Find hotels near Overlook Mountain Trailhead, Woodstock from CA $129

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Overlook Mountain Trailhead hotels

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, (206 reviews)
"Such a cute spot! Our room was super cozy, everything was clean and neat, very welcoming atmosphere and close to everything! Loved it! (We were in room 6, it’s small and perfect for a couple)"
United States
Avital
The price is CA $217
CA $261 total
includes taxes & fees
Jun 2 - Jun 3
Twin Gables of Woodstock

Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
3.4 km from Overlook Mountain Trailhead
9.6 out of 10, Exceptional, (270 reviews)
"Easy parking | easy walking | great location "
United States
Dardan
The price is CA $344
CA $438 total
includes taxes & fees
Jun 9 - Jun 10
Woodstock Way Hotel

The Herwood Inn

The Herwood Inn
4.5 star property
3.4 km from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (112 reviews)
"Beautifully designed place in the heart of Woodstock. The owners really know how to create a welcoming vibe. The rooms and cozy and warm and fully equipped. "
United States
juan
The price is CA $272
CA $304 total
includes taxes & fees
May 18 - May 19
The Herwood Inn

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, (209 reviews)
"LOVE the Woodstock Inn - always so relaxing!"
United States
Robert
The price is CA $245
CA $274 total
includes taxes & fees
May 12 - May 13
The Woodstock Inn on the Millstream

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
8.6 out of 10, Excellent, (157 reviews)
"I thoroughly enjoyed my stay! The hostess was warm and friendly and very accommodating, breakfast was fantastic. I stayed in the green room, and although had a "shared bathroom", I had it all to myself and felt very comfortable. I enjoyed hanging out in Woodstock - checking out the Kaaterskill waterfall and Platte Clove waterfall, shopping around town, having a beer with the locals. I had dinner right across the street at Alba's Kitchen - convenient and tasty. Great stay! Highly recommend this...
United States
Rachel
The price is CA $272
CA $305 total
includes taxes & fees
May 12 - May 13
Morning Glory B n B Woodstock NY

AutoCamp Catskills

AutoCamp Catskills
5.0 star property
8.9 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (494 reviews)
"Great stay"
United States
Hitesh
The price is CA $217
CA $297 total
includes taxes & fees
May 21 - May 22
AutoCamp Catskills

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, (1,005 reviews)
"Room was very clean and comfortable."
United States
Jose
The price is CA $115
CA $129 total
includes taxes & fees
May 31 - Jun 1
Super 8 by Wyndham Kingston

Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
14 km from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (558 reviews)
"Loved our stay. We'll be back"
United States
MIke
The price is CA $272
CA $294 total
includes taxes & fees
May 19 - May 20
Hotel Mountain Brook

The Leeway

The Leeway
2.0 star property
13.4 km from Overlook Mountain Trailhead
10.0 out of 10, Exceptional, (21 reviews)
"The leeway was very beautiful perfect for 2 people big cozy bed and nice living room area there are most definitely many places to eat nearby and lots of trails to walk and be one with nature and the small stream at the end was a breath taking view so beautiful in the morning with coffee i will be coming back "
United States
Delmy
The price is CA $304
CA $340 total
includes taxes & fees
May 13 - May 14
The Leeway

Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
13.9 km from Overlook Mountain Trailhead
9.2 out of 10, Wonderful, (67 reviews)
"Just all around a good experience "
United States
Mihai
The price is CA $264
CA $296 total
includes taxes & fees
May 27 - May 28
Emerson Resort & Spa

Hampton Inn Kingston

Hampton Inn Kingston
2.5 star property
15.7 km from Overlook Mountain Trailhead
9.0 out of 10, Wonderful, (1,008 reviews)
"We got in fairly late and the front desk staff were amazing! Great sleep and excellent breakfast/coffee"
United States
Sailor
The price is CA $200
CA $224 total
includes taxes & fees
May 17 - May 18
Hampton Inn Kingston

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, (937 reviews)
"really beautiful spot with great amenities, friendly staff, relaxed environment "
United States
Ryan
The price is CA $190
CA $235 total
includes taxes & fees
May 17 - May 18
Hunter Lodge, a Bluebird by Lark

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
12.4 km from Overlook Mountain Trailhead
7.4 out of 10, Good, (1,005 reviews)
"Trucker hotel. But not bad."
United States
Justin
The price is CA $168
CA $188 total
includes taxes & fees
May 25 - May 26
Howard Johnson by Wyndham Saugerties

Overlook Hotel

Overlook Hotel
2.0 star property
13 km from Overlook Mountain Trailhead
8.8 out of 10, Excellent, (31 reviews)
"Very nice staff. Our room was comfortable and clean. The place has a very cool vibe. "
United States
Stephanie
The price is CA $281
CA $315 total
includes taxes & fees
May 26 - May 27
Overlook Hotel

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, (1,005 reviews)
"Always a great stay here! "
United States
CODY ANN
The price is CA $190
CA $213 total
includes taxes & fees
May 17 - May 18
Courtyard by Marriott Kingston

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, (1,006 reviews)
"Clean and tidy with very kind helpful staff. "
United States
Crystal
The price is CA $185
CA $207 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express & Suites Kingston-Ulster by IHG

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, (921 reviews)
"Spacious room, good breakfast, nice lobby area with fireplace and beer in tap. "
United States
Jennifer
The price is CA $204
CA $228 total
includes taxes & fees
May 17 - May 18
Residence Inn by Marriott Kingston

Diamond Mills Resort

Diamond Mills Resort
3.5 star property
14.2 km from Overlook Mountain Trailhead
9.4 out of 10, Exceptional, (369 reviews)
"Great for a quick getaway. Nice sized rooms, heated bathroom floors. Overall great experience."
United States
Stephen
The price is CA $364
CA $441 total
includes taxes & fees
May 13 - May 14
Diamond Mills Resort

The Graham & Co.

The Graham & Co.
3.0 star property
16.2 km from Overlook Mountain Trailhead
9.8 out of 10, Exceptional, (35 reviews)
"The staff is super friendly and the place is fun"
United States
Naheima Nathalie
The price is CA $221
CA $248 total
includes taxes & fees
May 26 - May 27
The Graham & Co.
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.

Compare popular hotels close to Overlook Mountain Trailhead

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Books, music library, stereo
Twin Gables of Woodstock
3.0 star property
9.8
Exceptional
206 reviews
View
Superior Room, Fireplace, River View | View from room
Woodstock Way Hotel
4.0 star property
9.6
Exceptional
270 reviews
View
Outdoor spa tub
The Herwood Inn
4.5 star property
9.8
Exceptional
112 reviews
View
Lobby
The Woodstock Inn on the Millstream
3.0 star property
9.0
Wonderful
209 reviews
View
Studio, Private Bathroom, Garden View (Dove  house on Tannery br) | View from property
Morning Glory B n B Woodstock NY
3.0 star property
8.6
Excellent
157 reviews
View

Top Overlook Mountain Trailhead Hotel Reviews

Hotels near other Overlook Mountain Trailhead attractions

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 Vacation

Brigadoon 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 Inn

The 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 Woodstock

Twin 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 $129 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 Vacation

Located 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 Inn

The 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 Hotel

Woodstock 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 Vacation

Located 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 Woodstock

Just 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 Hotel

With 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 Vacation

Located 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 Woodstock

Twin 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 Millstream

Just 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 Vacation

Brigadoon 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 Inn

The 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 Hotel

Woodstock 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.
Can I find Expedia discounts for hotels near Overlook Mountain Trailhead?
Sign in to your account to unlock instant savings and access Member Prices on Expedia. Members always get our best prices, so join for free and look for great discounts on top hotels near Overlook Mountain Trailhead.

Explore a world of travel with Expedia