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Hinsdale Hotels with Swimming Pool

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Check availability on Hinsdale Hotels with Swimming Pools

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Hinsdale hotels with a pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is RM547
RM611 total
includes taxes & fees
5 Jan - 6 Jan 2026
Element Lenox Berkshires
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1003)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is RM357
RM399 total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool, seasonal outdoor pool, pool loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is RM410
RM458 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is RM413
RM461 total
includes taxes & fees
28 Jan - 29 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
Cozy Corner Motel

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (887)
"Clean, Great Staff, Quiet"
United States
john
The price is RM288
RM340 total
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy Corner Motel
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is RM320
RM357 total
includes taxes & fees
30 Dec - 31 Dec
Howard Johnson by Wyndham Lenox
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Very comfortable beds! "
United States
Gerald
The price is RM450
RM503 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (798)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is RM400
RM537 total
includes taxes & fees
12 Jan - 13 Jan 2026
Berkshire Mountain Lodge
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (592)
"Cute place"
United States
Lisa
The price is RM401
RM448 total
includes taxes & fees
30 Dec - 31 Dec
Maple Terrace Motel
Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is RM603
RM855 total
includes taxes & fees
26 Jan - 27 Jan 2026
The Red Lion 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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Top Hinsdale Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!"
Chris 1-night trip
Posted 3 days ago
The Red Lion Inn

Frequently asked questions

What are some accommodation options with pools in Hinsdale?
Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Williams Inn: Features a seasonal outdoor pool, an indoor pool and buffet. The Yankee, Trademark Collection by Wyndham: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features free self parking, an indoor pool and complimentary wireless Internet access.
What is there to see and do in Hinsdale?
Make a point to visit attractions such as Kennedy Park and Berkshire Museum. Discover sights such as Bas Ridge Golf Course during your stay.
When is the best time to book a hotel with a pool in Hinsdale?
Taking the local weather in Hinsdale 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 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Hinsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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