New York State may have travel restrictions in place, including self-quarantine, due to COVID-19.

Find out moreOpens in new tab or window
Photo by Marina Timo

Find Historic Hotels in Woodstock, NY from $299

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Top Woodstock Historic Hotels

Mountain Studio  
Escape NYC Fall🍁
Hikers SEPT/NOV 
near ski 
Sun-Th $specials
The price is $299 per night from Oct 31 to Nov 1
4.9/5Exceptional! (27 reviews)
Heaven on Earth

"If you want a beautiful and quiet location, this us the place to be."…"

Reviewed on Sep 29, 2020

Mountain Studio Escape NYC Fall🍁 Hikers SEPT/NOV near ski Sun-Th $specials
Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
4.9/5Exceptional! (10 reviews)
Peaceful cottage just outside of town

"This was an excellent option for staying in Woodstock. Having booked without knowing the town we were delighted that the cottage was a a short drive and situated in a quite area with beautiful views. We particularly enjoyed the visit from deer in the mornings. Ike was incredibly helpful and knows ..."…"

Reviewed on Aug 19, 2019

Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
Don't see what you're looking for?
We've got more Historic Hotels. Find the right one for you.
View all properties
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.

About Woodstock Historic Hotels

When you go on a Woodstock getaway, it is easy to pick a chain you are familiar with, or a modern hotel. You may be used to your room having all the familiar amenities. But sometimes choosing to stay in a more distinctive hotel can enrich your trip. A stay in a Woodstock historic hotel still gives you a well-appointed room and one with tons of character. Additionally, it provides you the opportunity to immerse yourself in Woodstock's past.

Grab Your Place in History

Many of the traditional hotels give you a feel for a bygone era right from the start. With unique architectures and locations in the heart of Woodstock, it will become obvious what makes Woodstock renowned. Luckily, you aren't required to live like the hotel's past guest. Although these hotels may be vintage, they have most up-to-date amenities to help you relax or keep in touch on your stay. You'll notice rooms outfitted with a comfy bed and just about everything else you may want for a marvelous visit.

After you have explored your hotel, you can continue to take in this culturally-rich region by exploring the museums and famous landmarks. Undoubtedly, all this time traveling will work up an appetite. Make sure to scan the comments and read the recommendations other travelers to Woodstock believe is merit a visit. You can also ask your hotel's front desk so you can get recommendations where their favorite areas to enjoy a drink or dinner in Woodstock are.

Book a Woodstock Historic Hotel!

Woodstock has 107 vintage hotels that possess the look and feel of another era. Some of these hotels are where respected novelists may have stayed. You are sure to reserve a hotel that has all the in-room amenities as well as the old-world charm you wish for. Be sure to book your vintage hotel soon, or you could miss out on staying in one of these unique accommodations.

Frequently asked questions

What should I expect on my historical trip to Woodstock?
A trip to the historical places in Woodstock is probably on top of your sightseeing itinerary. During your visit, why not check out the art scene and forests?
What's the best hotel in Woodstock to learn about local history?
Based on our travel expertise, Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village is a top historic cottage bookable on our site and it features private pools. Overlook Mountain Trailhead is a short 11-minute drive away. If you’re interested in local history, another choice for your stay is Mountain Studio Escape NYC Fall🍁Hikers SEPT/NOV near ski Sun-Th $specials.
How many historically relevant hotels will I find in Woodstock?
In Woodstock, there are 109 hotels and other accommodations bookable on Expedia, including 2 historic hotels or hotels close to historic sites.
What are the must-see historical places and other sights in Woodstock?
Woodstock is notable for landmarks like Overlook Mountain Trailhead. Additionally, in the area you’ll find Hunter Mountain and Catskill Mountains.
What is a historic hotel like in Woodstock?
By booking a historic hotel, guests can spend a night or two in a place that has a national historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be turned into a historic hotel provided that it’s of special interest. Traditional architecture and period features are typically found within the guestrooms or public spaces of historic hotels in Woodstock, giving a real sense of character.
What is the difference between a historic hotel and a heritage hotel?
“Heritage hotel” is more common in Asia and Europe, while “historic hotel” is a term often used in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels tend to be the most important aspect. For a heritage hotel, it’s mainly the cultural value along with how it shaped the community.
Do historic hotels in Woodstock have modern facilities?
Hotels have the safety features and modern conveniences you expect to find, but every effort is made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, free WiFi, and the amenities found in any hotel will also be available in a historic hotel. When you book a historic hotel in Woodstock, don’t worry that you’ll find yourself staying at a place that’s uncomfortable or rundown.

More trip options