An aerial view of a town with autumn-colored trees, a central green field, and surrounding residential areas.

Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Pittsfield holiday homes

Terrace/patio

1. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Pittsfield
9.8 out of 10, Exceptional, (10 reviews)
"Great host great stay"
United States
thomas v.
The price is AU$326
includes taxes & fees
25 Oct - 26 Oct
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
IMG 7964

2. Pine Tree Trail Lodge

Pine Tree Trail Lodge
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
The price is AU$813
includes taxes & fees
17 Nov - 18 Nov
Pine Tree Trail Lodge
A living room with a blue armchair, a beige armchair, a patterned rug, and a bookshelf with books and a plant.

3. Pretty Old House in Newport

Pretty Old House in Newport
Newport
8.0 out of 10, Very good, (2 reviews)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
The price is AU$429
includes taxes & fees
14 Nov - 15 Nov
Pretty Old House in Newport
A cozy living room with a sofa, ottoman, and dining table with chairs. There are windows with curtains, a wooden ceiling, and a view of the outdoors.

4. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Canaan
9.8 out of 10, Exceptional, (9 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
The price is AU$561
includes taxes & fees
22 Nov - 23 Nov
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
A wooden building with a red roof and a bell tower, surrounded by a well-maintained lawn and vibrant flowers.

5. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (25 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is AU$837
includes taxes & fees
24 Oct - 25 Oct
Peaceful, Spacious Lodge with Golf & Sunset Views
A modern building with a black exterior and a large glass entrance.

6. Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.4 out of 10, Exceptional, (9 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is AU$208
includes taxes & fees
25 Oct - 26 Oct
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

7. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
The price is AU$362
includes taxes & fees
2 Nov - 3 Nov
Cozy House in the heart of Waterville Maine.
Living area

8. Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard

Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Sangerville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
The price is AU$438
includes taxes & fees
30 Oct - 31 Oct
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
A wooden deck with outdoor furniture, a large potted plant, and string lights.

9. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, Exceptional, (18 reviews)
"We loved staying at the farm! My kids enjoyed meeting the horse and donkey on property. It was perfect for our family!"
United States
Shana S.
The price is AU$546
includes taxes & fees
4 Nov - 5 Nov
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

10. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is AU$530
includes taxes & fees
25 Oct - 26 Oct
Once Upon a Time — A Peaceful Maine Escape
A wooden kitchen with a large window, a black countertop, and three bar stools.

11. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (4 reviews)
"Great for kids. Lots of space. Convenient location. Plenty to do locally or venture out to explore. Recommend renting the golf cart to get back and forth down the camp road to the dock.. water is clear and clean, rock bottom at shore. Fast response from host who lives close by."
United States
Melissa B.
The price is AU$1,003
includes taxes & fees
24 Oct - 25 Oct
Welcome to "the east Madison chapel"
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

12. China Lake, Dog Friendly, Lots of space for family gatherings

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (5 reviews)
"We will miss this house and would be happy to come back again. The ac in every bedroom plus the main floor made the most humid days comfortable. And China Lake is a wonderful place to have a piece of to yourself."
United States
Lisa J.
The price is AU$721
includes taxes & fees
19 Nov - 20 Nov
China Lake, Dog Friendly, Lots of space for family gatherings
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

8/10 Good
"Was as expected room was clean"
Patrick 1-night trip
Posted less than an hour ago
Fireside Inn & Suites Waterville

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
153
Accommodation
49 Holiday Homes
Lowest Price
AU$208
Highest Price
AU$1,003