Hotels with Swimming Pool in Hillsdale, New York

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Check availability on Hillsdale Hotels with Swimming Pool

Tonight
Aug 1 - Aug 2
Tomorrow
Aug 2 - Aug 3
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Hillsdale Hotels with Swimming Pool

Blackberry River Inn
Relax by the pool surrounded by lush greenery and comfortable lounge seating.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (120)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is P9,574
P11,010 total
includes taxes & fees
Aug 11 - Aug 12
Blackberry River Inn
The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (87)
"Beautiful room and property. Perfect weekend getaway!"
The price is P16,700
P20,151 total
includes taxes & fees
Aug 3 - Aug 4
The Old Inn On The Green
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (397)
"No frills but it was a great stay!"
The price is P6,334
P7,075 total
includes taxes & fees
Aug 18 - Aug 19
Sunset Inn
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Swim laps in a serene, well-lit pool surrounded by a simple, functional design.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (683)
"Terrific place. Spacious, clean, comfortable."
The price is P7,139
P8,779 total
includes taxes & fees
Aug 6 - Aug 7
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is P9,370
P10,467 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax by the pool surrounded by lounge chairs and sunbeds, with views of the surrounding area and greenery.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P10,143
P11,329 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Lenox
Enjoy a refreshing swim in our pool surrounded by a serene landscape.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (773)
"Was great loved the jacuzzi tub "
The price is P4,608
P5,147 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Lenox
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.

Top Hillsdale Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Loved our visit"
Barbara 1-night trip
Posted 2 days ago
The Red Lion Inn

Frequently asked questions

What are some accommodations with pools in Hillsdale?
The Brooks Motel: Features a sauna, an indoor pool, and free self parking. Postcard Cabins Eastern Catskills: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Features a health club, an indoor pool, and complimentary wired internet access. Howard Johnson by Wyndham Saugerties: Features free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Hillsdale?
Spend some time experiencing the great outdoors at Copake Lake and Mosquito Island. Discover sights such as Catamount Aerial Adventure Park, Catamount Ski Area, and Hillsdale Town Hall during your stay.
When is the best time to book a hotel with a pool in Hillsdale?
Taking into account the local weather in Hillsdale can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.