Search Cottages in Pittsfield

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Recommended hotels in Pittsfield

Exterior
Angel Mist Retreat Garage Apartment

Condo in Pittsfield

Angel Mist Retreat Garage Apartment
10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is AED 516
AED 1,135 total
includes taxes & fees
11 Jan - 12 January 2026
Angel Mist Retreat Garage Apartment
Exterior
The Cozy Home- New, Comfortable, Centrally located

Vacation Home in Pittsfield

The Cozy Home- New, Comfortable, Centrally located
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great host great stay"
United States
thomas v.
The price is AED 485
AED 917 total
includes taxes & fees
11 Jan - 12 January 2026
The Cozy Home- New, Comfortable, Centrally located
Exterior
Pine Tree Trail Lodge

Vacation Home in Pittsfield

Pine Tree Trail Lodge
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
The price is AED 545
AED 1,025 total
includes taxes & fees
1 Jan - 2 January 2026
Pine Tree Trail Lodge
Exterior
Pine Tree Trail Lodge

Bed & Breakfast in Pittsfield

Pine Tree Trail Lodge
3.0 star property
The price is AED 982
AED 1,598 total
includes taxes & fees
11 Jan - 12 January 2026
Pine Tree Trail Lodge
Exterior
Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi

Apartment in Pittsfield

Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi
The price is AED 509
AED 1,193 total
includes taxes & fees
13 Dec - 14 Dec
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
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 AED 331
AED 360 total
includes taxes & fees
8 Jan - 9 January 2026
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
8.8 out of 10, Excellent, (1001)
"Beautiful rooms, lovely staff, good breakfast selection. "
United States
Edwin
The price is AED 374
AED 408 total
includes taxes & fees
24 Dec - 25 Dec
Fireside Inn & Suites Waterville
Front of property
The Towne Motel

Motel in Skowhegan

The Towne Motel
2.5 star property
9.0 out of 10, Wonderful, (564)
"Very clean, would use again "
United States
Bill
The price is AED 364
AED 396 total
includes taxes & fees
11 Jan - 12 January 2026
The Towne Motel
Exterior
The Skowhegan By Kasa

The Skowhegan By Kasa

The Skowhegan By Kasa
2.0 star property
8.6 out of 10, Excellent, (50)
"Amazinf stay overall"
United States
MARK
The price is AED 415
AED 452 total
includes taxes & fees
19 Dec - 20 Dec
The Skowhegan By Kasa
Exterior
The Elmwood

Motel in Waterville

The Elmwood
2.5 star property
8.6 out of 10, Excellent, (502)
"Great place to stay. "
United States
Jacqueline
The price is AED 387
AED 421 total
includes taxes & fees
7 Jan - 8 January 2026
The Elmwood
Exterior
Hampton Inn Waterville

Hampton Inn Waterville

Hampton Inn Waterville
2.5 star property
9.2 out of 10, Wonderful, (590)
"Amazing breakfast, quiet and easy parking. "
United States
Samantha
The price is AED 464
AED 506 total
includes taxes & fees
29 Dec - 30 Dec
Hampton Inn Waterville
Exterior
Canaan Motel

Motel in Canaan

Canaan Motel
2.5 star property
9.8 out of 10, Exceptional, (51)
"Room was very clean and the beds were extremely comfortable. "
United States
John
The price is AED 448
AED 488 total
includes taxes & fees
14 Dec - 15 Dec
Canaan Motel
Exterior
The Cabin Skowhegan

Cabin in Skowhegan

The Cabin 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
The price is AED 367
AED 773 total
includes taxes & fees
11 Jan - 12 January 2026
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
7.4 out of 10, Good, (1000)
"Very helpful staff and a wonderful breakfast included."
United States
Pat
The price is AED 385
AED 419 total
includes taxes & fees
11 Jan - 12 January 2026
Best Western Plus Waterville Grand Hotel
Exterior
ON THE GO!

Apartment in Hartland

ON THE GO!
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.
The price is AED 331
AED 600 total
includes taxes & fees
21 Dec - 22 Dec
ON THE GO!
Outdoor dining
The heart of the Belgrade Lakes

Apartment in Oakland

The heart of the Belgrade Lakes
9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
The price is AED 296
AED 703 total
includes taxes & fees
12 Dec - 13 Dec
The heart of the Belgrade Lakes
Front of property
Budget Host Airport Inn

Motel in Waterville

Budget Host Airport Inn
2.0 star property
6.8 out of 10, (529)
"Very clean room and walls were thick-it was quiet."
United States
Melody
The price is AED 331
AED 360 total
includes taxes & fees
13 Dec - 14 Dec
Budget Host Airport Inn
Exterior
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails

Vacation Home in Oakland

Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails
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 AED 747
AED 1,425 total
includes taxes & fees
16 Dec - 17 Dec
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails
Exterior
Sister A-Frame in Woods B

Cabin in Oakland

Sister A-Frame in Woods B
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 443
AED 839 total
includes taxes & fees
15 Dec - 16 Dec
Sister A-Frame in Woods B
Exterior
Private cabin on 30 acres, close to skiing, snowmobile & amenities

Cabin in Madison

Private cabin on 30 acres, close to skiing, snowmobile & amenities
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.
The price is AED 459
AED 1,249 total
includes taxes & fees
11 Jan - 12 January 2026
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.
View all properties
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

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

Frequently asked questions

Why book your cottage in Pittsfield with Expedia?
Expedia has some wonderful cottages in Pittsfield, so start packing your bags for an unforgettable vacation on nature's doorstep. If you have a certain budget, select how much you'd like to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect fit whatever your escape looks like.
How can I find cheap cottages in Pittsfield?
Expedia is here to help you look for cheap cottages in Pittsfield. To book a superb stay in a few quick keystrokes, simply use our convenient filter tool to refine your search by star rating, amenities and budget.