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Check availability on Hillsdale Hotels with Pool

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

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, (1,002 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is ฿4,220
฿4,714 total
includes taxes & fees
7 Jul - 8 Jul
The Yankee Inn
Seasonal outdoor pool

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (304 reviews)
  • cleanliness
    Immerse in the sun-drenched seasonal outdoor pool surrounded by lush resort grounds and full-service spa amenities.
The price is ฿8,032
฿9,237 total
includes taxes & fees
19 Jul - 20 Jul
Interlaken Inn & Resort
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (481 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is ฿2,239
฿2,508 total
includes taxes & fees
6 Jul - 7 Jul
Berkshire Travel Lodge
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is ฿5,166
฿5,940 total
includes taxes & fees
8 Jul - 9 Jul
Blackberry River Inn
Indoor pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (791 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
The price is ฿6,740
฿7,528 total
includes taxes & fees
19 Jul - 20 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Meeting facility

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is ฿5,866
฿8,034 total
includes taxes & fees
22 Jul - 23 Jul
The Red Lion Inn
Indoor pool

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, (784 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is ฿5,474
฿6,115 total
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is ฿7,315
฿8,193 total
includes taxes & fees
23 Jul - 24 Jul
Little Cat Lodge
Desk, laptop workspace, iron/ironing board, free cots/infant beds

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (576 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is ฿3,716
฿4,150 total
includes taxes & fees
7 Jul - 8 Jul
The Little Lion
Outdoor pool

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (879 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is ฿3,284
฿3,669 total
includes taxes & fees
6 Jul - 7 Jul
Howard Johnson by Wyndham Lenox
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 Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Staff was very helpful particularly Jerry in outside cafe. Grounds keeper did a beautiful job! Outdoor pool was amazing! Will be back to swim in in the winter. Loved the shops located in the main building. We stayed in Maple Glen which was lovely. I was disappointed my room was dark but now know to ask for a sunnier room when booking."
Jayne 1-night trip
Posted 9 hours ago
The Red Lion Inn

Frequently asked questions

What are some accommodation options with pools in Hillsdale?
The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn: Provides 3 restaurants, an outdoor pool and spa services. Berkshires Untold: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Provides 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.