The Best Hotels Closest to Overlook Mountain Trailhead in Woodstock 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.

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

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

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

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

14.5 km from Overlook Mountain Trailhead

Timothy

SAR 488

SAR 547 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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.

2. Hunter Lodge, a Bluebird by Lark

15.8 km from Overlook Mountain Trailhead

Marina

SAR 476

SAR 595 total

includes taxes & fees

8 Nov - 9 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 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 large garage and a vintage camper parked in the driveway.

3. AutoCamp Catskills

8.9 km from Overlook Mountain Trailhead

Raquel

SAR 492

SAR 698 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

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

4. Courtyard by Marriott Kingston

15.9 km from Overlook Mountain Trailhead

George

SAR 476

SAR 533 total

includes taxes & fees

25 Oct - 26 Oct

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".

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

5. Hampton Inn Kingston

15.7 km from Overlook Mountain Trailhead

Jennifer

SAR 459

SAR 514 total

includes taxes & fees

8 Nov - 9 Nov

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

A spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

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

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

6. Emerson Resort & Spa

13.9 km from Overlook Mountain Trailhead

Ashley

SAR 618

SAR 693 total

includes taxes & fees

1 Nov - 2 Nov

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 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.

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

7. Hotel Mountain Brook

14 km from Overlook Mountain Trailhead

Kristen

SAR 916

SAR 990 total

includes taxes & fees

9 Nov - 10 Nov

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 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.

8. Woodstock Way Hotel

3.4 km from Overlook Mountain Trailhead

Vannetta

SAR 1,227

SAR 1,521 total

includes taxes & fees

20 Oct - 21 Oct

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.

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.

9. Residence Inn by Marriott Kingston

16.1 km from Overlook Mountain Trailhead

Lamisa

SAR 503

SAR 564 total

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

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

10. Diamond Mills Resort

14.2 km from Overlook Mountain Trailhead

SAR 1,188

SAR 1,425 total

includes taxes & fees

13 Oct - 14 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 hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

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

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

12.4 km from Overlook Mountain Trailhead

Linda

SAR 477

SAR 534 total

includes taxes & fees

11 Nov - 12 Nov

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

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.

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

12. Twin Gables of Woodstock

3.4 km from Overlook Mountain Trailhead

Coleen

SAR 541

SAR 606 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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.

13. Overlook Hotel

13 km from Overlook Mountain Trailhead

Leonardo

SAR 651

SAR 729 total

includes taxes & fees

13 Oct - 14 Oct

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 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.

16.2 km from Overlook Mountain Trailhead

Daniel

SAR 587

SAR 657 total

includes taxes & fees

2 Nov - 3 Nov

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.

15. Howard Johnson by Wyndham Saugerties

12.4 km from Overlook Mountain Trailhead

Shirley

SAR 412

SAR 462 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

16. The Woodstock Inn on the Millstream

3.8 km from Overlook Mountain Trailhead

Carolyn

SAR 860

SAR 963 total

includes taxes & fees

13 Oct - 14 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 cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

17. Kaatskill Mountain Club & Condos by Vail Resorts

16.7 km from Overlook Mountain Trailhead

Ryan

SAR 670

SAR 797 total

includes taxes & fees

10 Nov - 11 Nov

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.

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

18. Phoenicia Lodge

17 km from Overlook Mountain Trailhead

Thomas

SAR 650

SAR 728 total

includes taxes & fees

13 Oct - 14 Oct

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

A cabin with a red roof, surrounded by a gravel path and rocks, with dense forest in the background.

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

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

19. The Leeway

13.4 km from Overlook Mountain Trailhead

Shih-Chun

SAR 859

SAR 963 total

includes taxes & fees

2 Nov - 3 Nov

A restaurant with orange seating, white tablecloths, and potted plants.

A living room with a red patterned rug, a blue armchair, a yellow sofa, and a black coffee table.

A cozy living room with a wood-burning stove, wicker furniture, and a bookshelf.

A room with a red accent wall, a large potted plant, and a small stool.

20. Hotel Kinsley

17.4 km from Overlook Mountain Trailhead

Daile

SAR 891

SAR 1,160 total

includes taxes & fees

10 Nov - 11 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 1,004 reviews	View
Hunter Lodge, a Bluebird by Lark	9.2 Wonderful 1,003 reviews	View
AutoCamp Catskills	9.0 Wonderful 584 reviews	View
Courtyard by Marriott Kingston	8.8 Excellent 1,005 reviews	View
Hampton Inn Kingston	9.0 Wonderful 1,001 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."

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

10/10 Excellent

"What a fun get away! The house was neat clean spacious and had everything that we needed for our stay. The hot tub was easy to use and clean on a fall afternoon. The outdoor porch plus other sitting areas were enjoyable to take in the natural scenery from all v as stage points. Just 5 minutes to town which made it very convenient also!Lisa & John"

Pet Friendly Cabin Doh-Ray up @ 1500 ft

10/10 Excellent

"What we needed and expected. Amble space for two (or even four). Lovely setting and easy outdoor exercise. Convenient drive to town or hiking. All is well maintained. Hosts respond quickly and kindly.Thanks for this stay!"

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."

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

8/10 Good

"We loved sitting outside on the back deck, watching the deer and chipmunks in the open forest. The house has a well-stocked kitchen with plenty of amenities, with several nice areas to sit for a meal or read a book.The only reason I can't give 5* is the house needs more proactive maintenance. Some electrical issue took out the upstairs A/C right before we arrived. The property manager was good at communicating, but getting emergency repairs in a small town on a holiday weekend was hard. We also had poor water pressure starting out. They sent a handyman who managed to change a filter that solved most of it, but there was still an issue with the kitchen cold water after he left. Some caveats: - If you are much over 6 feet tall, you may feel crowded. The ceilings in the older section of the house (the kitchen is newer) are only about 6'-4" high, lower in a couple of spots.- This house may not be the best choice if you have mobility issues. The stairs are steep, narrow, and well-polished wood that is somewhat slippery. And, as with many old houses, some of the doors can stick from settling.- Some people claimed this is walkable distance from town. The distance is walkable, but the road is not. We tried one time, and with the blind curves and hills and negligible shoulder, felt we took our lives in our hands. Drive to the free municipal lot and park.All in all, still a great little place for a couple."

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

10/10 Excellent

"Gorgeous yard, cozy layout, well-equipped kitchen, comfy living room that opens into a fairly spacious dining room area. Would rent again in a heartbeat."

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 trip 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 forest or experience its art scene.

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Levon Helm Studios

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

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Colony

You can get tickets for a performance at Colony during your stay in Woodstock. Amble around this relaxing area's forest 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 browsing the exhibits at Woodstock Artists Association and Museum in Woodstock. Amble around this relaxing area's forest or experience its art scene.

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SweetHeart Gallery

9.4/10 (3 reviews)

You can spend an afternoon exploring the galleries in 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 hotel to stay close to Overlook Mountain Trailhead?

Woodstock Way Hotel is one of the top choices for your stay based on our traveler 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 accommodations 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, the majority of hotel reservations are refundable if you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to cancel it and receive a refund within 24 hours of your booking. Enter dates in and click on "Search", then use the filter option "fully refundable" to get the top deals on offer near Overlook Mountain Trailhead.

Where can I learn more about changing or cancelling my trip in the area near Overlook Mountain Trailhead?

For more information about changing or cancelling your stay near Overlook Mountain Trailhead, head over to our customer service page.

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.

Find hotels near Overlook Mountain Trailhead, Woodstock from SAR 462

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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. Hunter Lodge, a Bluebird by Lark

3. AutoCamp Catskills

4. Courtyard by Marriott Kingston

5. Hampton Inn Kingston

6. Emerson Resort & Spa

7. Hotel Mountain Brook

8. Woodstock Way Hotel

9. Residence Inn by Marriott Kingston

10. Diamond Mills Resort

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

12. Twin Gables of Woodstock

13. Overlook Hotel

14. The Graham & Co.

15. Howard Johnson by Wyndham Saugerties

16. The Woodstock Inn on the Millstream

17. Kaatskill Mountain Club & Condos by Vail Resorts

18. Phoenicia Lodge

19. The Leeway

20. Hotel Kinsley

Compare popular hotels close to Overlook Mountain Trailhead

Top Overlook Mountain Trailhead Hotel Reviews

The Herwood Inn

Twin Gables of Woodstock

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

Pet Friendly Cabin Doh-Ray up @ 1500 ft

Botanical Studio Retreat in the Heart of Woodstock

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

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