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

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

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 AED 437
AED 845 total
includes taxes & fees
18 Aug - 19 Aug
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 AED 516
AED 1,147 total
includes taxes & fees
31 Aug - 1 Sep
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 AED 5,212
AED 6,440 total
includes taxes & fees
9 Sep - 10 Sep
Pine Tree Trail Lodge
Books, offices

4. Pretty old house in Newport with WiFi

Pretty old house in Newport with WiFi
Newport
The price is AED 544
AED 1,229 total
includes taxes & fees
8 Sep - 9 Sep
Pretty old house in Newport with WiFi
Terrace/patio

5. 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 AED 661
AED 825 total
includes taxes & fees
18 Aug - 19 Aug
Lakefront Retreat on Sebasticook Lake
Interior

6. 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 AED 716
AED 1,349 total
includes taxes & fees
9 Sep - 10 Sep
Blake's Cabin
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, (16 reviews)
"Private clean cabin! Host came to check on us , All amenities available! Thank you"
United States
Tammy
The price is AED 606
AED 757 total
includes taxes & fees
21 Aug - 22 Aug
Gorgeous 2-bedroom cottage with AC in charming Stetson
Exterior

8. 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 AED 1,055
AED 2,230 total
includes taxes & fees
13 Aug - 14 Aug
Peaceful, Spacious Lodge with Golf & Sunset Views
Interior

9. 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 AED 331
AED 520 total
includes taxes & fees
31 Aug - 1 Sep
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Exterior

10. 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

11. 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 AED 443
AED 963 total
includes taxes & fees
13 Aug - 14 Aug
Sister A-Frame in Woods B
Fireplace

12. 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 AED 659
AED 1,051 total
includes taxes & fees
13 Aug - 14 Aug
Forest Cabin w/ Stunning Wall of Windows
Smart TV

13. 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 AED 413
AED 631 total
includes taxes & fees
19 Aug - 20 Aug
Charming cabin in the birches right on the atv trail!
Exterior

14. 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 AED 423
AED 541 total
includes taxes & fees
25 Aug - 26 Aug
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
2 bedrooms, WiFi, bed sheets

15. 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 AED 422
AED 869 total
includes taxes & fees
14 Aug - 15 Aug
The heart of the Belgrade Lakes
Property grounds

16. 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 AED 547
AED 1,369 total
includes taxes & fees
3 Sep - 4 Sep
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Paper towels

17. 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 AED 477
AED 601 total
includes taxes & fees
12 Sep - 13 Sep
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Outdoor dining

18. Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Oakland
10.0 out of 10, Exceptional, (14 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
The price is AED 868
AED 1,717 total
includes taxes & fees
10 Sep - 11 Sep
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Smart TV, fireplace, DVD player, books

19. 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 AED 502
AED 1,176 total
includes taxes & fees
24 Aug - 25 Aug
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
Outdoor dining

20. 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 AED 584
AED 933 total
includes taxes & fees
17 Aug - 18 Aug
Minutes to Colby
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

The Skowhegan By Kasa

The Skowhegan By Kasa

10/10 Excellent
"Very cool recently updated property in an old mill with very high ceilings and exposed brick. Everything was super clean. Our room was more like a suite with a separate bedroom and a sitting area(both with TV's). Small fridge and microwave perfect for storing drinks and heating up leftovers. Bathroom was large and modern. Few things to note - this is an unstaffed hotel so all communication is via text. Also there is no coffeemaker in the room - there is a kettle and coffee and tea bags, but the on-site restaurant has coffee and opens at 7AM."
Ruth 2-night trip
Posted 9 hours ago
The Skowhegan By Kasa

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.