Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Pittsfield vacation 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 R$ 698
R$ 1.531 total
includes taxes & fees
2 May - 3 May
Angel Mist Retreat Garage Apartment
Terrace/patio

The Cozy Home- New, Comfortable, Book Swap

The Cozy Home- New, Comfortable, Book Swap
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great host great stay"
United States
thomas v.
The price is R$ 557
R$ 1.144 total
includes taxes & fees
2 May - 3 May
The Cozy Home- New, Comfortable, Book Swap
House (2 Bedrooms) | Interior

Trout Ponds & Sauna: Unique Log Cabin in Freedom

Trout Ponds & Sauna: Unique Log Cabin in Freedom
3.0 star property
Freedom
The price is R$ 905
R$ 1.667 total
includes taxes & fees
19 May - 20 May
Trout Ponds & Sauna: Unique Log Cabin in Freedom
Property grounds

Cabin on 30 acre of privacy. Fire pit, picnic table, trails & close to town.

Cabin on 30 acre of privacy. Fire pit, picnic table, trails & close to town.
Madison
10.0 out of 10, Exceptional, (43 reviews)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
The price is R$ 647
R$ 1.713 total
includes taxes & fees
3 May - 4 May
Cabin on 30 acre of privacy. Fire pit, picnic table, trails & close to town.
Terrace/patio

The Beach Bum | Modern Cabin on the Sand

The Beach Bum | Modern Cabin on the Sand
Burnham
10.0 out of 10, Exceptional, (2 reviews)
"Nice cottage. Perfect location. Everything you need for a quiet beach stay on Unity pond. "
United States
Albert
The price is R$ 828
R$ 2.018 total
includes taxes & fees
3 May - 4 May
The Beach Bum | Modern Cabin on the Sand
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 R$ 508
R$ 1.055 total
includes taxes & fees
4 May - 5 May
The Cabin Skowhegan
On the beach

The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!
Burnham
9.0 out of 10, Wonderful, (7 reviews)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
The price is R$ 992
R$ 2.546 total
includes taxes & fees
3 May - 4 May
The Maine Lake House with an Amazing Sand Beach!
Exterior

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
The price is R$ 990
R$ 1.799 total
includes taxes & fees
8 May - 9 May
Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
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 R$ 627
R$ 1.502 total
includes taxes & fees
4 May - 5 May
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
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 R$ 572
R$ 1.155 total
includes taxes & fees
8 May - 9 May
The heart of the Belgrade Lakes
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 R$ 863
R$ 1.361 total
includes taxes & fees
22 May - 23 May
Forest Cabin with Wall of Windows
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 R$ 448
R$ 813 total
includes taxes & fees
1 May - 2 May
ON THE GO!
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 R$ 600
R$ 1.288 total
includes taxes & fees
13 May - 14 May
Sister A-Frame in Woods B
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is R$ 517
R$ 1.065 total
includes taxes & fees
4 May - 5 May
Discover Oakland charm near Colby College 10 min
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 R$ 1.119
R$ 1.990 total
includes taxes & fees
25 May - 26 May
Blake's Cabin
Private kitchen

Gorgeous 2-bedroom cottage with AC in charming Stetson

Gorgeous 2-bedroom cottage with AC in charming Stetson
Stetson
The price is R$ 739
R$ 924 total
includes taxes & fees
3 May - 4 May
Gorgeous 2-bedroom cottage with AC in charming Stetson
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 R$ 560
R$ 854 total
includes taxes & fees
2 May - 3 May
Charming cabin in the birches right on the atv trail!
Exterior detail

Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
The price is R$ 638
R$ 804 total
includes taxes & fees
2 May - 3 May
Spacious modern living in a quite neighborhood
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 R$ 560
R$ 718 total
includes taxes & fees
13 May - 14 May
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Microwave, oven, stovetop

Superb 2-bedroom Home with AC in Detroit

Superb 2-bedroom Home with AC in Detroit
Detroit
The price is R$ 463
R$ 886 total
includes taxes & fees
5 May - 6 May
Superb 2-bedroom Home with AC in Detroit
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

Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

8/10 Good
"Breakfast food and staff fabulous! Rooms a little dated, but they really make up for it in cleanliness and friendlyness."
Wendy J 3-night trip
Posted 4 hours ago
Holiday Inn Express & Suites Waterville - North by IHG

Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, we have vacation rentals near popular points of interest in Pittsfield, or you can select a more remote option if you're looking for relaxation. 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.

How many vacation rentals will I find in Pittsfield?

Expedia has 3 vacation 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 larger area.

What are vacation rentals like in Pittsfield?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Pittsfield. Vacation rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.