The Best Hotels Closest to Overlook Mountain Trailhead in Woodstock for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Overlook Mountain Trailhead hotels

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

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

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

A Holiday Inn Express & Suites sign with a clear view of the hotel building in the background.

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

12.4 km from Overlook Mountain Trailhead

Linda

SAR 462

SAR 517 total

includes taxes & fees

15 Nov - 16 Nov

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 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.

2. Twin Gables of Woodstock

3.4 km from Overlook Mountain Trailhead

Coleen

SAR 540

SAR 605 total

includes taxes & fees

16 Nov - 17 Nov

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 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.

3. Courtyard by Marriott Kingston

15.9 km from Overlook Mountain Trailhead

Ana

SAR 475

SAR 532 total

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.

4. Hampton Inn Kingston

15.7 km from Overlook Mountain Trailhead

Jennifer

SAR 459

SAR 514 total

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 large garage and a vintage camper parked in the driveway.

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.

5. AutoCamp Catskills

8.9 km from Overlook Mountain Trailhead

Raquel

SAR 539

SAR 751 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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.

6. SunView Motel

13.9 km from Overlook Mountain Trailhead

Furquan

SAR 490

SAR 530 total

includes taxes & fees

17 Nov - 18 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 hotel room with two beds, a TV, a dresser, and a door leading to another room.

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

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

8. Hunter Lodge, a Bluebird by Lark

15.8 km from Overlook Mountain Trailhead

Marina

SAR 475

SAR 594 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

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.

9. Residence Inn by Marriott Kingston

16.1 km from Overlook Mountain Trailhead

Lamisa

SAR 537

SAR 601 total

includes taxes & fees

15 Nov - 16 Nov

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.

10. Emerson Resort & Spa

13.9 km from Overlook Mountain Trailhead

Lisa

SAR 618

SAR 692 total

includes taxes & fees

15 Nov - 16 Nov

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.

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

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

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

14.5 km from Overlook Mountain Trailhead

Timothy

SAR 458

SAR 513 total

includes taxes & fees

15 Nov - 16 Nov

A landscaped garden with coniferous trees and a bed of yellow flowers.

A compact kitchenette with a microwave, a small refrigerator, and a flat-screen TV mounted on the wall.

A flat-screen TV mounted on a wall above a wooden countertop.

12. Hudson Valley 9w Motel

14.7 km from Overlook Mountain Trailhead

Jerome

SAR 357

SAR 587 total

includes taxes & fees

18 Oct - 19 Oct

A living room with a leather sofa, a wooden coffee table, a TV on a wooden stand, and a window with curtains.

A storefront with a 'DEFACE' sign, a 'NO PETS' notice, and various seasonal decorations including pumpkins and flowers.

A hotel room with two beds, a wooden dresser, a television, and a stone wall.

A swimming pool with lounge chairs and a red building in the background.

13. Red Ranch Motel

17 km from Overlook Mountain Trailhead

Oleg

SAR 401

SAR 433 total

includes taxes & fees

3 Nov - 4 Nov

An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.

A hotel room with a bed, a desk, a sofa, and two lamps.

A buffet area with various food items, a coffee machine, and a refrigerator.

A hotel room with a bed, desk, chair, TV, and kitchenette.

14. Comfort Inn Saugerties

12.5 km from Overlook Mountain Trailhead

John

SAR 537

SAR 601 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a nightstand, a lamp, and two framed pictures on the wall.

A multi-story hotel with a flat roof, large windows, and a brick facade.

A bathroom with a walk-in shower, grab bars, and a white tiled wall.

A hotel lobby with a reception desk, two armchairs, a small table, and a lamp.

15. Super 8 by Wyndham Kingston

16.8 km from Overlook Mountain Trailhead

BOCHENG

SAR 316

SAR 354 total

includes taxes & fees

17 Nov - 18 Nov

A swimming pool with a glass ceiling, indoor seating, and a brick wall.

A restaurant with booths, tables, and a bar area.

A bar area with a long counter, multiple bar stools, and a television mounted above the bar.

A hotel room with a sofa, ottoman, desk, chair, television, and a mirror.

16. Kingston Regency Inn

16.7 km from Overlook Mountain Trailhead

Stephen

SAR 473

SAR 581 total

includes taxes & fees

2 Nov - 3 Nov

View all properties

Compare popular hotels close to Overlook Mountain Trailhead

Property	Property class	Guest rating
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG	8.8 Excellent 814 reviews	View
Twin Gables of Woodstock	9.8 Exceptional 229 reviews	View
Courtyard by Marriott Kingston	8.8 Excellent 1,002 reviews	View
Hampton Inn Kingston	9.0 Wonderful 1,002 reviews	View
AutoCamp Catskills	9.0 Wonderful 586 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."

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"

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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 354

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 Saugerties - Hudson Valley by IHG

2. Twin Gables of Woodstock

3. Courtyard by Marriott Kingston

4. Hampton Inn Kingston

5. AutoCamp Catskills

6. SunView Motel

7. Howard Johnson by Wyndham Saugerties

8. Hunter Lodge, a Bluebird by Lark

9. Residence Inn by Marriott Kingston

10. Emerson Resort & Spa

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

12. Hudson Valley 9w Motel

13. Red Ranch Motel

14. Comfort Inn Saugerties

15. Super 8 by Wyndham Kingston

16. Kingston Regency Inn

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

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

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

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