Find Hotels with a Pool in Hillsdale, NY

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Check availability on Hillsdale Hotels with a Pool

Tonight
Mar 8 - Mar 9
Tomorrow
Mar 9 - Mar 10
Next weekend
Mar 13 - Mar 15
In two weeks
Mar 20 - Mar 22

Our top choices for Hillsdale hotels with a pool

Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (22 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
The price is NT$4,404
NT$4,919 total
includes taxes & fees
Mar 15 - Mar 16
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,010 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is NT$2,935
NT$3,279 total
includes taxes & fees
Mar 15 - Mar 16
The Yankee, Trademark Collection by Wyndham
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (743 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is NT$3,390
NT$3,786 total
includes taxes & fees
Mar 15 - Mar 16
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (869 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is NT$3,369
NT$4,471 total
includes taxes & fees
Apr 1 - Apr 2
Berkshire Mountain Lodge
Indoor pool

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1,005 reviews)
  • cleanliness
    Swim in style at this Saugerties retreat with a year-round indoor pool and relaxing sauna for post-adventure recovery.
The price is NT$3,136
NT$3,513 total
includes taxes & fees
Mar 9 - Mar 10
Howard Johnson by Wyndham Saugerties
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (554 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is NT$3,485
NT$3,893 total
includes taxes & fees
Mar 9 - Mar 10
The Little Lion
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (411 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is NT$3,010
NT$3,362 total
includes taxes & fees
Mar 9 - Mar 10
Sunset Inn
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (21 reviews)
  • cleanliness
    Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
The price is NT$6,209
NT$7,998 total
includes taxes & fees
Mar 9 - Mar 10
Prospect Berkshires
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (74 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
Little Cat Lodge
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,003 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is NT$4,023
NT$4,494 total
includes taxes & fees
Mar 31 - Apr 1
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included
4 stars

Top Hillsdale Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
" The overall property was clean and well kept the pool and Hot Tub are very nice. The breakfast was excellent. The room we stayed in was clean. Beds were comfortable however the room was a little dated."
Frank 2-night trip
Posted 12 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are some accommodations with pools in Hillsdale?
The Brooks Motel: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Features a seasonal outdoor pool, an indoor pool, and buffet. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Offers a health club, an indoor pool, and complimentary wired internet access. The Yankee, Trademark Collection by Wyndham: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers buffet, an indoor pool, and free self parking.
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.