A rural landscape with snow-covered fields, a winding road, and scattered trees.

Hillsdale Hotel Guide - Hotels with Pool in Hillsdale, New York

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Check availability on Hillsdale Hotels 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, (1,013 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is €148
includes taxes & fees
12 Jul - 13 Jul
The Yankee Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (580 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is €109
includes taxes & fees
13 Jul - 14 Jul
The Little Lion
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (127 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is €154
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,011 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is €207
includes taxes & fees
22 Jul - 23 Jul
The Red Lion Inn
Deep-tissue massages, Swedish massages, facials, 5 treatment rooms

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.6 out of 10, Excellent, (54 reviews)
The price is €239
includes taxes & fees
10 Aug - 11 Aug
Pocketbook Hotel and Bath
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (95 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is €167
includes taxes & fees
13 Jul - 14 Jul
Little Cat Lodge
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is €66
includes taxes & fees
19 Jul - 20 Jul
Berkshire Travel Lodge
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (881 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is €97
includes taxes & fees
12 Jul - 13 Jul
Howard Johnson by Wyndham Lenox
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (423 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Centre, offering a sunny retreat in a peaceful location.
The price is €107
includes taxes & fees
22 Jul - 23 Jul
Sunset Inn
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (875 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is €88
includes taxes & fees
22 Jul - 23 Jul
Berkshire 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.
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Choose what matters most at hotels with a pool in Hillsdale

Breakfast included
4 stars

Top Hillsdale Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Front desk staff was very accommodating. She was kind to let us check in as soon as rooms were cleaned. We traveled from California and were very sleepy and that made our stay more enjoyable."
MARIA THERESA 2-night trip
Posted 14 hours ago
The Yankee Inn

Frequently asked questions

What are some accommodation options with pools in Hillsdale?
It's All About the Mountain Views, Modern Farmhouse: Offers a seasonal outdoor pool, an indoor pool and buffet. The Yankee Inn: Provides free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool and spa services. Berkshires Untold: 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.
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.