Woodstock Vacation Packages 2026 from $1,288

Woodstock flight + hotel vacation packages

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

Discounted Winter Rates! Ski Retreat, Hot Tub, Fire Pit Windham Mountain House

Save 100% on your flight

$1,288

per person

May 29 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Hudson (HCC)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.

Secluded Catskills Retreat Heated Pool Hot Tub Game Rooms The Hilltop Hideaway by Avantstay

Save 100% on your flight

$3,203

per person

May 29 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Hudson (HCC)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Bring the family and enjoy the arcade/game room, along with volleyball. An outdoor pool is also provided.

Scenic Catskills Retreat Pool, Hot Tub, Game Room, Lake & Views Mountainview Estate by Avantstay

Save 100% on your flight

$3,841

per person

May 29 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Hudson (HCC)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and barbecue grills. An outdoor pool and a terrace are also provided.

Mins to Hunter Mountain Sleeps 36 Pool, Spa, Games & Bar Cozy Peaks Lodge by Avantstay

Save 100% on your flight

$3,501

per person

May 29 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Hudson (HCC)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Save 100% on your flight

$2,742

per person

May 29 - Jun 1

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Hudson (HCC)

This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.

Top Woodstock hotels deals

Woodstock Way Hotel

10 Waterfall Way Woodstock NY

$276 nightly

$305 total

Mar 8 - Mar 9

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.

The Herwood Inn

148 Tinker St Woodstock NY

$168 nightly

$189 total

Mar 23 - Mar 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.

Hotel Dylan

320 Maverick Rd Woodstock NY

Free Cancellation

Reserve now, pay when you stay

$160 nightly

$180 total

Mar 11 - Mar 12

Total with 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.

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY

Get rates

This cottage includes a garden and barbecue grills.

Residence Inn by Marriott Kingston

800 Frank Sottile Boulevard Kingston NY

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$132 total

Mar 15 - Mar 16

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.

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

282 Cairo Junction Rd Catskill NY

$149 nightly

$161 total

Mar 11 - Mar 12

Total with taxes and fees

This cabin features a virtual front desk. Take advantage of the free self parking.

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.

Popular places to visit

Woodstock Music Shop

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.

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 $1,288. 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.