Woodstock, NY

Travel Guide

Woodstock
Woodstock
Woodstock
Woodstock
Woodstock

Where to stay in Woodstock

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Shady

If you're looking for some top things to see and do in Shady and surrounding area, you can visit Overlook Mountain Trailhead and Byrdcliffe Barn.

Shady
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
$396 nightly
The price is $439 total per night from Aug 25 to Aug 26
$439 total
Aug 25 - Aug 26
Total includes taxes and fees
Stay at this 4-star hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (168 reviews)
Highly recommend this tranquil gem
"I stayed here two years ago and have been hoping to be able to come back since then. The rooms are so beautiful and comfortable, the setting just gorgeous. Everything is a convenient walk away. Staff are laid back, friendly, and helpful."

Reviewed on Aug 15, 2025

Woodstock Way Hotel
Hotel Dylan

Hotel Dylan

2 out of 5
320 Maverick Rd, Woodstock, NY
$218 nightly
The price is $245 total per night from Aug 25 to Aug 26
$245 total
Aug 25 - Aug 26
Total includes taxes and fees
Book a stay at this golf motel in Woodstock. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ashokan Rail Trail- Woodstock Dike Trailhead ...
9.2/10 Wonderful! (28 reviews)
"amazing place"

Reviewed on Jul 31, 2025

Hotel Dylan
The Herwood Inn

The Herwood Inn

4.5 out of 5
148 Tinker St, Woodstock, NY
$251 nightly
The price is $281 total per night from Sep 16 to Sep 17
$281 total
Sep 16 - Sep 17
Total includes taxes and fees
Stay at this 4.5-star luxury guesthouse in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions The Comeau Property and Woodstock ...
9.6/10 Exceptional! (82 reviews)
"We enjoyed the convenience and walkability. Downtown Woodstock is about a 10 to 15 minute easy walk to shops and eateries. We stayed in the King Suite, a 2nd floor lodging that was clean, spacious and included pretty much all you need for a stay (games, books, kitchenette, toaster oven, pots, pans, ..."

Reviewed on Aug 7, 2025

The Herwood Inn
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.
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
Stay at this cottage in Woodstock. Enjoy tennis courts, patios, and an in-room coffeemaker. Popular attractions The Comeau Property and Woodstock Public Library ...
9/10 Wonderful! (36 reviews)
Writing and Relaxing
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster ..."

Reviewed on Aug 4, 2025

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock

Woodstock
Stay at this cottage in Woodstock. Enjoy free WiFi, a garden, and patios. Our guests praise the property condition in our reviews. Popular attractions Woodstock ...
9.8/10 Exceptional! (217 reviews)
"Where do we start? We wanted something comfortable and peaceful for a short getaway and the Streamside Cottage was beyond our expectations! First off, it was very clean but also so cute and charming. Plenty of space for the two of us. Each morning, we had a peaceful breakfast on the deck and enjoyed ..."

Reviewed on Aug 14, 2025

Streamside Cottage Half Mile to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Woodstock
Stay at this cottage in Woodstock. Enjoy free WiFi, a garden, and patios. Popular attractions Woodstock Public Library and Colony are located nearby.
10/10 Exceptional! (70 reviews)
"Wonderful Little Cottage. Clean, well put together, would definitely recommend."

Reviewed on Jul 27, 2025

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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.

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