Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Pine Tree Trail Lodge

2.0 star property
Pittsfield
10.0 out of 10, Exceptional, (1)
"Great place. The host so helpful. I would definitely stay here again. "
United States
Amber G.
The price is NZ$427
includes taxes & fees
15 Dec - 16 Dec
Pine Tree Trail Lodge

Angel Mist Retreat Garage Apartment

Pittsfield
10.0 out of 10, Exceptional, (14)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is NZ$535
includes taxes & fees
9 Dec - 10 Dec
Angel Mist Retreat Garage Apartment

Classy AF Home Steps from Colby and Trails

Oakland
10.0 out of 10, Exceptional, (49)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails

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

Smithfield
10.0 out of 10, Exceptional, (66)
"Awesome place for our vacation!!! Had a great time fishing and enjoying each other’s company while hanging around the fire pit!!"
United States
Craig C.
Large Secluded Cabin on the Lake - Now booking 2+ night stays

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

Exeter
9.8 out of 10, Exceptional, (135)
"Wonderful and very nice property. Owner more than gracious and hospitable. Would highly recommend."
United States
LMB
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"Very clean, great view, quiet, serene location right on the lake."
United States
katherine b.
Lakefront Cabin

The Cabin Skowhegan

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
The price is NZ$364
includes taxes & fees
9 Dec - 10 Dec
The Cabin Skowhegan

My Valhalla Farm

3.5 star property
Oakland
My Valhalla Farm

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Albion
9.8 out of 10, Exceptional, (37)
"Nice place, great fishing. "
United States
Bryan W.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is NZ$396
includes taxes & fees
9 Dec - 10 Dec
Sister A-Frame in Woods B

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

Exeter
9.8 out of 10, Exceptional, (166)
"This is the second year in a row that we went there, it was exuberant and wonderful, relaxing, and enjoying"
United States
Nathan H.
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding

Maplewood Lakehouse in Newport

Newport
10.0 out of 10, Exceptional, (8)
"Maplewood Lakehouse was clean, spacious, accommodating, and everything our large group needed."
United States
Jane H.
Maplewood Lakehouse in Newport

Lakefront cabin on North Pond with private beach

Smithfield
9.6 out of 10, Exceptional, (7)
"We came to Maine to relax and decompress. This spot was perfect for that The quiet was just what we needed and the property was clean, spacious and comfortable."
United States
Michael C.
Lakefront cabin on North Pond with private beach

The Hideout Cabin | Steps to the Beach

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.
The price is NZ$761
includes taxes & fees
9 Dec - 10 Dec
The Hideout Cabin | Steps to the Beach

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2.0 star property
Oakland
10.0 out of 10, Exceptional, (4)
"We had an excellent stay on the lake. The property is beautiful and the house has everything, with great views from all 3 levels. We would love to stay again! "
United States
Ashley L.
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Family-friendly Troy Getaway With Furnished Deck!

3.0 star property
Troy
10.0 out of 10, Exceptional, (1)
"Great property and the owner was very welcoming and accommodating. Would recommend!!"
United States
Bonnie
Family-friendly Troy Getaway With Furnished Deck!

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

Newport
10.0 out of 10, Exceptional, (121)
"Very relaxing place"
United States
Fabiana W.
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug

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

Oakland
9.2 out of 10, Wonderful, (26)
"Adorable cabin well stocked with plenty of space. Beautiful view! Nice and Clean. Needed help with the door lock and they were quick to respond and help. "
United States
Angela
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

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

Dexter
10.0 out of 10, Exceptional, (23)
"We’ve enjoyed staying at this location!"
United States
Ted G.
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!

Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach

Madison
9.6 out of 10, Exceptional, (72)
"Such a cute home with lots of personality and "
United States
Heidi F.
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
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

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$364 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?

Pine Tree Trail Lodge: This highly rated holiday home rental in Pittsfield offers a fireplace, an arcade/games room and a BBQ 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 that you can cook with friends or family.

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.