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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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.
$208 nightly
The price is $227
Sep 13 - Sep 14
Total with taxes and fees
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.
$282 nightly
The price is $308
Sep 13 - Sep 14
Total with taxes and fees
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.
$1,782 nightly
The price is $1,801
Oct 7 - Oct 8
Total with taxes and fees
Pine Tree Trail Lodge
Exterior

4. Peaceful, Spacious Lodge with Golf & Sunset Views

Peaceful, Spacious Lodge with Golf & Sunset Views
Palmyra
10.0 out of 10, Exceptional, (24 reviews)
"Gorgeous property, very clean"
United States
Aaliya J.
$528 nightly
The price is $576
Sep 13 - Sep 14
Total with taxes and fees
Peaceful, Spacious Lodge with Golf & Sunset Views
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.
$333 nightly
The price is $363
Sep 10 - Sep 11
Total with taxes and fees
Blake's Cabin
Terrace/patio

6. Lakefront Retreat on Sebasticook Lake

Lakefront Retreat on Sebasticook Lake
Newport
9.0 out of 10, Wonderful, (4 reviews)
"Great property, would definitely stay again!"
United States
Skyla C.
$217 nightly
The price is $237
Sep 10 - Sep 11
Total with taxes and fees
Lakefront Retreat on Sebasticook Lake
DVD player, books, offices

7. Pretty Old House in Newport

Pretty Old House in Newport
Newport
$257 nightly
The price is $280
Sep 15 - Sep 16
Total with taxes and fees
Pretty Old House in Newport
Outdoor dining

8. 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, (18 reviews)
"Very nice. Will stay there again"
United States
Andy O.
$189 nightly
The price is $206
Sep 10 - Sep 11
Total with taxes and fees
Gorgeous 2-bedroom cottage with AC in charming Stetson
Smart TV, books

9. 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, (8 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
$419 nightly
The price is $456
Sep 13 - Sep 14
Total with taxes and fees
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Fireplace

10. Forest Cabin w/ Stunning Wall of Windows

Forest Cabin w/ Stunning Wall of Windows
Jackson
10.0 out of 10, Exceptional, (5 reviews)
"The space was warm and clean and had everything we needed. The hosts were incredibly friendly and helpful. "
United States
Ally L.
$260 nightly
The price is $283
Sep 13 - Sep 14
Total with taxes and fees
Forest Cabin w/ Stunning Wall of Windows
Private kitchen

11. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Great for kids. Lots of space. Convenient location. Plenty to do locally or venture out to explore. Recommend renting the golf cart to get back and forth down the camp road to the dock.. water is clear and clean, rock bottom at shore. Fast response from host who lives close by."
United States
Melissa B.
$657 nightly
The price is $716
Sep 10 - Sep 11
Total with taxes and fees
Welcome to "the east Madison chapel"
Smart TV

12. 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.
$158 nightly
The price is $172
Sep 11 - Sep 12
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
Outdoor dining

13. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (25 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$230 nightly
The price is $251
Sep 10 - Sep 11
Total with taxes and fees
Minutes to Colby
Property grounds

14. 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
9.8 out of 10, Exceptional, (46 reviews)
"Great experience"
United States
Chase D.
$323 nightly
The price is $352
Sep 16 - Sep 17
Total with taxes and fees
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Terrace/patio

15. China Lake, Dog Friendly, Lots of space for family gatherings

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (3 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
$606 nightly
The price is $661
Sep 16 - Sep 17
Total with taxes and fees
China Lake, Dog Friendly, Lots of space for family gatherings
Exterior

16. 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, (9 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
$133 nightly
The price is $144
Sep 13 - Sep 14
Total with taxes and fees
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Exterior

17. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
$264 nightly
The price is $288
Sep 28 - Sep 29
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Exterior

18. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$238 nightly
The price is $259
Sep 10 - Sep 11
Total with taxes and fees
Sister A-Frame in Woods B
2 bedrooms, WiFi, bed sheets

19. 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
$215 nightly
The price is $234
Sep 10 - Sep 11
Total with taxes and fees
The heart of the Belgrade Lakes
Smart TV, fireplace, DVD player, books

20. 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, (12 reviews)
"Beautiful place and location. Highly recommend and would stay here again."
United States
Michelle W.
$285 nightly
The price is $311
Sep 10 - Sep 11
Total with taxes and fees
Charming 2-bedroom house in awesome Sangerville with WiFi, AC and big yard
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

10/10 Excellent
"A lovely alternative to the chain hotels in Waterville. Everything was great. We had breakfast at the attached restaurant and it was quite good."
Ariel M 1-night trip
Posted 1 day ago
Fireside Inn & Suites Waterville

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $142 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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.