Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Our top choices for Pittsfield holiday rentals

Angel Mist Retreat Garage Apartment

10.0 out of 10, Exceptional, (13)
"Beautifully presented. Exceptionally well equipped ."
The price is NZ$522
includes taxes & fees
14 Sept - 15 Sept
Angel Mist Retreat Garage Apartment

Family, Friends and Fun for all

2.0 star property
9.6 out of 10, Exceptional, (7)
"The property was very nice. Lots of rooms, fun environment, prompt communication. Worked great for our group."
The price is NZ$613
includes taxes & fees
8 Sept - 9 Sept
Family, Friends and Fun for all

Log cabin, King bed!!! Private beach!!

9.8 out of 10, Exceptional, (31)
"Its a great place to relax and slow down."
Log cabin, King bed!!! Private beach!!

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (43)
"Loved the cozy home! We would stay there again in a heartbeat. The only thing that we would have been nice is if there was a tv in the main bedroom, but that’s just a personal preference. "
Cozy House in the heart of Waterville Maine.

Large Secluded Cabin on the Lake - Now booking 2+ night stays

10.0 out of 10, Exceptional, (59)
"Canin was well stocked, easy to access. Perfect for what we needed. "
Large Secluded Cabin on the Lake - Now booking 2+ night stays

Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

9.8 out of 10, Exceptional, (161)
"Debbie was an absolutely wonderful host! Her cabin was incredibly clean, quiet and beautiful! Highly recommend!! We will definitely be booking her property again! "
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

9.2 out of 10, Wonderful, (24)
"Had a wonderful time. Loon Cove is exactly that, the Loons were everywhere. The cabin was comfortable and well appointed. I really enjoyed my stay. I have one criticism, the sheer curtains in the bedrooms and bathrooms need to have a privacy/darkening option. The sun comes up at 4:30am and the trash guy, landscaper and nature viewers were on and around the property throughout my stay. "
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

10.0 out of 10, Exceptional, (117)
"We totally loved our stay. We are talking about our next stay. "
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (60)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

10.0 out of 10, Exceptional, (128)
"We had a family gathering in the area and this was perfect for our family of 4. "
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

The Dexter Suite. Now with Plants! Vintage-styled 1-bedroom apt near downtown

10.0 out of 10, Exceptional, (1)
"It was cozy and very close to everything we needed. The host was kind, and the place was clean. "
The price is NZ$237
includes taxes & fees
8 Sept - 9 Sept
The Dexter Suite. Now with Plants! Vintage-styled 1-bedroom apt near downtown

Lakefront Cabin

10.0 out of 10, Exceptional, (26)
"Enjoyed an awesome stay on the lake!! House was super and Kennith was a great host!"
Lakefront Cabin

ON THE GO!

10.0 out of 10, Exceptional, (1)
"Very clean, owner nearby and responsive to all requests. This is not the Taj Mahal, but it serves it purpose. Will consider again next visit to Hartland."
The price is NZ$261
includes taxes & fees
14 Sept - 15 Sept
ON THE GO!

3-bedroom lake house, medical cannabis WiFi, kayaks, dock, walking trail & more

10.0 out of 10, Exceptional, (1)
"Family of five stayed for 5 nights to recharge before school started. We all rested well & enjoyed dawn and dusk fishing."
3-bedroom lake house, medical cannabis WiFi, kayaks, dock, walking trail & more

Central Maine Waterfront

9.8 out of 10, Exceptional, (7)
"This property was full off character with barn wood lined walls and cute fixtures. John was incredibly hospitable and made us feel like family. "
Central Maine Waterfront

The Modern Maine Retreat

8.8 out of 10, Excellent, (11)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

10.0 out of 10, Exceptional, (15)
"Great stay, the place is wonderful and the host is fantastic looking forward to staying again in the future "
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (4)
"Great stay. Would stay here again if in the area."
The price is NZ$391
includes taxes & fees
8 Sept - 9 Sept
Sister A-Frame in Woods B

Minutes to Colby

8.8 out of 10, Excellent, (17)
"This was such a wonderful option. Location, clean, and adorable. "
The price is NZ$429
includes taxes & fees
8 Sept - 9 Sept
Minutes to Colby

Classy AF Home Steps from Colby and Trails

10.0 out of 10, Exceptional, (45)
"Wonderful house in a great location. Hosts were fantastic. "
Classy AF Home Steps from Colby and Trails
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

Find out more about Pittsfield

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsfield holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as NZ$237 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 holiday 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 holiday.

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 holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Pittsfield has to offer?

Cozy House in the heart of Waterville Maine.: This holiday home rental outside of Pittsfield is equipped with a garden, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Pittsfield?

Expedia has 3 holiday 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 wider area.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a small group gathering.