Find Hotels with a Pool in Pittsfield, MA
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Check availability on Pittsfield Hotels with a Pool
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Sep 18 - Sep 19Tomorrow
Sep 19 - Sep 20This weekend
Sep 18 - Sep 20Next weekend
Sep 25 - Sep 27Our top choices for Pittsfield hotels with a pool
1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$108 nightly
$120 total
Oct 18 - Oct 19
Total with taxes and fees
2. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
- Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
$109 nightly
$122 total
Oct 19 - Oct 20
Total with taxes and fees
3. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
- Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
$139 nightly
$155 total
Sep 20 - Sep 21
Total with taxes and fees
4. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
- Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
$114 nightly
$127 total
Oct 19 - Oct 20
Total with taxes and fees
5. Berkshire Inn
Berkshire InnPittsfield
- Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
$79 nightly
$88 total
Oct 18 - Oct 19
Total with taxes and fees
6. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$116 nightly
$130 total
Sep 22 - Sep 23
Total with taxes and fees
7. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
- Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
$128 nightly
$143 total
Sep 29 - Sep 30
Total with taxes and fees
8. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
- Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$79 nightly
$88 total
Sep 20 - Sep 21
Total with taxes and fees
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Top Pittsfield Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Room was clean when we arrived. Check in was quick and easy, desk clerk friendly and helpful. We had my granddaughter with us so utilized the pool area and game room, nice to have those activities so available."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Excellent location. Excellent adjacent restaurant "Door Prize". Will definitely stay again"
The Red Lion Inn
8/10 Good
"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Nice place, would stay again"
Quality Inn Great Barrington
10/10 Excellent
"Beds were comfortable but the pillows not so great but clean and quiet."
Hilton Garden Inn Lenox Pittsfield
8/10 Good
"Hotel was very clean, spacious, and staff was very courteous. Bar and restaurant onsite are hood, Guidos market is right in front and is AMAZING!! Definitely a great value and comfortable!"
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