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.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,384, price is now $1,214 per person
$1,214
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Hudson (HCC)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $6,209, price is now $4,909 per person
$4,909
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Hudson (HCC)
An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $5,947, price is now $4,707 per person
$4,707
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Hudson (HCC)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Price was $3,326, price is now $3,054 per person
$3,054
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Hudson (HCC)
This chalet features a hot tub and a sauna. Free self parking and a terrace are also offered on site.
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,654, price is now $1,332 per person
$1,332
per person
Oct 14 - Oct 20
found 8 hours ago
Roundtrip non-stop flight included
Portland (PDX) 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.

Top Woodstock hotels deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way Woodstock NY
$381 nightly
The price is $422 total per night
$422 total
Aug 31 - Sep 1
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

The Herwood Inn

4.5 out of 5
148 Tinker St Woodstock NY
$231 nightly
The price is $259 total per night
$259 total
Sep 23 - Sep 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.
Hot Tub
Pet friendly
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St Woodstock NY
$189 nightly
The price is $227 total per night
$227 total
Sep 16 - Sep 17
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
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3 out of 5
141 Tinker Street Woodstock NY
$209 nightly
The price is $234 total per night
$234 total
Sep 6 - Sep 7
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.
Parking included
Free WiFi
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock NY
$275 nightly
The price is $308 total per night
$308 total
Sep 7 - Sep 8
Total with taxes and fees
This cottage includes a garden and barbecue grills.
Kitchen
Free WiFi
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $202 total per night
$202 total
Aug 31 - Sep 1
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
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.

Stay near popular Woodstock attractions

Woodstock Music Shop

9.6/10 (18 reviews)
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.
See properties

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, which include hotels and flights in Woodstock, start from as little as $1,214. 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

Browse Woodstock vacation photos for more inspiration

A calm lake with a sunset reflecting on the water, surrounded by forested hills.
Dramatic Sunset with Blue Sky at the Ashokan Reservoir in Ulster County in New York. Golden light reflects on the Mountains and calm reservoir surface.
A stone signpost with 'Minnewaska State Park Preserve' written on it, surrounded by trees and rocks.
An aerial view of a town with a river, surrounded by autumn-colored trees and a bridge.
A calm pond with rocks, a wooden bridge, and a boat dock.

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