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Our top choices for Overlook Mountain Trailhead hotels

Books, music library, stereo
Twin Gables of Woodstock

Twin Gables of Woodstock

Twin Gables of Woodstock
3.0 star property
3.4 km from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (192)
"Amazing stay!!! Super hippie vibe and lived every minute of it. "
United States
Heather
The price is ฿4,052
฿4,538 total
includes taxes & fees
4 Jan - 5 Jan 2026
Twin Gables of Woodstock
Exterior detail
The Herwood Inn

The Herwood Inn

The Herwood Inn
4.5 star property
3.4 km from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (92)
"Quaint, quirky, very environmentally conscious, fun old vinyls, and a cedar fragrant hot tub!"
United States
Dietlinde
The price is ฿5,251
฿5,882 total
includes taxes & fees
20 Jan - 21 Jan 2026
The Herwood Inn
Superior Room, Fireplace, River View | Egyptian cotton sheets, premium bedding, down duvets, minibar
Woodstock Way Hotel

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
3.4 km from Overlook Mountain Trailhead
9.6 out of 10, Exceptional, (216)
"The room and views were lovely, and we loved the Tannery cafe!"
United States
Katherine
Woodstock Way Hotel
Room, Ensuite (Superior Main Lodge Room) - This unit is not pet friendly | Premium bedding, bed sheets
Hotel Mountain Brook

Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
14 km from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (516)
"everything was excellent amazing place and great location"
United States
Grigoriy
The price is ฿4,680
฿5,054 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Mountain Brook
Reception
Hotel Dylan

Hotel Dylan

Hotel Dylan
2.0 star property
7.6 km from Overlook Mountain Trailhead
9.4 out of 10, Exceptional, (40)
"Close to restaurants and shopping. Nice vibe."
United States
sara
The price is ฿5,136
฿5,753 total
includes taxes & fees
23 Dec - 24 Dec
Hotel Dylan
Lobby
The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream
3.0 star property
3.8 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (203)
"Love this place!"
United States
Robert
The price is ฿5,622
฿6,297 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Woodstock Inn on the Millstream
Seasonal outdoor pool
The Graham & Co.

The Graham & Co.

The Graham & Co.
3.0 star property
16.2 km from Overlook Mountain Trailhead
9.6 out of 10, Exceptional, (22)
"A beautiful and relaxing getaway in the Catskills. Highly recommended. The room and grounds are clean and well maintained. The staff is friendly and attentive without being intrusive."
United States
Brian
The price is ฿4,871
฿5,456 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Graham & Co.
Free daily continental breakfast
Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG
2.5 star property
14.5 km from Overlook Mountain Trailhead
9.4 out of 10, Exceptional, (1002)
"Great room, friendly staff "
United States
Jamila
The price is ฿3,675
฿4,116 total
includes taxes & fees
18 Jan - 19 Jan 2026
Holiday Inn Express & Suites Kingston-Ulster by IHG
Deluxe Room, 1 King Bed, Balcony | Premium bedding, pillow-top beds, minibar, in-room safe
Diamond Mills Resort

Diamond Mills Resort

Diamond Mills Resort
3.5 star property
14.2 km from Overlook Mountain Trailhead
9.4 out of 10, Exceptional, (346)
"Amazing view from the room. We had a great stay. "
United States
Adam
The price is ฿7,715
฿9,427 total
includes taxes & fees
8 Jan - 9 Jan 2026
Diamond Mills Resort
Premium bedding, down duvets, Tempur-Pedic beds, in-room safe
AutoCamp Catskills

AutoCamp Catskills

AutoCamp Catskills
5.0 star property
8.9 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (442)
"Great location. Amazing views. "
United States
Sarig
The price is ฿5,060
฿6,898 total
includes taxes & fees
4 Jan - 5 Jan 2026
AutoCamp Catskills
Front of property – evening/night
Emerson Resort & Spa

Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
13.9 km from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (46)
"Very clean and cozy "
United States
Robert
The price is ฿7,509
฿9,252 total
includes taxes & fees
4 Jan - 5 Jan 2026
Emerson Resort & Spa
Lobby sitting area
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
15.8 km from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (828)
"Wonderful views, location, and accommodations. I would gladly return to Hunter Lodge"
United States
Russel
The price is ฿4,844
฿5,910 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hunter Lodge, a Bluebird by Lark
Reception
Hampton Inn Kingston

Hampton Inn Kingston

Hampton Inn Kingston
2.5 star property
15.7 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (1007)
"The hotel is great and great location. "
United States
Thomas
The price is ฿3,580
฿4,009 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Kingston
Exterior
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
16.7 km from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (322)
"Beautiful resort. "
United States
Kelly
The price is ฿6,878
฿8,191 total
includes taxes & fees
6 Jan - 7 Jan 2026
Kaatskill Mountain Club & Condos by Vail Resorts
Dining
Phoenicia Lodge

Phoenicia Lodge

Phoenicia Lodge
2.0 star property
17 km from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (32)
"Had a great stay! "
United States
Lace
The price is ฿4,549
฿5,094 total
includes taxes & fees
23 Dec - 24 Dec
Phoenicia Lodge
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY
3.0 star property
3.4 km from Overlook Mountain Trailhead
8.4 out of 10, Very good, (155)
"Beautiful historic home. We had a nice stay. "
United States
Anonymous traveller
The price is ฿5,936
฿6,648 total
includes taxes & fees
4 Jan - 5 Jan 2026
Morning Glory B n B Woodstock NY
Restaurant
Hotel Kinsley

Hotel Kinsley

Hotel Kinsley
3.5 star property
17.4 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (331)
"Room was great and staff very friendly"
Canada
Byron
The price is ฿6,914
฿9,001 total
includes taxes & fees
20 Jan - 21 Jan 2026
Hotel Kinsley
Exterior
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
2.5 star property
12.4 km from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (691)
"Clean rooms, very friendly and accommodating staff. Breakfast was very nice. Just overall wonderful hotel"
United States
Gideon
The price is ฿4,366
฿4,890 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
Front of property
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
3.0 star property
15.9 km from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (1002)
"Great stay!!"
United States
Anita
The price is ฿3,711
฿4,156 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Kingston
View from property
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston
3.0 star property
16.1 km from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (799)
"This was perfect for our family of 5. The beds were very comfortable. My son said he had the best shower of his life. The breakfast was very good with lots of options. A perfect overnight after the Polar Express."
United States
John
The price is ฿3,581
฿4,010 total
includes taxes & fees
1 Jan - 2 Jan 2026
Residence Inn by Marriott Kingston
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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Top Overlook Mountain Trailhead Hotel Reviews

Hotels near other Overlook Mountain Trailhead attractions

Woodstock Music Shop

4.5/5 (6 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

Karma Triyana Dharmachakra Monastery

5.0/5 (4 reviews)
Learn about the local history of Woodstock with a stop at Karma Triyana Dharmachakra Monastery. 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 225 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 225 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?
Get outside and spend some time strolling around The Comeau Property, Woodstock Dog Park and Thorn Preserve - Catskill Center. For cultural attractions near Overlook Mountain Trailhead, head to Bethel Woods Museum, Colony and SweetHeart Gallery. Explore nature at Platte Clove Preserve - Catskill Center and Opus 40.