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Top Holiday Rentals in Pittsfield

Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
9.8 out of 10, Exceptional, (102)
"This is a great place to stay if you're looking to enjoy peace and quiet in a true countryside environment. Debbie is super friendly and accommodating; she already had a lot of the things we were worried about needing to bring. You'll have the opportunity to enjoy wildlife, stargazing, and nature in an area with rich history."
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Family and pet friendly ME cabin, private, Trails, close to town.
10.0 out of 10, Exceptional, (18)
"It Was great cozy perfect little getaway"
The price is £302
per night
14 May - 15 May
Family and pet friendly ME cabin, private, Trails, close to town.
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
7.8 out of 10, Good, (6)
"Everything we had hoped for. :)"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
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Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
9.8 out of 10, Exceptional, (130)
"The location is remote and very peaceful! Cabin is clean and stocked with everything we needed (pots, pans, utensils, plenty of towels and extra bedding.) Debbie was a great host- she helped us find local farm fresh eggs & answered any questions we had. Will definitely be staying here again in the future!"
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
The Cabin - Skowhegan
9.6 out of 10, Exceptional, (24)
"I liked everything about this cabin and the large yard to walk my dog . "
The price is £138
per night
5 May - 6 May
The Cabin - Skowhegan
Three waterfront cottages with private sandy beach - Family Getaway
10.0 out of 10, Exceptional, (20)
"WE HAD AN AMAZING STAY! MOST ENJOYABLE AND BEAUTIFUL PROPERTY"
Three waterfront cottages with private sandy beach - Family Getaway
Elegant Newport Cabin w/ Porch & Lake Access
10.0 out of 10, Exceptional, (1)
"Absolutely beautiful location and we loved our stay. Had some issues with the well water but owner was very responsive and it will be corrected. The home was cozy and warm and we will be back !!! Thank you Ben and Lisa"
Elegant Newport Cabin w/ Porch & Lake Access
The Modern Maine Retreat
The Modern Maine Retreat
Waterville Home Rental w/ Private Yard + Deck!
Waterville Home Rental w/ Private Yard + Deck!
Central Maine Waterfront
9.6 out of 10, Exceptional, (4)
"Great place went hunting Dailey Clean quiet. Washer and dryer is a big plus for 2 guys hunting."
Central Maine Waterfront
Cozy cabin with 200’ of waterfront on Whites Pond
9.6 out of 10, Exceptional, (25)
"My wife and I had a great stay. Lovely little cabin. We would love to stay in the summer time."
Cozy cabin with 200’ of waterfront on Whites Pond
Minutes to Colby
The price is £204
per night
6 May - 7 May
Minutes to Colby
Blake's Cabin
9.4 out of 10, Exceptional, (13)
"Nice place!"
The price is £310
per night
6 May - 7 May
Blake's Cabin
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
10.0 out of 10, Exceptional, (16)
"It was a great place to be Private and quiet except for the trafic noise. Wonderful vacation"
Unique Maine Log Cabin w/ Trout Ponds & Sauna!
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok
7.6 out of 10, Good, (9)
"The house and surrounding were very nice. Exactly as described and had some nice touches left by the management company- extra soap, laundry pods, doggie poop bags. The only concerns were that the keypad on the door was temperamental and didn’t work our entire visit (thankfully there was a key in a lockbox so we could get inside when it was cold and raining) and there were several dishes put away dirty. Overall it was a great property that we hope to return to in warmer weather and enjoy the...
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok
The Hideout - Just Steps to the Beach!
10.0 out of 10, Exceptional, (4)
"Let me start with the view: oh what is it beautiful! A little regret that we came when the temperatures were still chilly, so we only took it in from the windows. But still! Just a lovely setting! The house was simple, but so well maintained. The kitchen had even more gear than I expected. Everything about it was comfortable. My college daughter liked having “her space” in the loft. The property owners were very responsive. For an individual, a couple or a small family looking for peace and...
The price is £345
per night
6 May - 7 May
The Hideout - Just Steps to the Beach!
Waterfront Lakehouse
9.8 out of 10, Exceptional, (46)
"Wonderful place to stay! Our family loves coming here."
Waterfront Lakehouse
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
10.0 out of 10, Exceptional, (96)
"Great"
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
9.8 out of 10, Exceptional, (19)
"This is the second stay for our group on the 3rd week in September. Jason's camp has everything we need. Room for 4 adults, a nicely laid out kitchen for cooking, and a beautiful view of Lovejoy Pond (this time complete with a bald eagle flying overhead). Clean, comfortable, and convenient. Thanks Jason!"
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, (42)
"The picture you show was the owners 1st property and we could not access the property with my elderly family. When I called the owner, he offered me a second option of another property. That is the property I rated. It was very kind of the owner to accomodate us. It was a lit more driving than we intended but the accommodstions were much better for us."
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Don't see what you're looking for?
See all available properties in Pittsfield
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.

Pittsfield Holiday Rental Travel Info

Popular accommodation
Pittsfield private holiday homes
Known landmarks
JW Parks Golf Course
International airport
Bangor, ME (BGR-Bangor Intl.)

Other types of properties in Pittsfield you may be interested in

Holiday Inn Express & Suites Waterville - North, an IHG Hotel
2.5 star property
8.6 out of 10, Excellent, (583)
"Good value for the price we paid."
The price is £125
per night
27 May - 28 May
Holiday Inn Express & Suites Waterville - North, an IHG Hotel
The Elmwood
2.5 star property
8.8 out of 10, Excellent, (257)
"great!"
The price is £130
per night
5 May - 6 May
The Elmwood
Fireside Inn & Suites Waterville
2.0 star property
8.8 out of 10, Excellent, (1000)
"Very nice staff. Clean and comfortable rooms. Convenient location."
The price is £152
per night
5 May - 6 May
Fireside Inn & Suites Waterville
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.

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, apart-hotels, 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 £138 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?

Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok: This holiday home rental outside of Pittsfield is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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.

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