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Check availability on Hillsdale Hotels with Swimming Pool

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, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is ₹12,631
₹14,108 total
includes taxes & fees
26 Jan - 27 Jan
Element Lenox Berkshires
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, (723 reviews)
"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"
United States
Domenic
The price is ₹9,541
₹10,658 total
includes taxes & fees
21 Jan - 22 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (1,006 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is ₹8,905
₹9,947 total
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, seasonal outdoor pool, pool loungers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The hotel is very nice and clean. From the moment we checked in to check out, we had an amazing time. "
United States
Gina
The price is ₹8,419
₹9,404 total
includes taxes & fees
27 Jan - 28 Jan
The Yankee, Trademark Collection by Wyndham
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (549 reviews)
"Perfect for pets "
United States
Maria
The price is ₹9,995
₹11,165 total
includes taxes & fees
21 Jan - 22 Jan
The Little Lion
Indoor pool

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (662 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ₹11,620
₹12,980 total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Lenox Pittsfield
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"All was great! The atmosphere, food, and rooms were very clean. "
United States
Brent
The price is ₹13,100
₹18,692 total
includes taxes & fees
26 Jan - 27 Jan
The Red Lion Inn
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (824 reviews)
"Great overnights stay, wish I was here longer "
United States
Thomas
The price is ₹10,228
₹13,202 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (829 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is ₹7,179
₹8,018 total
includes taxes & fees
23 Jan - 24 Jan
Howard Johnson by Wyndham Lenox
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (816 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is ₹8,967
₹12,046 total
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge
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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Top Hillsdale Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"As usual at the Yankee, check-in was friendly and quick. Room was clean and had everything in order. Rate was very reasonable.,"
Nathaniel 1-night trip
Posted 5 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are some accommodation options with pools in Hillsdale?
The Brooks Motel: Provides free self parking, an indoor pool and complimentary wireless Internet access. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access. Berkshire Mountain Lodge: Offers 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a seasonal outdoor pool, an indoor pool and buffet. 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 the local weather in Hillsdale into account can help you maximise your time at the pool during your trip. 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 Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.