Pittsfield Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Pittsfield

Angel Mist Retreat Garage Apartment
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$537
includes taxes & fees
2 Nov - 3 Nov
Angel Mist Retreat Garage Apartment
Large Secluded Cabin on the Lake - Now booking 2+ night stays
10.0 out of 10, Exceptional, (66)
"It was a relaxing week It was fully equipped with everything we expected and more"
United States
Leslie R.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
10.0 out of 10, Exceptional, (132)
"The cabin was very comfortable and well equipped. Beautiful setting!Owner was friendly and helpful with several suggestions for activities. "
United States
Sharon J.
Cabin in scenic woods with hiking trails, firepit, horseback riding nearby
Sister A-Frame in Woods B
10.0 out of 10, Exceptional, (7)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is NZ$399
includes taxes & fees
28 Oct - 29 Oct
Sister A-Frame in Woods B
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.4 out of 10, Exceptional, (65)
"Great family camp right on the water with great views and paddle boats to play and fish the lake. Nice host, it was a peaceful stay!"
United States
Michael L.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Classy AF Home Steps from Colby and Trails
10.0 out of 10, Exceptional, (48)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
9.8 out of 10, Exceptional, (37)
"House was great! Clean, bright, comfortable."
United States
Emily C.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Lakefront Cabin
10.0 out of 10, Exceptional, (27)
"My family and I attended a concert at the Bowl in the Pines and wanted to make a weekend out of it and found this perfect little cabin right on the lake! Kids absolutely loved swimming, fishing and canoeing! Great spot for family bonding! Thank you! "
United States
Laura L.
Lakefront Cabin
The Cabin 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$366
includes taxes & fees
27 Oct - 28 Oct
The Cabin Skowhegan
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
9.8 out of 10, Exceptional, (164)
"Beautiful, peaceful location. This was the perfect place to stay while my family was waiting for our house to be ready."
United States
Sara L.
Cabin Rental in scenic Maine woods with hiking trails, firepit, horseback riding
Lovely private cabin on 30 acres with walking trails & fire pit. 1 pet allowed
10.0 out of 10, Exceptional, (40)
"Short stay to family and friends, the house was nice as always. "
United States
Al Q.
The price is NZ$602
includes taxes & fees
5 Nov - 6 Nov
Lovely private cabin on 30 acres with walking trails & fire pit. 1 pet allowed
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!
10.0 out of 10, Exceptional, (21)
"We’ve enjoyed staying at this location!"
United States
Ted G.
Rail Trail Retreat! Recently remodeled cozy home on Snowmobile/ATV Trail!
Cozy House in the heart of Waterville Maine.
9.6 out of 10, Exceptional, (46)
"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. "
United States
Michelle
Cozy House in the heart of Waterville Maine.
Blake's Cabin
9.6 out of 10, Exceptional, (23)
"Had a great stay. Quiet and peaceful week on the lake"
United States
Jacob S.
The price is NZ$629
includes taxes & fees
28 Oct - 29 Oct
Blake's Cabin
The Modern Maine Retreat
8.6 out of 10, Excellent, (13)
"Place was very clean, local to everything that we needed. Plenty of room for all 4 of us. I would definitely come back to this house if staying in Oakland again"
United States
Mark P.
The Modern Maine Retreat
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
10.0 out of 10, Exceptional, (121)
"This is an excellent 1 bedroom vacation cabin on Lake Sebasticook. We had everything we needed for a nice stay."
United States
Kenneth M.
10 Steps And You're In Sebasticook Lake. This Is Where You Go To Unplug
Lakefront cabin on North Pond with private beach
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
Minutes to Colby
8.6 out of 10, Excellent, (19)
"Andriana was great with communication and allowing us to get in to the Vrbo an hour earlier. Great location, everything was right there. "
United States
Colleen W.
The price is NZ$438
includes taxes & fees
27 Oct - 28 Oct
Minutes to Colby
Quiet setting 1 minute drive to China lake boat launch and ATV trail
10.0 out of 10, Exceptional, (33)
"Since the place had no air conditioning and it wa very hot, Don got us extra fans and made a place in the cool basement for our dogs. Beds were comfy and we had all we needed."
United States
Luann K.
Quiet setting 1 minute drive to China lake boat launch and ATV trail
the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater
8.6 out of 10, Excellent, (13)
"This stay was nice. I enjoyed my time in a clean and comfortable little house. The interior was made to be old fashioned and was decorated nicely still maintaining an modern feel. A microwave wolves been nice to have in the kitchen, but other than that it was nice."
United States
Benjamin P.
the Corner cottage: Overlooking Hayden Brook, Steps to Lakewood Summer Theater
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.
Save an average of 15% on thousands of hotels when you're signed in

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$366 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?

Classy AF Home Steps from Colby and Trails: This holiday home rental outside of Pittsfield offers a private garden, a selection of games and a BBQ to help you feel perfectly comfortable 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.

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.