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

Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Pittsfield holiday rentals

A spacious kitchen with wooden cabinets, a microwave, and a stove.

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

The Libby House – Fast WiFi, Parking & Full Kitchen
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place!"
United States
mary jane c.
The price is HK$800
HK$975 total
includes taxes & fees
10 Nov - 11 Nov
The Libby House – Fast WiFi, Parking & Full Kitchen
Terrace/patio

2. 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)
"I recommend this property to anyone staying in the Pittsfield area. I’ve already suggested it to our friends who live there as great option for guests. Very clean and comfortable and a good value."
United States
Anonymous traveller
The price is HK$934
HK$1,633 total
includes taxes & fees
5 Nov - 6 Nov
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.

3. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Very quiet and lovely apartment. The host was very accommodating and attentive to my questions."
United States
Ruth W.
The price is HK$1,101
HK$2,304 total
includes taxes & fees
3 Nov - 4 Nov
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 HK$2,526
HK$4,472 total
includes taxes & fees
30 Nov - 1 Dec
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, (2 reviews)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
The price is HK$1,020
HK$2,326 total
includes taxes & fees
15 Nov - 16 Nov
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 HK$1,262
HK$3,197 total
includes taxes & fees
12 Nov - 13 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, (25 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is HK$2,252
HK$4,490 total
includes taxes & fees
12 Nov - 13 Nov
Peaceful, Spacious Lodge with Golf & Sunset Views
A two-story house with a wooden staircase and a balcony, two garage doors, and two ATVs parked in front.

8. 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)
"Our 3 night stay was quiet. Even with the other unit occupied, we were very comfortable."
United States
Thayne I.
The price is HK$685
HK$1,277 total
includes taxes & fees
3 Nov - 4 Nov
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
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 HK$745
HK$1,129 total
includes taxes & fees
19 Nov - 20 Nov
Charming cabin in the birches right on the atv trail!
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 HK$706
HK$1,659 total
includes taxes & fees
3 Nov - 4 Nov
Sister A-Frame in Woods B
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.

11. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
The price is HK$1,161
HK$1,898 total
includes taxes & fees
8 Nov - 9 Nov
Cozy House in the heart of Waterville Maine.
A modern kitchen with a dining area, a sofa, and a window with a view.

12. Forest Cabin w/ Stunning Wall of Windows

Forest Cabin w/ Stunning Wall of Windows
Jackson
10.0 out of 10, Exceptional, (7 reviews)
"The space was warm and clean and had everything we needed. The hosts were incredibly friendly and helpful. "
United States
Ally L.
Forest Cabin w/ Stunning Wall of Windows
Living area

13. 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, (13 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
The price is HK$1,059
HK$2,343 total
includes taxes & fees
3 Nov - 4 Nov
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.

14. 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)
"Really neat cabin that has been added onto. The backstory was really cool to read. Highly recommend this cabin. Extremely peaceful and private. Highly recommend this host and staying here!"
United States
Blake B.
The price is HK$1,052
HK$2,609 total
includes taxes & fees
3 Nov - 4 Nov
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A modern building with a black exterior and a large glass entrance.

15. 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, (10 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is HK$883
HK$1,065 total
includes taxes & fees
3 Nov - 4 Nov
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A hot tub with a fire pit and chairs in a backyard with tall trees.

16. Dog Friendly, Steps to Lake, Golf, & Theate

Dog Friendly, Steps to Lake, Golf, & Theate
Madison
10.0 out of 10, Exceptional, (1 review)
"The house is really nice convenient local area. We would stay there again when we come into town."
United States
Al Q.
The price is HK$1,616
HK$4,061 total
includes taxes & fees
3 Nov - 4 Nov
Dog Friendly, Steps to Lake, Golf, & Theate
A living room with a sofa, a fireplace, a television, and a plant.

17. Minimal & Cozy Victorian Private Room in Downtown Skowhegan

Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Skowhegan
The price is HK$1,569
HK$2,531 total
includes taxes & fees
8 Nov - 9 Nov
Minimal & Cozy Victorian Private Room in Downtown Skowhegan
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

18. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is HK$2,118
HK$3,626 total
includes taxes & fees
3 Nov - 4 Nov
Once Upon a Time — A Peaceful Maine Escape
A bathroom with a white shower curtain, a sink with a marble countertop, and a mirror above the sink.

19. 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 HK$902
HK$1,753 total
includes taxes & fees
3 Nov - 4 Nov
The heart of the Belgrade Lakes
A rustic stone house with a metal roof, surrounded by a grassy field and a large tree.

20. 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 HK$941
HK$1,129 total
includes taxes & fees
3 Nov - 4 Nov
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
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

Belmont Motel

Belmont Motel

8/10 Good
"Room was nice the shower had a hole in it from where a bar used to be but other than that it was good the room was big but the tv was in a bad spot to watch while in bed"
Kaitlyn 2-night trip
Posted 5 hours ago
Belmont Motel

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:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

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

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Pittsfield has to offer?

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95: This highly rated holiday home rental in Pittsfield 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 holiday rentals will I find in Pittsfield?

Expedia has 3 holiday 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 wider area.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.