overlook Mountain Trailhead

Richard

£117

includes taxes & fees

13 Oct - 14 Oct

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

19. Phoenicia Lodge

10.6 mi from Overlook Mountain Trailhead

Thomas

£146

includes taxes & fees

28 Oct - 29 Oct

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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 1,002 reviews	View
AutoCamp Catskills	9.0 Wonderful 574 reviews	View
Hunter Lodge, a Bluebird by Lark	9.2 Wonderful 1,020 reviews	View
Courtyard by Marriott Kingston	8.8 Excellent 1,006 reviews	View
Hotel Mountain Brook	9.8 Exceptional 603 reviews	View

Top Overlook Mountain Trailhead Hotel Reviews

Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!

10/10 Excellent

"Judy’s place was so charming! My wife and I eloped in Kingston and the cottage was a perfect place for us to celebrate and have a getaway for the weekend. We would absolutely return!"

The Herwood Inn

10/10 Excellent

"Wonderful experience! The room was beautiful and equipped with everything you could think of. We had such a lovely,relaxing stay."

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10/10 Excellent

"Everything about our stay at Junebug was top shelf. For a part of two it is ideal, and even with us having a third adult with us (for an extra, very reasonable fee), who used the LR with the pull-out sofa, there was plenty of private space, and a cozy kitchenette common space. Well stocked, well layed out kitchen. No range, but there is an electric portable burner if needed, and an outside grill. The place is spotless, and the hosts, who are next door, respect your privacy yet are available if you have questions. How perfect is that?Plus we had special medical needs that were easily accommodated. (I advise you check before booking, as we did). We hope to stay there again, it’s like a little wonderland in the country. Thank you, John and Molly!"

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

10/10 Excellent

"Lovely location, wind blowing through the trees, rain pattering, just beautiful scenery and wildlife. Great places to eat nearby, The Red Onion is excellent, Bread Alone was busy but good, so much we did not get to do, but the town seems cozy and fun!"

Botanical Studio Retreat in the Heart of Woodstock

10/10 Excellent

"The location is beyond perfect. Everything I wanted to explore was within a 4–10 minute walk, and I discovered so many cool spots just by wandering. A few places, like Bearsville Theatre, were a quick drive — but absolutely worth it. The host is incredibly accommodating, which made the stay feel even more relaxed and welcoming."

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

10/10 Excellent

"We had a wonderful weekend! The house was clean, big, beautiful and very well equipped. The host Greg was super responsive. The pool is nice and the outside space is great. There are many hiking trails around and the town is super cute, many restaurants cafes and small shops. We are planning to return in the future!"

Maple House: Private/Romantic Walk-to-Town Oasis

10/10 Excellent

"Beautiful property, inside and out!"

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

10/10 Excellent

"A beautiful spot just outside of main street woodstock. would book it again"

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

10/10 Excellent

"Great little apartment in the perfect location to explore Woodstock. I didn't have a car & it was very easy to walk to great restaurants and shops."

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.

Search Hotels Near Overlook Mountain Trailhead, Woodstock

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Overlook Mountain Trailhead hotels

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

2. AutoCamp Catskills

3. Hunter Lodge, a Bluebird by Lark

4. Courtyard by Marriott Kingston

5. Hotel Mountain Brook

6. Diamond Mills Resort

7. SunView Motel

8. Hampton Inn Kingston

9. Woodstock Way Hotel

10. Twin Gables of Woodstock

11. The Herwood Inn

12. Residence Inn by Marriott Kingston

13. Overlook Hotel

14. The Graham & Co.

15. Emerson Resort & Spa

16. The Woodstock Inn on the Millstream

17. Kaatskill Mountain Club & Condos by Vail Resorts

18. Howard Johnson by Wyndham Saugerties

19. Phoenicia Lodge

Compare popular hotels close to Overlook Mountain Trailhead

Top Overlook Mountain Trailhead Hotel Reviews

Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!

The Herwood Inn

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

Botanical Studio Retreat in the Heart of Woodstock

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

Maple House: Private/Romantic Walk-to-Town Oasis

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

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