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

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, (8 reviews)
"Great host great stay"
United States
thomas v.
The price is €203
includes taxes & fees
7 Sept - 8 Sept
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Fridge, microwave, oven, stovetop

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 €1,567
includes taxes & fees
15 Sept - 16 Sept
Pine Tree Trail Lodge
Books, offices

3. Pretty Old House in Newport

Pretty Old House in Newport
Newport
The price is €275
includes taxes & fees
7 Sept - 8 Sept
Pretty Old House in Newport
Exterior

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 €512
includes taxes & fees
7 Sept - 8 Sept
Peaceful, Spacious Lodge with Golf & Sunset Views
Smart TV, books

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 €427
includes taxes & fees
13 Sept - 14 Sept
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Exterior

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 €147
includes taxes & fees
4 Oct - 5 Oct
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Smart TV, fireplace, DVD player, books

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 €281
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Exterior

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 €260
includes taxes & fees
28 Sept - 29 Sept
Discover Oakland charm near Colby College 10 min
Smart TV, DVD player, books

9. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
Once Upon a Time — A Peaceful Maine Escape
Outdoor dining

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 €377
includes taxes & fees
15 Sept - 16 Sept
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Private kitchen

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 €625
includes taxes & fees
4 Sept - 5 Sept
Welcome to "the east Madison chapel"
Terrace/patio

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

8/10 Good
"Great place - would get another star if restaurant or snack bar was open for breakfast"
Andrea 1-night trip
Posted 20 hours ago
The Skowhegan By Kasa

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
4,955
Accommodation
58 Holiday Homes
Lowest Price
€99
Highest Price
€243