Deals on vacations and trips to Woodstock

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Woodstock flight + hotel vacation packages

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

The Hidden Inn

4 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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.
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this holiday park. Guests will appreciate free perks like free self parking and WiFi in public areas. A grocery/convenience store, a lobby fireplace, and a communal living room are also on offer.
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
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

The Herwood Inn

4.5 out of 5
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hudson (HCC)
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.

Top Woodstock hotels deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
$378 nightly
The price is $418 total per night
$418 total
Jul 28 - Jul 29
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
Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $223 total per night
$223 total
Aug 19 - Aug 20
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
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St, Woodstock, NY
$264 nightly
The price is $296 total per night
$296 total
Aug 4 - Aug 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
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3 out of 5
141 Tinker Street, Woodstock, NY
$199 nightly
The price is $223 total per night
$223 total
Jul 21 - Jul 22
Total includes 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
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St, Woodstock, NY
$249 nightly
The price is $279 total per night
$279 total
Jul 28 - Jul 29
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
The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream

3 out of 5
48 Tannery Brook Rd, Woodstock, NY
$229 nightly
The price is $256 total per night
$256 total
Jul 23 - Jul 24
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
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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.

Overlook Mountain Trailhead

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.

Karma Triyana Dharmachakra Monastery

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.

Woodstock Music Shop

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, which include hotels and flights in Woodstock, start from as little as $438. 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.

Photos of local treasures

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