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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Pittsfield vacation 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 AED 437
AED 833 total
includes taxes & fees
5 Oct - 6 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 AED 5,052
AED 6,267 total
includes taxes & fees
3 Nov - 4 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, (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 AED 477
AED 1,145 total
includes taxes & fees
5 Oct - 6 Oct
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 AED 639
AED 1,561 total
includes taxes & fees
7 Oct - 8 Oct
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, (24 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is AED 1,055
AED 2,198 total
includes taxes & fees
5 Oct - 6 Oct
Peaceful, Spacious Lodge with Golf & Sunset Views
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.

6. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (63 reviews)
"Less than 5 minutes to Colby. We were there for a camp. AC in both bedrooms. Nice artwork and decor."
United States
Leslie G.
The price is AED 544
AED 945 total
includes taxes & fees
15 Oct - 16 Oct
Cozy House in the heart of Waterville Maine.
A modern building with a black exterior and a large glass entrance.

7. 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 AED 413
AED 530 total
includes taxes & fees
12 Oct - 13 Oct
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
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, (19 reviews)
"Great communication. The location was excellent for a few day trips. Very clean and well maintained. Would definitely stay here again if in the area."
United States
Patricia
The price is AED 400
AED 809 total
includes taxes & fees
25 Oct - 26 Oct
Discover Oakland charm near Colby College 10 min
Living area

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 AED 496
AED 1,153 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
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 AED 734
AED 1,469 total
includes taxes & fees
5 Oct - 6 Oct
Once Upon a Time — A Peaceful Maine Escape
A wooden deck with outdoor furniture, a large potted plant, and string lights.

11. 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, (17 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 AED 752
AED 1,306 total
includes taxes & fees
18 Oct - 19 Oct
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.

12. 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 AED 1,469
AED 2,630 total
includes taxes & fees
10 Oct - 11 Oct
Welcome to "the east Madison chapel"
A two-story house with a balcony, surrounded by trees and a grassy yard.

13. Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach

Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
Smithfield
10.0 out of 10, Exceptional, (3 reviews)
"Best vacation home ever!!! Host, property, and home met all of our families expections. Just perfect !"
United States
Dianne S.
The price is AED 1,392
AED 3,243 total
includes taxes & fees
6 Oct - 7 Oct
Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
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 Elmwood

The Elmwood

8/10 Good
"Great"
Allan 7-night trip
Posted less than an hour ago
The Elmwood