Hotels with Swimming Pool in Hillsdale, New York

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Check availability on Hillsdale Hotels with Swimming Pool

Tonight
Jan 8 - Jan 9
Tomorrow
Jan 9 - Jan 10
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Hillsdale hotels with a pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (15)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is P8,227
P9,190 total
includes taxes & fees
Jan 21 - Jan 22
Element Lenox Berkshires
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (716)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is P5,817
P6,497 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is P12,548
P16,000 total
includes taxes & fees
Feb 4 - Feb 5
Prospect Berkshires
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1002)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is P5,817
P6,498 total
includes taxes & fees
Jan 23 - Jan 24
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is P4,676
P5,223 total
includes taxes & fees
Jan 10 - Jan 11
Howard Johnson by Wyndham Lenox
Exterior
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"Perfect for pets "
United States
Maria
The price is P6,511
P7,273 total
includes taxes & fees
Jan 12 - Jan 13
The Little Lion
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Everything was great! "
Canada
Daphne
The price is P6,004
P6,706 total
includes taxes & fees
Jan 19 - Jan 20
The Yankee, Trademark Collection by Wyndham
2 indoor pools, 2 outdoor pools, pool umbrellas, sun 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

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, (818)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is P5,540
P7,346 total
includes taxes & fees
Jan 15 - Jan 16
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Very comfortable beds! "
United States
Gerald
The price is P6,600
P7,373 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn & Suites Berkshires-Lenox
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (661)
" Nice staff - beautiful hotel!"
United States
MARY
The price is P7,590
P8,478 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield
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

Top Hillsdale Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Perfectly Clean. Great Service. Beautiful Place!"
Joseph 1-night trip
Posted 9 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

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

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