A lush green golf course with a lake and trees in the background.

Find Hotels with a Pool in Roscoe, NY

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Roscoe Hotels with a Pool

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Roscoe hotels with a pool

A house with a swimming pool, a deck, and a fenced yard.
A cozy living room with a fireplace, a sofa, a chair, a bookshelf, and a large window.
A wooden staircase leading to a landing with a white railing, a wooden door with a glass panel, and a small wooden bench.
A modern kitchen with a large island, bar stools, wooden accents, and stainless steel appliances.

1. Cozy Wood Stove * Chef’s Kitchen * Private Stream

Cozy Wood Stove * Chef’s Kitchen * Private Stream
Roscoe
$715 nightly
$804 total
Nov 3 - Nov 4
Total with taxes and fees
Cozy Wood Stove * Chef’s Kitchen * Private Stream
A hot tub with a view of a house and trees.
A covered porch with a sofa, a large window with a view of a grassy area, and a decorative metal gate.
A rustic cabin with a metal roof, surrounded by a lush green lawn and a flowing stream.
A cozy cabin interior with a stone fireplace, wooden floors, a leather recliner, and a sofa with patterned cushions.

2. 🏞️ Creekside Catskills Escape | Pool, Hot Tub, Sauna & Fire Pit 🔥

🏞️ Creekside Catskills Escape | Pool, Hot Tub, Sauna & Fire Pit 🔥
Roscoe
🏞️ Creekside Catskills Escape | Pool, Hot Tub, Sauna & Fire Pit 🔥
An outdoor swimming pool with a wooden deck, a red cabin, and a fenced area.
A hammock between trees, a wooden cabin, and a red building with a metal roof.
A kitchen with wooden cabinets, a microwave, a sink, and a window with a view.
Interior

3. Luxury Catskills Creekside Cabin | Pool, Sauna & Fire Pit Retreat

Luxury Catskills Creekside Cabin | Pool, Sauna & Fire Pit Retreat
Roscoe
Luxury Catskills Creekside Cabin | Pool, Sauna & Fire Pit Retreat
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building.
A modern cabin with a wooden deck, large windows, and a black roof, surrounded by dense forest.
An indoor venue with wooden beams, tables set for dining, and hanging greenery.
A triangular tent-style room with a bed, a small table, and a red lamp.

4. Callicoon Hills

Callicoon Hills
Callicoon Center
$261 nightly
$295 total
Oct 8 - Oct 9
Total with taxes and fees
Callicoon Hills
A modern lobby with a curved sofa, a reception desk, and a flat-screen TV.
A banquet hall with round tables covered in white tablecloths and chairs, a carpeted floor, and a ceiling with recessed lighting.
A hotel room with two beds, a desk, a chair, and a large painting on the wall.
A spacious indoor area with multiple tables and chairs, a kitchen area with a counter, and a large window providing natural light.

5. Days Inn by Wyndham Liberty/Monticello

Days Inn by Wyndham Liberty/Monticello
Liberty
  • Dive into poolside serenity at this Liberty hotel, where comfortable loungers invite all-day relaxation beside sparkling waters.
$87 nightly
$98 total
Nov 1 - Nov 2
Total with taxes and fees
Days Inn by Wyndham Liberty/Monticello
A large indoor swimming pool with a wooden deck and lounge chairs.
A modern living room with two sofas, a glass coffee table, and a painting of a horse.
A modern bathroom with a glass shower enclosure, a toilet, and a towel rack with folded towels.
A reception area with a marble counter, a wall-mounted artwork, and a ceiling with recessed lighting.

6. Best Western Monticello

Best Western Monticello
Monticello
  • Dive into refreshing leisure at this hotel's indoor pool sanctuary, complete with sun loungers and a rejuvenating sauna.
$114 nightly
$128 total
Oct 14 - Oct 15
Total with taxes and fees
Best Western Monticello
A water park with a water play structure and people enjoying the water.
A wooden building with a staircase leading to a balcony, surrounded by snow and trees.
A hotel lobby with round tables, cushioned chairs, a large pillar, and a projection screen displaying a movie.
A fountain with water jets in the center, surrounded by a circular stone border. In the background, there is a building with a balcony and arched windows.

7. Villa Roma Resort and Conference Center

Villa Roma Resort and Conference Center
Callicoon
  • Year-round aquatic adventures await at this resort with indoor and seasonal outdoor pools, a waterslide, and poolside bar.
$205 nightly
$231 total
Oct 8 - Oct 9
Total with taxes and fees
Villa Roma Resort and Conference Center
A cozy indoor seating area with wooden beams, string lights, and potted plants.
A wooden building with a sign reading "The Arnold" and a garden with daffodils.
A covered outdoor dining area with wooden tables and benches, large windows, and a view of a garden.
A cozy log cabin interior with a central seating area, wooden walls, and large windows.

8. The Arnold House

The Arnold House
Livingston Manor
  • Dive into seasonal bliss at this mountain hotel with a refreshing outdoor pool and poolside bar for a summer escape.
$420 nightly
$475 total
Oct 8 - Oct 9
Total with taxes and fees
The Arnold House
A poolside area with lounge chairs and striped umbrellas, surrounded by a wooden fence and trees.
A spacious dining area with multiple tables and chairs, large potted plants, and a view of the outdoors through large windows.
A large white house with a green roof, surrounded by a well-maintained lawn and a view of a lake.
A sunroom with wooden beams, large windows, and a variety of potted plants.

9. Kenoza Hall

Kenoza Hall
Kenoza Lake
  • Seasonal outdoor pool sanctuary offers sun-soaked relaxation amid hiking trails at this indulgent spa retreat in the countryside.
$400 nightly
$451 total
Oct 18 - Oct 19
Total with taxes and fees
Kenoza Hall
An above-ground swimming pool with a built-in ladder, surrounded by a gravel border and grass.
A living room with a wooden floor, a sofa, a dining table with chairs, and a door leading outside.
A bedroom with a bed, two wicker chairs, a ceiling fan, and a window with curtains.
A living room with a wooden staircase, a black leather sofa, a TV on a stand, and a patterned rug.

10. 5 minutes from original Woodstock site.

5 minutes from original Woodstock site.
Mongaup Valley
  • Splash into serenity at this historic retreat with private and outdoor pools near Woodstock.
$309 nightly
$348 total
Oct 8 - Oct 9
Total with taxes and fees
5 minutes from original Woodstock site.
View all properties

Choose what matters most at hotels with a pool in Roscoe

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Roscoe Hotel Reviews

Days Inn by Wyndham Liberty/Monticello

Days Inn by Wyndham Liberty/Monticello

10/10 Excellent
"Restaurant was amazing . Staff very informative about history of Woodstock"
Mary 1-night trip
Posted 4 days ago
Days Inn by Wyndham Liberty/Monticello

Frequently asked questions

What are some hotels with pools in Roscoe?
Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy: Provides a sauna, a pool, and complimentary wireless internet access. Roscoe Mountain Club: Features a children's pool, a seasonal outdoor pool, and 3 restaurants. Winterberry Pond, Converted Barn & Hot Tub: Offers daily, a pool, and free self parking. Roscoe Coop Clucking Crazy Hut: Hotel located near Resorts World Catskills. Offers a sauna, an indoor pool, and buffet. Property of Big Foot Roscoe, NY: Hotel located near Resorts World Catskills. Features a full-service spa, an indoor pool, and a sauna.
What is there to see and do in Roscoe?
Spend some time experiencing the great outdoors at Tennanah Lake and Willowemoc Wild Forest. Discover sights such as Catskill State Park during your stay.
When is the best time to book a hotel with a pool in Roscoe?
Taking into account the local weather in Roscoe 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 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Roscoe are January, February, December, and March, with each month seeing an average of 9 inches of snowfall.

Explore a world of travel with Expedia