Woodstock, NY

Travel Guide

A calm lake with a sunset reflecting on the water, surrounded by forested hills.
A sunset over a calm lake with mountains in the background.
A stone signpost with 'Minnewaska State Park Preserve' written on it, surrounded by trees and rocks.
An aerial view of a town with a river, surrounded by autumn-colored trees and a bridge.
A calm lake at sunset with a canoe tied to a dock, surrounded by trees and hills.
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way Woodstock NY
$352 nightly
The price is $390 total per night from Dec 1 to Dec 2
$390 total
Dec 1 - Dec 2
Total with taxes and fees
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (326 reviews)
"It's a nice place but for the price I would have expected more attention to detail in the room. There are also minimal amenities. Also, the images give you the impression it is in a very private, quiet area which is not the case. However, it is in a great location because it's right in the heart ..."

Reviewed on Nov 4, 2026

Woodstock Way Hotel
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St Woodstock NY
$174 nightly
The price is $195 total per night from Nov 16 to Nov 17
$195 total
Nov 16 - Nov 17
Total with taxes and fees
Stay at this hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Woodstock Public Library and SweetHeart Gallery are located ...
9.8/10 Exceptional! (232 reviews)
"Our room and the common spaces were clean and cozy. Breakfast was lovely and our non-dairy needs were able to be accommodated. We didn’t interact much with any staff but each process was such a breeze that we really didn’t need to. The hotel is in such a great, central location and is an easy walk ..."

Reviewed on Nov 1, 2026

Twin Gables of Woodstock
The Herwood Inn

The Herwood Inn

4 out of 5
148 Tinker St Woodstock NY
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions The Comeau Property and Woodstock Public ...
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The Herwood Inn
See all 2,424 properties in Woodstock
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.
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY
Stay at this cottage in Woodstock. Enjoy free WiFi, a garden, and patios. Our guests praise the property condition in our reviews. Popular attractions Woodstock ...
Streamside Cottage Half Mile to Town of Woodstock
Oscar winning living @ Livingstations

Oscar winning living @ Livingstations

Woodstock NY
Stay at this vacation home in Woodstock. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Levon Helm Studios and Overlook Mountain ...
10/10 Exceptional! (3 reviews)
"Beautiful and really unique property that is close to town but still very private. Ari was very communicative and responsive to any questions leading up to the stay and while we were there. The view from the outdoor sauna is definitely a highlight! Can't wait to come back!"

Reviewed on Nov 2, 2026

Oscar winning living @ Livingstations
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
9.6/10 Exceptional! (339 reviews)
"The cabin itself wasn’t very spacious, but it was well-equipped with everything we needed. The bathroom and shower were clean and comfortable. Our only difficulty was that there wasn’t enough outdoor lighting after sunset, which made cooking outside a bit challenging."

Reviewed on Nov 6, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all properties in Woodstock
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.

Stay near popular Woodstock attractions

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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Frequently asked questions

Is Woodstock worth visiting?
Woodstock is worth visiting for its outdoor activities and diverse dining scene. Travelers can enjoy hiking at the Overlook Mountain Trailhead for scenic views. The area also offers a variety of food options, including North American favorites and Italian dishes like pasta and pizza, ensuring satisfying meals after a day of exploration.
When is the best time to visit Woodstock?
The best time to visit Woodstock is from May through September, when the weather is typically mild to warm, perfect for exploring. For fewer crowds and better value, the quieter months of December through March are a good bet, offering a cooler, potentially snowy experience.
What is Woodstock known for?
Woodstock is known for its scenic Overlook Mountain Trailhead and cultural landmarks such as Colony and Bearsville Theater. This city, home to these notable spots, also offers travelers a chance to experience a rich North American food culture.
What is a good itinerary length for Woodstock?
A good itinerary length for Woodstock is two to three days to experience highlights like the Overlook Mountain Trailhead, Colony, and Bearsville Theater, along with a Rock and Roll History Tour. For a deeper visit, consider four to five days to fully explore these sites and enjoy the local vibe. See Woodstock Activities.
What are the top things to do in and around Woodstock?
Woodstock offers a mix of outdoor adventure, music history, and unique local spots:


How do I plan a trip to Woodstock?
To plan your trip to Woodstock, search for places to stay on Expedia and book flights and rental cars in advance. Consider booking a Woodstock Rock and Roll History Tour to explore landmarks like Colony and Bearsville Theater. For outdoor activities at Overlook Mountain Trailhead, pair your plans with indoor backups for weather flexibility.
What cuisines can you find in Woodstock?
In Woodstock, travelers can find New American cuisine, featuring dishes like gourmet burgers, seasonal salads, and creative entrees. You'll also discover Southern soul food, with options such as fried chicken and mac and cheese, alongside Italian, Mexican, and various Asian dishes like Chinese and Thai.
Can I book a refundable hotel in Woodstock?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Woodstock by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Woodstock with Expedia?
Expedia makes it easier to plan your Woodstock trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Woodstock?
The best choice depends on your travel style. Hotels in Woodstock can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Woodstock trip on Expedia?
Once you've booked your Woodstock trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Woodstock trip?
Expedia offers customer support before, during, and after your Woodstock trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Woodstock?
If it's your first trip to Woodstock, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Woodstock hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Woodstock hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Woodstock

A river with a red bridge, surrounded by autumn-colored trees and houses.

Saugerties

A calm harbor with several boats docked, a lighthouse, and a rocky breakwater.

Kingston

A river winding through a forested valley with autumn foliage.

Bearsville

A mountainous landscape with autumn foliage and a river.

Elka Park

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