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Find Hotels with a Pool in Windsor, MA from CA $125

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Check availability on Windsor Hotels with a Pool

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Windsor hotels with a pool

A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A modern bathroom with a glass-enclosed shower, a toilet, and a towel rack.

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
CA $138
CA $154 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A modern cafe with a counter, seating area, and large windows.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

2. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
CA $135
CA $151 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
CA $121
CA $167 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
An indoor swimming pool with blue tiles, a wooden wall, and a blue and white color scheme.
A modern interior with a large window, a wooden table, and bar stools.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

4. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
  • Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.
CA $169
CA $188 total
includes taxes & fees
Nov 17 - Nov 18
Hotel Downstreet, an Ascend Collection Hotel
Indoor pool
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.
A spacious living room with a fireplace, comfortable seating, and large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

5. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
CA $114
CA $142 total
includes taxes & fees
Nov 17 - Nov 18
Vacation Village in the Berkshires
A hot tub with a tiled floor and a metal ladder.
Room
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.

6. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
CA $146
CA $163 total
includes taxes & fees
Nov 14 - Nov 15
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A bathroom with a bathtub, toilet, and shower.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
A motel with a parking lot, a swimming pool, and outdoor seating.

7. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
CA $117
CA $130 total
includes taxes & fees
Nov 17 - Nov 18
Berkshire Inn
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A modern bathroom with a bathtub, shower, and handrails.
A hotel room with a bed, a desk, a chair, and a carpeted floor.

8. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
CA $155
CA $173 total
includes taxes & fees
Nov 16 - Nov 17
Hampton Inn & Suites Berkshires-Lenox
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
CA $112
CA $125 total
includes taxes & fees
Oct 30 - Oct 31
Howard Johnson by Wyndham Lenox
A poolside area with lounge chairs, umbrellas, and a swimming pool.
A patio area with outdoor furniture, a fire pit, and potted plants.
A cozy living room with a stone fireplace, comfortable seating, and a television.
A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

10. The Springs Motel

The Springs Motel
New Ashford
  • Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
CA $150
CA $165 total
includes taxes & fees
Nov 1 - Nov 2
The Springs Motel
View all properties

Choose what matters most at hotels with a pool in Windsor

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Windsor Hotel Reviews

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

8/10 Good
"Property was clean and in excellent shape overall. Pros: Food at the Bistro was excellent quality, and large portions. Room was clean and comfortable, slept well while staying there. Onsite laundry was a very helpful option and the washer and dryer, while expensive at $4.00 a load, were in excellent condition and did the job very well. Pool and hot tub were excellent. Cons: The light switches governing the various lights in the room were a little confusing at first. The free HBO had severe buffering issues, making watching anything on it tough. The controls for the automatic curtain open/shut were broken, making one start the open and shut manually. Overall, the Pros well outweighed the Cons."
William 2-night trip
Posted 4 hours ago
Courtyard by Marriott Lenox Berkshires
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The staff was very helpful. The were lots of activities offered including the pool, hot tub, movie theater , and renting movies for free. The unit was very spacious and comfortable. We could hear the people above us stomping around a bit but that’s to be expected."
Jessica 1-night trip
Posted 6 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Good stay"
Jared 1-night trip
Posted 7 hours ago
The Red Lion Inn
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."
Luisa 1-night trip
Posted 11 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

Frequently asked questions

What are some accommodations with pools in Windsor?
Vacation Village in the Berkshires: Aparthotel, 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. The Yankee Inn: Provides a seasonal outdoor pool, an indoor pool, and buffet. Berkshires Untold: Offers daily, an indoor pool, and free self parking. Hotel Downstreet, an Ascend Collection Hotel: Features 3 restaurants, an outdoor pool, and spa services.
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 Wahconah Falls State Park, Mount Greylock State Reservation Visitor Center, and Pontoosuc Lake 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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