Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Family, Friends and Fun for all

2.0 star property
10.0 out of 10, Exceptional, (2)
"We booked this location for our workers for the 2025 Master Amateur Invitational due to its proximity to the event grounds. The place was amazing and perfect for this event. The staff and the hosts were very responsive and accommodating to all our needs. I would recommend this place to anyone staying in the Pittsfield, ME area."
The price is NZ$654
includes taxes & fees
20 July - 21 July
Family, Friends and Fun for all

Discover Oakland charm near Colby College 10 min

2.0 star property
10.0 out of 10, Exceptional, (2)
"New, clean and had everything we needed. "
The price is NZ$436
includes taxes & fees
4 Aug - 5 Aug
Discover Oakland charm near Colby College 10 min

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (2)
"Great stay. Would stay here again if in the area."
The price is NZ$388
includes taxes & fees
23 July - 24 July
Sister A-Frame in Woods B

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

10.0 out of 10, Exceptional, (2)
"The property was very clean & in a quiet area. Very comfortable & inviting."
The price is NZ$356
includes taxes & fees
30 July - 31 July
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Cozy unique studio with Sauna, WiFi and AC and in peaceful Skowhegan

The price is NZ$303
includes taxes & fees
18 July - 19 July
Cozy unique studio with Sauna, WiFi and AC and in peaceful Skowhegan

Glamping in Amish Country

The price is NZ$389
includes taxes & fees
21 July - 22 July
Glamping in Amish Country

Minimal & Cozy Victorian Private Room in Downtown Skowhegan

The price is NZ$592
includes taxes & fees
27 July - 28 July
Minimal & Cozy Victorian Private Room in Downtown Skowhegan

The Beach Bum | Modern Cabin on the Sand

The price is NZ$896
includes taxes & fees
21 July - 22 July
The Beach Bum | Modern Cabin on the Sand

The Maine Lake House with an Amazing Sand Beach!

8.8 out of 10, Excellent, (6)
"Great stay, property was a great fit for a few day stay to visit family."
The price is NZ$1,266
includes taxes & fees
18 July - 19 July
The Maine Lake House with an Amazing Sand Beach!
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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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?

Family, Friends and Fun for all: This highly rated holiday home rental in Pittsfield offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.