A calm lake with a sunset reflecting on the water, surrounded by forested hills.

Woodstock Hotel Guide - Hotels with Pool in Woodstock, New York

  • 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 Pool

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Woodstock hotels with a pool

A white house with a green door, black trim, and a porch with a lantern.

1. Twin Gables of Woodstock

Twin Gables of Woodstock
3.0 star property
Woodstock
9.8 out of 10, Exceptional, (232 reviews)
"Location in downtown Woodstock was great- parking was easy. Loved the rooftop patio - great place to enjoy a coffee. Rooms were very nice and large."
United States
Barbara
The price is €144
includes taxes & fees
16 Nov - 17 Nov
Twin Gables of Woodstock
A wooden cabin with large windows overlooking a forested area with a waterfall.

2. Woodstock Way Hotel

Woodstock Way Hotel
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (325 reviews)
"The staff was amazing… the waterfall was blissful"
United States
Wayne
The price is €311
includes taxes & fees
1 Dec - 2 Dec
Woodstock Way Hotel
A white house with a porch, a bicycle, and a chair in the yard.

3. The Woodstock Inn on the Millstream

The Woodstock Inn on the Millstream
3.0 star property
Woodstock
9.0 out of 10, Wonderful, (227 reviews)
"Breakfast was less than I expected. Mostly breads dry cereal, some fruit. Breads were cold and hard, had to be toasted. Not enough places to sit inside."
United States
Arthur
The price is €229
includes taxes & fees
12 Nov - 13 Nov
The Woodstock Inn on the Millstream
A serene garden with a stone pathway, a small bridge, and a bench.

4. Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY
3.0 star property
Woodstock
8.6 out of 10, Excellent, (171 reviews)
"We had a great time! The host was super sweet and helpful, and the breakfast was delicious. Would stay again!"
United States
Lucian
The price is €219
includes taxes & fees
9 Nov - 10 Nov
Morning Glory B n B Woodstock NY
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

Choose what matters most at hotels with a pool in Woodstock

Breakfast included
Hot tub

Top Woodstock Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Second time staying, it's a great place. Would have given it 5 stars across the board, but the sauna was being worked on and it's one of the reasons why I book the place. That was disappointing, but the rest was all good."
Michelle 1-night trip
Posted 11 hours ago
Hotel Vienna

Frequently asked questions

What are some hotels with pools in Woodstock?
Woodstock Way Hotel: Features sunloungers, a pool and complimentary wireless Internet access. Twin Gables of Woodstock: Offers a steam room, 3 indoor swimming pools and spa services. The Herwood Inn: Offers a snack bar/deli, an indoor pool and free self parking. Streamside Cottage Half Mile to Town of Woodstock: Provides a sauna, an indoor pool and free self parking. Beekman Arms and Delamater Inn: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Woodstock?
The picturesque setting of Overlook Mountain Trailhead and The Comeau Property showcase the area's natural beauty. During your stay, visit sights such as Bearsville Theater, Catskill State Park and Woodstock Music Shop. 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 the local weather in Woodstock into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Woodstock are January, February, March and April, with each month seeing an average of 17 cm of snowfall.