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Search Hotels with Swimming Pool in Pittsfield

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Check availability on Pittsfield Hotels with Swimming Pool

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Pittsfield hotels with a pool

A building entrance with a large planter with purple flowers and a small tree.

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (978 reviews)
"Very nice hotel"
United States
Philip
The price is ₹11,000
₹12,287 total
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

2. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (434 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is ₹9,380
₹10,477 total
includes taxes & fees
11 Nov - 12 Nov
The Central Downtown Inn & Suites
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

3. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (941 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is ₹7,658
₹8,554 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Inn
An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (257 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is ₹9,380
₹10,477 total
includes taxes & fees
4 Dec - 5 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

5. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is ₹11,244
₹12,560 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

6. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,001 reviews)
"Room was spacious and clean"
United States
James
The price is ₹8,857
₹9,893 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,255 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is ₹7,272
₹10,240 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (934 reviews)
"Friendly staff"
United States
William
The price is ₹6,736
₹7,525 total
includes taxes & fees
8 Nov - 9 Nov
FairBridge Inn Express
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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Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Enjoyable stay. We will come back."
Joseph 1-night trip
Posted 10 hours ago
The Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Office staff wonderful! Room clean but older carpet and bathroom looked dingy."
Martha 1-night trip
Posted 1 day ago
Quality Inn Great Barrington

Frequently asked questions

What are some accommodation options with pools in Pittsfield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. FairBridge Inn Express: Provides buffet, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Hotel On North: Provides a health club, an indoor pool and free valet parking. Best Western Plus Berkshire Hills Inn & Suites: Features a snack bar/deli, a pool and complimentary high-speed (wired) Internet access.
What is there to see and do in Pittsfield?
Surround yourself with nature at Housatonic River and Onota Lake. During your stay, visit sights such as Berkshire Museum, Colonial Theater and Bousquet Ski Area. The sporting events and theatre scene are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Pittsfield?
Taking the local weather in Pittsfield 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 Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's the best way to travel around Pittsfield?
Knowing the transportation options in Pittsfield can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have very many public transport options, so consider a car rental to maximise your time.

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