Pittsfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

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 ￥21,998
￥48,229 total
includes taxes & fees
May 12 - May 13
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 ￥18,645
￥35,523 total
includes taxes & fees
May 17 - May 18
The Cozy Home- New, Comfortable, Book Swap
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 ￥18,488
￥36,205 total
includes taxes & fees
May 18 - May 19
The Cabin Skowhegan
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 ￥25,978
￥63,092 total
includes taxes & fees
May 12 - May 13
The Beach Bum | Modern Cabin on the Sand
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 ￥18,896
￥40,919 total
includes taxes & fees
May 12 - May 13
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 ￥15,511
￥32,960 total
includes taxes & fees
May 25 - May 26
Discover Oakland charm near Colby College 10 min
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 ￥17,627
￥26,899 total
includes taxes & fees
May 12 - May 13
Charming cabin in the birches right on the atv trail!
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 ￥14,101
￥25,617 total
includes taxes & fees
May 14 - May 15
ON THE GO!
Private kitchen

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, (2 reviews)
"We ended up not bringing the dogs, but the property was pet friendly. The host was very accommodating. The property was immaculate. Please note that GPS is not accurate. The cabin is the white property at the end of the lane, lakeside."
United States
Holly C.
The price is ￥23,267
￥28,948 total
includes taxes & fees
May 12 - May 13
Gorgeous 2-bedroom cottage with AC in charming Stetson
Property grounds

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, (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 ￥23,189
￥57,383 total
includes taxes & fees
Jun 4 - Jun 5
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
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 ￥19,742
￥47,307 total
includes taxes & fees
May 12 - May 13
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 ￥18,018
￥36,889 total
includes taxes & fees
May 12 - May 13
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 ￥27,419
￥52,942 total
includes taxes & fees
Jun 4 - Jun 5
Blake's Cabin
Outdoor dining

Pool, fire pit & minutes to Messalonskee Lake!

Pool, fire pit & minutes to Messalonskee Lake!
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 ￥35,253
￥57,179 total
includes taxes & fees
May 12 - May 13
Pool, fire pit & minutes to Messalonskee Lake!
Exterior detail

Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
The price is ￥20,094
￥25,318 total
includes taxes & fees
May 12 - May 13
Spacious modern living in a quite neighborhood
Microwave, oven, stovetop

Superb 2-bedroom Home with AC in Detroit

Superb 2-bedroom Home with AC in Detroit
Detroit
The price is ￥15,370
￥28,708 total
includes taxes & fees
May 12 - May 13
Superb 2-bedroom Home with AC in Detroit
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, (1 review)
"Cozy room, very nice bathroom and shower, beautiful setti ng and very accomadating and available host"
United States
Judith L.
The price is ￥13,960
￥27,171 total
includes taxes & fees
May 12 - May 13
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
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 ￥21,575
￥36,154 total
includes taxes & fees
May 16 - May 17
Forest Cabin with Wall of Windows
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 ￥28,516
￥52,496 total
includes taxes & fees
May 19 - May 20
Trout Ponds & Sauna: Unique Log Cabin in Freedom
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 ￥31,101
￥79,488 total
includes taxes & fees
May 12 - May 13
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Lockwood Hotel

Lockwood Hotel

10/10 Excellent
"We have stayed multiple time. Perfect central location in Waterville."
Kimberly 1-night trip
Posted 14 hours ago
Lockwood 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
  • 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 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.

What's the top vacation rental in Pittsfield?

The Cozy Home- New, Comfortable, Book Swap: Visitors like this Pittsfield vacation home rental. It 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 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.