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30 Sep - 1 Oct
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1 Oct - 2 Oct
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Our top choices for Overlook Mountain Trailhead hotels

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.
A park with picnic tables and chairs, a tall cylindrical structure, and autumn-colored trees.
A large tree in a grassy area with a small white building in the background.
A bathroom with three sinks, a trash can, and a chair.

1. SunView Motel

SunView Motel
13.9 km from Overlook Mountain Trailhead
United States
Victoria
AED 383
AED 414 total
includes taxes & fees
1 Oct - 2 Oct
SunView Motel
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.
A cozy lounge area with a sofa, armchairs, a coffee table, and a bookshelf.
A modern living room with a large window, a blue sofa, a wooden coffee table, and a rustic wooden wall.
A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.

2. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
15.8 km from Overlook Mountain Trailhead
United States
Shubhangi
AED 528
AED 649 total
includes taxes & fees
26 Oct - 27 Oct
Hunter Lodge, a Bluebird by Lark
A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.
A reception area with a wooden desk, a blue wall with a logo, and shelves with products.
A historic hotel with a prominent tower and a brick facade.
A dining area with a brick fireplace, wooden beams, and a chandelier.

3. Diamond Mills Resort

Diamond Mills Resort
14.2 km from Overlook Mountain Trailhead
United States
Al
AED 976
AED 1,185 total
includes taxes & fees
5 Oct - 6 Oct
Diamond Mills Resort
A wooden cabin with large windows overlooking a forested area with a waterfall.
A two-story wooden house with a stone retaining wall, a stone pathway, and a small garden with various plants.
A modern living room with a grey sofa, a small round table, and a hanging light fixture.
A modern bedroom with a wooden bed, a desk, and large windows.

4. Woodstock Way Hotel

Woodstock Way Hotel
3.4 km from Overlook Mountain Trailhead
United States
Vannetta
AED 1,262
AED 1,557 total
includes taxes & fees
20 Oct - 21 Oct
Woodstock Way Hotel
A modern two-story house with a dark exterior, a front porch, and a small outdoor seating area.
A bedroom with a bed, desk, chair, and a window with curtains.
A room with a wooden desk, a chair, a coffee maker, a framed picture, a vase with flowers, and a bed.
A modern building with a large driveway, a covered outdoor seating area, and a large tree in the background.

5. Overlook Hotel

Overlook Hotel
13 km from Overlook Mountain Trailhead
United States
Leonardo
AED 636
AED 713 total
includes taxes & fees
5 Oct - 6 Oct
Overlook Hotel
An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.
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.
A hotel room with two beds, a TV, a dresser, and a door leading to another room.

6. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
12.4 km from Overlook Mountain Trailhead
United States
Richard
AED 510
AED 571 total
includes taxes & fees
13 Oct - 14 Oct
Howard Johnson by Wyndham Saugerties
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.
A modern interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.
A modern house with a sloped roof, large windows, and a well-maintained lawn.
A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.

7. AutoCamp Catskills

AutoCamp Catskills
8.9 km from Overlook Mountain Trailhead
United States
Raquel
AED 528
AED 735 total
includes taxes & fees
29 Oct - 30 Oct
AutoCamp Catskills
A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.
A campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.
A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.
A corridor with white walls, wooden slats, and a concrete floor.

8. The Graham & Co.

The Graham & Co.
16.2 km from Overlook Mountain Trailhead
United States
Daniel
AED 663
AED 742 total
includes taxes & fees
1 Oct - 2 Oct
The Graham & Co.
A spacious living area with a fireplace, a dining table with chairs, and a television mounted on the wall.
An indoor swimming pool with clear water, a 5 feet deep sign, and a tiled floor.
A Hampton Inn hotel with a modern facade, multiple entry points, and a well-lit entrance.
A candy store with shelves of various treats and a sign that reads "TREATS".

9. Hampton Inn Kingston

Hampton Inn Kingston
15.7 km from Overlook Mountain Trailhead
United States
stephen
AED 514
AED 576 total
includes taxes & fees
26 Oct - 27 Oct
Hampton Inn Kingston
A hotel room with two beds, a desk, and a large window.
A stone building with multiple windows and a door, situated on a street corner.
A modern building with multiple windows and a landscaped area with decorative pumpkins and a tree.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

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

Holiday Inn Express & Suites Kingston-Ulster by IHG
14.5 km from Overlook Mountain Trailhead
United States
Cindy
AED 511
AED 572 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express & Suites Kingston-Ulster by IHG
A spacious lobby with a fireplace, comfortable seating, and large windows.
An outdoor patio with a fire pit, wicker furniture, and a red building in the background.
A multi-story hotel with a well-lit entrance, a flag, and a sign indicating it is a Marriott Residence Inn.
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.

11. Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston
16.1 km from Overlook Mountain Trailhead
United States
Harold
AED 525
AED 588 total
includes taxes & fees
4 Oct - 5 Oct
Residence Inn by Marriott Kingston
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.
A couple standing on a wooden deck overlooking a landscaped garden with a river view.
A hallway with intricate carvings on the walls and a large vase in the center.
A spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

12. Emerson Resort & Spa

Emerson Resort & Spa
13.9 km from Overlook Mountain Trailhead
Canada
Ashley
AED 776
AED 869 total
includes taxes & fees
1 Oct - 2 Oct
Emerson Resort & Spa
A white house with a porch, surrounded by lush greenery and two green Adirondack chairs.
A spacious living room with a fireplace, two sofas, a coffee table, and a TV mounted above the fireplace.
A picnic setup with a table, food, drinks, and binoculars by a stream.
A bedroom with a large bed, a fireplace, a TV, and a painting on the wall.

13. The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream
3.8 km from Overlook Mountain Trailhead
United States
Carolyn
AED 841
AED 942 total
includes taxes & fees
1 Oct - 2 Oct
The Woodstock Inn on the Millstream
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 bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.
A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

14. Hotel Mountain Brook

Hotel Mountain Brook
14 km from Overlook Mountain Trailhead
United States
Kristen
AED 970
AED 1,047 total
includes taxes & fees
20 Oct - 21 Oct
Hotel Mountain Brook
A living room with a fireplace, green sofa, and a leopard print armchair.
A wooden deck with outdoor seating and a house in the background.
A white house with a green door, black trim, and a porch with a lantern.
A hallway with a patterned floor, a potted plant, a chandelier, and a door with a decorative mirror.

15. Twin Gables of Woodstock

Twin Gables of Woodstock
3.4 km from Overlook Mountain Trailhead
United States
Coleen
AED 859
AED 1,031 total
includes taxes & fees
28 Oct - 29 Oct
Twin Gables of Woodstock
A multi-story building with outdoor seating and a stone-paved patio.
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.
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

16. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
16.7 km from Overlook Mountain Trailhead
United Kingdom
Ryan
AED 736
AED 877 total
includes taxes & fees
28 Oct - 29 Oct
Kaatskill Mountain Club & Condos by Vail Resorts
A dining area with a stone fireplace, wooden beams, and large windows.
Exterior
A row of red buildings with a gravel driveway and a bench outside.
A spacious living room with a stone fireplace, wooden beams, and large windows.

17. Phoenicia Lodge

Phoenicia Lodge
17 km from Overlook Mountain Trailhead
United States
Thomas
AED 636
AED 712 total
includes taxes & fees
28 Oct - 29 Oct
Phoenicia Lodge
A serene garden with a stone pathway, a small bridge, and a bench.
A hallway with a framed portrait on the wall, a door to the right, and a window on the left.
A room with a large tapestry, two wicker chairs, a small table, and a globe lamp.
A dining area with a wooden table, chairs, a chandelier, and a view of the outdoors through large windows.

18. Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY
3.4 km from Overlook Mountain Trailhead
United States
Lucian
AED 841
AED 942 total
includes taxes & fees
6 Oct - 7 Oct
Morning Glory B n B Woodstock NY
A snow-covered lodge with a stone chimney, lit windows, and snow-laden trees in front.
A wooden deck with a fire pit surrounded by Adirondack chairs.
A wooden interior with a staircase, a wooden desk with a lamp, and a vase with flowers.
A bar area with wooden bar stools, a fireplace, and a variety of bottles and glasses on shelves.

19. Deer Mountain Inn

Deer Mountain Inn
16.7 km from Overlook Mountain Trailhead
United States
Julia
AED 1,440
AED 1,654 total
includes taxes & fees
27 Oct - 28 Oct
Deer Mountain Inn
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Top Overlook Mountain Trailhead Hotel Reviews

Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!

Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!

10/10 Excellent
"Judy’s place was so charming! My wife and I eloped in Kingston and the cottage was a perfect place for us to celebrate and have a getaway for the weekend. We would absolutely return!"
Elena D. 3-night trip
Posted 22 hours ago
Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!
The Herwood Inn

The Herwood Inn

10/10 Excellent
"Wonderful experience! The room was beautiful and equipped with everything you could think of. We had such a lovely,relaxing stay."
Diana 1-night trip
Posted 2 days ago
The Herwood Inn
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10/10 Excellent
"Everything about our stay at Junebug was top shelf. For a part of two it is ideal, and even with us having a third adult with us (for an extra, very reasonable fee), who used the LR with the pull-out sofa, there was plenty of private space, and a cozy kitchenette common space. Well stocked, well layed out kitchen. No range, but there is an electric portable burner if needed, and an outside grill. The place is spotless, and the hosts, who are next door, respect your privacy yet are available if you have questions. How perfect is that?Plus we had special medical needs that were easily accommodated. (I advise you check before booking, as we did). We hope to stay there again, it’s like a little wonderland in the country. Thank you, John and Molly!"
Natalie M. 2-night trip
Posted 3 days ago
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

10/10 Excellent
"Lovely location, wind blowing through the trees, rain pattering, just beautiful scenery and wildlife. Great places to eat nearby, The Red Onion is excellent, Bread Alone was busy but good, so much we did not get to do, but the town seems cozy and fun!"
Mary E. 7-night trip
Posted 4 days ago
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
Botanical Studio Retreat in the Heart of Woodstock

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."
Jeffrey 3-night trip
Posted 5 days ago
Botanical Studio Retreat in the Heart of Woodstock
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

10/10 Excellent
"We had a wonderful weekend! The house was clean, big, beautiful and very well equipped. The host Greg was super responsive. The pool is nice and the outside space is great. There are many hiking trails around and the town is super cute, many restaurants cafes and small shops. We are planning to return in the future!"
Anonymous traveler 3-night trip
Posted 2 weeks ago
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
Maple House: Private/Romantic Walk-to-Town Oasis

Maple House: Private/Romantic Walk-to-Town Oasis

10/10 Excellent
"Beautiful property, inside and out!"
Tracy B. 3-night trip
Posted 2 weeks ago
Maple House: Private/Romantic Walk-to-Town Oasis
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

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"
mark c. 3-night trip
Posted 2 months ago
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

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."
Denise W. 6-night trip
Posted 2 months ago
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.