Photo by Marina Timo

Find Hotels with a Pool in Woodstock, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Woodstock Hotels with a Pool

Our top choices for Woodstock hotels with a pool

Reception
Hotel Dylan

Hotel Dylan

Hotel Dylan
2.0 star property
Woodstock
9.4 out of 10, Exceptional, (40)
"Close to restaurants and shopping. Nice vibe."
United States
sara
The price is ￥23,595
￥26,427 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel Dylan
Outdoor pool
Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House
Woodstock
10.0 out of 10, Exceptional, (6)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
The price is ￥85,953
￥150,186 total
includes taxes & fees
Dec 14 - Dec 15
Woodstock Historic Artist Estate - The Museum House
Indoor pool
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz
2.5 star property
New Paltz
9.4 out of 10, Exceptional, (1000)
"The hotel is quiet and clean and had a very comfortable bed."
United States
Carolyn
The price is ￥17,318
￥19,397 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Hampton Inn by Hilton New Paltz
Indoor pool
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston
3.0 star property
Kingston
8.8 out of 10, Excellent, (1001)
" Lean room, quiet location and comfortable bed."
United States
Barbara
The price is ￥17,077
￥19,126 total
includes taxes & fees
Dec 14 - Dec 15
Courtyard by Marriott Kingston
Indoor pool, sun loungers
Hampton Inn Kingston

Hampton Inn Kingston

Hampton Inn Kingston
2.5 star property
Kingston
9.0 out of 10, Wonderful, (1001)
"Everything was amazing! The room was great and the staff is superb!"
United States
Danielle
The price is ￥17,318
￥19,397 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Kingston
Indoor pool
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center
2.5 star property
Kingston
7.6 out of 10, Good, (1001)
"Nice staff, clean room, breakfast was tasty."
United States
Sarah
The price is ￥15,197
￥17,021 total
includes taxes & fees
Dec 21 - Dec 22
Best Western Plus Kingston Hotel And Conference Center
Indoor pool
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1002)
"Easy check in, friendly staff. "
United States
Daniel
The price is ￥16,197
￥18,141 total
includes taxes & fees
Dec 14 - Dec 15
Howard Johnson by Wyndham Saugerties
Indoor pool
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
2.5 star property
Saugerties
8.8 out of 10, Excellent, (690)
"Clean rooms, very friendly and accommodating staff. Breakfast was very nice. Just overall wonderful hotel"
United States
Gideon
The price is ￥19,779
￥22,152 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
Seasonal outdoor pool
The Graham & Co.

The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.6 out of 10, Exceptional, (22)
"A beautiful and relaxing getaway in the Catskills. Highly recommended. The room and grounds are clean and well maintained. The staff is friendly and attentive without being intrusive."
United States
Brian
The price is ￥24,323
￥27,240 total
includes taxes & fees
Dec 14 - Dec 15
The Graham & Co.
Indoor pool
Hotel Vienna

Hotel Vienna

Hotel Vienna
2.5 star property
Windham
9.4 out of 10, Exceptional, (717)
"Great place to stay with family room it's very clear 👌"
United States
jaisson
Hotel Vienna
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.
View all properties

Top Woodstock Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Love this place when its available. Low key, clean and conveniently near BOTH Hunter and Windham ski areas!"
Bruce 1-night trip
Posted 2 days ago
Hotel Vienna

Explore a world of travel with Expedia

Frequently asked questions

What are some hotels with pools in Woodstock?
Woodstock Way Hotel: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel Dylan: Provides sun loungers, a pool, and complimentary wireless internet access. Twin Gables of Woodstock: Features buffet, an indoor pool, and complimentary wired internet access. The Herwood Inn: Provides a snack bar/deli, an indoor pool, and buffet. Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream: Hotel located near Windham Mountain Resort. Features daily, an indoor pool, and free self parking.
What is there to see and do in Woodstock?
Explore places like Hunter Mountain while you're in the area. The picturesque setting of Overlook Mountain Trailhead and The Comeau Property showcase the area's natural beauty. Broaden your horizons with the local art scene in Woodstock.
When is the best time to book a hotel with a pool in Woodstock?
Taking into account the local weather in Woodstock is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Woodstock are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.