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

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

1. Hunter Lodge, a Bluebird by Lark

15.8 km from Overlook Mountain Trailhead

Shubhangi

SAR 475

SAR 595 total

includes taxes & fees

8 Nov - 9 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 wooden deck with outdoor seating and a house in the background.

2. Twin Gables of Woodstock

3.4 km from Overlook Mountain Trailhead

Coleen

SAR 616

SAR 690 total

includes taxes & fees

8 Nov - 9 Nov

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

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

3. SunView Motel

13.9 km from Overlook Mountain Trailhead

Victoria

SAR 391

SAR 423 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

4. Emerson Resort & Spa

13.9 km from Overlook Mountain Trailhead

Ashley

SAR 618

SAR 692 total

includes taxes & fees

1 Nov - 2 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 interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.

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.

5. AutoCamp Catskills

8.9 km from Overlook Mountain Trailhead

Raquel

SAR 475

SAR 680 total

includes taxes & fees

4 Nov - 5 Nov

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 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.

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

6. The Herwood Inn

3.4 km from Overlook Mountain Trailhead

Diana

SAR 1,099

SAR 1,230 total

includes taxes & fees

22 Oct - 23 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 hotel room with two beds, a desk, a chair, and a large window with curtains.

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

7. Courtyard by Marriott Kingston

15.9 km from Overlook Mountain Trailhead

Ana

SAR 475

SAR 532 total

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 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 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.

8. Hotel Mountain Brook

14 km from Overlook Mountain Trailhead

Kristen

SAR 991

SAR 1,070 total

includes taxes & fees

4 Nov - 5 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 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.

9. Overlook Hotel

13 km from Overlook Mountain Trailhead

Leonardo

SAR 650

SAR 728 total

includes taxes & fees

12 Oct - 13 Oct

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

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.

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

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

14.5 km from Overlook Mountain Trailhead

Cindy

SAR 458

SAR 513 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

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

11. The Graham & Co.

16.2 km from Overlook Mountain Trailhead

Daniel

SAR 586

SAR 657 total

includes taxes & fees

3 Nov - 4 Nov

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.

12. Diamond Mills Resort

14.2 km from Overlook Mountain Trailhead

SAR 1,188

SAR 1,424 total

includes taxes & fees

11 Oct - 12 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 two-story wooden house with a stone retaining wall, a stone pathway, and a small garden with various plants.

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.

13. Woodstock Way Hotel

3.4 km from Overlook Mountain Trailhead

Vannetta

SAR 1,227

SAR 1,520 total

includes taxes & fees

20 Oct - 21 Oct

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

A Howard Johnson Inn with a beige facade, red trim, and a clear blue sky with clouds.

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.

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

15. Kaatskill Mountain Club & Condos by Vail Resorts

16.7 km from Overlook Mountain Trailhead

Ryan

SAR 644

SAR 767 total

includes taxes & fees

15 Oct - 16 Oct

A snow-covered lodge with a stone chimney, lit windows, and snow-laden trees in front.

A wooden deck with a fire pit surrounded by Adirondack chairs.

A wooden interior with a staircase, a wooden desk with a lamp, and a vase with flowers.

A bar area with wooden bar stools, a fireplace, and a variety of bottles and glasses on shelves.

16. Deer Mountain Inn

16.7 km from Overlook Mountain Trailhead

Julia

SAR 1,486

SAR 1,707 total

includes taxes & fees

27 Oct - 28 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 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.

17. Phoenicia Lodge

17 km from Overlook Mountain Trailhead

Thomas

SAR 650

SAR 728 total

includes taxes & fees

26 Oct - 27 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 wooden deck with two Adirondack chairs and a red-framed window.

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

18. The Leeway

13.4 km from Overlook Mountain Trailhead

Shih-Chun

SAR 859

SAR 962 total

includes taxes & fees

2 Nov - 3 Nov

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

A hotel room with a large window, two blue armchairs, a round table with a plant, and a bed with a white blanket.

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

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

19. Hotel Kinsley

17.4 km from Overlook Mountain Trailhead

Daile

SAR 890

SAR 1,159 total

includes taxes & fees

8 Nov - 9 Nov

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Top Overlook Mountain Trailhead Hotel Reviews

The Herwood Inn

10/10 Excellent

"Beautiful property. Would stay again!"

Twin Gables of Woodstock

8/10 Good

"The location was good and there was plenty of close parking. The bed was comfortable with clean, crisp sheets. The bathroom was very small but the shower was nice and there was plenty of hot water, we were on the 3rd floor with 2 long flights of stairs but it was much more private than being on the first floor where there was a lot of activity. The third floor had slanted ceilings which made it hard for one side of the bed to get out of without hitting your head, you constantly had to be aware. Breakfast was plentiful but the kitchen where there was one long table, was also the office."

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"

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."

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

10/10 Excellent

"It took us several years to find a place in Woodstock that we wanted to return to annually. The location is perfect in that it is just on the edge of town but we walk to everywhere in town in a matter of minutes. The bathroom was recently redone and is beautiful. When we leave at the end of our stay it feels like we're leaving home. As long as this property is available it will be the only place we stay in Woodstock."

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 423

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Be picky

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Our top choices for Overlook Mountain Trailhead hotels

1. Hunter Lodge, a Bluebird by Lark

2. Twin Gables of Woodstock

3. SunView Motel

4. Emerson Resort & Spa

5. AutoCamp Catskills

6. The Herwood Inn

7. Courtyard by Marriott Kingston

8. Hotel Mountain Brook

9. Overlook Hotel

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

11. The Graham & Co.

12. Diamond Mills Resort

13. Woodstock Way Hotel

14. Howard Johnson by Wyndham Saugerties

15. Kaatskill Mountain Club & Condos by Vail Resorts

16. Deer Mountain Inn

17. Phoenicia Lodge

18. The Leeway

19. Hotel Kinsley

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

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

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

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