Find Hotels with a Pool in Pittsfield, MA
Check availability on Pittsfield Hotels with a Pool
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Aug 13 - Aug 14Tomorrow
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Aug 21 - Aug 23Our 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.
$125 nightly
$139 total
Aug 31 - Sep 1
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.
$119 nightly
$133 total
Sep 13 - Sep 14
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.
$155 nightly
$173 total
Sep 13 - Sep 14
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.
$131 nightly
$146 total
Sep 7 - Sep 8
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.
$87 nightly
$97 total
Sep 13 - Sep 14
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.
$165 nightly
$184 total
Sep 7 - Sep 8
Total with taxes and fees
7. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
- Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$77 nightly
$86 total
Sep 13 - Sep 14
Total with taxes and fees
8. 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.
$130 nightly
$146 total
Sep 13 - Sep 14
Total with taxes and fees
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Top Pittsfield Hotel Reviews
The Yankee Inn
10/10 Excellent
"Nice facility, good location, clean room, helpful staff. The pool was great as well. The breakfast could be enhanced with real eggs, some gluten free option. Also, I asked one of the servers who was replenishing food containers if there was an alternative to dairy milk for my oatmeal and she said no. Another guest heard my question and pointed me to the almond milk. It would be helpful if your staff could be aware of all of the offerings! Otherwise, we had a wonderful stay."
Quality Inn Great Barrington
10/10 Excellent
"Great place to stay and a great price"
Comfort Inn & Suites East Greenbush - Albany
10/10 Excellent
"Perfect for our needs , excellent location"
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Nice!"
Berkshire Inn
10/10 Excellent
"He stayed here in August 2026, and we have been staying here in August from at least 2019 or so except for last year. Keep in mind that you get what you pay for and we were not paying for luxury or five star amenities. We were staying for a couple of days and we wanted someplace clean and near downtown Pittsfield, decent and with a pool. This is exactly what we got. It is a quiet, clean, decently maintained property with ample parking and a pool, decent cable and excellent shower pressure. Cold water comes from the tap when you want a cold, none of this lukewarm stuff coming out of the cold water tap. The property itself and the rooms have been upgraded and modernized since our last day in 2024. Is it perfect no. But the beds are comfortable, the pool is enjoyable, it is close to the hot dog ranch, and I really have no complaints about it at all. The two less than perfect things are that the owners or managers on check-in are not the warmest and most welcoming, but they are fine and there is nothing objectionable about them. And the housekeeping staff is absolutely wonderful. The only other thing is that it sits off of busy Housatonic/Route 20 so sometimes to get to downtown Pittsfield instead of turning left when it’s busy, you will want to turn right and turn around or go the back way. This will add approximately two minutes to your drive. I have no doubt that we will stay there next year!"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"
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