An aerial view of a town with autumn-colored trees, a central green field, and surrounding residential areas.

Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Pittsfield vacation rentals

Terrace/patio

1. Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95

Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Pittsfield
9.8 out of 10, Exceptional, (8 reviews)
"Great host great stay"
United States
thomas v.
The price is ￥18,773
￥35,767 total
includes taxes & fees
Aug 18 - Aug 19
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
Exterior

2. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is ￥22,150
￥49,250 total
includes taxes & fees
Aug 21 - Aug 22
Angel Mist Retreat Garage Apartment
Fridge, microwave, oven, stovetop

3. Pine Tree Trail Lodge

Pine Tree Trail Lodge
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
The price is ￥223,877
￥276,616 total
includes taxes & fees
Sep 9 - Sep 10
Pine Tree Trail Lodge
Terrace/patio

4. Lakefront Retreat on Sebasticook Lake

Lakefront Retreat on Sebasticook Lake
Newport
8.8 out of 10, Excellent, (3 reviews)
"Beautiful cottage on the water, beautiful views and peaceful"
United States
Erin B.
The price is ￥28,397
￥35,424 total
includes taxes & fees
Aug 18 - Aug 19
Lakefront Retreat on Sebasticook Lake
Interior

5. Blake's Cabin

Blake's Cabin
Hartland
9.6 out of 10, Exceptional, (26 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 ￥30,763
￥57,950 total
includes taxes & fees
Sep 1 - Sep 2
Blake's Cabin
Exterior

6. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (22 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is ￥45,293
￥95,798 total
includes taxes & fees
Aug 18 - Aug 19
Peaceful, Spacious Lodge with Golf & Sunset Views
Outdoor dining

7. 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, (15 reviews)
"Private clean cabin! Host came to check on us , All amenities available! Thank you"
United States
Tammy
The price is ￥26,030
￥32,500 total
includes taxes & fees
Aug 16 - Aug 17
Gorgeous 2-bedroom cottage with AC in charming Stetson
Interior

8. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
8.0 out of 10, Very Good, (1 review)
"Very clean and comfortable. Nice view of river. Very quiet & comfortable."
United States
Jack F.
The price is ￥14,198
￥22,354 total
includes taxes & fees
Aug 26 - Aug 27
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Smart TV

9. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 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 ￥17,748
￥27,084 total
includes taxes & fees
Aug 20 - Aug 21
Charming cabin in the birches right on the atv trail!
Fireplace

10. Forest Cabin w/ Stunning Wall of Windows

Forest Cabin w/ Stunning Wall of Windows
Jackson
10.0 out of 10, Exceptional, (4 reviews)
"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 ￥28,326
￥44,632 total
includes taxes & fees
Aug 13 - Aug 14
Forest Cabin w/ Stunning Wall of Windows
Exterior

11. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (15 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
Discover Oakland charm near Colby College 10 min
Exterior

12. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is ￥19,026
￥41,373 total
includes taxes & fees
Aug 20 - Aug 21
Sister A-Frame in Woods B
Exterior

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.4 out of 10, Exceptional, (8 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is ￥18,600
￥23,713 total
includes taxes & fees
Aug 24 - Aug 25
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Exterior

14. 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, (3 reviews)
"Cozy room, very nice bathroom and shower, beautiful setti ng and very accomadating and available host"
United States
Judith L.
The price is ￥13,630
￥26,894 total
includes taxes & fees
Aug 16 - Aug 17
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Smart TV, fireplace, DVD player, books

15. 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 ￥21,499
￥50,339 total
includes taxes & fees
Aug 12 - Aug 13
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
2 bedrooms, WiFi, bed sheets

16. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
The price is ￥18,142
￥36,627 total
includes taxes & fees
Aug 12 - Aug 13
The heart of the Belgrade Lakes
Property grounds

17. 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, (45 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 ￥23,506
￥58,810 total
includes taxes & fees
Sep 8 - Sep 9
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Outdoor dining

18. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (24 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is ￥25,084
￥40,066 total
includes taxes & fees
Aug 20 - Aug 21
Minutes to Colby
Paper towels

19. 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
10.0 out of 10, Exceptional, (2 reviews)
"WE were delighted in our accommodations. The apartment was lovely and very clean. Lynne was very responsive to my numerous questions. The location was centralized to hiking and biking trails and a quick jaunt to Augusta for the triathlon. I have to say that I slept like a baby too which is not a normal occurence for me. The mattress was so very comfortable. We would not hesitate to book here again. Thank you for a lovely visit."
United States
Cheri A.
The price is ￥20,509
￥25,794 total
includes taxes & fees
Aug 12 - Aug 13
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Property grounds

20. Minimal & Cozy Victorian Private Room in Downtown Skowhegan

Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Skowhegan
The price is ￥31,552
￥54,167 total
includes taxes & fees
Aug 17 - Aug 18
Minimal & Cozy Victorian Private Room in Downtown Skowhegan
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

8/10 Good
"Nice to stay"
vipul 1-night trip
Posted 2 hours ago
Fireside Inn & Suites Waterville

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:

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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- close to I95: 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.