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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Pittsfield vacation 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, (9 reviews)
"Great host great stay"
United States
thomas v.
The price is ￥18,669
￥35,568 total
includes taxes & fees
Sep 23 - Sep 24
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 ￥219,381
￥282,075 total
includes taxes & fees
Sep 29 - Sep 30
Pine Tree Trail Lodge
A wooden building with a red roof and a bell tower, surrounded by a well-maintained lawn and vibrant flowers.

3. 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 ￥45,040
￥93,896 total
includes taxes & fees
Sep 23 - Sep 24
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.

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, (8 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
The price is ￥27,372
￥66,358 total
includes taxes & fees
Oct 18 - Oct 19
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
A living room with a blue armchair, a beige armchair, a patterned rug, and a bookshelf with books and a plant.

5. Pretty Old House in Newport

Pretty Old House in Newport
Newport
8.0 out of 10, Very good, (1 review)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
The price is ￥20,394
￥48,905 total
includes taxes & fees
Sep 23 - Sep 24
Pretty Old House in Newport
A wooden kitchen with a large window, a black countertop, and three bar stools.

6. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (3 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 ￥62,752
￥112,346 total
includes taxes & fees
Sep 25 - Sep 26
Welcome to "the east Madison chapel"
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

7. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (17 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is ￥21,806
￥40,355 total
includes taxes & fees
Sep 24 - Sep 25
Discover Oakland charm near Colby College 10 min
A modern building with a black exterior and a large glass entrance.

8. 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 ￥17,931
￥22,965 total
includes taxes & fees
Sep 23 - Sep 24
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

9. 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 ￥21,179
￥49,248 total
includes taxes & fees
Sep 25 - Sep 26
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.

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 ￥32,121
￥57,882 total
includes taxes & fees
Sep 28 - Sep 29
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

11. 100 Ft Private Sandy Beach | Newly Renovated 4BR Retreat

100 Ft Private Sandy Beach | Newly Renovated 4BR Retreat
China
100 Ft Private Sandy Beach | Newly Renovated 4BR Retreat
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

12. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is ￥33,979
￥66,530 total
includes taxes & fees
Sep 24 - Sep 25
Once Upon a Time — A Peaceful Maine Escape
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

10/10 Excellent
"Front Desk were extremely helpful."
Tena 1-night trip
Posted 14 hours ago
Fireside Inn & Suites Waterville

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
3,101
Accommodation
51 Vacation Homes
Lowest Price
￥17,955
Highest Price
￥42,509