Hillsdale Hotel with Pool

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Check availability on Hillsdale Hotel with Pool

Our top choices for Hillsdale hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

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.
The price is HK$854
HK$953 total
includes taxes & fees
19 May - 20 May
The Yankee Inn
Indoor pool

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.
The price is HK$687
HK$942 total
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge
Exterior

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.
The price is HK$619
HK$691 total
includes taxes & fees
19 May - 20 May
Howard Johnson by Wyndham Lenox
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is HK$995
HK$1,111 total
includes taxes & fees
28 May - 29 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior

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.
The price is HK$744
HK$831 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion
Seasonal outdoor pool

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.
The price is HK$601
HK$672 total
includes taxes & fees
26 May - 27 May
Berkshire Inn
Seasonal outdoor pool

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.
The price is HK$1,191
HK$1,334 total
includes taxes & fees
20 May - 21 May
Little Cat Lodge
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 HK$1,226
HK$1,720 total
includes taxes & fees
27 May - 28 May
The Red Lion Inn
Seasonal outdoor pool, open 10 AM to 8 PM, pool umbrellas, pool loungers

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.
The price is HK$836
HK$903 total
includes taxes & fees
19 May - 20 May
Red Ranch Motel
Indoor pool

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 price is HK$1,308
HK$1,461 total
includes taxes & fees
25 May - 26 May
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.
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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included
4 stars

Top Hillsdale Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

8/10 Good
"its dated old and it was sitll very clean every thing worked Room care was good. The microwave and the frig were nice. but got to give a thumbs down to no coffee in the rooom"
Harry 2-night trip
Posted 13 hours ago
Monument Mountain Motel

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. 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 high-speed (wired) Internet access. The Red Lion Inn: Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Hampton Inn & Suites Berkshires-Lenox: Offers a steam room, 3 indoor swimming 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 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.

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