Photo of a sunset through the trees at Mill Pond, Pittsfield, Maine, the USA

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Pittsfield vacation rentals

Terrace/patio

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome
Pittsfield
9.6 out of 10, Exceptional, (5 reviews)
"Great host great stay"
United States
thomas v.
The price is ￥19,251
￥37,030 total
includes taxes & fees
Jun 28 - Jun 29
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome
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 ￥22,682
￥50,257 total
includes taxes & fees
Jun 28 - Jun 29
Angel Mist Retreat Garage Apartment
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
Riverside Loft – Cozy 1BR w/ Sebasticook River Views & Trail Access + Wi-Fi
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 ￥18,174
￥27,735 total
includes taxes & fees
Jun 30 - Jul 1
Charming cabin in the birches right on the atv trail!
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 ￥15,993
￥33,809 total
includes taxes & fees
Jul 9 - Jul 10
Discover Oakland charm near Colby College 10 min
Outdoor dining

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, (6 reviews)
"Private clean cabin! Host came to check on us , All amenities available! Thank you"
United States
Tammy
The price is ￥26,656
￥33,281 total
includes taxes & fees
Jul 9 - Jul 10
Gorgeous 2-bedroom cottage with AC in charming Stetson
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 ￥20,937
￥26,342 total
includes taxes & fees
Jun 28 - Jun 29
Charming 1-bedroom building with WiFi, AC in brilliant Madison 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 ￥21,677
￥44,964 total
includes taxes & fees
Jul 15 - Jul 16
Sister A-Frame in Woods B
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 ￥14,394
￥28,016 total
includes taxes & fees
Jun 28 - Jun 29
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
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 ￥25,363
￥60,927 total
includes taxes & fees
Jul 14 - Jul 15
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
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 ￥50,205
￥101,639 total
includes taxes & fees
Jun 30 - Jul 1
The Getaway- A Cozy Lakeside Cabin
On the beach

The Retreat- A Relaxing Beachside Bungalow

The Retreat- A Relaxing Beachside Bungalow
Burnham
10.0 out of 10, Exceptional, (3 reviews)
"Great cabin and location "
United States
John V.
The price is ￥36,696
￥77,923 total
includes taxes & fees
Jun 28 - Jun 29
The Retreat- A Relaxing Beachside Bungalow
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 ￥14,559
￥26,449 total
includes taxes & fees
Jun 30 - Jul 1
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 ￥18,578
￥37,683 total
includes taxes & fees
Jul 2 - Jul 3
The heart of the Belgrade Lakes
Fridge, microwave, oven, stovetop

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 ￥22,617
￥28,174 total
includes taxes & fees
Jun 29 - Jun 30
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Paper towels

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Smithfield
10.0 out of 10, Exceptional, (1 review)
"Clean and new."
United States
erik s.
The price is ￥22,648
￥28,213 total
includes taxes & fees
Jun 29 - Jun 30
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
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 ￥31,502
￥58,638 total
includes taxes & fees
Jun 29 - Jun 30
Blake's Cabin
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 Beach Bum | Modern Cabin on the Sand
Terrace/patio

Lakefront Retreat on Sebasticook Lake

Lakefront Retreat on Sebasticook Lake
Newport
The price is ￥29,079
￥35,746 total
includes taxes & fees
Jul 2 - Jul 3
Lakefront Retreat on Sebasticook Lake
TV

Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is ￥30,533
￥63,216 total
includes taxes & fees
Jun 30 - Jul 1
Once Upon a Time — A Peaceful Maine Escape
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
"Recommend"
Sheala 3-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Waterville - North by IHG

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
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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?

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome: 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.