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4 Oct - 5 Oct
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9 Oct - 11 Oct
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Our top choices for Overlook Mountain Trailhead hotels

An outdoor patio with a fire pit, seating, and a building in the background.
A modern hotel room with a grey sofa, an orange armchair, a small wooden table, and a large window with sheer curtains.
A modern cafe with a wooden counter, bar stools, and a menu board above the counter.
A Courtyard by Marriott hotel with a modern facade, large windows, and a well-maintained entrance area.

1. Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
15.9 km from Overlook Mountain Trailhead
Canada
Ana
SAR 476
SAR 533 total
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott Kingston
A room with two beds, wooden headboards, a red accent wall, and wooden flooring.
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.
A park with picnic tables and chairs, a tall cylindrical structure, and autumn-colored trees.

2. SunView Motel

SunView Motel
13.9 km from Overlook Mountain Trailhead
United States
Victoria
SAR 391
SAR 423 total
includes taxes & fees
5 Oct - 6 Oct
SunView Motel
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 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.
A modern house with a sloped roof, large windows, and a well-maintained lawn.
A modern interior with a wooden dining table, chairs, a sofa, and a bar area with wine bottles.

3. AutoCamp Catskills

AutoCamp Catskills
8.9 km from Overlook Mountain Trailhead
United States
Raquel
SAR 476
SAR 680 total
includes taxes & fees
4 Nov - 5 Nov
AutoCamp Catskills
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.
A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.
A bedroom with a large window offering a view of a forested mountain.
A cozy lounge area with a sofa, armchairs, a coffee table, and a bookshelf.

4. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
15.8 km from Overlook Mountain Trailhead
United States
Shubhangi
SAR 507
SAR 629 total
includes taxes & fees
1 Nov - 2 Nov
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 bar with a patterned floor, bar stools, and a bar counter with taps.
A dining area with a brick fireplace, wooden beams, and a chandelier.

5. Diamond Mills Resort

Diamond Mills Resort
14.2 km from Overlook Mountain Trailhead
United States
Al
SAR 1,188
SAR 1,424 total
includes taxes & fees
5 Oct - 6 Oct
Diamond Mills Resort
An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.
A hotel room with two beds, a TV, a dresser, and a door leading to another room.
A Howard Johnson Inn with a beige facade, red trim, and a clear blue sky with clouds.
A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.

6. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
12.4 km from Overlook Mountain Trailhead
United States
Richard
SAR 412
SAR 462 total
includes taxes & fees
2 Nov - 3 Nov
Howard Johnson by Wyndham Saugerties
A modern two-story house with a dark exterior, a front porch, and a small outdoor seating area.
A modern bathroom with a marble floor, a large mirror, and a towel rack.
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.

7. Overlook Hotel

Overlook Hotel
13 km from Overlook Mountain Trailhead
United States
Leonardo
SAR 651
SAR 729 total
includes taxes & fees
5 Oct - 6 Oct
Overlook Hotel
A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.
A pool area with a wooden deck, benches, and umbrellas.
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
SAR 586
SAR 657 total
includes taxes & fees
2 Nov - 3 Nov
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
SAR 517
SAR 579 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Kingston
A hotel room with two beds, a desk, and a large window.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.
A modern building with multiple windows and a landscaped area with decorative pumpkins and a tree.
An outdoor patio with a round table and orange chairs, a black metal fence, and string lights.

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
SAR 488
SAR 547 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express & Suites Kingston-Ulster by IHG
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.
A bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.
A modern hotel lobby with a wooden floor, a reception desk, two patterned armchairs, a chandelier, and a view of the outdoors through a glass door.
A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

11. Hotel Mountain Brook

Hotel Mountain Brook
14 km from Overlook Mountain Trailhead
United States
Kristen
SAR 879
SAR 949 total
includes taxes & fees
3 Nov - 4 Nov
Hotel Mountain Brook
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 room with a bed, a window with curtains, a nightstand with a lamp, and a vase with flowers.
A wooden interior with a staircase, a wooden desk with a lamp, and a vase with flowers.

12. Deer Mountain Inn

Deer Mountain Inn
16.7 km from Overlook Mountain Trailhead
United States
Julia
SAR 1,487
SAR 1,707 total
includes taxes & fees
27 Oct - 28 Oct
Deer Mountain Inn
A wooden cabin with large windows overlooking a forested area with a waterfall.
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.
A two-story wooden house with a stone retaining wall, a stone pathway, and a small garden with various plants.

13. Woodstock Way Hotel

Woodstock Way Hotel
3.4 km from Overlook Mountain Trailhead
United States
Vannetta
SAR 1,227
SAR 1,521 total
includes taxes & fees
2 Nov - 3 Nov
Woodstock Way Hotel
A living room with a fireplace, green sofa, and a leopard print armchair.
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.
A wooden deck with outdoor seating and a house in the background.

14. Twin Gables of Woodstock

Twin Gables of Woodstock
3.4 km from Overlook Mountain Trailhead
United States
Coleen
SAR 728
SAR 874 total
includes taxes & fees
2 Nov - 3 Nov
Twin Gables of Woodstock
A multi-story building with outdoor seating and a stone-paved patio.
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
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.

15. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
16.7 km from Overlook Mountain Trailhead
United Kingdom
Ryan
SAR 670
SAR 797 total
includes taxes & fees
2 Nov - 3 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A blue door with a white frame, a small table with a chair, a rug, and potted plants on the porch.
A room with a dark wooden chair, a small round table with potted plants, and a framed picture on the wall.
A red brick building with a blue door, white windows, and a small garden with a chair and plants.
A living room with a sofa, a round table, and a wooden bench. There is a door and a framed picture on the wall.

16. The Wiltwyck

The Wiltwyck
17.5 km from Overlook Mountain Trailhead
United States
ALEJANDRO
SAR 510
SAR 782 total
includes taxes & fees
21 Oct - 22 Oct
The Wiltwyck
A dining area with a stone fireplace, wooden beams, and large windows.
A spacious living room with a stone fireplace, wooden beams, and large windows.
A row of red buildings with a gravel driveway and a bench outside.
A hammock between trees, a red cabin, and a blue chair in a wooded area.

17. Phoenicia Lodge

Phoenicia Lodge
17 km from Overlook Mountain Trailhead
United States
Thomas
SAR 650
SAR 728 total
includes taxes & fees
28 Oct - 29 Oct
Phoenicia Lodge
A serene garden with a stone pathway, a small bridge, and a bench.
A dining area with a wooden table, chairs, a chandelier, and a view of the outdoors through large windows.
A rustic wooden pergola in a garden with a house in the background.
A hallway with a framed portrait on the wall, a door to the right, and a window on the left.

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
SAR 822
SAR 921 total
includes taxes & fees
2 Nov - 3 Nov
Morning Glory B n B Woodstock NY
A modern house with a wooden deck, a fire pit, and a covered outdoor seating area.
A modern kitchen with a wooden island, black cabinets, and a built-in refrigerator. There are hanging plants, a coffee machine, and shelves with dishes and utensils.
A wooden sign with the text "Mitchell Manor" hanging from a building.
A two-story house with a porch, a sign for 'The Herwood Inn', and a well-maintained lawn.

19. The Herwood Inn

The Herwood Inn
3.4 km from Overlook Mountain Trailhead
United States
Diana
SAR 1,020
SAR 1,143 total
includes taxes & fees
7 Oct - 8 Oct
The Herwood Inn
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Top Overlook Mountain Trailhead Hotel Reviews

The Herwood Inn

The Herwood Inn

10/10 Excellent
"Loved our cozy, retro studio. All our necessities were addressed from beautiful thick bath towels to luxurious bedding & complimentary coffee. A turntable with records and lovely soaps and air freshener were added surprises. Location was extremely convenient for walking to shops & restaurants. Adam, our host was very helpful with restaurant suggestions and he made sure we were comfortable. We highly recommend a stay at the Herwood!"
Diana 1-night trip
Posted 2 days ago
The Herwood Inn
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 7 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 9 days ago
Botanical Studio Retreat in the Heart of Woodstock
Maple House: Private/Romantic Walk-to-Town Oasis

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

10/10 Excellent
"Gorgeous yard, cozy layout, well-equipped kitchen, comfy living room that opens into a fairly spacious dining room area. Would rent again in a heartbeat."
Laura J. 3-night trip
Posted 2 weeks ago
Maple House: Private/Romantic Walk-to-Town Oasis
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

10/10 Excellent
"It took us several years to find a place in Woodstock that we wanted to return to annually. The location is perfect in that it is just on the edge of town but we walk to everywhere in town in a matter of minutes. The bathroom was recently redone and is beautiful. When we leave at the end of our stay it feels like we're leaving home. As long as this property is available it will be the only place we stay in Woodstock."
D 3-night trip
Posted 1 month ago
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
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!
Woodstock House on 35 private acres Mountain Views

Woodstock House on 35 private acres Mountain Views

10/10 Excellent
"Love it. Have stayed multiple times."
Steve G. 8-night trip
Posted 2 months ago
Woodstock House on 35 private acres Mountain Views
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

10/10 Excellent
"Michael was a very responsive host and answered my question about check in accurately and quickly. The apartment was quaint and decorated nicely. Great sink and refrigerator. A/C, when the outside temp was 88 degrees, was an excellent relief. You couldn’t ask for a more central location to all of the shopping and restaurants that Woodstock has to offer. The beautiful claw foot tub was great and relaxing after a full day of walking and dancing after enjoying an epic concert at the Bearsville Theater. If there is one critique I could make would be to get a memory foam mattress topper for the bed. We found it too hard for our old bones.Would definitely stay there again."
Joanne K. 1-night trip
Posted 2 months ago
Colorful Modern Hideaway In Downtown 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.