Hotels with Pool & Resorts in Hillsdale from AU$122

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Check availability on Hillsdale Hotels with Pool

Tonight
27 Apr - 28 Apr
Tomorrow
28 Apr - 29 Apr
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

Our top choices for Hillsdale hotels with a pool

Indoor pool, seasonal outdoor pool, 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 AU$161
includes taxes & fees
3 May - 4 May
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (916 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating spa pool experiences.
The price is AU$167
includes taxes & fees
26 May - 27 May
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (91 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a spa pool to soothe tired muscles.
The price is AU$198
includes taxes & fees
4 May - 5 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, (556 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is AU$172
includes taxes & fees
28 Apr - 29 Apr
The Little Lion
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (852 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is AU$123
includes taxes & fees
28 Apr - 29 Apr
Howard Johnson by Wyndham Lenox
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is AU$276
includes taxes & fees
30 Apr - 1 May
The Red Lion Inn
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (76 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is AU$238
includes taxes & fees
28 Apr - 29 Apr
Little Cat Lodge
Indoor pool

Element Lenox Berkshires

Element 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 AU$277
includes taxes & fees
3 May - 4 May
Element Lenox Berkshires
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is AU$196
includes taxes & fees
17 May - 18 May
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (854 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is AU$122
includes taxes & fees
25 May - 26 May
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

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
Mark 1-night trip
Posted 7 hours ago
Monument Mountain Motel

Frequently asked questions

What are some accommodation options with pools in Hillsdale?
Berkshires Untold: Offers free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Features 3 restaurants, an outdoor pool and spa services. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy: Hotel located near National Shrine of the Divine Mercy. Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. The Red Lion Inn: Provides a sauna, an indoor pool and free self parking. Quality Inn Great Barrington: Offers buffet, an indoor pool and free self parking.
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.