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Our top choices for Overlook Mountain Trailhead hotels

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 4.713.249 ₫
5.278.839 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
The Woodstock Inn on the Millstream
Outdoor spa tub
The Herwood Inn

The Herwood Inn

The Herwood Inn
4.5 star property
3.4 km from Overlook Mountain Trailhead
9.6 out of 10, Exceptional, (90)
"Just lovely all around! I loved the attention to detail inside and on the grounds."
United States
karen
The price is 4.952.861 ₫
5.547.206 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
The Herwood Inn
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 4.978.071 ₫
5.575.440 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Morning Glory B n B Woodstock NY
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 4.306.145 ₫
4.822.880 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hotel Dylan
Reception
AutoCamp Catskills

AutoCamp Catskills

AutoCamp Catskills
5.0 star property
8.9 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (441)
"Great location. Amazing views. "
United States
Sarig
The price is 3.696.872 ₫
5.172.988 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
AutoCamp Catskills
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, (690)
"Clean rooms, very friendly and accommodating staff. Breakfast was very nice. Just overall wonderful hotel"
United States
Gideon
The price is 3.660.009 ₫
4.099.209 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
In-room safe, desk, laptop workspace, blackout curtains
Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston
2.5 star property
16.8 km from Overlook Mountain Trailhead
6.2 out of 10, (1002)
"Wonderful and friendly staff!"
United States
Ashley
The price is 2.170.991 ₫
2.431.668 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Super 8 by Wyndham Kingston
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, (1000)
"The hotel is great and great location. "
United States
Thomas
The price is 3.001.207 ₫
3.361.354 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn Kingston
View from room
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 6.468.210 ₫
7.902.986 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Diamond Mills Resort
Outdoor dining
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, (1000)
" Lean room, quiet location and comfortable bed."
United States
Barbara
The price is 2.887.194 ₫
3.233.658 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Courtyard by Marriott Kingston
Lobby
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, (790)
"Very nice stay"
United States
LOIS
The price is 3.001.734 ₫
3.361.941 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Residence Inn by Marriott Kingston
Indoor pool
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
12.4 km from Overlook Mountain Trailhead
7.6 out of 10, Good, (1001)
"Easy check in, friendly staff. "
United States
Daniel
The price is 2.817.417 ₫
3.155.505 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Howard Johnson by Wyndham Saugerties
Exterior
Overlook Hotel

Overlook Hotel

Overlook Hotel
2.0 star property
13 km from Overlook Mountain Trailhead
8.4 out of 10, Very good, (22)
"Owners were super friendly and location was great! "
United States
Elliott
The price is 5.805.985 ₫
6.502.702 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Overlook Hotel
Indoor pool
Comfort Inn Saugerties

Comfort Inn Saugerties

Comfort Inn Saugerties
2.5 star property
12.5 km from Overlook Mountain Trailhead
7.2 out of 10, Good, (712)
"This hotel is accommodating homeless people in the cold weather. ( I appreciate the need). I would have liked to know that before… my stay was diminished because I felt like I was staying at a homeless shelter and not a hotel that I paid $$ for. We won’t stay there again. "
United States
Janet
The price is 3.324.815 ₫
3.723.794 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn Saugerties
Front of property
Hudson Valley 9w Motel

Hudson Valley 9w Motel

Hudson Valley 9w Motel
2.0 star property
14.7 km from Overlook Mountain Trailhead
8.2 out of 10, Very good, (68)
"trains wake us up at 5 and 5:30 AM. affordable and convenient otherwise."
United States
Joe
The price is 2.501.445 ₫
4.118.168 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Hudson Valley 9w Motel
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, (1000)
"Great stay"
United States
Siju
The price is 3.028.065 ₫
3.391.434 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express & Suites Kingston-Ulster by IHG
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 3.813.519 ₫
4.270.888 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Phoenicia Lodge
Indoor pool
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center
2.5 star property
16.8 km from Overlook Mountain Trailhead
7.6 out of 10, Good, (1005)
"Nice staff, clean room, breakfast was tasty."
United States
Sarah
The price is 2.569.379 ₫
2.877.704 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Best Western Plus Kingston Hotel And Conference Center
Restaurant
Hotel Kinsley

Hotel Kinsley

Hotel Kinsley
3.5 star property
17.4 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (330)
"Room was great and staff very friendly"
Canada
Byron
The price is 5.798.531 ₫
7.547.914 ₫ total
includes taxes & fees
18 Jan - 19 Jan 2026
Hotel Kinsley
Exterior
Deer Mountain Inn

Deer Mountain Inn

Deer Mountain Inn
2.0 star property
16.7 km from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (5)
"Amazing!"
United States
gabrielle
The price is 10.427.076 ₫
11.919.517 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Deer Mountain Inn
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.
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.