Search for Cheap Deals on
Hotels in Woodstock

Choose from 2465 Woodstock Hotel Deals

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way Woodstock NY
  • 5 min drive from Overlook Mountain Trailhead
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and onsite spa services. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.6/10 Exceptional! (324 reviews)
"The room was very clean and comfortable. If you arrive after 3:00pm and have an upstairs room I recommend either not bringing a large suitcase or having someone strong to carry your bags upstairs as staff is limited to just the person at the front desk."

Reviewed on Oct 31, 2026

Woodstock Way Hotel
Twin Gables of Woodstock

Twin Gables of Woodstock

3 out of 5
73 Tinker St Woodstock NY
  • 5 min drive from Overlook Mountain Trailhead
Stay at this hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Woodstock Public Library and SweetHeart Gallery are located ...
9.8/10 Exceptional! (232 reviews)
"Our room and the common spaces were clean and cozy. Breakfast was lovely and our non-dairy needs were able to be accommodated. We didn’t interact much with any staff but each process was such a breeze that we really didn’t need to. The hotel is in such a great, central location and is an easy walk ..."

Reviewed on Nov 1, 2026

Twin Gables of Woodstock
The Herwood Inn

The Herwood Inn

4 out of 5
148 Tinker St Woodstock NY
  • 5 min drive from Overlook Mountain Trailhead
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions The Comeau Property and Woodstock Public ...
The Herwood Inn
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3 out of 5
141 Tinker Street Woodstock NY
  • 5 min drive from Overlook Mountain Trailhead
Stay at this B&B in Woodstock. Enjoy free parking, a garden, and an outdoor tennis court. Popular attractions The Comeau Property and Woodstock Public Library ...
Morning Glory B n B Woodstock NY
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
  • 28 min drive from Overlook Mountain Trailhead
Book a stay at this business-friendly inn in Rhinebeck. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (1,014 reviews)
"Needs some tlc everywhere; new bathroom fixtures that aren’t stained and scratched, old hair blower wall bracket removed, last guest’s cot removed from room , just a overall dullness"

Reviewed on Nov 2, 2026

Beekman Arms and Delamater Inn
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
  • 22 min drive from Overlook Mountain Trailhead
Stay at this hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.2/10 Wonderful! (1,004 reviews)
"The hotel is in a perfect location, close to everything we wanted to do in the area (hiking, restaurants, etc.) The staff was very nice and accommodating. I found the bed to be uncomfortable though, it creaked at every little movement and the mattress dipped in the middle which made for a restless ..."

Reviewed on Nov 2, 2026

Hunter Lodge, a Bluebird by Lark
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

4.5 out of 5
549 Washington Street Hudson NY
  • 33 min drive from Overlook Mountain Trailhead
Book a stay at this luxury hotel in Hudson. Enjoy free WiFi, free parking, and 3 indoor pools. Popular attractions Oakdale Beach and Hudson Area Library are ...
8.6/10 Excellent! (103 reviews)
"not worth the price!"

Reviewed on Nov 2, 2026

Pocketbook Hotel and Bath
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

3 out of 5
500 Frank Sottile Blvd Kingston NY
  • 19 min drive from Overlook Mountain Trailhead
Book a stay at this business-friendly hotel in Kingston. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,003 reviews)
"Nice weekend stay! Room was clean and staff was very nice."

Reviewed on Nov 1, 2026

Courtyard by Marriott Kingston
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

2.5 out of 5
4 South Putt Corners Road New Paltz NY
  • 55 min drive from Overlook Mountain Trailhead
Book a stay at this business-friendly hotel in New Paltz. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
9.4/10 Exceptional! (1,004 reviews)
"Very clean hotel, nice bright hallways with lovely carpeting, lobby fresh and welcoming. Would highly recommend."

Reviewed on Oct 31, 2026

Hampton Inn by Hilton New Paltz
Kingston Regency Inn

Kingston Regency Inn

2.5 out of 5
503 Washington Avenue Kingston NY
  • 23 min drive from Overlook Mountain Trailhead
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
6.2/10 (113 reviews)
"Ty"

Reviewed on Nov 2, 2026

Kingston Regency Inn
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
  • 31 min drive from Overlook Mountain Trailhead
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
  • 6 min drive from Overlook Mountain Trailhead
Book a stay at this luxury holiday park in Saugerties. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
AutoCamp Catskills
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.

Find cheap hotels in Woodstock

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Woodstock hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Woodstock.

Choosing the right hotel in New York has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Woodstock’s 2,465 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $123. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Woodstock hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Woodstock. No matter your reason for visiting Woodstock, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Woodstock hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Woodstock for as low as $123.

How many hotels are there in Woodstock?

With over 2,465 hotels in Woodstock, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $123.

How to find cheap car rentals in Woodstock?

Finding a cheap car rental deal in Woodstock is as easy as scoring cheap hotels in Woodstock. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.