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

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 ￥18,784
￥35,788 total
includes taxes & fees
Oct 19 - Oct 20
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

2. 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 ￥22,162
￥48,589 total
includes taxes & fees
Oct 12 - Oct 13
Angel Mist Retreat Garage Apartment
IMG 7964

3. 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 ￥53,026
￥92,368 total
includes taxes & fees
Nov 3 - Nov 4
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.

4. 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 ￥20,521
￥49,209 total
includes taxes & fees
Oct 7 - Oct 8
Pretty Old House in Newport
A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

5. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.6 out of 10, Exceptional, (5 reviews)
The price is ￥12,076
￥20,046 total
includes taxes & fees
Oct 7 - Oct 8
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
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 ￥30,118
￥70,509 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥45,319
￥94,477 total
includes taxes & fees
Oct 7 - Oct 8
Peaceful, Spacious Lodge with Golf & Sunset Views
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

8. 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 ￥17,758
￥27,100 total
includes taxes & fees
Oct 7 - Oct 8
Charming cabin in the birches right on the atv trail!
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.

9. 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 ￥23,362
￥40,089 total
includes taxes & fees
Nov 2 - Nov 3
Cozy House in the heart of Waterville Maine.
A wooden cabin with a porch, a door, and a green chair.

10. 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 ￥15,785
￥36,992 total
includes taxes & fees
Nov 2 - Nov 3
Sister A-Frame in Woods B
A modern building with a black exterior and a large glass entrance.

11. 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 ￥17,758
￥22,798 total
includes taxes & fees
Oct 12 - Oct 13
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.

12. 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 ￥17,206
￥34,756 total
includes taxes & fees
Oct 25 - Oct 26
Discover Oakland charm near Colby College 10 min
A two-story house with a wooden staircase and a balcony, two garage doors, and two ATVs parked in front.

13. 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 ￥13,780
￥27,065 total
includes taxes & fees
Oct 7 - Oct 8
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
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 ￥23,185
￥38,176 total
includes taxes & fees
Nov 1 - Nov 2
Forest Cabin w/ Stunning Wall of Windows
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

15. 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 ￥18,153
￥36,992 total
includes taxes & fees
Oct 7 - Oct 8
The heart of the Belgrade Lakes
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 ￥20,521
￥25,809 total
includes taxes & fees
Oct 12 - Oct 13
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Living area

17. 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 ￥21,310
￥49,553 total
includes taxes & fees
Oct 7 - Oct 8
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

18. 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 ￥21,168
￥55,248 total
includes taxes & fees
Oct 12 - Oct 13
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A wooden deck with a table and chairs, a view of a house, and a tree.

19. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (26 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is ￥25,098
￥39,917 total
includes taxes & fees
Oct 7 - Oct 8
Minutes to Colby
A modern building with a black exterior, a wooden-framed entrance, and a stone staircase leading up to a glass door.

20. 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 ￥20,244
￥25,507 total
includes taxes & fees
Oct 12 - Oct 13
Spacious modern living in a quite neighborhood
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

Best Western Plus Waterville Grand Hotel

Best Western Plus Waterville Grand Hotel

10/10 Excellent
"Good"
Debra 1-night trip
Posted 4 hours ago
Best Western Plus Waterville Grand Hotel

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pittsfield!

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.