Find Hotels with a Pool in Hillsdale, NY

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Check availability on Hillsdale Hotels with a Pool

Tonight
29 Nov - 30 Nov
Tomorrow
30 Nov - 1 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Hillsdale Hotels with a Pool

Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1011)
Shimmering waters beckon at dual pool options, where indoor relaxation meets seasonal outdoor splendor. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is AED 229
AED 256 total
includes taxes & fees
7 Dec - 8 Dec
The Yankee, Trademark Collection by Wyndham
Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
Swimming enthusiasts appreciate the serene indoor pool that provides year-round aquatic enjoyment regardless of weather. After energizing laps, guests gather at the outdoor firepit or enjoy a complimentary manager's reception before retreating to individually furnished rooms.
The price is AED 481
AED 537 total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.2 out of 10, Wonderful, (63)
Plunge into the indoor pool open from 8:00 AM to 10:00 PM after exploring nearby Tanglewood Music Center. Soothing hot tub sessions complement winter activities like cross-country skiing, while attentive staff ensure a refreshingly clean, well-maintained aquatic retreat.
The price is AED 350
AED 391 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Indoor pool
8.0 out of 10, Very Good, (973)
Swimmers splash in the pristine indoor pool from 7 AM to 9 PM, complemented by an on-site health club for complete wellness. Hiking trails and skiing opportunities nearby make this centrally located hotel an ideal family-friendly retreat.
The price is AED 341
AED 381 total
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
  • Outdoor pool
7.6 out of 10, Good, (827)
Sparkling waters beckon at the inviting outdoor pool, a refreshing retreat after exploring nearby Tanglewood Music Center. Deep soaking bathtubs and hydromassage showers in clean, spacious rooms complement this conveniently located getaway.
The price is AED 290
AED 324 total
includes taxes & fees
30 Nov - 1 Dec
Howard Johnson by Wyndham Lenox
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

2.0 star property
Copake Falls
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.4 out of 10, Exceptional, (65)
Seasonal outdoor swimming provides mountain refreshment after exploring nearby hiking trails or skiing adventures. Relaxation continues in the sauna, while evenings bring gatherings around the firepit under starry skies after a delicious continental breakfast.
Little Cat Lodge
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
  • Outdoor pool
  • Pool loungers
9.6 out of 10, Exceptional, (15)
Mountain adventures begin at the outdoor pool, complete with sun loungers and umbrellas for post-hike relaxation. Sauna sessions, complimentary bicycles, and nearby hiking trails complement the experience at this scenic Berkshire retreat.
The price is AED 955
AED 1,190 total
includes taxes & fees
3 Dec - 4 Dec
Prospect Berkshires
2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (790)
Swimming enthusiasts rejoice at this four-pool paradise nestled in the Berkshires. Families appreciate the well-maintained waters complemented by sun loungers, umbrellas, and refreshing poolside drinks, creating memorable mountain getaways year-round.
The price is AED 391
AED 488 total
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Seasonal outdoor pool
Berkshire Inn

Berkshire Inn

2.0 star property
Pittsfield
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
7.8 out of 10, Good, (839)
Seasonal outdoor pool beckons sun-seekers from June through August at this spotless, centrally located motel. After a day of skiing or downtown exploration, guests appreciate comfortable beds, updated rooms with refrigerators, and friendly service.
The price is AED 300
AED 335 total
includes taxes & fees
30 Nov - 1 Dec
Berkshire Inn
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (771)
Plunge into the pristine indoor pool after exploring hiking trails or nearby Tanglewood Music Center. Sun loungers invite relaxation while the hot tub soothes tired muscles. Beyond aquatic pleasures, this lodge offers fitness facilities and an arcade room.
Berkshire Mountain Lodge
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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Top Hillsdale Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Love this place! Great rooms, view of the lake, Indian restaurant inside, and wonderful breakfast choices. We’ll be back. "
Keville 1-night trip
Posted 4 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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Frequently asked questions

What are some accommodations with pools in Hillsdale?
The Brooks Motel: Offers free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Provides a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Features a seasonal outdoor pool, an indoor pool, and buffet.
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.