Find Hotels with a Pool in Hillsdale, NY

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Check availability on Hillsdale Hotels with a Pool

Tonight
Jan 7 - Jan 8
Tomorrow
Jan 8 - Jan 9
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, (14)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is ￥21,767
￥24,314 total
includes taxes & fees
Jan 19 - Jan 20
Element Lenox Berkshires
Meeting facility
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, (1000)
"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 ￥15,347
￥17,143 total
includes taxes & fees
Jan 23 - Jan 24
Holiday Inn & Suites Pittsfield-Berkshires 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 ￥33,199
￥42,330 total
includes taxes & fees
Jan 26 - Jan 27
Prospect 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 ￥15,347
￥17,143 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Great Barrington 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 ￥12,371
￥13,818 total
includes taxes & fees
Jan 8 - Jan 9
Howard Johnson by Wyndham Lenox
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
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 ￥17,226
￥19,242 total
includes taxes & fees
Jan 11 - Jan 12
The Little Lion
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (807)
"great stall and friendly pet friendly place"
United States
bonnie
The price is ￥15,455
￥20,762 total
includes taxes & fees
Feb 1 - Feb 2
Berkshire Mountain Lodge
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, (1010)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ￥15,840
￥17,692 total
includes taxes & fees
Jan 14 - Jan 15
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, (817)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ￥16,640
￥21,649 total
includes taxes & fees
Jan 8 - Jan 9
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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, (660)
" Nice staff - beautiful hotel!"
United States
MARY
The price is ￥20,026
￥22,369 total
includes taxes & fees
Jan 30 - Jan 31
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.
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Top Hillsdale Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Very clean, modern hotel. Would definitely stay here again. "
Debra 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox

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.