Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

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$1,098
HK$2,417 total
includes taxes & fees
2 Mar - 3 Mar
Angel Mist Retreat Garage Apartment
Terrace/patio

The Cozy Home- New, Comfortable, Centrally located

The Cozy Home- New, Comfortable, Centrally located
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great host great stay"
United States
thomas v.
The price is HK$1,291
HK$2,260 total
includes taxes & fees
19 Mar - 20 Mar
The Cozy Home- New, Comfortable, Centrally located
Microwave, oven, stovetop

Superb 2-bedroom Home with AC in Detroit

Superb 2-bedroom Home with AC in Detroit
Detroit
The price is HK$739
HK$1,402 total
includes taxes & fees
2 Mar - 3 Mar
Superb 2-bedroom Home with AC in Detroit
Exterior

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (52 reviews)
"Very quiet and relaxing - just what we wanted."
United States
Mary D.
The price is HK$782
HK$1,646 total
includes taxes & fees
2 Mar - 3 Mar
The Cabin Skowhegan
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
9.2 out of 10, Wonderful, (7 reviews)
"Very neat cabin. Spacious all utilities and a fire pit"
United States
Lisa O.
The price is HK$880
HK$1,343 total
includes taxes & fees
2 Mar - 3 Mar
Charming cabin in the birches right on the atv trail!
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$943
HK$1,787 total
includes taxes & fees
4 Mar - 5 Mar
Sister A-Frame in Woods B
1 bedroom, WiFi, bed sheets

ON THE GO!

ON THE GO!
Hartland
10.0 out of 10, Exceptional, (2 reviews)
"It was a clean and quiet room. The property was also clean and quiet. "
United States
Sarah F.
The price is HK$704
HK$1,279 total
includes taxes & fees
2 Mar - 3 Mar
ON THE GO!
2 bedrooms, WiFi, bed sheets

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is HK$900
HK$1,833 total
includes taxes & fees
1 Apr - 2 Apr
The heart of the Belgrade Lakes
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$1,369
HK$2,652 total
includes taxes & fees
2 Mar - 3 Mar
Blake's Cabin
Exterior

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.2 out of 10, Wonderful, (5 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is HK$951
HK$1,207 total
includes taxes & fees
4 Mar - 5 Mar
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Property grounds

Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths

Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Everything was amazing"
United States
Antwan B.
The price is HK$1,197
HK$2,925 total
includes taxes & fees
2 Mar - 3 Mar
Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is HK$697
HK$1,962 total
includes taxes & fees
9 Mar - 10 Mar
Discover Oakland charm near Colby College 10 min
Fireplace

Forest Cabin with Wall of Windows

Forest Cabin with Wall of Windows
Jackson
10.0 out of 10, Exceptional, (1 review)
"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$1,080
HK$1,808 total
includes taxes & fees
3 Mar - 4 Mar
Forest Cabin with Wall of Windows
Terrace/patio

The Escape | Steps to the Sand

The Escape | Steps to the Sand
Burnham
The Escape | Steps to the Sand
Exterior

Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is HK$1,526
HK$2,803 total
includes taxes & fees
2 Mar - 3 Mar
Cozy getaway: farmhouse with wood stove & jacuzzi tub
Exterior detail

Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
The price is HK$951
HK$1,207 total
includes taxes & fees
3 Mar - 4 Mar
Spacious modern living in a quite neighborhood
On the beach

The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!
Burnham
8.8 out of 10, Excellent, (6 reviews)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
The price is HK$1,553
HK$4,037 total
includes taxes & fees
2 Mar - 3 Mar
The Maine Lake House with an Amazing Sand Beach!
Property grounds

The Water's Edge | Peaceful Lakeside Cabin

The Water's Edge | Peaceful Lakeside Cabin
Hartland
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay! "
United States
Michaela W.
The price is HK$1,297
HK$3,370 total
includes taxes & fees
2 Mar - 3 Mar
The Water's Edge | Peaceful Lakeside Cabin
Outdoor dining

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22 reviews)
"Easy check in and spacious apartment. Excellent location- within minutes of Colby and downtown restaurants. Super comfy living room to relax in after a full day of Parents Weekend:"
United States
Jodie M.
The price is HK$861
HK$1,492 total
includes taxes & fees
2 Mar - 3 Mar
Minutes to Colby
Smart TV, books

Salt water hot tub, king size beds, dog friendly, ice fishing

Salt water hot tub, king size beds, dog friendly, ice fishing
Canaan
10.0 out of 10, Exceptional, (4 reviews)
"We had such a wonderful time here! It was so cozy during the snowstorm and had everything we needed and more. We enjoyed the hot tub and snowmobiling on the lake was awesome. The host was quick at responding and so helpful! We will definitely stay here again. "
United States
Ashley G.
The price is HK$1,216
HK$2,954 total
includes taxes & fees
4 Mar - 5 Mar
Salt water hot tub, king size beds, dog friendly, ice fishing
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

Large Secluded Cabin on the Lake - Now booking 2+ night stays

Large Secluded Cabin on the Lake - Now booking 2+ night stays

10/10 Excellent
"Great place to stay "
samuel g. 7-night trip
Posted 2 days ago
Large Secluded Cabin on the Lake - Now booking 2+ night stays

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?

Cozy getaway: farmhouse with wood stove & jacuzzi tub: This holiday home rental outside of Pittsfield is located in a rural location, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 Lovejoy Pond. 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.