Deals on vacations and trips to Woodstock

Save when you book Woodstock package deals

Choose two or more items and save on your trip:

Top Woodstock hotels deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way Woodstock NY
$381 nightly
The price is $422 total per night
$422 total
Sep 7 - Sep 8
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
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St Woodstock NY
$297 nightly
The price is $333 total per night
$333 total
Aug 23 - Aug 24
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
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St Woodstock NY
$189 nightly
The price is $227 total per night
$227 total
Sep 8 - Sep 9
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
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3 out of 5
141 Tinker Street Woodstock NY
$209 nightly
The price is $234 total per night
$234 total
Sep 6 - Sep 7
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
The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream

3 out of 5
48 Tannery Brook Rd Woodstock NY
$229 nightly
The price is $256 total per night
$256 total
Aug 17 - Aug 18
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A terrace, a garden, and a picnic area are also on offer.
Breakfast included
Parking included
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY
$284 nightly
The price is $318 total per night
$318 total
Sep 7 - Sep 8
Total with taxes and fees
This cottage includes a garden and barbecue grills.
Kitchen
Free WiFi
Don't see what you're looking for?
See all available properties in Woodstock
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.

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.
See properties

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, which include hotels and flights in Woodstock, start from as little as . Make your travel dreams come true and book your trip with Travelocity today.
How long should my Woodstock vacation be?
Typically, 2 nights is how long the majority of travelers spend exploring the attractions of Woodstock. Wondering whether that'll be enough time to get to all the things on your sightseeing list? Stay another night or two and experience everything this place has to offer.
Where can I get the best vacation package deals for Woodstock?
You'll come across an amazing range of Woodstock package deals on Travelocity. With 400 air carriers and 1,000,000 properties across the globe, arranging your ideal getaway will be a breeze.
Why should I purchase my Woodstock vacation package via Travelocity?
We offer destinations to suit every type of globetrotter, superb service and support available 24/7. And to top all that off, we'll match any cheaper price you find with our Price Match Guarantee.
Will I save money on my Woodstock car rental if I combine it with hotels and flights?
With a Woodstock vacation package, you can bundle your flight, car and hotel bookings and save tons. When you're ready to uncover the best of this awesome location, why not head to Times Square? This famous attraction is 90 mi from Woodstock. With a rental car, you'll be there belong long.
Which airport is best for Woodstock?
One of the handiest options is Albany Intl. Airport (ALB), located 50 mi north of the hustle and bustle of downtown Woodstock. You can also jet into Stewart Intl. Airport (SWF), 35 mi away from central Woodstock).
What is there to do in Woodstock?
Woodstock is brimming with sights to explore, such as Overlook Mountain Trailhead and Karma Triyana Dharmachakra Monastery. These two fantastic attractions top most people's travel itineraries.
Where should I stay when visiting Woodstock?
If you're after a place to base yourself, consider the Morning Glory B N B Woodstock Ny. It's the top pick for many travelers.

Photos of local treasures

Browse Woodstock vacation photos for more inspiration

A calm lake with a sunset reflecting on the water, surrounded by forested hills.
Dramatic Sunset with Blue Sky at the Ashokan Reservoir in Ulster County in New York. Golden light reflects on the Mountains and calm reservoir surface.
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 pond with rocks, a wooden bridge, and a boat dock.

Explore More Ways to Travel with Travelocity