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Check prices for these dates

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14 Nov - 15 Nov
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15 Nov - 16 Nov
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20 Nov - 22 Nov
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Our top choices for Overlook Mountain Trailhead hotels

A buffet with various food items, including omelets and baked goods, served in metal containers.

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

Holiday Inn Express & Suites Kingston-Ulster by IHG
2.5 star property
9 mi from Overlook Mountain Trailhead
9.4 out of 10, Exceptional, (1,000 reviews)
"The room was clean and spacious. The bathroom was suitable for elderly guests such as my mother. The buffet breakfast was excellent too"
United States
Timothy
The price is £97
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express & Suites Kingston-Ulster by IHG
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

2. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
9.8 mi from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (1,002 reviews)
"Always a nice stay."
United States
Marina
The price is £126
includes taxes & fees
29 Nov - 30 Nov
Hunter Lodge, a Bluebird by Lark
A white house with a green door, black trim, and a porch with a lantern.

3. Twin Gables of Woodstock

Twin Gables of Woodstock
3.0 star property
2.1 mi from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (233 reviews)
"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."
United States
Barbara
The price is £147
includes taxes & fees
17 Nov - 18 Nov
Twin Gables of Woodstock
A wooden cabin with large windows overlooking a forested area with a waterfall.

4. Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
2.1 mi from Overlook Mountain Trailhead
9.6 out of 10, Exceptional, (328 reviews)
"We had an amazing time and would highly recommend this beautiful hotel to anyone who’s looking for a retreat like atmosphere and lovely amenities. We will definitely be back."
United States
Amy
The price is £263
includes taxes & fees
16 Nov - 17 Nov
Woodstock Way Hotel
Bar (on property)

5. Howland House

Howland House
2.0 star property
8 mi from Overlook Mountain Trailhead
9.4 out of 10, Exceptional, (11 reviews)
"Beautiful refinished bed and breakfast with friendly staff and a great restaurant."
Canada
Ben
The price is £139
includes taxes & fees
17 Nov - 18 Nov
Howland House
An outdoor patio with a fire pit, seating, and a building in the background.

6. Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
3.0 star property
9.9 mi from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (1,007 reviews)
"Very nice hotel in a convenient area too."
United States
Yvette
The price is £93
includes taxes & fees
3 Dec - 4 Dec
Courtyard by Marriott Kingston
A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

7. The Graham & Co.

The Graham & Co.
3.0 star property
10.1 mi from Overlook Mountain Trailhead
9.4 out of 10, Exceptional, (69 reviews)
"Wonderful Stay"
United States
Daniel
The price is £93
includes taxes & fees
15 Nov - 16 Nov
The Graham & Co.
A multi-story building with outdoor seating and a stone-paved patio.

8. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
10.4 mi from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (452 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is £141
includes taxes & fees
29 Nov - 30 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

9. Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
8.7 mi from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (615 reviews)
"Overall amazing stay! Location, staff, food, aesthetic and coziness all 10/10!"
United States
Kim
The price is £175
includes taxes & fees
2 Dec - 3 Dec
Hotel Mountain Brook
A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.

10. Hampton Inn Kingston

Hampton Inn Kingston
2.5 star property
9.7 mi from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (1,000 reviews)
"Great stay. Great breakfast!"
United States
stephen
The price is £97
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn Kingston
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
2.5 star property
7.7 mi from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (831 reviews)
"Room was nice and spacious Breakfast was tasty done with a class and quick service"
United States
Artur
The price is £111
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

12. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
8.7 mi from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (120 reviews)
"Lovely setting, room was clean and comfortable. We ate dinner and breakfast at the hotel restaurant and enjoyed both meals."
United States
Kathleen
The price is £131
includes taxes & fees
13 Dec - 14 Dec
Emerson Resort & Spa
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.

13. AutoCamp Catskills

AutoCamp Catskills
5.0 star property
5.5 mi from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (597 reviews)
"Very nice área to camp, everything was super clean. Would go back anytime of the year"
United States
Natalia Pérez
The price is £115
includes taxes & fees
10 Dec - 11 Dec
AutoCamp Catskills
A dining area with a stone fireplace, wooden beams, and large windows.

14. Phoenicia Lodge

Phoenicia Lodge
2.0 star property
10.6 mi from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (73 reviews)
"friendly atmosphere, great area, cabin experience."
United States
Thomas
The price is £127
includes taxes & fees
15 Nov - 16 Nov
Phoenicia Lodge
A modern two-story house with a dark exterior, a front porch, and a small outdoor seating area.

15. Overlook Hotel

Overlook Hotel
2.0 star property
8 mi from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (66 reviews)
"Great space to comfortable fit a family of 4."
United States
Julie
The price is £147
includes taxes & fees
23 Nov - 24 Nov
Overlook Hotel
A spacious lobby with a fireplace, comfortable seating, and large windows.

16. Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston
3.0 star property
10 mi from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (1,004 reviews)
"It is close to everything and a well maintained property."
United States
Wendy
The price is £106
includes taxes & fees
13 Dec - 14 Dec
Residence Inn by Marriott Kingston
A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

17. SunView Motel

SunView Motel
2.5 star property
8.6 mi from Overlook Mountain Trailhead
8.6 out of 10, Excellent, (652 reviews)
"Very clean helpful staff lots of parking and very close to all stores."
United States
Deodat
The price is £113
includes taxes & fees
15 Nov - 16 Nov
SunView Motel
An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

18. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
7.7 mi from Overlook Mountain Trailhead
7.4 out of 10, Good, (1,001 reviews)
"Comfortable beds"
United States
Margaret
The price is £99
includes taxes & fees
6 Dec - 7 Dec
Howard Johnson by Wyndham Saugerties
A cozy room with wooden walls, a dining table with chairs, a fireplace, and a staircase.

19. The Leeway

The Leeway
2.0 star property
8.3 mi from Overlook Mountain Trailhead
10.0 out of 10, Exceptional, (24 reviews)
"Staff was helpful and friendly. Cabin was great"
Taiwan
Shih-Chun
The price is £178
includes taxes & fees
17 Nov - 18 Nov
The Leeway
A restaurant with orange seating, white tablecloths, and potted plants.

20. Hotel Kinsley

Hotel Kinsley
3.5 star property
10.8 mi from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (416 reviews)
"I would not stay here."
United States
Christopher
The price is £226
includes taxes & fees
13 Dec - 14 Dec
Hotel Kinsley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Compare popular hotels close to Overlook Mountain Trailhead

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Kingston-Ulster by IHG
2.5 star property
9.4
Exceptional
1,000 reviews
View
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.
Hunter Lodge, a Bluebird by Lark
3.0 star property
9.2
Wonderful
1,002 reviews
View
A white house with a green door, black trim, and a porch with a lantern.
Twin Gables of Woodstock
3.0 star property
9.8
Exceptional
233 reviews
View
A wooden cabin with large windows overlooking a forested area with a waterfall.
Woodstock Way Hotel
4.0 star property
9.6
Exceptional
328 reviews
View
Bar (on property)
Howland House
2.0 star property
9.4
Exceptional
11 reviews
View

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.
See properties

Top Overlook Mountain Trailhead Hotel Reviews

A white house with a green door, black trim, and a porch with a lantern.
Twin Gables of Woodstock

Twin Gables of Woodstock

Twin Gables of Woodstock
Woodstock

10/10 Excellent

Beautifully decorated in a homely style and in keeping with the Woodstock vibe. Excellent location for all the excellent bars and restaurants and shops. We also appreciated a TV free property!
United Kingdom
Kevin
Reviewed September 20, 2025
Twin Gables of Woodstock

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.