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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pittsfield holiday homes

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, (8 reviews)
"Great host great stay"
United States
thomas v.
The price is AU$318
includes taxes & fees
7 Sept - 8 Sept
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

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$2,425
includes taxes & fees
16 Sept - 17 Sept
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
The price is AU$418
includes taxes & fees
5 Oct - 6 Oct
Pretty Old House in Newport
A wooden building with a red roof and a bell tower, surrounded by a well-maintained lawn and vibrant flowers.

4. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (24 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is AU$825
includes taxes & fees
16 Sept - 17 Sept
Peaceful, Spacious Lodge with Golf & Sunset Views
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.

5. 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, (8 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
The price is AU$611
includes taxes & fees
7 Sept - 8 Sept
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
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, (8 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is AU$209
includes taxes & fees
13 Sept - 14 Sept
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

7. 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$446
includes taxes & fees
8 Sept - 9 Sept
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

8. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is AU$425
includes taxes & fees
28 Sept - 29 Sept
Discover Oakland charm near Colby College 10 min
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

9. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is AU$621
includes taxes & fees
9 Sept - 10 Sept
Once Upon a Time — A Peaceful Maine Escape
A wooden deck with outdoor furniture, a large potted plant, and string lights.

10. 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, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
The price is AU$592
includes taxes & fees
7 Sept - 8 Sept
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
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, (2 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$995
includes taxes & fees
7 Sept - 8 Sept
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, (3 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
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

The Skowhegan By Kasa

The Skowhegan By Kasa

10/10 Excellent
"Lovely property. Spacious room. Thankfully greeted by a staff member."
Lynn 1-night trip
Posted 3 hours ago
The Skowhegan By Kasa

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
58
Accommodation
51 Holiday Homes
Lowest Price
AU$209
Highest Price
AU$2,425