Hotels with Swimming Pool in Hillsdale, New York

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Check availability on Hillsdale Hotels with Swimming Pool

Our top choices for Hillsdale hotels with a pool

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
"Pool and hot tub are terrific, great breakfast spread, convenient location, super comfortable mattress."
United States
Emma
The price is P6,728
P7,515 total
includes taxes & fees
May 26 - May 27
The Yankee Inn

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (938 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
"Spacious, clean, and the pool was warm and perfect for family swimming"
United States
Danielle
The price is P5,414
P7,427 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
"Plenty of parking and nice pool."
United States
Dan
The price is P4,876
P5,447 total
includes taxes & fees
May 19 - May 20
Howard Johnson by Wyndham Lenox

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
"Clean rooms, friendly staff, pool was very clean"
United States
Camille
The price is P7,839
P8,756 total
includes taxes & fees
May 28 - May 29
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
"we loved using the pool at the beautiful Red Lion"
United States
Lisa
The price is P5,864
P6,550 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (855 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
"This is a very convenient motel -- it is easy to get to, has a nice pool, quiet area, comfortable room,"
United States
Donald W
The price is P4,937
P5,515 total
includes taxes & fees
May 25 - May 26
Berkshire Inn

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (78 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
"We look forward to returning and using the pool."
United States
Evelyn
The price is P9,388
P10,514 total
includes taxes & fees
May 27 - May 28
Little Cat Lodge

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
"The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night."
United States
Judith Pauline
The price is P9,666
P13,554 total
includes taxes & fees
May 28 - May 29
The Red Lion Inn

Red Ranch Motel

Red Ranch Motel
2.5 star property
Catskill
7.2 out of 10, Good, (496 reviews)
  • cleanliness
    Dive into seasonal poolside bliss with dedicated children's swimming areas and shady loungers at this Hudson Valley retreat.
"Had nice pool."
United States
Juan
The price is P6,592
P7,119 total
includes taxes & fees
May 20 - May 21
Red Ranch Motel

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
"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 P10,308
P11,514 total
includes taxes & fees
May 25 - May 26
Element by Marriott Lenox Berkshires
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.

Choose what matters most at hotels with a pool in Hillsdale

Top Hillsdale Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Hillsdale?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Features 3 restaurants, an outdoor pool, and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Offers buffet, an indoor pool, and complimentary wired internet access. The Red Lion Inn: Features 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Hampton Inn & Suites Berkshires-Lenox: Offers a steam room, 3 indoor pools, 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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