Best Resorts in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Resorts in Pittsfield

No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Fridge, microwave, oven, stovetop
Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment

Pittsfield
10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
$283 nightly
The price is $309
Dec 2 - Dec 3
Total with taxes and fees
Angel Mist Retreat Garage Apartment
Microwave, oven, stovetop, dishwasher
The Cozy Home- New, Comfortable, Centrally located

The Cozy Home- New, Comfortable, Centrally located

2.0 star property
Pittsfield
10.0 out of 10, Exceptional, (1)
"Great host great stay"
United States
thomas v.
$229 nightly
The price is $250
Dec 5 - Dec 6
Total with taxes and fees
The Cozy Home- New, Comfortable, Centrally located
Game room
Pine Tree Trail Lodge

Pine Tree Trail Lodge

3.0 star property
Pittsfield
$399 nightly
The price is $435
Dec 31 - Jan 1, 2026
Total with taxes and fees
Pine Tree Trail Lodge
Property grounds
Pine Tree Trail Lodge

Pine Tree Trail Lodge

2.0 star property
Pittsfield
$239 nightly
The price is $241
Dec 7 - Dec 8
Total with taxes and fees
Pine Tree Trail Lodge
Smart TV
Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi

Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi

Pittsfield
$300 nightly
The price is $327
Dec 2 - Dec 3
Total with taxes and fees
Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi
Fridge, microwave, oven, stovetop
RiverBend Loft | Modern Stay Near ATV & Snowmobile Trails

RiverBend Loft | Modern Stay Near ATV & Snowmobile Trails

Pittsfield
$300 nightly
The price is $327
Dec 2 - Dec 3
Total with taxes and fees
RiverBend Loft | Modern Stay Near ATV & Snowmobile Trails
Free buffet breakfast
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, (858)
"The front desk person when we checked in was amazing. Breakfast was awesome, room was clean! Would stay here again. "
Canada
Jennifer
$87 nightly
The price is $95
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Express & Suites Waterville - North by IHG
Breakfast, lunch, dinner served; American cuisine
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2.0 star property
Waterville
8.8 out of 10, Excellent, (1003)
"Clean room and friendly staff. "
United States
Julie
$99 nightly
The price is $108
Dec 25 - Dec 26
Total with taxes and fees
Fireside Inn & Suites Waterville
Desk, laptop workspace, free WiFi, bed sheets
The Elmwood

The Elmwood

2.5 star property
Waterville
8.6 out of 10, Excellent, (502)
"Great place to stay. "
United States
Jacqueline
$102 nightly
The price is $112
Dec 22 - Dec 23
Total with taxes and fees
The Elmwood
Exterior detail
The Towne Motel

The Towne Motel

2.5 star property
Skowhegan
9.0 out of 10, Wonderful, (563)
"Our room was neat and clean. The entire staff was very friendly and courteous. We would stay here again. "
United States
David
$99 nightly
The price is $108
Dec 3 - Dec 4
Total with taxes and fees
The Towne Motel
Lobby
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
$126 nightly
The price is $138
Dec 18 - Dec 19
Total with taxes and fees
Hampton Inn Waterville
2 restaurants, lunch, dinner served; American cuisine
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
$105 nightly
The price is $114
Dec 4 - Dec 5
Total with taxes and fees
Best Western Plus Waterville Grand Hotel
Exterior
The Skowhegan By Kasa

The Skowhegan By Kasa

2.0 star property
Skowhegan
8.6 out of 10, Excellent, (47)
"Amazinf stay overall"
United States
MARK
$135 nightly
The price is $147
Dec 16 - Dec 17
Total with taxes and fees
The Skowhegan By Kasa
Standard Room | Free WiFi, bed sheets
Canaan Motel

Canaan Motel

2.5 star property
Canaan
9.8 out of 10, Exceptional, (51)
"Room was very clean and the beds were extremely comfortable. "
United States
John
$122 nightly
The price is $133
Dec 2 - Dec 3
Total with taxes and fees
Canaan Motel
Terrace/patio
The Cabin Skowhegan

The Cabin Skowhegan

Skowhegan
9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
$193 nightly
The price is $210
Dec 2 - Dec 3
Total with taxes and fees
The Cabin Skowhegan
Fridge, microwave, oven, stovetop
Private cabin on 30 acres, close to skiing, snowmobile & amenities

Private cabin on 30 acres, close to skiing, snowmobile & amenities

Madison
10.0 out of 10, Exceptional, (41)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
$312 nightly
The price is $340
Dec 2 - Dec 3
Total with taxes and fees
Private cabin on 30 acres, close to skiing, snowmobile & amenities
Exterior
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.
$324 nightly
The price is $345
Dec 16 - Dec 17
Total with taxes and fees
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails
Exterior
Budget Host Airport Inn

Budget Host Airport Inn

2.0 star property
Waterville
6.8 out of 10, (529)
"Very clean room and walls were thick-it was quiet."
United States
Melody
$90 nightly
The price is $98
Dec 2 - Dec 3
Total with taxes and fees
Budget Host Airport Inn
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Dec 2 - Dec 3
Total with taxes and fees
Sister A-Frame in Woods B
Fridge, microwave, oven, stovetop
The Beach Bum | Modern Cabin on the Sand

The Beach Bum | Modern Cabin on the Sand

Burnham
10.0 out of 10, Exceptional, (2)
"Nice cottage. Perfect location. Everything you need for a quiet beach stay on Unity pond. "
United States
Albert
$375 nightly
The price is $409
Dec 2 - Dec 3
Total with taxes and fees
The Beach Bum | Modern Cabin on the Sand
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

10/10 Excellent
"The staff was amazing and very kind. The hotel itself is very comfortable, relaxing, and clean. My stay was in a family suite and i had 6 children with me. The staff was so understanding, kind, and hospitable that i instantly felt welcome and was able to relax and enjoy my stay. Thank you so much!"
Stephanie 1-night trip
Posted 3 days ago
Holiday Inn Express & Suites Waterville - North by IHG

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
Accommodation
 Resorts
Lowest Price
Highest Price

Frequently asked questions

What can I expect from a resort vacation in Pittsfield?
Longing for a relaxing getaway? You deserve all the comforts of a resort, where you can find everything you need for your trip from convenient food and drink options to activities and shopping. Browse the resort options in the area and discover the one that's best for you, whether you envision yourself sipping drinks by a sprawling pool or heading to the spa for a deep-tissue massage.
What's a favorite resort in Pittsfield?
Our highest-rated resorts around Pittsfield: North Woods 18' Teepee Resort - 16 mi (25.8 km) from Pittsfield. North Woods 12' Teepee Resort - 16 mi (25.8 km) from Pittsfield. North Woods 12' Teepee Resort - 16 mi (25.8 km) from Pittsfield. North Woods 16' Teepee Resort - 16 mi (25.8 km) from Pittsfield.
What can I do in Pittsfield?
JW Parks Golf Course, Sebasticook Lake, and Skowhegan State Fairgrounds are a few interesting places to visit nearby. In the area, other attractions include Sandy Pond and Kennebec River.
What's the weather like in Pittsfield?
The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 24°F. The snowiest months in Pittsfield are January, March, December, and February, with each month seeing an average of 9 inches of snowfall.
What's the best way to get to and around Pittsfield?
Fly into Waterville, ME (WVL-Robert Lafleur), which is located 22.6 mi (36.3 km) from the city center. Otherwise, look for flights into Bangor Intl. Airport (BGR), which is 27.9 mi (44.8 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia