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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pittsfield holiday 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, (8 reviews)
"Great host great stay"
United States
thomas v.
The price is HK$953
HK$1,791 total
includes taxes & fees
12 Sept - 13 Sept
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Exterior

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 HK$1,101
HK$2,413 total
includes taxes & fees
13 Sept - 14 Sept
Angel Mist Retreat Garage Apartment
Private kitchen

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 HK$11,018
HK$14,049 total
includes taxes & fees
7 Oct - 8 Oct
Pine Tree Trail Lodge
Private kitchen

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is HK$706
HK$1,111 total
includes taxes & fees
8 Sept - 9 Sept
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Living area

5. Pretty Old House in Newport

Pretty Old House in Newport
Newport
The price is HK$1,019
HK$2,444 total
includes taxes & fees
8 Sept - 9 Sept
Pretty Old House in Newport
Outdoor dining

6. Gorgeous 2-bedroom cottage with AC in charming Stetson

Gorgeous 2-bedroom cottage with AC in charming Stetson
Stetson
10.0 out of 10, Exceptional, (18 reviews)
"Very nice. Will stay there again"
United States
Andy O.
The price is HK$1,294
HK$1,615 total
includes taxes & fees
8 Sept - 9 Sept
Gorgeous 2-bedroom cottage with AC in charming Stetson
Interior

7. Blake's Cabin

Blake's Cabin
Hartland
9.6 out of 10, Exceptional, (26 reviews)
"Clean rooms and beautiful property and lake views. Host was always quick to answer questions. Would definitely stay here again. "
United States
Carmen B.
The price is HK$1,529
HK$2,846 total
includes taxes & fees
8 Sept - 9 Sept
Blake's Cabin
Terrace/patio

8. Lakefront Retreat on Sebasticook Lake

Lakefront Retreat on Sebasticook Lake
Newport
9.0 out of 10, Wonderful, (4 reviews)
"Great property, would definitely stay again!"
United States
Skyla C.
The price is HK$1,568
HK$1,931 total
includes taxes & fees
8 Sept - 9 Sept
Lakefront Retreat on Sebasticook Lake
Exterior

9. 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 HK$2,251
HK$4,727 total
includes taxes & fees
9 Sept - 10 Sept
Peaceful, Spacious Lodge with Golf & Sunset Views
Living area

10. 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 HK$1,516
HK$3,524 total
includes taxes & fees
9 Sept - 10 Sept
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Living area

11. Forest Cabin w/ Stunning Wall of Windows

Forest Cabin w/ Stunning Wall of Windows
Jackson
10.0 out of 10, Exceptional, (5 reviews)
"The space was warm and clean and had everything we needed. The hosts were incredibly friendly and helpful. "
United States
Ally L.
The price is HK$1,408
HK$2,218 total
includes taxes & fees
9 Sept - 10 Sept
Forest Cabin w/ Stunning Wall of Windows
Living area

12. 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 Host was great, I highly recommend this spot, everything was super smooth and the cabin was beautiful. "
United States
Jason B.
The price is HK$882
HK$1,346 total
includes taxes & fees
8 Sept - 9 Sept
Charming cabin in the birches right on the atv trail!
Exterior

13. 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, (8 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is HK$910
HK$1,163 total
includes taxes & fees
13 Sept - 14 Sept
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Exterior

14. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$946
HK$2,048 total
includes taxes & fees
10 Sept - 11 Sept
Sister A-Frame in Woods B
Property grounds

15. 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 HK$1,051
HK$2,744 total
includes taxes & fees
16 Sept - 17 Sept
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Living area

16. 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 HK$1,094
HK$2,525 total
includes taxes & fees
8 Sept - 9 Sept
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Room

17. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
The price is HK$902
HK$1,812 total
includes taxes & fees
8 Sept - 9 Sept
The heart of the Belgrade Lakes
Private kitchen

18. 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, (3 reviews)
"WE were delighted in our accommodations. The apartment was lovely and very clean. Lynne was very responsive to my numerous questions. The location was centralized to hiking and biking trails and a quick jaunt to Augusta for the triathlon. I have to say that I slept like a baby too which is not a normal occurence for me. The mattress was so very comfortable. We would not hesitate to book here again. Thank you for a lovely visit."
United States
Cheri A.
The price is HK$941
HK$1,196 total
includes taxes & fees
8 Sept - 9 Sept
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Exterior

19. 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 HK$833
HK$1,506 total
includes taxes & fees
8 Sept - 9 Sept
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Exterior

20. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is HK$1,411
HK$2,436 total
includes taxes & fees
28 Sept - 29 Sept
Discover Oakland charm near Colby College 10 min
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

8/10 Good
"Great to stay with pets, but room is a little outdated."
Alexandre 1-night trip
Posted 1 hour 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:

  • View our selection of featured holiday rentals in Pittsfield
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  • 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.