Hotels with Pool & Resorts in Windsor from AU$135

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Check availability on Windsor Hotels with Pool

Best Windsor Hotels with Pool

Indoor pool
Element Lenox Berkshires
Element Lenox Berkshires
3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
The price is AU$231
includes taxes & fees
9 Nov - 10 Nov
Element Lenox Berkshires
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (901)
"Excellent customer service and great rooms"
The price is AU$177
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (809)
"Good for the one night drive through! "
The price is AU$135
includes taxes & fees
22 Oct - 23 Oct
Howard Johnson by Wyndham Lenox
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (2065)
"Nice room clean and friendly staff"
The price is AU$174
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the 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
9.2 out of 10, Wonderful, (1003)
"Very clean, nice amenities , great location!!"
The price is AU$191
includes taxes & fees
13 Nov - 14 Nov
Hampton Inn & Suites Berkshires-Lenox
Exterior
Cozy Corner Motel
Cozy Corner Motel
2.0 star property
9.2 out of 10, Wonderful, (873)
"Very nice staff, nice breakfast"
The price is AU$135
includes taxes & fees
2 Nov - 3 Nov
Cozy Corner Motel
Seasonal outdoor pool
The Springs Motel
The Springs Motel
2.0 star property
9.2 out of 10, Wonderful, (78)
"The Springs Motel was a delight! Something away from the boring, staple type of hotel. The staff was so friendly and welcoming. The coffee and breakfast is a great touch! Can't wait to go back"
The price is AU$186
includes taxes & fees
15 Oct - 16 Oct
The Springs Motel
Indoor pool
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (701)
"Great stay, perfect "
The price is AU$194
includes taxes & fees
5 Nov - 6 Nov
Berkshire Mountain Lodge
Indoor pool, open 6:00 AM to 10 PM, pool loungers
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
8.8 out of 10, Excellent, (1006)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
The price is AU$222
includes taxes & fees
12 Nov - 13 Nov
Hotel Downstreet, an Ascend Collection Hotel
Seasonal outdoor pool
Apple Tree Inn
Apple Tree Inn
3.0 star property
8.6 out of 10, Excellent, (310)
"Very clean room and comfortable bed. Friendly staff and restaurant/bar on site. "
The price is AU$284
includes taxes & fees
15 Oct - 16 Oct
Apple Tree 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 Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"This place is just beyond incredible! It is our 40th wedding anniversary today and so happy we found this place. "
Patty 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires

Frequently asked questions

What are some accommodation options with pools in Windsor?
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. Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Berkshires Untold: Offers 3 restaurants, an outdoor pool and spa services. The Red Lion Inn: Features free self parking, an indoor pool and complimentary wireless Internet access.
What is there to see and do in Windsor?
Take a walk along the waterfront at Campers Beach and Iroquis Waterfront. Discover sights such as Mount Greylock State Reservation Visitor Center, Mount Greylock and Barrington Stage Company during your stay.
When is the best time to book a hotel with a pool in Windsor?
Taking the local weather in Windsor 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 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, March, February and November, with each month seeing an average of 17 cm of snowfall.