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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Pittsfield vacation rentals

A spacious kitchen with wooden cabinets, a microwave, and a stove.

1. The Libby House – Fast WiFi, Parking & Full Kitchen

The Libby House – Fast WiFi, Parking & Full Kitchen
Pittsfield
10.0 out of 10, Exceptional, (1 review)
"Great place!"
United States
mary jane c.
The price is CA $144
CA $214 total
includes taxes & fees
Nov 17 - Nov 18
The Libby House – Fast WiFi, Parking & Full Kitchen
Terrace/patio

2. 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, (10 reviews)
"I recommend this property to anyone staying in the Pittsfield area. I’ve already suggested it to our friends who live there as great option for guests. Very clean and comfortable and a good value."
United States
Anonymous traveller
The price is CA $168
CA $272 total
includes taxes & fees
Nov 12 - Nov 13
Quiet Maine Retreat- Fast Wi-Fi - Long Stays Welcome- close to I95
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

3. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Very quiet and lovely apartment. The host was very accommodating and attentive to my questions."
United States
Ruth W.
The price is CA $198
CA $419 total
includes taxes & fees
Nov 12 - Nov 13
Angel Mist Retreat Garage Apartment
IMG 7964

4. 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 CA $442
CA $784 total
includes taxes & fees
Dec 8 - Dec 9
Pine Tree Trail Lodge
A living room with a blue armchair, a beige armchair, a patterned rug, and a bookshelf with books and a plant.

5. Pretty Old House in Newport

Pretty Old House in Newport
Newport
8.0 out of 10, Very good, (2 reviews)
"Good place to stay for a night. Everything was clean. The location is not close to much."
United States
Sallie S.
The price is CA $184
CA $419 total
includes taxes & fees
Nov 21 - Nov 22
Pretty Old House in Newport
A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is CA $108
CA $167 total
includes taxes & fees
Nov 30 - Dec 1
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
A cozy living room with a sofa, ottoman, and dining table with chairs. There are windows with curtains, a wooden ceiling, and a view of the outdoors.

7. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Canaan
9.8 out of 10, Exceptional, (9 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
The price is CA $208
CA $533 total
includes taxes & fees
Nov 22 - Nov 23
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
A wooden building with a red roof and a bell tower, surrounded by a well-maintained lawn and vibrant flowers.

8. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (25 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
The price is CA $405
CA $814 total
includes taxes & fees
Nov 16 - Nov 17
Peaceful, Spacious Lodge with Golf & Sunset Views
A wooden cabin with a porch, a door, and a green chair.

9. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is CA $127
CA $302 total
includes taxes & fees
Nov 19 - Nov 20
Sister A-Frame in Woods B
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

10. 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 cabin was perfect for our two night stay. It was very clean and it felt just like being at home. Misty was a responsive host and I would definitely rent here again."
United States
Tonilynne D.
The price is CA $121
CA $189 total
includes taxes & fees
Nov 19 - Nov 20
Charming cabin in the birches right on the atv trail!
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

11. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
The price is CA $223
CA $345 total
includes taxes & fees
Nov 18 - Nov 19
Cozy House in the heart of Waterville Maine.
A two-story house with a wooden staircase and a balcony, two garage doors, and two ATVs parked in front.

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

New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
Sangerville
7.2 out of 10, Good, (5 reviews)
"Our 3 night stay was quiet. Even with the other unit occupied, we were very comfortable."
United States
Thayne I.
New Stylish Guest Suite – Cozy & Quiet Stay in charming Sangerville
A modern kitchen with a dining area, a sofa, and a window with a view.

13. Forest Cabin w/ Stunning Wall of Windows

Forest Cabin w/ Stunning Wall of Windows
Jackson
10.0 out of 10, Exceptional, (7 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 CA $233
CA $370 total
includes taxes & fees
Dec 6 - Dec 7
Forest Cabin w/ Stunning Wall of Windows
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

14. 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, (4 reviews)
"A lovely spot. It is extremely clean. The hostess has thought of everything! There are plenty of nice towels and facecloths and bedding. The bed is very comfortable. We have enjoyed our stay"
Canada
Sherrie
The price is CA $169
CA $203 total
includes taxes & fees
Nov 14 - Nov 15
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A modern building with a black exterior and a large glass entrance.

15. 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, (10 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is CA $184
CA $209 total
includes taxes & fees
Nov 24 - Nov 25
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Living area

16. 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, (13 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
The price is CA $191
CA $426 total
includes taxes & fees
Nov 12 - Nov 13
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

17. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
The price is CA $162
CA $315 total
includes taxes & fees
Nov 14 - Nov 15
The heart of the Belgrade Lakes
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

18. 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)
"Really neat cabin that has been added onto. The backstory was really cool to read. Highly recommend this cabin. Extremely peaceful and private. Highly recommend this host and staying here!"
United States
Blake B.
The price is CA $189
CA $453 total
includes taxes & fees
Nov 24 - Nov 25
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A modern building with a black exterior, a wooden-framed entrance, and a stone staircase leading up to a glass door.

19. Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Mila was always available when I needed anything. Very flexible and the place was nice."
United States
Donna B.
The price is CA $174
CA $208 total
includes taxes & fees
Nov 15 - Nov 16
Spacious modern living in a quite neighborhood
A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

20. 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
8.0 out of 10, Very good, (1 review)
"Very clean and centrally located for the Belgrade Lakes. Nice people and I will definitely stay again."
United States
Mike F.
The price is CA $169
CA $203 total
includes taxes & fees
Nov 19 - Nov 20
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
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

Lockwood Hotel

Lockwood Hotel

10/10 Excellent
"Had a wonderful stay at the Lockwood. The room, hotel and staff were all top shelf!"
Jeanne 1-night trip
Posted 22 hours ago
Lockwood Hotel

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield vacation rentals we have selected for you start as low as CA $167 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 offers a patio, a selection of books, and air-conditioning to help you feel perfectly comfortable in your new surroundings. 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.