Woodstock Vacation Packages 2026 from $499

Woodstock flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Vienna

$499

per person

Jun 24 - Jun 26

found 8 hours ago

Roundtrip flight included

Islip (ISP) to Hudson (HCC)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.

Wylder Hotel Windham

$643

per person

Jun 24 - Jun 26

found 8 hours ago

Roundtrip flight included

Islip (ISP) to Hudson (HCC)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.

Eastwind Windham

$540

per person

Jun 24 - Jun 26

found 8 hours ago

Roundtrip flight included

Islip (ISP) to Hudson (HCC)

This hotel features a restaurant and 2 bars/lounges. Enjoy the sauna and perks like free self parking and free WiFi. A lobby fireplace, a communal living room, and a picnic area are also on offer.

The Haüs Windham

$674

per person

Jun 24 - Jun 26

found 8 hours ago

Roundtrip flight included

Islip (ISP) to Hudson (HCC)

This hotel 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. A 24-hour gym and barbecue grills are also provided.

Top Woodstock hotels deals

Woodstock Way Hotel

10 Waterfall Way Woodstock NY

$258 nightly

$285 total

Apr 28 - Apr 29

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

148 Tinker St Woodstock NY

$176 nightly

$197 total

Apr 22 - Apr 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.

Hot Tub

Pet friendly

Twin Gables of Woodstock

73 Tinker St Woodstock NY

$139 nightly

$167 total

May 3 - May 4

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.

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY

Get rates

This cottage includes a garden and barbecue grills.

Kitchen

Free WiFi

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock NY

$276 nightly

$309 total

May 3 - May 4

Total with taxes and fees

This cottage features barbecue grills.

Residence Inn by Marriott Kingston

800 Frank Sottile Boulevard Kingston NY

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$156 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and dry cleaning are also provided.

Breakfast included

Pet friendly

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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.

Popular places to visit

Woodstock Music Shop

4/5(1 review)

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.

Overlook Mountain Trailhead

Learn about the local history of Woodstock when you take a trip to Overlook Mountain Trailhead. Discover the mountain views while you're in the area.

Woodstock Public Library

4.5/5(20 reviews)

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.

Frequently asked questions

How much are vacation packages to Woodstock?

Packages, which include hotels and flights in Woodstock, start from as little as $499. 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.