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Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Pittsfield hotels with a pool

Pool
Lobby
Lobby
Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$108 nightly
$120 total
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
Pool
Exterior
Exterior
Room

2. 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.
$118 nightly
$132 total
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pool
Room
Reception
Exterior

3. 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.
$118 nightly
$132 total
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Indoor pool
Lobby
Restaurant
Terrace/patio

4. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
  • Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
$148 nightly
$165 total
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Pool
Property grounds
Pool
Standard Room, Accessible | Hand-held showerhead

5. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
$86 nightly
$96 total
Sep 2 - Sep 3
Total with taxes and fees
Berkshire Inn
Outdoor pool
Superior Room, 1 King Bed, Jetted Tub | Jetted tub
Superior Room, 1 King Bed, Jetted Tub
View from room

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$100 nightly
$112 total
Sep 28 - Sep 29
Total with taxes and fees
The Yankee Inn
Pool
One King Bed, Non-Smoking, Accessible Roll in shower | Bathroom shower
Exterior
Breakfast area

7. 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.
$121 nightly
$135 total
Sep 30 - Oct 1
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
Exterior
Bathroom
Room
Exterior

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$79 nightly
$88 total
Sep 3 - Sep 4
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Indoor pool
Exterior
Front of property - evening/night
Lobby sitting area

9. 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.
$106 nightly
$118 total
Sep 3 - Sep 4
Total with taxes and fees
Vacation Village in the Berkshires
Pool
Restaurant
Exterior
View from property

10. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
$178 nightly
$198 total
Sep 7 - Sep 8
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub
Spa
4 stars
5 stars

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The Red Lion Inn is always charming and comfortable!"
Maureen R 1-night trip
Posted 2 hours ago
The Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Nice property, quiet and comfortable. Asked to upgrade but was denied."
Stephen 5-night trip
Posted 4 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Easy access friendly staff clean rooms"
Veronica 1-night trip
Posted 8 hours ago
Quality Inn Great Barrington
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Conveniently located to Tanglewood and Jacob's pillow and other attractions in towns in western Mass. All brand new decorated room. Neighborhood is a little down market but safe and quiet at night. Good value for money."
Judith 1-night trip
Posted 5 days ago
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Clean comfortable; difficult to see sign locating property"
Doreen 1-night trip
Posted 9 days ago
Hilton Garden Inn Lenox Pittsfield

Frequently asked questions

What are some accommodations 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 wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Features a health club, an indoor pool, and free valet parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Best Western Plus Berkshire Hills Inn & Suites: Features a snack bar/deli, a pool, and complimentary wired internet access.
What is there to see and do in Pittsfield?
Surround yourself with nature at Pontoosuc Lake and Housatonic River. During your stay, check out sights such as Berkshire Museum, Colonial Theater, and Barrington Stage Company. The sporting events and theater 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 into account the local weather in Pittsfield 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 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches 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 many public transit options to choose from so consider a car rental to maximize your time.

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