Hotels with Swimming Pools in Windsor

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Check availability on Windsor Hotels with Swimming Pools

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Hotels with Swimming Pools in Windsor

Hotel Downstreet, Ascend Hotel Collection
Enjoy a lively swim in our indoor pool, featuring a vibrant mural and easy access via a ladder.

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Clean,friendly staff and great location."
The price is S$206
includes taxes & fees
7 Sept - 8 Sept
Hotel Downstreet, Ascend Hotel Collection
The Porches Inn at Mass MoCA
Outdoor pool

The Porches Inn at Mass MoCA

3.5 star property
9.4 out of 10, Exceptional, (405)
"Very comfortable room that worked great for our family. "
The price is S$299
includes taxes & fees
2 Sept - 3 Sept
The Porches Inn at Mass MoCA
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (400)
"No frills but it was a great stay!"
The price is S$156
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
Devonfield Inn B&B
Enjoy a romantic meal for two on this serene patio, surrounded by lush greenery and a beautiful view.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Swim laps in a serene, well-lit pool surrounded by a simple, functional design.

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

3.5 star property
9.0 out of 10, Wonderful, (686)
"Had a great time"
The price is S$163
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
9.6 out of 10, Exceptional, (11)
"Really enjoyed my stay here, definitely need a car to get around"
The price is S$218
includes taxes & fees
18 Aug - 19 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax by the pool surrounded by lounge chairs and sunbeds, with views of the surrounding area and greenery.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is S$221
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Lenox Pittsfield
Howard Johnson by Wyndham Lenox
Enjoy a refreshing swim in our pool surrounded by a serene landscape.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (778)
"My stay was perfect. I can't wait to stay there again. "
The price is S$113
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
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.

Top Windsor Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Studio was nice and spacious. I got there late and left early so didn’t take advantage of amenities but they looked nice."
Mitchell 1-night trip
Posted 2 days 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. Hotel Downstreet, Ascend Hotel Collection: Offers free self parking, an indoor pool and complimentary wireless Internet access. Red Roof Inn PLUS+ South Deerfield – Amherst: Offers a health club, an indoor pool and complimentary high-speed (wired) Internet access. The Williams Inn: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Offers a seasonal outdoor pool, an indoor pool and buffet.
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.