Woodstock Vacation Packages 2026 from $1,116

Woodstock flight + hotel vacation packages

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

Eastwind Windham

Save 100% on your flight

$1,116

per person

Jun 6 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) 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.

Secluded Retreat w/ Pool, Hot Tub, Fire Pit, Views Windham Mountain House

Save 100% on your flight

$2,379

per person

Jun 6 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) 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.

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

$12,573

per person

Jul 19 - Jul 26

found 11 hours ago

Roundtrip flight included

Houston (HOU) 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.

The Haüs Windham

$1,384

per person

Jul 19 - Jul 26

found 11 hours ago

Roundtrip flight included

Houston (HOU) 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.

Perfect Family Vacation Home in the Mountains

Save 100% on your flight

$2,134

per person

Jun 6 - Jun 13

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Hudson (HCC)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

Top Woodstock hotels deals

Woodstock Way Hotel

10 Waterfall Way Woodstock NY

$286 nightly

$315 total

May 4 - May 5

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

May 6 - May 7

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.

Breakfast included

Parking included

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY

Get rates

This cottage includes a garden and barbecue grills.

Kitchen

Free WiFi

Best Western Plus Kingston Hotel And Conference Center

503 Washington Ave Kingston NY

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$98 total

May 6 - May 7

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a garden, and a grocery/convenience store are also offered.

Pet friendly

Parking included

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

282 Cairo Junction Rd Catskill NY

$199 nightly

$215 total

May 5 - May 6

Total with taxes and fees

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

Kitchen

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 $1,116. 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.