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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Pittsfield holiday rentals

Exterior

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is HK$1,101
HK$2,414 total
includes taxes & fees
28 Jul - 29 Jul
Angel Mist Retreat Garage Apartment
Terrace/patio

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, (6 reviews)
"Great host great stay"
United States
thomas v.
The price is HK$933
HK$1,778 total
includes taxes & fees
23 Jul - 24 Jul
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Fridge, microwave, oven, stovetop

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$11,749
HK$13,968 total
includes taxes & fees
30 Jul - 31 Jul
Pine Tree Trail Lodge
Outdoor dining

Tiny House Oasis in beautiful Waldo County, Maine. Dogs welcome!

Tiny House Oasis in beautiful Waldo County, Maine. Dogs welcome!
Jackson
The price is HK$917
HK$1,171 total
includes taxes & fees
27 Jul - 28 Jul
Tiny House Oasis in beautiful Waldo County, Maine. Dogs welcome!
Fireplace

Forest Cabin w/ Stunning Wall of Windows

Forest Cabin w/ Stunning Wall of Windows
Jackson
10.0 out of 10, Exceptional, (4 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$1,482
HK$2,308 total
includes taxes & fees
20 Aug - 21 Aug
Forest Cabin w/ Stunning Wall of Windows
Outdoor dining

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, (12 reviews)
"Private clean cabin! Host came to check on us , All amenities available! Thank you"
United States
Tammy
The price is HK$1,294
HK$1,615 total
includes taxes & fees
26 Jul - 27 Jul
Gorgeous 2-bedroom cottage with AC in charming Stetson
TV

Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is HK$2,456
HK$4,224 total
includes taxes & fees
8 Aug - 9 Aug
Once Upon a Time — A Peaceful Maine Escape
On the beach

The Retreat- A Relaxing Beachside Bungalow

The Retreat- A Relaxing Beachside Bungalow
Burnham
10.0 out of 10, Exceptional, (3 reviews)
"Great cabin and location "
United States
John V.
The price is HK$2,001
HK$4,063 total
includes taxes & fees
23 Jul - 24 Jul
The Retreat- A Relaxing Beachside Bungalow
Exterior

Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (22 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is HK$2,315
HK$3,061 total
includes taxes & fees
30 Jul - 31 Jul
Peaceful, Spacious Lodge with Golf & Sunset Views
Smart TV, fireplace, DVD player, books

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, (11 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
The price is HK$1,058
HK$2,461 total
includes taxes & fees
2 Aug - 3 Aug
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Exterior

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

New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Sangerville
8.0 out of 10, Very good, (3 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$847
HK$1,530 total
includes taxes & fees
23 Jul - 24 Jul
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Interior

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
The price is HK$706
HK$1,111 total
includes taxes & fees
29 Jul - 30 Jul
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
1 bedroom, WiFi, bed sheets

ON THE GO!

ON THE GO!
Hartland
10.0 out of 10, Exceptional, (3 reviews)
"Host friendly. Great place to stay in the area."
United States
Loretta
ON THE GO!
Interior

Blake's Cabin

Blake's Cabin
Hartland
9.6 out of 10, Exceptional, (25 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
28 Jul - 29 Jul
Blake's Cabin
Outdoor dining

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is HK$1,247
HK$1,991 total
includes taxes & fees
28 Jul - 29 Jul
Minutes to Colby
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (14 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is HK$792
HK$1,667 total
includes taxes & fees
29 Jul - 30 Jul
Discover Oakland charm near Colby College 10 min
Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9 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
29 Jul - 30 Jul
Sister A-Frame in Woods B
Outdoor dining

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Oakland
10.0 out of 10, Exceptional, (14 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
The price is HK$2,346
HK$4,255 total
includes taxes & fees
17 Aug - 18 Aug
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Smart TV

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
4 Aug - 5 Aug
Charming cabin in the birches right on the atv trail!
2 bedrooms, WiFi, bed sheets

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$1,837 total
includes taxes & fees
24 Jul - 25 Jul
The heart of the Belgrade 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 Skowhegan By Kasa

The Skowhegan By Kasa

8/10 Good
"The place was beautiful, It could use an easy chair to sit in to read, in both the bedroom and the living room. I would stay there again if I was back that way. The bench in the shower was not near the shower."
David 1-night trip
Posted less than an hour ago
The Skowhegan By Kasa

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 is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. 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.