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

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Pittsfield vacation rentals

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
13 Oct - 14 Oct
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
A single bed with a metal frame, two bedside tables with lamps, and a door to the right.

2. The Libby House – Fast WiFi, Parking & Full Kitchen

The Libby House – Fast WiFi, Parking & Full Kitchen
Pittsfield
The price is AED 375
AED 488 total
includes taxes & fees
19 Oct - 20 Oct
The Libby House – Fast WiFi, Parking & Full Kitchen
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

3. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is AED 516
AED 1,131 total
includes taxes & fees
18 Oct - 19 Oct
Angel Mist Retreat Garage Apartment
IMG 7964

4. 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 1,233
AED 2,148 total
includes taxes & fees
9 Nov - 10 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.

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 AED 477
AED 1,109 total
includes taxes & fees
12 Oct - 13 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.

6. 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
8 Nov - 9 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.

7. 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
12 Oct - 13 Oct
Peaceful, Spacious Lodge with Golf & Sunset Views
A wooden cabin with a porch, a door, and a green chair.

8. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 367
AED 865 total
includes taxes & fees
3 Nov - 4 Nov
Sister A-Frame in Woods B
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

9. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 reviews)
"The cabin was perfect for our two night stay. It was very clean and it felt just like being at home. Misty was a responsive host and I would definitely rent here again."
United States
Tonilynne D.
The price is AED 459
AED 681 total
includes taxes & fees
3 Nov - 4 Nov
Charming cabin in the birches right on the atv trail!
A modern building with a black exterior and a large glass entrance.

10. 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 two-story house with a wooden staircase and a balcony, two garage doors, and two ATVs parked in front.

11. New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville

New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Sangerville
7.2 out of 10, Good, (5 reviews)
"Cozy room, very nice bathroom and shower, beautiful setti ng and very accomadating and available host"
United States
Judith L.
The price is AED 317
AED 626 total
includes taxes & fees
12 Oct - 13 Oct
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

12. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (20 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 415
AED 829 total
includes taxes & fees
12 Oct - 13 Oct
Discover Oakland charm near Colby College 10 min
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.

13. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (64 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 933 total
includes taxes & fees
2 Nov - 3 Nov
Cozy House in the heart of Waterville Maine.
A modern kitchen with a dining area, a sofa, and a window with a view.

14. Forest Cabin w/ Stunning Wall of Windows

Forest Cabin w/ Stunning Wall of Windows
Jackson
10.0 out of 10, Exceptional, (7 reviews)
"The location of the property is perfect--there's easy access and it's a great spot to call homebase while exploring the Maine Coast. The cabin peaceful and cozy and had most everything I needed. The decor is tasteful and calming and the hosts provide all sorts of varied amenities including homemade soaps."
United States
Laura
The price is AED 539
AED 888 total
includes taxes & fees
1 Nov - 2 Nov
Forest Cabin w/ Stunning Wall of Windows
Living area

15. 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
15 Oct - 16 Oct
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

16. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, Exceptional, (4 reviews)
"A lovely spot. It is extremely clean. The hostess has thought of everything! There are plenty of nice towels and facecloths and bedding. The bed is very comfortable. We have enjoyed our stay"
Canada
Sherrie
The price is AED 477
AED 601 total
includes taxes & fees
16 Oct - 17 Oct
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

17. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
The price is AED 422
AED 861 total
includes taxes & fees
12 Oct - 13 Oct
The heart of the Belgrade Lakes
A modern building with a black exterior, a wooden-framed entrance, and a stone staircase leading up to a glass door.

18. Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Mila was always available when I needed anything. Very flexible and the place was nice."
United States
Donna B.
The price is AED 471
AED 594 total
includes taxes & fees
16 Oct - 17 Oct
Spacious modern living in a quite neighborhood
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

19. Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Madison
10.0 out of 10, Exceptional, (45 reviews)
"Great experience"
United States
Chase D.
The price is AED 493
AED 1,286 total
includes taxes & fees
12 Oct - 13 Oct
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A wooden deck with outdoor furniture, a large potted plant, and string lights.

20. 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
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
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

10/10 Excellent
"Large double room. Nice shower. Fridge and microwave. Comfortable bed. Clean."
Marion 5-night trip
Posted 8 hours ago
The Elmwood

Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, we have vacation rentals near popular points of interest in Pittsfield, or you can select a more remote option if you're looking for relaxation. Pittsfield is known for its restaurants and shopping. Make sure you have time to check out the golf courses while you're in the area.

What's the top vacation rental in Pittsfield?

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95: Visitors like this Pittsfield vacation home rental. It offers a patio, a selection of books, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals will I find in Pittsfield?

Expedia has 3 vacation rentals for your stay in Pittsfield.

What can I see and do in Pittsfield?

Explore the area and family-friendly sights such as First Congregational Church, or get out into nature at a spot like Sebasticook Lake. JW Parks Golf Course and Skowhegan State Fairgrounds are a couple of places you'll find in the larger area.

What are vacation rentals like in Pittsfield?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Pittsfield. Vacation rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.