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Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Exterior
Angel Mist Retreat Garage Apartment

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.
$285 nightly
The price is $311
Dec 12 - Dec 13
Total with taxes and fees
Angel Mist Retreat Garage Apartment
Exterior
The Cozy Home- New, Comfortable, Centrally located

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 13 - Dec 14
Total with taxes and fees
The Cozy Home- New, Comfortable, Centrally located
Exterior
Pine Tree Trail Lodge

Pine Tree Trail Lodge

Pine Tree Trail Lodge
2.0 star property
Pittsfield
10.0 out of 10, Exceptional, (1)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
$271 nightly
The price is $273
Dec 15 - Dec 16
Total with taxes and fees
Pine Tree Trail Lodge
Exterior
Pine Tree Trail Lodge

Pine Tree Trail Lodge

Pine Tree Trail Lodge
3.0 star property
Pittsfield
$399 nightly
The price is $435
Jan 10 - Jan 11, 2026
Total with taxes and fees
Pine Tree Trail Lodge
Exterior
Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi

Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi

Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi
Pittsfield
$298 nightly
The price is $325
Dec 13 - Dec 14
Total with taxes and fees
Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi
Exterior
Holiday Inn Express & Suites Waterville - North by IHG

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
$90 nightly
The price is $98
Jan 8 - Jan 9, 2026
Total with taxes and fees
Holiday Inn Express & Suites Waterville - North by IHG
Front of property
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville
2.0 star property
Waterville
8.8 out of 10, Excellent, (1001)
"Beautiful rooms, lovely staff, good breakfast selection. "
United States
Edwin
$102 nightly
The price is $111
Dec 24 - Dec 25
Total with taxes and fees
Fireside Inn & Suites Waterville
Front of property
The Towne Motel

The Towne Motel

The Towne Motel
2.5 star property
Skowhegan
9.0 out of 10, Wonderful, (564)
"Very clean, would use again "
United States
Bill
$99 nightly
The price is $108
Dec 14 - Dec 15
Total with taxes and fees
The Towne Motel
Exterior
The Skowhegan By Kasa

The Skowhegan By Kasa

The Skowhegan By Kasa
2.0 star property
Skowhegan
8.6 out of 10, Excellent, (49)
"Amazinf stay overall"
United States
MARK
$119 nightly
The price is $129
Dec 13 - Dec 14
Total with taxes and fees
The Skowhegan By Kasa
Exterior
The Elmwood

The Elmwood

The Elmwood
2.5 star property
Waterville
8.6 out of 10, Excellent, (502)
"Great place to stay. "
United States
Jacqueline
$105 nightly
The price is $115
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Elmwood
Exterior
Hampton Inn Waterville

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 29 - Dec 30
Total with taxes and fees
Hampton Inn Waterville
Front of property
Canaan Motel

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 12 - Dec 13
Total with taxes and fees
Canaan Motel
Exterior
The Cabin Skowhegan

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 12 - Dec 13
Total with taxes and fees
The Cabin Skowhegan
Exterior
Best Western Plus Waterville Grand Hotel

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 14 - Dec 15
Total with taxes and fees
Best Western Plus Waterville Grand Hotel
Exterior
ON THE GO!

ON THE GO!

ON THE GO!
Hartland
10.0 out of 10, Exceptional, (1)
"It was a clean and quiet room. The property was also clean and quiet. "
United States
Sarah F.
$150 nightly
The price is $164
Dec 12 - Dec 13
Total with taxes and fees
ON THE GO!
Outdoor dining
The heart of the Belgrade Lakes

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
$176 nightly
The price is $191
Dec 12 - Dec 13
Total with taxes and fees
The heart of the Belgrade Lakes
Free self parking
Budget Host Airport Inn

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 12 - Dec 13
Total with taxes and fees
Budget Host Airport Inn
Exterior
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails

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.
$334 nightly
The price is $355
Dec 16 - Dec 17
Total with taxes and fees
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails
Exterior
Sister A-Frame in Woods B

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 15 - Dec 16
Total with taxes and fees
Sister A-Frame in Woods B
Property grounds
Private cabin on 30 acres, close to skiing, snowmobile & amenities

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, (42)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
$311 nightly
The price is $339
Dec 16 - Dec 17
Total with taxes and fees
Private cabin on 30 acres, close to skiing, snowmobile & amenities
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

Pine Tree Trail Lodge

Pine Tree Trail Lodge

10/10 Excellent
"Great place. The host so helpful. I would definitely stay here again. "
Amber G. 4-night trip
Posted 4 days ago
Pine Tree Trail Lodge

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
5,274
Accommodation
38 Cottages
Lowest Price
$98
Highest Price
$435

Frequently asked questions

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What is there to do in Pittsfield near my cottage?
The most useful travel accessory is a well-thought-out travel plan. JW Parks Golf Course is a great place to start your exploration of Pittsfield.

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