The 10 Best Hotels Near Overlook Mountain Trailhead, Woodstock from CA $153

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Our top choices for Overlook Mountain Trailhead hotels

A hotel room with two beds, a desk, and a large window.

An outdoor patio with a round table and orange chairs, a black metal fence, and string lights.

A stone building with multiple windows and a door, situated on a street corner.

A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

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

14.5 km from Overlook Mountain Trailhead

Bailey

CA $184

CA $206 total

includes taxes & fees

Oct 25 - Oct 26

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

A bathroom with three sinks, a trash can, and a chair.

A hallway with a wooden door leading to a bathroom, a blue couch with a cushion, and a kitchen area with cabinets and a sink.

A large tree in a grassy area with a small white building in the background.

2. SunView Motel

13.9 km from Overlook Mountain Trailhead

Victoria

CA $147

CA $159 total

includes taxes & fees

Oct 1 - Oct 2

A balcony with a table featuring a bottle, glasses, and binoculars, overlooking a river, greenery, and a house.

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

14.2 km from Overlook Mountain Trailhead

CA $376

CA $456 total

includes taxes & fees

Sep 28 - Sep 29

A spacious lobby with a fireplace, comfortable seating, and large windows.

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.

An outdoor patio with a fire pit, wicker furniture, and a red building in the background.

4. Residence Inn by Marriott Kingston

16.1 km from Overlook Mountain Trailhead

Harold

CA $202

CA $227 total

includes taxes & fees

Oct 4 - Oct 5

A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.

A campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.

A corridor with white walls, wooden slats, and a concrete floor.

5. The Graham & Co.

16.2 km from Overlook Mountain Trailhead

Daniel

CA $241

CA $270 total

includes taxes & fees

Sep 28 - Sep 29

A cozy room with wooden walls, a dining table with chairs, a fireplace, and a staircase.

A wooden deck with two Adirondack chairs and a red-framed window.

A rustic interior with wooden walls, a dining table with a bench, a sofa, and a hanging light fixture.

A cozy living room with a sofa, a dining table, and a fireplace.

6. The Leeway

13.4 km from Overlook Mountain Trailhead

Shih-Chun

CA $356

CA $399 total

includes taxes & fees

Sep 28 - Sep 29

A wooden cabin with large windows overlooking a forested area with a waterfall.

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.

A modern living room with a grey sofa, a small round table, and a hanging light fixture.

7. Woodstock Way Hotel

3.4 km from Overlook Mountain Trailhead

Vannetta

CA $486

CA $599 total

includes taxes & fees

Oct 20 - Oct 21

An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.

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.

8. Howard Johnson by Wyndham Saugerties

12.4 km from Overlook Mountain Trailhead

Richard

CA $197

CA $220 total

includes taxes & fees

Sep 29 - Sep 30

A living room with a fireplace, green sofa, and a leopard print armchair.

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.

A white house with a green door, black trim, and a porch with a lantern.

9. Twin Gables of Woodstock

3.4 km from Overlook Mountain Trailhead

Coleen

CA $317

CA $380 total

includes taxes & fees

Sep 28 - Sep 29

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 bedroom with a bed, desk, chair, and a window with curtains.

A modern building with a large driveway, a covered outdoor seating area, and a large tree in the background.

10. Overlook Hotel

13 km from Overlook Mountain Trailhead

Leonardo

CA $247

CA $277 total

includes taxes & fees

Sep 28 - Sep 29

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 cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.

A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

11. Kaatskill Mountain Club & Condos by Vail Resorts

16.7 km from Overlook Mountain Trailhead

Nuria

CA $279

CA $332 total

includes taxes & fees

Oct 26 - Oct 27

A dining area with a stone fireplace, wooden beams, and large windows.

A hammock between trees, a red cabin, and a blue chair in a wooded area.

A row of red buildings with a gravel driveway and a bench outside.

12. Phoenicia Lodge

17 km from Overlook Mountain Trailhead

Thomas

CA $245

CA $274 total

includes taxes & fees

Sep 28 - Sep 29

A restaurant with orange seating, white tablecloths, and potted plants.

A living room with a red patterned rug, a blue armchair, a yellow sofa, and a black coffee table.

A room with a red accent wall, a large potted plant, and a small stool.

A cozy living room with a wood-burning stove, wicker furniture, and a bookshelf.

13. Hotel Kinsley

17.4 km from Overlook Mountain Trailhead

Daile

CA $335

CA $437 total

includes taxes & fees

Oct 26 - Oct 27

A large, multi-story house with a prominent tower, surrounded by a well-maintained lawn and trees.

A richly decorated living room with a sofa, a coffee table, and a colorful stained glass lamp.

A covered porch with a red floor, potted plants, and red umbrellas.

A dining area with wooden furniture, a stained glass window, and a cabinet with glass doors.

14. Fairlawn Inn

17.4 km from Overlook Mountain Trailhead

Rachel

CA $366

CA $396 total

includes taxes & fees

Oct 4 - Oct 5

A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

A hallway with intricate carvings on the walls and a large vase in the center.

A well-maintained garden with a red bridge, a welcome sign, and a building with a gabled roof.

A spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

15. Emerson Resort & Spa

13.9 km from Overlook Mountain Trailhead

Ashley

CA $292

CA $328 total

includes taxes & fees

Sep 29 - Sep 30

A wooden deck with a flower pot and a view of a playground area with picnic tables and a small shed.

A hotel room with two beds, a nightstand with a lamp, and a window with floral curtains.

A picnic table, playground equipment, and a swimming pool within a fenced area.

A motel with a porch, a small stream, and parked vehicles.

16. Four Seasons Motel

19.9 km from Overlook Mountain Trailhead

Jabari

CA $141

CA $153 total

includes taxes & fees

Sep 28 - Sep 29

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

A wooden-paneled bedroom with a bed, bedside tables, and a hanging light fixture.

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.

17. Hotel Mountain Brook

14 km from Overlook Mountain Trailhead

Kristen

CA $317

CA $342 total

includes taxes & fees

Sep 30 - Oct 1

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 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.

A modern house with a large garage and a vintage camper parked in the driveway.

18. AutoCamp Catskills

8.9 km from Overlook Mountain Trailhead

Raquel

CA $214

CA $295 total

includes taxes & fees

Oct 20 - Oct 21

A landscaped garden with coniferous trees and a bed of yellow flowers.

A compact kitchenette with a microwave, a small refrigerator, and a flat-screen TV mounted on the wall.

A framed landscape painting, a clock, and various decorative items on a shelf.

19. Hudson Valley 9w Motel

14.7 km from Overlook Mountain Trailhead

Jerome

CA $134

CA $221 total

includes taxes & fees

Sep 28 - Sep 29

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Compare popular hotels close to Overlook Mountain Trailhead

Property	Star rating	Guest rating
Holiday Inn Express & Suites Kingston-Ulster by IHG	9.4 Exceptional 1,002 reviews	View
SunView Motel	8.6 Excellent 618 reviews	View
Diamond Mills Resort	9.4 Exceptional 394 reviews	View
Residence Inn by Marriott Kingston	9.0 Wonderful 995 reviews	View
The Graham & Co.	9.6 Exceptional 62 reviews	View

Top Overlook Mountain Trailhead Hotel Reviews

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!"

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."

The Herwood Inn

10/10 Excellent

"What a fabulous find. The Herwood is Woodstock hippie chic fabulous. We loved our stay. Thank you to Adam and Carmen for being such wonderful hosts."

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

10/10 Excellent

"The cottage itself is perfect, no notes. It has everything you need and a welcome binder to guide you through your stay on the property. It’s a 15-minute walk to town and there are no set paths so expect to drive the 4 minutes into town. Communication with the host was very easy - John was available and accommodating. I wish Junebug could house me everywhere I go. Thank you for the wonderful stay."

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!"

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

10/10 Excellent

"Beautiful property, inside and out!"

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"

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."

Woodstock House on 35 private acres Mountain Views

10/10 Excellent

"Love it. Have stayed multiple times."

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 are the top-rated hotels near Overlook Mountain Trailhead?

Discovering the ideal stay near Overlook Mountain Trailhead is essential for enjoying the stunning landscapes of Woodstock. Here are some top-rated hotels that offer both comfort and excellent amenities for travellers.Brigadoon--3 BR Magical Farmhouse for a Romantic or Family VacationBrigadoon is a charming farmhouse just 6.8 km from Overlook Mountain Trailhead, with an impressive review rating of 10. This picturesque retreat features a cozy fireplace and a beautiful garden, perfect for unwinding after a day of exploration. Guests will appreciate the well-equipped kitchen and the hot tub for relaxing evenings. Outdoor enthusiasts can enjoy nearby hiking and biking trails, bringing the natural beauty of Woodstock right to their doorstep.The Herwood InnThe Herwood Inn is a luxurious 4.5-star hotel located just 5.0 km from Overlook Mountain Trailhead, with a stellar review rating of 9.8. This romantic getaway features designer toiletries and premium bedding, ensuring a restful stay. Guests can indulge in the hot tub or enjoy a quiet moment on the furnished balcony overlooking the mountains. With a kitchenette and complimentary parking, The Herwood Inn is a fantastic choice for travellers seeking both comfort and convenience.Twin Gables of WoodstockTwin Gables of Woodstock is a delightful 3-star hotel located only 4.5 km from Overlook Mountain Trailhead, enjoying a review rating of 9.8. This Victorian hotel offers a tranquil atmosphere with a beautiful terrace and garden. Guests can start their day with a complimentary continental breakfast and take advantage of the daily housekeeping. The stunning mountain views and nearby hiking and biking trails make it an excellent base for outdoor adventures.

How much is a hotel near Overlook Mountain Trailhead?

Staying near Overlook Mountain Trailhead is a treat, with plenty of hotels from CA $153 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, especially in peak season. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

What are the most popular family-friendly hotels near Overlook Mountain Trailhead?

For families seeking the perfect stay near Overlook Mountain Trailhead, these top-rated hotels offer a blend of comfort and family-friendly amenities.Brigadoon--3 BR Magical Farmhouse for a Romantic or Family VacationLocated 6.8 km from Overlook Mountain Trailhead, Brigadoon is a charming farmhouse rated 10 by travellers. Perfect for families, it offers a kitchen, outdoor patio, and games for children, ensuring a memorable stay. Guests can also take advantage of onsite golf, a hot tub, and nearby hiking trails, making it ideal for both relaxation and adventure.The Herwood InnThe Herwood Inn, a 4.5-star hotel only 5.0 km from Overlook Mountain Trailhead, enjoys a stellar review rating of 9.8. This family-friendly inn offers secured yard space for children, free cribs, and a lovely garden. Additional amenities include an espresso maker, hot tub, and easy access to nearby skiing, making it a perfect retreat for families seeking both comfort and activities.Woodstock Way HotelWoodstock Way Hotel is a 4-star gem just 4.3 km from Overlook Mountain Trailhead, an impressive 9.6 travellers' rating. This family-friendly hotel features a fully equipped kitchen, free cribs, and a delightful garden area for kids to explore. Guests can also enjoy amenities like a spa, terrace, and self-parking, making it a fantastic choice for families looking to unwind after a day of adventure.

Which hotels near Overlook Mountain Trailhead offer the best views?

Discovering the best hotels with stunning views near Overlook Mountain Trailhead can elevate any outdoor adventure in Woodstock.Brigadoon--3 BR Magical Farmhouse for a Romantic or Family VacationLocated just 6.8 km from Overlook Mountain Trailhead, this enchanting farmhouse boasts a perfect blend of rustic charm and modern comfort. Rated 10 by travellers, it features breathtaking mountain views that can be enjoyed from the patio or garden. Guests will appreciate the hot tub for relaxation after a day of hiking, along with amenities like a fully equipped kitchen and onsite golf privileges, making it an ideal choice for both romance and adventure.Twin Gables of WoodstockJust 4.5 km from Overlook Mountain Trailhead, Twin Gables of Woodstock is rated 9.8 by travellers and offers a quaint Victorian design complemented by picturesque mountain views. This charming 3-star hotel provides free continental breakfast and a lovely terrace for travellers to enjoy the surrounding natural beauty. With daily housekeeping and access to hiking and biking trails, it's an excellent choice for those seeking comfort and convenience.Woodstock Way HotelWith a stellar review rating of 9.6 and located only 4.3 km from Overlook Mountain Trailhead, the Woodstock Way Hotel offers contemporary elegance with stunning mountain views. This 4-star hotel features a relaxing spa, complete with various massage options, and a terrace that provides a perfect spot to unwind. Guests can also enjoy the onsite shopping and fitness facilities, ensuring a luxurious stay in the heart of Woodstock.

What are the best affordable hotels near Overlook Mountain Trailhead?

For outdoor enthusiasts looking to explore Overlook Mountain Trailhead without breaking the bank, these top-rated affordable hotels provide comfortable stays and easy access to adventure.Brigadoon--3 BR Magical Farmhouse for a Romantic or Family VacationLocated just 6.8 km from Overlook Mountain Trailhead, Brigadoon offers a magical farmhouse experience perfect for families or couples. Rated 10 by travellers, this hotel features a fully equipped kitchen, a cozy fireplace, and a relaxing hot tub. Guests can enjoy the outdoor patio and nearby hiking trails, making it an ideal base for exploring the beautiful surroundings.Twin Gables of WoodstockTwin Gables of Woodstock is a charming 3-star hotel located only 4.5 km from Overlook Mountain Trailhead. With a review rating of 9.8, this hotel offers a free continental breakfast and WiFi to ensure a delightful stay. Its Victorian design and beautiful mountain views create a serene atmosphere, while the nearby hiking and biking opportunities cater to outdoor lovers of all ages.The Woodstock Inn on the MillstreamJust 4.7 km from Overlook Mountain Trailhead, The Woodstock Inn on the Millstream boasts an impressive 8.8 review rating. This 3-star inn features free continental breakfast and WiFi, ensuring travellers start their day right. With spacious rooms that include kitchen amenities, a fireplace, and easy access to local hiking spots, this inn perfectly balances comfort with convenience for travellers seeking adventure.

What are the best pet-friendly hotels near Overlook Mountain Trailhead?

Finding the perfect pet-friendly stay near Overlook Mountain Trailhead ensures both you and your furry friend can enjoy the beauty of Woodstock together. Here are some top-rated options that cater to your needs.Brigadoon--3 BR Magical Farmhouse for a Romantic or Family VacationBrigadoon is a unique, pet-friendly farmhouse located 6.8 km from Overlook Mountain Trailhead, with a perfect review rating of 10. This enchanting retreat permits dogs and offers a spacious environment for families or romantic getaways. Guests can enjoy amenities like a hot tub, a well-equipped kitchen, and beautiful mountain views, ensuring a memorable stay in the heart of nature.The Herwood InnThe Herwood Inn, a 4.5-star hotel located just 5.0 km from Overlook Mountain Trailhead, boasts an impressive review rating of 9.8. This pet-friendly haven welcomes dogs and provides essential amenities like food and water bowls, ensuring a comfortable stay for your furry companion. Guests can also enjoy a hot tub, a terrace, and free self-parking, making it an ideal spot for relaxation after a day of outdoor adventures.Woodstock Way HotelWoodstock Way Hotel is a charming 4-star accommodation situated only 4.3 km from Overlook Mountain Trailhead, featuring a great traveler rating score of 9.6. This hotel is pet-friendly, allowing dogs and providing a welcoming atmosphere for pet owners. Guests will appreciate amenities such as an onsite spa, fitness facilities, and daily housekeeping, making it a fantastic choice for a comfortable and enjoyable stay.

Can I book a fully refundable hotel close to Overlook Mountain Trailhead?

Most bookings on Expedia are refundable if canceled within 24-48 hours of arrival, though this depends on the hotel's individual cancellation policy, which you should check in your booking confirmation. If free cancellation is available, you can cancel directly through your Expedia account by going to "My Trips" and selecting your reservation. To find fully refundable hotel options, simply enter "Overlook Mountain Trailhead", set your travel dates, and use the "Fully refundable" filter under "Deals & Discounts" on the results page. Alternatively, explore deals with free cancellation options on Expedia.

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Woodstock Vacation Rentals

Find hotels near Overlook Mountain Trailhead, Woodstock from CA $153

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Overlook Mountain Trailhead hotels

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

2. SunView Motel

3. Diamond Mills Resort

4. Residence Inn by Marriott Kingston

5. The Graham & Co.

6. The Leeway

7. Woodstock Way Hotel

8. Howard Johnson by Wyndham Saugerties

9. Twin Gables of Woodstock

10. Overlook Hotel

11. Kaatskill Mountain Club & Condos by Vail Resorts

12. Phoenicia Lodge

13. Hotel Kinsley

14. Fairlawn Inn

15. Emerson Resort & Spa

16. Four Seasons Motel

17. Hotel Mountain Brook

18. AutoCamp Catskills

19. Hudson Valley 9w Motel

Compare popular hotels close to Overlook Mountain Trailhead

Top Overlook Mountain Trailhead Hotel Reviews

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

Botanical Studio Retreat in the Heart of Woodstock

The Herwood Inn

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

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

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

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Woodstock House on 35 private acres Mountain Views

Other attractions near Overlook Mountain Trailhead

Woodstock Music Shop

Karma Triyana Dharmachakra Monastery

Byrdcliffe Barn

Levon Helm Studios

Colony

Woodstock Public Library

Woodstock Artists Association and Museum

SweetHeart Gallery

Frequently asked questions

Explore a world of travel with Expedia