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

Hillsdale Hotel with Pool

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Check availability on Hillsdale Hotel with Pool

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Hillsdale hotels with a pool

1. Little Cat Lodge

Little Cat Lodge
Copake Falls
  • Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
HK$1,051
HK$1,177 total
includes taxes & fees
25 Aug - 26 Aug
Little Cat Lodge

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
HK$964
HK$1,077 total
includes taxes & fees
23 Sept - 24 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG

3. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
HK$882
HK$985 total
includes taxes & fees
1 Sept - 2 Sept
The Little Lion

4. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
HK$2,575
HK$3,139 total
includes taxes & fees
17 Sept - 18 Sept
Prospect Berkshires

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
HK$1,526
HK$1,705 total
includes taxes & fees
30 Aug - 31 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

6. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
HK$1,235
HK$1,769 total
includes taxes & fees
8 Sept - 9 Sept
The Red Lion Inn

7. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
HK$917
HK$1,178 total
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort

8. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
HK$529
HK$593 total
includes taxes & fees
1 Sept - 2 Sept
Berkshire Travel Lodge

9. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
HK$1,239
HK$1,384 total
includes taxes & fees
14 Sept - 15 Sept
The Yankee Inn

10. Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
Hudson
HK$1,757
HK$2,340 total
includes taxes & fees
31 Aug - 1 Sept
Pocketbook Hotel and Bath
View all properties

Choose what matters most at hotels with a pool in Hillsdale

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Hillsdale Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Front desk staff was great! Simple hot breakfast was good. Plenty of onsite parking. Conveniently located close to the town and shops."
Anuvrath 3-night trip
Posted 15 hours ago
Quality Inn Great Barrington
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

10/10 Excellent
"Very great stay and cleanest!"
Nancy 1-night trip
Posted 21 hours ago
Howard Johnson by Wyndham Saugerties
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"I liked the balcony overlooking the lake"
Rinat 3-night trip
Posted 22 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 2 days ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Evan M 1-night trip
Posted 2 days ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 3 days ago
Howard Johnson by Wyndham Lenox

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. FairBridge Inn Express: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Berkshires Untold: Offers 3 restaurants, an outdoor pool and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Features free self parking, an outdoor pool and flat-screen televisions.
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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