Woodstock Vacation Packages 2026

Top Woodstock hotels deals

Woodstock Way Hotel

10 Waterfall Way Woodstock NY

$409 nightly

$454 total

Nov 2 - Nov 3

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.

Twin Gables of Woodstock

73 Tinker St Woodstock NY

$194 nightly

$233 total

Nov 2 - Nov 3

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.

The Herwood Inn

148 Tinker St Woodstock NY

$297 nightly

$333 total

Oct 22 - Oct 23

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.

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY

$313 nightly

$351 total

Oct 20 - Oct 21

Total with taxes and fees

This cottage includes a garden and barbecue grills.

Beekman Arms and Delamater Inn

6387 MILL ST Rhinebeck NY

$152 nightly

$172 total

Oct 25 - Oct 26

Total with taxes and fees

A restaurant and a bar/lounge are featured at this inn. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

Free Cancellation

Reserve now, pay when you stay

$269 nightly

$304 total

Nov 1 - Nov 2

Total with taxes and fees

This smoke-free hotel features 3 indoor pools, a restaurant, and a bar/lounge. Enjoy the steam room and perks like free valet parking and free WiFi. Free self parking, a coffee shop, and a garden are also offered.

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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

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.