Book a hotel near Overlook Mountain Trailhead, Woodstock
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Top hotels close to Overlook Mountain Trailhead
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
Woodstock NY
0.88 mi from Overlook Mountain Trailhead
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Woodstock NY
1.44 mi from Overlook Mountain Trailhead
This cottage features a terrace, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Pet friendly
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Woodstock NY
1.61 mi from Overlook Mountain Trailhead
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Woodstock House on 35 private acres Mountain Views
Woodstock NY
1.64 mi from Overlook Mountain Trailhead
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Woodstock NY
1.71 mi from Overlook Mountain Trailhead
This cottage includes a garden and barbecue grills.
Kitchen
Free WiFi
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!
Woodstock NY
2.05 mi from Overlook Mountain Trailhead
$269 nightly
The price is $301 total per night
$301 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Stay at this apartment in Woodstock. Enjoy balconies and air conditioning. Popular attractions Woodstock Music Shop and Woodstock Artists Association and Museum are located nearby.
Kitchen
Air conditioning
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
Woodstock NY
2.05 mi from Overlook Mountain Trailhead
$308 nightly
The price is $345 total per night
$345 total
Dec 25 - Dec 26
Total with taxes and fees
Stay at this apartment in Woodstock. Enjoy balconies, an in-room coffeemaker, and air conditioning. Popular attractions Woodstock Music Shop and Woodstock Artists Association and Museum are located nearby.
Kitchen
Air conditioning
The Herwood Inn
148 Tinker St Woodstock NY
2.12 mi from Overlook Mountain Trailhead
$144 nightly
The price is $162 total per night
$162 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a hot tub on site, and a terrace and a garden are also provided.
Hot Tub
Pet friendly
Morning Glory B n B Woodstock NY
141 Tinker Street Woodstock NY
2.13 mi from Overlook Mountain Trailhead
$189 nightly
The price is $212 total per night
$212 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
An outdoor tennis court, free self parking, and wedding services are featured at this bed & breakfast. WiFi in public areas is free. A garden is also provided.
Parking included
Free WiFi
Twin Gables of Woodstock
73 Tinker St Woodstock NY
2.13 mi from Overlook Mountain Trailhead
$129 nightly
The price is $144 total per night
$144 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and a lobby fireplace are also on offer.
Breakfast included
Parking included
Woodstock Way Hotel
10 Waterfall Way Woodstock NY
2.14 mi from Overlook Mountain Trailhead
$277 nightly
The price is $305 total per night
$305 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
A bar/lounge and a coffee shop are featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.
Spa
Pet friendly
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See all available properties in Overlook Mountain Trailhead
View all propertiesLowest 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.
Overlook Mountain Trailhead hotels essential information
Accommodation | 1,078 hotels |
|---|---|
Lowest Price | $144 |
Highest Price | $345 |
Popular hotels | Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres, Woodstock Way Hotel, NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!, ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi, Woodstock House on 35 private acres Mountain Views, Junebug Cottage: peace, love and privacy a short walk to Woodstock village green, Twin Gables of Woodstock, The Herwood Inn, Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!, Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi, Morning Glory B n B Woodstock NY, TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage |
Recent Overlook Mountain Trailhead hotel reviews by fellow wanderers
The Herwood Inn
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Quaint, quirky, very environmentally conscious, fun old vinyls, and a cedar fragrant hot tub!"
A verified traveler stayed at The Herwood Inn
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