Hotels with Swimming Pools in Hillsdale

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Hillsdale Hotels with Swimming Pools

Our top choices for Hillsdale hotels with a pool

Porch

Four Seasons Motel

Four Seasons Motel
2.0 star property
Catskill
8.2 out of 10, Very good, (208 reviews)
  • cleanliness
    Seasonal mountain pool paradise invites guests to cool off with refreshing dips from May to September.
The price is S$138
includes taxes & fees
13 Apr - 14 Apr
Four Seasons Motel
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (846 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is S$112
includes taxes & fees
13 Apr - 14 Apr
Howard Johnson by Wyndham Lenox
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is S$157
includes taxes & fees
14 Apr - 15 Apr
The Little Lion
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (901 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is S$152
includes taxes & fees
12 May - 13 May
Berkshire Mountain Lodge
Indoor pool

Element Lenox Berkshires

Element 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 price is S$209
includes taxes & fees
19 Apr - 20 Apr
Element Lenox Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is S$158
includes taxes & fees
27 Apr - 28 Apr
Hampton Inn & Suites Berkshires-Lenox
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (88 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is S$168
includes taxes & fees
16 Apr - 17 Apr
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property grounds

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 price is S$248
includes taxes & fees
21 Apr - 22 Apr
The Red Lion Inn
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (75 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is S$243
includes taxes & fees
16 Apr - 17 Apr
Little Cat Lodge
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is S$203
includes taxes & fees
19 Apr - 20 Apr
Blackberry River Inn
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

Choose what matters most at hotels with a pool in Hillsdale

Breakfast included
4 stars

Top Hillsdale Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"would come again to stay if around the area compared to Red Lion. "
Juliet 1-night trip
Posted 16 hours ago
Quality Inn Great Barrington

Frequently asked questions

What are some accommodation options with pools in Hillsdale?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Hotel located near National Shrine of the Divine Mercy. Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Berkshires Untold: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features a seasonal outdoor pool, an indoor pool and buffet. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel, 15-minute walk from National Shrine of the Divine Mercy. 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.

Explore a world of travel with Expedia