Woodstock Vacation Packages 2025 from $901

Woodstock flight + hotel vacation packages

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

Inn at Pine Plains

per person

Jul 11 - Jul 14

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Hudson (HCC)

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A garden and a picnic area are also provided.

Top Woodstock hotels deals

Woodstock Way Hotel

10 Waterfall Way, Woodstock, NY

$382 nightly

$424 total

Jun 8 - Jun 9

Total includes 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

Twin Gables of Woodstock

73 Tinker St, Woodstock, NY

$149 nightly

$167 total

Jun 24 - Jun 25

Total includes 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

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

$277 nightly

$310 total

Jun 8 - Jun 9

Total includes taxes and fees

This cottage features barbecue grills.

Kitchen

Pet friendly

The Herwood Inn

148 Tinker St, Woodstock, NY

$198 nightly

$222 total

Jun 4 - Jun 5

Total includes 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

The Woodstock Inn on the Millstream

48 Tannery Brook Rd, Woodstock, NY

$219 nightly

$245 total

Jun 4 - Jun 5

Total includes 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

Hotel Dylan

320 Maverick Rd, Woodstock, NY

$175 nightly

$197 total

Jun 11 - Jun 12

Total includes taxes and fees

This motel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop is also provided.

Pool

Parking included

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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

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 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.

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.

Frequently asked questions

How much are vacation packages to Woodstock?

Packages, which include hotels and flights in Woodstock, start from as little as $901. 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.