Hotels near Overlook Mountain Trailhead

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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, (193)
"Amazing stay!!! Super hippie vibe and lived every minute of it. "
United States
Heather
The price is P7,576
P8,486 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Twin Gables of Woodstock
Outdoor spa tub
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, (93)
"Quaint, quirky, very environmentally conscious, fun old vinyls, and a cedar fragrant hot tub!"
United States
Dietlinde
The price is P10,454
P11,708 total
includes taxes & fees
Jan 20 - Jan 21, 2026
The Herwood Inn
View from room
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, (217)
"The room and views were lovely, and we loved the Tannery cafe!"
United States
Katherine
Woodstock Way Hotel
Exterior
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, (517)
"everything was excellent amazing place and great location"
United States
Grigoriy
The price is P8,751
P9,451 total
includes taxes & fees
Jan 6 - Jan 7, 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 P9,605
P10,758 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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 P10,513
P11,775 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Woodstock Inn on the Millstream
Fireplace
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 P9,109
P10,202 total
includes taxes & fees
Jan 6 - Jan 7, 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, (1000)
"Great room, friendly staff "
United States
Jamila
The price is P7,297
P8,173 total
includes taxes & fees
Dec 28 - Dec 29
Holiday Inn Express & Suites Kingston-Ulster by IHG
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 P14,428
P17,628 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Diamond Mills Resort
Reception
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 P9,480
P12,924 total
includes taxes & fees
Jan 4 - Jan 5, 2026
AutoCamp Catskills
Dinner served
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 P9,075
P11,072 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hunter Lodge, a Bluebird by Lark
Property grounds
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 P14,042
P17,300 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Emerson Resort & Spa
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, (323)
"Beautiful resort. "
United States
Kelly
The price is P12,862
P15,317 total
includes taxes & fees
Jan 6 - Jan 7, 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 P6,223
P6,970 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Phoenicia Lodge
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, (1001)
"The hotel is great and great location. "
United States
Thomas
The price is P6,707
P7,512 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hampton Inn Kingston
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)
"I loved the guest room with the pool table and self attend bar."
United States
Chavez
Deer Mountain Inn
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 traveler
The price is P11,100
P12,432 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Morning Glory B n B Woodstock NY
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, (694)
"Nice clean rooms, excellent coffee at breakfast and my son loved the pancakes."
United States
Gary
The price is P8,180
P9,161 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
Restaurant
Hotel Kinsley

Hotel Kinsley

Hotel Kinsley
3.5 star property
17.4 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (332)
"Room was great and staff very friendly"
Canada
Byron
The price is P12,930
P16,831 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Hotel Kinsley
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, (803)
"Staff was very kind and courteous "
United States
Natasha
The price is P6,695
P7,499 total
includes taxes & fees
Jan 8 - Jan 9, 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

Woodstock Way Hotel

Woodstock Way Hotel

10/10 Excellent
"The room and views were lovely, and we loved the Tannery cafe!"
Katherine 1-night trip
Posted 12 days ago
Woodstock Way Hotel
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

10/10 Excellent
"great reception!"
travel 1-night trip
Posted 3 months ago
Morning Glory B n B Woodstock NY

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 trip 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 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 225 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.
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.