Hotels with Swimming Pool in Hillsdale, New York

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Check availability on Hillsdale Hotels with Swimming Pool

Tonight
Jan 4 - Jan 5
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Jan 5 - Jan 6
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Jan 9 - Jan 11
In two weeks
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 P8,182
P9,139 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, (1006)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is P5,768
P6,443 total
includes taxes & fees
Jan 9 - Jan 10
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 P14,833
P18,541 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 P5,768
P6,443 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 P4,650
P5,194 total
includes taxes & fees
Jan 5 - Jan 6
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 P6,475
P7,232 total
includes taxes & fees
Jan 5 - Jan 6
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, (804)
"great stall and friendly pet friendly place"
United States
bonnie
The price is P5,809
P7,803 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 P5,954
P6,651 total
includes taxes & fees
Jan 11 - Jan 12
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, (814)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is P6,622
P8,547 total
includes taxes & fees
Jan 7 - Jan 8
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 P7,527
P8,408 total
includes taxes & fees
Jan 9 - Jan 10
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Nice warm pool and hot tub. Good little fitness center. "
Fawn 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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: Features 3 restaurants, an outdoor pool, and spa services. Berkshire Mountain Lodge: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
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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