Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Pittsfield

Fridge, microwave, oven, stovetop
Angel Mist Retreat Garage Apartment

Condo in Pittsfield

10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
$283 nightly
The price is $309
Dec 7 - Dec 8
Total with taxes and fees
Angel Mist Retreat Garage Apartment
Microwave, oven, stovetop, dishwasher
The Cozy Home- New, Comfortable, Centrally located

Vacation Home in Pittsfield

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great host great stay"
United States
thomas v.
$229 nightly
The price is $250
Dec 8 - Dec 9
Total with taxes and fees
The Cozy Home- New, Comfortable, Centrally located
Property grounds
Pine Tree Trail Lodge

Vacation Home in Pittsfield

2.0 star property
$239 nightly
The price is $241
Dec 7 - Dec 8
Total with taxes and fees
Pine Tree Trail Lodge
Smart TV
Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi

Apartment in Pittsfield

$300 nightly
The price is $327
Dec 7 - Dec 8
Total with taxes and fees
Downtown Loft Pittsfield | Furnished 1BR + Wi-Fi
Fridge, microwave, oven, stovetop
RiverBend Loft | Modern Stay Near ATV & Snowmobile Trails

Apartment in Pittsfield

$300 nightly
The price is $327
Dec 7 - Dec 8
Total with taxes and fees
RiverBend Loft | Modern Stay Near ATV & Snowmobile Trails
Terrace/patio
The Cabin Skowhegan

Cabin in Skowhegan

9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
$193 nightly
The price is $210
Dec 7 - Dec 8
Total with taxes and fees
The Cabin Skowhegan
Living area
The heart of the Belgrade Lakes

Apartment in Oakland

9.0 out of 10, Wonderful, (9)
"Host was very accommodating "
United States
Maureen
$176 nightly
The price is $191
Dec 7 - Dec 8
Total with taxes and fees
The heart of the Belgrade Lakes
Exterior
Sister A-Frame in Woods B

Cabin in Oakland

10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$210 nightly
The price is $228
Dec 8 - Dec 9
Total with taxes and fees
Sister A-Frame in Woods B
1 bedroom, WiFi, bed sheets
ON THE GO!

Apartment in Hartland

10.0 out of 10, Exceptional, (1)
"It was a clean and quiet room. The property was also clean and quiet. "
United States
Sarah F.
$150 nightly
The price is $164
Dec 7 - Dec 8
Total with taxes and fees
ON THE GO!
Exterior
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails

Vacation Home in Oakland

10.0 out of 10, Exceptional, (7)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
$366 nightly
The price is $388
Dec 16 - Dec 17
Total with taxes and fees
Cozy winter farmhouse with wood stove & jacuzzi tub near snow trails
Fridge, microwave, oven, stovetop
Private cabin on 30 acres, close to skiing, snowmobile & amenities

Cabin in Madison

10.0 out of 10, Exceptional, (42)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
$312 nightly
The price is $340
Dec 7 - Dec 8
Total with taxes and fees
Private cabin on 30 acres, close to skiing, snowmobile & amenities
On the beach
The Getaway- A Cozy Lakeside Cabin

Cabin in Burnham

10.0 out of 10, Exceptional, (6)
"Such a great cabin and location. Super clean and a perfect getaway, we can’t wait to go back!"
United States
Sara D.
$405 nightly
The price is $442
Dec 7 - Dec 8
Total with taxes and fees
The Getaway- A Cozy Lakeside Cabin
Fridge, microwave, oven, stovetop
The Beach Bum | Modern Cabin on the Sand

Cabin in Burnham

10.0 out of 10, Exceptional, (2)
"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
Fridge, microwave, oven, stovetop
The Hideout Cabin | Steps to the Beach

Cabin in Burnham

10.0 out of 10, Exceptional, (9)
"Amenities were great. Property was clean and quiet. Perfect for teens. Great view of the lake. Updated kitchen and grill was great for making family meals. Enjoyed making s'mores in the fire pit. Kayaks were so much fun. "
United States
Jamie M.
$405 nightly
The price is $442
Dec 7 - Dec 8
Total with taxes and fees
The Hideout Cabin | Steps to the Beach
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min

Vacation Home in Oakland

2.0 star property
10.0 out of 10, Exceptional, (6)
"New, clean and had everything we needed. "
United States
Lara B.
$238 nightly
The price is $260
Dec 22 - Dec 23
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
Interior
Ice fishing, king size beds, dog friendly

Vacation Home in Canaan

10.0 out of 10, Exceptional, (3)
"Awesome stay right on the water. "
United States
Timothy S.
$299 nightly
The price is $326
Dec 8 - Dec 9
Total with taxes and fees
Ice fishing, king size beds, dog friendly
Exterior
Pretty old house in Newport with WiFi

Vacation Home in Newport

2.0 star property
$248 nightly
The price is $270
Dec 8 - Dec 9
Total with taxes and fees
Pretty old house in Newport with WiFi
Exterior
Blake's Cabin

Cabin in Hartland

9.6 out of 10, Exceptional, (24)
"We had a great time. "
United States
Candy C.
$334 nightly
The price is $364
Dec 7 - Dec 8
Total with taxes and fees
Blake's Cabin
Outdoor dining
Minutes to Colby

Apartment in Waterville

8.8 out of 10, Excellent, (22)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
$174 nightly
The price is $190
Dec 8 - Dec 9
Total with taxes and fees
Minutes to Colby
Exterior
Stylish Guest Loft – Cozy & Quiet Stay in charming Sangerville

Apartment in Sangerville

2.0 star property
$117 nightly
The price is $128
Dec 7 - Dec 8
Total with taxes and fees
Stylish Guest Loft – Cozy & Quiet Stay in charming Sangerville
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

10/10 Excellent
"The staff was amazing and very kind. The hotel itself is very comfortable, relaxing, and clean. My stay was in a family suite and i had 6 children with me. The staff was so understanding, kind, and hospitable that i instantly felt welcome and was able to relax and enjoy my stay. Thank you so much!"
Stephanie 1-night trip
Posted 7 days ago
Holiday Inn Express & Suites Waterville - North by IHG

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 $210 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?

Pine Tree Trail Lodge: Visitors like this Pittsfield vacation home rental. It offers a fireplace, an arcade game room, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.