Find Hotels with a Pool in Windsor, MA

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Check availability on Windsor Hotels with a Pool

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Oct 7 - Oct 8
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Oct 8 - Oct 9
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Oct 10 - Oct 12
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Oct 17 - Oct 19

Top Windsor Hotels with a Pool

Berkshire Travel Lodge
Outdoor pool

Berkshire Travel Lodge

2.5 star property
5.4 out of 10, (447)
"The motel seems to be managed and cleaned by the owners. Not the ritz, but clean and a bargain compared with other lodging in the area. The owner was very responsive. "
$75 nightly
The price is $84
Oct 8 - Oct 9
Total with taxes and fees
Berkshire Travel Lodge
The Springs Motel
Seasonal outdoor pool

The Springs Motel

2.0 star property
9.2 out of 10, Wonderful, (73)
"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"
$97 nightly
The price is $107
Oct 8 - Oct 9
Total with taxes and fees
The Springs Motel
Willows Motel Williamstown
Outdoor pool

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (958)
"Very quaint inn, comfortable beds, very clean. Most cheerful staff and great fresh fruit and variety at breakfast."
$99 nightly
The price is $111
Oct 8 - Oct 9
Total with taxes and fees
Willows Motel Williamstown
Berkshire Mountain Lodge
Indoor pool

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (678)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
$97 nightly
The price is $108
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Mountain Lodge
Huttopia Berkshires
Outdoor pool

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
$98 nightly
The price is $109
Oct 9 - Oct 10
Total with taxes and fees
Huttopia Berkshires
Element Lenox Berkshires
Indoor pool

Element Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
$143 nightly
The price is $160
Nov 2 - Nov 3
Total with taxes and fees
Element Lenox Berkshires
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (805)
"Great place to stay for overnight stays. Breakfast was appreciated."
$79 nightly
The price is $88
Oct 19 - Oct 20
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (869)
"Very nice staff, nice breakfast"
$79 nightly
The price is $88
Nov 2 - Nov 3
Total with taxes and fees
Cozy Corner Motel
Maple Terrace Motel
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (579)
"Excellent place. Bountiful view. "
$99 nightly
The price is $111
Nov 2 - Nov 3
Total with taxes and fees
Maple Terrace Motel
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Very clean, nice amenities , great location!!"
$130 nightly
The price is $146
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Berkshires-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.
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Top Windsor Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Clean venue. Very quiet and I highly recommend renting a kayak. You might see a bald eagle:)"
soren 1-night trip
Posted 18 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What are some accommodations 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 pools, 2 outdoor pools, and a snack bar/deli. Berkshires Untold: Offers 3 restaurants, an outdoor pool, and spa services. The Red Lion Inn: Provides 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 into account the local weather in Windsor can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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