Woodstock Vacation Packages 2025/2026 from $436

Woodstock flight + hotel vacation packages

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

The Hidden Inn

$436

per person

Oct 10 - Oct 13

found 11 hours ago

Roundtrip flight included

Orlando (MCO) to Hudson (HCC)

A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.

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

Save 100% on your flight

$3,259

per person

Oct 10 - Oct 13

found 12 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Hotel Vienna

Save 100% on your flight

$566

per person

Oct 10 - Oct 13

found 11 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Save 100% on your flight

$903

per person

Oct 10 - Oct 13

found 11 hours ago

Roundtrip flight included

Orlando (MCO) to Hudson (HCC)

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

Kaatskill Mountain Club at Hunter Mountain

$485

per person

Oct 10 - Oct 13

found 11 hours ago

Roundtrip flight included

Orlando (MCO) to Hudson (HCC)

A restaurant and an outdoor pool are featured at this hotel. Enjoy the sauna and perks like free WiFi. A lobby fireplace, a picnic area, and luggage storage are also on offer.

Top Woodstock hotels deals

Woodstock Way Hotel

10 Waterfall Way, Woodstock, NY

$350 nightly

$388 total

Sep 1 - Sep 2

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

Hotel Dylan

320 Maverick Rd, Woodstock, NY

$219 nightly

$246 total

Sep 3 - Sep 4

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.

Pool

Parking included

Morning Glory B n B Woodstock NY

141 Tinker Street, Woodstock, NY

$199 nightly

$223 total

Sep 3 - Sep 4

Total with taxes and fees

An outdoor tennis court, free self parking, and wedding services are featured at this bed & breakfast. WiFi in public areas is free. A garden is also provided.

Breakfast included

Parking included

The Herwood Inn

148 Tinker St, Woodstock, NY

$253 nightly

$283 total

Sep 2 - Sep 3

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

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

$275 nightly

$308 total

Sep 7 - Sep 8

Total with taxes and fees

This cottage features barbecue grills.

Kitchen

Pet friendly

Americas Best Value Inn New Paltz

7 Terwilliger Ln, New Paltz, NY

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$118 total

Sep 3 - Sep 4

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

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.

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.

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.

Frequently asked questions

How much are vacation packages to Woodstock?

Packages, which include hotels and flights in Woodstock, start from as little as $436. 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.