Photo by Joe Vickiana

Find Hotels with Pool in Oliverea, NY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
12 Nov - 13 Nov
Tomorrow
13 Nov - 14 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

Our top choices for Oliverea hotels with a pool

A pool area with a wooden deck, benches, and a lifebuoy.

1. Eastwind Oliverea Valley

Eastwind Oliverea Valley
3.5 star property
Big Indian
9.4 out of 10, Exceptional, (62 reviews)
The price is £225
includes taxes & fees
13 Dec - 14 Dec
Eastwind Oliverea Valley
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.

2. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (335 reviews)
  • cleanliness
    Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
The price is £120
includes taxes & fees
15 Nov - 16 Nov
Shandaken Inn
A log cabin with a tower, a swimming pool, and lounge chairs.

3. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.2 out of 10, Wonderful, (119 reviews)
  • cleanliness
    Seasonal outdoor pool beckons with shady umbrellas in the heart of Catskill Mountains.
The price is £127
includes taxes & fees
22 Nov - 23 Nov
Emerson Resort & Spa
A pool area with a wooden deck, benches, and umbrellas.

4. The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.4 out of 10, Exceptional, (69 reviews)
  • cleanliness
    Splash into poolside fun at this Catskill Mountains motel, where seasonal swimming meets adventure in a charming outdoor oasis.
The price is £92
includes taxes & fees
15 Nov - 16 Nov
The Graham & Co.
A swimming pool with lounge chairs and a building in the background.

5. Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.0 out of 10, Very good, (276 reviews)
  • cleanliness
    Serene seasonal pool oasis nestled in the Catskill Mountains offers perfect summer refreshment.
The price is £123
includes taxes & fees
14 Nov - 15 Nov
Catskill Seasons Inn
A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.

6. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (912 reviews)
  • cleanliness
    Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
The price is £104
includes taxes & fees
23 Nov - 24 Nov
Hotel Vienna
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

7. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (452 reviews)
  • cleanliness
    Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
The price is £152
includes taxes & fees
29 Nov - 30 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

8. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (139 reviews)
  • cleanliness
    Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
The price is £189
includes taxes & fees
23 Nov - 24 Nov
Wylder Hotel Windham
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

9. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (377 reviews)
  • cleanliness
    Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
The price is £137
includes taxes & fees
18 Nov - 19 Nov
The Winwood Condominiums
A swimming pool with lounge chairs and potted plants.

10. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (185 reviews)
  • cleanliness
    Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
The price is £97
includes taxes & fees
15 Nov - 16 Nov
Moore's Motel
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 Oliverea

Breakfast included
4 stars

Top Oliverea Hotel Reviews

A pool area with a wooden deck, benches, and a lifebuoy.
Eastwind Oliverea Valley

Eastwind Oliverea Valley

Eastwind Oliverea Valley
Big Indian

10/10 Excellent

Very nice place to stay. Staff very friendly and welcoming . Lovely breakfast baskets available (additional charge). Only improvement would be cleaning of room . We got a message while out asking if we would like the room cleaned that day with a circa 3 hour window that cleaners were available . We asked for it to be and unfortunately it wasn’t when we returned. Put it down to message system delays but think better system needed than this. Definately worth visiting though .
United Kingdom
Cheryl
Reviewed July 21, 2025
Eastwind Oliverea Valley

Frequently Asked Questions

What are some accommodation options with pools in Oliverea?

Urban Cowboy Lodge: Offers a sauna, an outdoor pool and spa services. Eastwind Oliverea Valley: Provides kitchens, a communal pool and televisions. Cold Spring Lodge - Cabin 5: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli. Hunter Lodge, a Bluebird by Lark: Hotel located near Windham Mountain Resort. Features daily, an indoor pool and free self parking. Emerson Resort & Spa: Hotel, 1-minute walk from Hunter Mountain. Offers 2 hot tubs, an outdoor pool and a sauna.

What is there to see and do in Oliverea?

Surround yourself with nature at Giant Ledge Trailhead and Esopus Creek. Discover sights such as Catskill State Park, Belleayre Beach and Belleayre Mountain Ski Center during your stay.

When is the best time to book a hotel with a pool in Oliverea?

Taking the local weather in Oliverea 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 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Oliverea are January, February, December and March, with each month seeing an average of 24 cm of snowfall.