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 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.

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

12.4 km from Overlook Mountain Trailhead

Eleanor

SAR 462

SAR 517 total

includes taxes & fees

22 Nov - 23 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 cafe with a wooden counter, bar stools, and a menu board above the counter.

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

2. Courtyard by Marriott Kingston

15.9 km from Overlook Mountain Trailhead

Roberta

SAR 444

SAR 497 total

includes taxes & fees

1 Nov - 2 Nov

A room with a leather armchair, a floor lamp, and a radiator.

3. Howland House

12.9 km from Overlook Mountain Trailhead

Ben

SAR 630

SAR 706 total

includes taxes & fees

23 Nov - 24 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.

4. Kaatskill Mountain Club & Condos by Vail Resorts

16.7 km from Overlook Mountain Trailhead

Nabeel

SAR 613

SAR 730 total

includes taxes & fees

23 Nov - 24 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.

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

A candy store with shelves of various treats and a sign that reads "TREATS".

5. Hampton Inn Kingston

15.7 km from Overlook Mountain Trailhead

Jennifer

SAR 459

SAR 514 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Overlook Hotel

13 km from Overlook Mountain Trailhead

Leonardo

SAR 650

SAR 728 total

includes taxes & fees

26 Oct - 27 Oct

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 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.

7. Residence Inn by Marriott Kingston

16.1 km from Overlook Mountain Trailhead

Kathy Reilly

SAR 522

SAR 584 total

includes taxes & fees

23 Nov - 24 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 hallway with intricate carvings on the walls and a large vase in the center.

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

8. Emerson Resort & Spa

13.9 km from Overlook Mountain Trailhead

Jeremy

SAR 624

SAR 699 total

includes taxes & fees

5 Nov - 6 Nov

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

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

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.

9. Hotel Mountain Brook

14 km from Overlook Mountain Trailhead

Stephen

SAR 915

SAR 988 total

includes taxes & fees

26 Oct - 27 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.

10. Howard Johnson by Wyndham Saugerties

12.4 km from Overlook Mountain Trailhead

Shirley

SAR 405

SAR 454 total

includes taxes & fees

15 Nov - 16 Nov

A hotel with a covered entrance, stone facade, and a sign indicating it is a Holiday Inn Express & Suites.

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

A row of refrigerators with shelves stocked with beverages and condiments.

A hotel reception area with a modern design, featuring a reception desk, a wall-mounted sign, and a decorative panel.

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

22 Nov - 23 Nov

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 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.

12. The Leeway

13.4 km from Overlook Mountain Trailhead

Shih-Chun

SAR 859

SAR 962 total

includes taxes & fees

2 Nov - 3 Nov

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 cozy lobby with patterned sofas, a wooden reception desk, and a mirror reflecting the interior.

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

13. Red Ranch Motel

17 km from Overlook Mountain Trailhead

Oleg

SAR 442

SAR 477 total

includes taxes & fees

1 Nov - 2 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.

14. Hudson Valley 9w Motel

14.7 km from Overlook Mountain Trailhead

Jerome

SAR 357

SAR 587 total

includes taxes & fees

25 Oct - 26 Oct

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

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

15. Comfort Inn Saugerties

12.5 km from Overlook Mountain Trailhead

Tevfik

SAR 537

SAR 602 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

16. Kingston Regency Inn

16.7 km from Overlook Mountain Trailhead

Stephen

SAR 469

SAR 577 total

includes taxes & fees

12 Nov - 13 Nov

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

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

A compact hotel room with a wooden dresser, a television, a microwave, a small refrigerator, a trash bin, and a chair.

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

17. Super 8 by Wyndham Kingston

16.8 km from Overlook Mountain Trailhead

BOCHENG

SAR 316

SAR 354 total

includes taxes & fees

1 Nov - 2 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 816 reviews	View
Courtyard by Marriott Kingston	8.8 Excellent 1,006 reviews	View
Howland House	9.2 Wonderful 10 reviews	View
Kaatskill Mountain Club & Condos by Vail Resorts	9.2 Wonderful 440 reviews	View
Hampton Inn Kingston	9.0 Wonderful 1,002 reviews	View

Top Overlook Mountain Trailhead Hotel Reviews

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

10/10 Excellent

"My Wife and I enjoyed our stay. The Accommodations were perfect for a getaway weekend in the Town Of Woodstock, Felt very private nestled back in the woods. The House was perfect."

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

10/10 Excellent

"Grat place to stay while exploring the Catskills"

Twin Gables of Woodstock

10/10 Excellent

"Location in downtown Woodstock was great- parking was easy. Loved the rooftop patio - great place to enjoy a coffee. Rooms were very nice and large."

Woodstock House on 35 private acres Mountain Views

10/10 Excellent

"Vicky's property was truly exceptional. The house felt like a cared-for and well-maintained place where friends and family stay, not just an anonymous property being managed by an absent landlord. It was so refreshing to have comprehensive instructions for the house, an immaculately kept space, and a location that's convenient to Woodstock while still remaining secluded and private. Couldn't recommend more highly!"

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."

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.

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. Courtyard by Marriott Kingston

3. Howland House

4. Kaatskill Mountain Club & Condos by Vail Resorts

5. Hampton Inn Kingston

6. Overlook Hotel

7. Residence Inn by Marriott Kingston

8. Emerson Resort & Spa

9. Hotel Mountain Brook

10. Howard Johnson by Wyndham Saugerties

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

12. The Leeway

13. Red Ranch Motel

14. Hudson Valley 9w Motel

15. Comfort Inn Saugerties

16. Kingston Regency Inn

17. Super 8 by Wyndham Kingston

Compare popular hotels close to Overlook Mountain Trailhead

Top Overlook Mountain Trailhead Hotel Reviews

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

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

Twin Gables of Woodstock

Woodstock House on 35 private acres Mountain Views

Pet Friendly Cabin Doh-Ray up @ 1500 ft

Botanical Studio Retreat in the Heart of Woodstock

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