Woodstock Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Woodstock Vacation
Book a tailored Woodstock vacation package that includes only the things you need and nothing you don't. Great for families, festivals and markets, think about basing yourself in the neighborhood of Kingston Stockade District. If a sightseeing tour is part of the program during your trip to Woodstock, visit big attractions like Overlook Mountain Trailhead, Bethel Woods Museum and Opus 40. Don't put off visiting this destination any longer. The perfect Woodstock vacation is a couple of clicks away with Expedia.
Woodstock Hotel Deals
Woodstock Way Hotel
10 Waterfall Way Woodstock NY
9.6/10 Exceptional! (235 reviews)
The room was in great condition and the staff was very nice. I enjoyed all the amenities.
Reviewed on Feb 19, 2026
The Herwood Inn
148 Tinker St Woodstock NY
The price is CA $218 per night from Mar 23 to Mar 24
CA $218
CA $245 total
Mar 23 - Mar 24
includes taxes & fees
9.8/10 Exceptional! (101 reviews)
Loved the layout of the Inn. Great vibe…peace, love and music. Self-serve concept was very convenient. Clean room and beautifully decorated and fully stocked with all the amenities of home. Located close to downtown and only 5 mins from the Bearsville Theater. We will definitely be back!
Reviewed on Feb 15, 2026
Hotel Dylan
320 Maverick Rd Woodstock NY
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Feb 25 to Feb 26
CA $210
CA $236 total
Feb 25 - Feb 26
includes taxes & fees
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.
Discover the most popular places to visit in Woodstock
Karma Triyana Dharmachakra Monastery
Learn about the local history of Woodstock with a stop at Karma Triyana Dharmachakra Monastery. Discover the mountain views while you're in the area.
Woodstock Public Library
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.
What to do in Woodstock
Discover New York City: 6+ Must-See Self-Guided Walking Audio Tours
CA $68
per traveller
Explore a world of travel with Expedia
- 3 Star Hotels in Shady
- Hotels near Ashokan Rail Trail- Woodstock Dike Trailhead
- B&B in Bearsville
- Chalets in Bearsville
- Cottages in Bearsville
- Guest Houses in Bearsville
- Holiday Park Resorts in Bearsville
- Luxury Hotels in Bearsville
- Bearsville Hotels
- Inns in Bearsville
- Lodges in Bearsville
- Motels in Bearsville
- Hotels near Bethel Woods Museum
- Holiday Park Resorts in Glenford
- Independent Hotels in Glenford
- Glenford Hotels
- Hotels near Indian Head Mountain
- Country Houses in Lake Hill
- Cheap Hotels in Lake Hill
- Luxury Hotels in Lake Hill
- Lake Hill Hotels
- Motels in Lake Hill
- Resorts in Lake Hill
- Lake Katrine Hotels
- Resorts in Lake Katrine
- New York Hotels
- Hotels near Opus 40
- Hotels near Overlook Mountain Trailhead
- B&B in Ruby
- Ruby Hotels
- Adults Only Resorts & in Shady
- Shady Hotels
- B&B in Shokan
- Guest Houses in Shokan
- Cheap Hotels in Shokan
- Luxury Hotels in Shokan
- Shokan Hotels
- Resorts in Shokan
- Cheap Hotels in West Hurley
- Luxury Hotels in West Hurley
- West Hurley Hotels
- Resorts in West Hurley
- West Saugerties Hotels
- Farmstay in Willow
- Aparthotels in Willow
- Apartments in Willow
- B&B in Willow
- Chalets in Willow
- Guest Houses in Willow
- Holiday Park Resorts in Willow
- Hostels in Willow
- Beach Hotel Hotels in Willow
- Luxury Hotels in Willow
- Spa Hotels in Willow
- Willow Hotels
- Inns in Willow
- Lodges in Willow
- Motels in Willow
- Resorts in Willow
- Aparthotels in Zena
- Chalets in Zena
- Zena Hotels
- Resorts in Zena
- Accord Vacations
- Acra Vacations
- Belleayre Beach at Pine Hill Lake
- Big Indian Vacations
- Cairo Vacations
- Catskill Mountains
- Catskill State Park
- Catskill Vacations
- Dietz Stadium
- Esopus Falls
- Federated Church of Kerhonkson
- Franklin D. Roosevelt Presidential Library and Museum
- Hudson Valley Vacations
- Hunter Vacations
- Hyde Park Station
- Karma Triyana Dharmachakra Monastery
- Kingston Vacations
- Leeds Vacations
- Museum of Rhinebeck History
- Olana State Historic Site
- Omega Institute
- Pine Hill Vacations
- Poet's Walk Park
- Red Hill Fire Tower
- Rhinebeck Vacations
- Saugerties Village Beach
- Vanderbilt Mansion National Historic Site
- Visit West Saugerties
- Windham Mountain Resort
- Woodstock Public Library
- World's Second Largest Garden Gnome
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
