Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Pittsfield vacation rentals

Exterior detail

Riverside Loft – Cozy 1BR w/ Sebasticook River Views & Trail Access + Wi-Fi

Riverside Loft – Cozy 1BR w/ Sebasticook River Views & Trail Access + Wi-Fi
Pittsfield
The price is ￥21,199
￥51,252 total
includes taxes & fees
Jun 2 - Jun 3
Riverside Loft – Cozy 1BR w/ Sebasticook River Views & Trail Access + Wi-Fi
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 ￥22,362
￥48,680 total
includes taxes & fees
Jun 2 - Jun 3
Angel Mist Retreat Garage Apartment
Terrace/patio

The Cozy Home- New, Comfortable, Book Swap

The Cozy Home- New, Comfortable, Book Swap
Pittsfield
9.6 out of 10, Exceptional, (4 reviews)
"Great host great stay"
United States
thomas v.
The price is ￥18,953
￥35,936 total
includes taxes & fees
Jun 2 - Jun 3
The Cozy Home- New, Comfortable, Book Swap
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)
"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 ￥13,618
￥22,657 total
includes taxes & fees
Jun 2 - Jun 3
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, (3 reviews)
"Host friendly. Great place to stay in the area."
United States
Loretta
The price is ￥14,334
￥26,040 total
includes taxes & fees
Jun 30 - Jul 1
ON THE GO!
Exterior

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (53 reviews)
"Beautifully furnished cozy cabin and great hospitality from Larry and Lisa! Nice and toasty when we arrived and every detail was expertly crafted for a pleasant stay. Thank you so much for hosting our weekend in Skowhegan."
United States
Josh W.
The price is ￥18,953
￥36,804 total
includes taxes & fees
Jun 15 - Jun 16
The Cabin Skowhegan
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 ￥15,768
￥33,506 total
includes taxes & fees
Jun 7 - Jun 8
Discover Oakland charm near Colby College 10 min
Exterior

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

New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Sangerville
7.0 out of 10, Good, (2 reviews)
"Cozy room, very nice bathroom and shower, beautiful setti ng and very accomadating and available host"
United States
Judith L.
The price is ￥14,191
￥27,621 total
includes taxes & fees
Jun 2 - Jun 3
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
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 ￥20,068
￥47,915 total
includes taxes & fees
Jun 2 - Jun 3
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Private kitchen

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
The price is ￥22,298
￥27,777 total
includes taxes & fees
Jun 14 - Jun 15
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
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 ￥19,208
￥41,595 total
includes taxes & fees
Jun 2 - Jun 3
Sister A-Frame in Woods B
Exterior detail

Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
The price is ￥20,426
￥25,736 total
includes taxes & fees
Jun 2 - Jun 3
Spacious modern living in a quite neighborhood
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, (44 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 ￥23,731
￥58,331 total
includes taxes & fees
Jun 17 - Jun 18
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
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 ￥18,205
￥23,316 total
includes taxes & fees
Jun 9 - Jun 10
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Outdoor dining

Pool, fire pit & minutes to Messalonskee Lake!

Pool, fire pit & minutes to Messalonskee Lake!
Oakland
10.0 out of 10, Exceptional, (12 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
The price is ￥39,818
￥67,662 total
includes taxes & fees
Jun 8 - Jun 9
Pool, fire pit & minutes to Messalonskee Lake!
On the beach

The Getaway- A Cozy Lakeside Cabin

The Getaway- A Cozy Lakeside Cabin
Burnham
10.0 out of 10, Exceptional, (6 reviews)
"Such a great cabin and location. Super clean and a perfect getaway, we can’t wait to go back!"
United States
Sara D.
The price is ￥27,275
￥70,501 total
includes taxes & fees
Jun 2 - Jun 3
The Getaway- A Cozy Lakeside Cabin
Terrace/patio

The Escape | Steps to the Sand

The Escape | Steps to the Sand
Burnham
The price is ￥26,407
￥64,308 total
includes taxes & fees
Jun 2 - Jun 3
The Escape | Steps to the Sand
Shower, towels, soap, toilet paper

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, (4 reviews)
"The cottage was very clean with plenty of room and privacy. The cottage sat on a nice lot overlooking the lake.The owner greeted us on arrival and was very friendly offering his availability for anything that we may need."
United States
Keith W.
The price is ￥23,652
￥29,601 total
includes taxes & fees
Jun 6 - Jun 7
Gorgeous 2-bedroom cottage with AC in charming Stetson
Shower, hair dryer, towels, shampoo

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Smithfield
The price is ￥22,298
￥27,777 total
includes taxes & fees
Jun 14 - Jun 15
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
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 ￥27,872
￥53,817 total
includes taxes & fees
Jun 4 - Jun 5
Blake's Cabin
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 Elmwood

The Elmwood

10/10 Excellent
"V"
Francine 1-night trip
Posted less than an hour ago
The Elmwood

Find out more about Pittsfield

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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.