Hotels with Pool & Resorts in Pittsfield from AU$148

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Check availability on Pittsfield Hotels with Pool

Our top choices for Pittsfield hotels with a pool

Indoor pool
Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

2.5 star property
Waterville
8.6 out of 10, Excellent, (860)
"Room was Clean.hot coffee served and good. Breakfast was good too. 2nd time we stayed will return again"
United States
Clinton
The price is AU$148
includes taxes & fees
8 Jan - 9 Jan 2026
Holiday Inn Express & Suites Waterville - North by IHG
Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool loungers
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2.0 star property
Waterville
8.8 out of 10, Excellent, (1000)
"Clean room and friendly staff. "
United States
Julie
The price is AU$164
includes taxes & fees
24 Dec - 25 Dec
Fireside Inn & Suites Waterville
Outdoor pool
The Towne Motel

The Towne Motel

2.5 star property
Skowhegan
9.0 out of 10, Wonderful, (564)
"Our room was neat and clean. The entire staff was very friendly and courteous. We would stay here again. "
United States
David
The price is AU$163
includes taxes & fees
11 Dec - 12 Dec
The Towne Motel
Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
Hampton Inn Waterville

Hampton Inn Waterville

2.5 star property
Waterville
9.2 out of 10, Wonderful, (590)
"Amazing breakfast, quiet and easy parking. "
United States
Samantha
The price is AU$205
includes taxes & fees
29 Dec - 30 Dec
Hampton Inn Waterville
Indoor pool
Best Western Plus Waterville Grand Hotel

Best Western Plus Waterville Grand Hotel

3.0 star property
Waterville
7.4 out of 10, Good, (1000)
"Very helpful staff and a wonderful breakfast included."
United States
Pat
The price is AU$172
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus Waterville Grand Hotel
Property grounds
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails

Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails

Oakland
10.0 out of 10, Exceptional, (7)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is AU$589
includes taxes & fees
17 Dec - 18 Dec
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails
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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Top Pittsfield Hotel Reviews

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Clean, spacious room with comfortable beds. All staff mem bers were friendly, accommodating, professional and courteous. This is a dog friendly hotel so we could bring our black lab with us! When we come back again to the Waterville area this is the place we will stay!"
Elaine 1-night trip
Posted 5 days ago
Fireside Inn & Suites Waterville

Frequently asked questions

What are some hotels with pools in Pittsfield?
Pine Tree Trail Lodge: Provides daily, a seasonal outdoor pool and free self parking. Angel Mist Retreat Garage Apartment: Offers a snack bar/deli, an indoor pool and buffet. Fireside Inn & Suites Waterville: Features 2 restaurants, an indoor pool and free self parking. The Skowhegan By Kasa: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn Express & Suites Waterville - North by IHG: Features a snack bar/deli, a seasonal outdoor pool and free self parking.
What is there to see and do in Pittsfield?
The picturesque settings of Sebasticook Lake and Sandy Pond showcase the area's natural beauty. Discover sights such as JW Parks Golf Course during your stay.
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 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Pittsfield are January, March, December and February, with each month seeing an average of 23 cm of snowfall.