Pittsfield Holiday Rentals

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Our top choices for Pittsfield holiday rentals

Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail

Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail
Warren
10.0 out of 10, Exceptional, (22 reviews)
"Great place to stay, it is always my go to spot when staying in Warren. Everything is clean and comfortable and feels like home."
Canada
Colleen L.
The price is AU$283
includes taxes & fees
22 Feb - 23 Feb
Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail

Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA

Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA
Tionesta
10.0 out of 10, Exceptional, (17 reviews)
"The cabin was clean and beautiful "
United States
Lisa
The price is AU$291
includes taxes & fees
5 Mar - 6 Mar
Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA

Charming 2-bedroom apartment in peaceful Warren with AC

Charming 2-bedroom apartment in peaceful Warren with AC
Warren
9.8 out of 10, Exceptional, (11 reviews)
"The rooms were spacious, the loft was very clean the host even had a good basket for us. "
United States
Brian F.
The price is AU$167
includes taxes & fees
22 Feb - 23 Feb
Charming 2-bedroom apartment in peaceful Warren with AC

River view getaway

River view getaway
Warren
9.8 out of 10, Exceptional, (47 reviews)
"It was a great place to stay!"
United States
Lindsey F.
The price is AU$370
includes taxes & fees
24 Feb - 25 Feb
River view getaway

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak
Clymer
9.8 out of 10, Exceptional, (11 reviews)
"My family had a wonderful time staying at this condo. It was conveniently close to Peek’n Peak ski resort."
United States
Nathaniel B.
Sun and Snow Escape: Ski/Golf Condo in Peek'n Peak

Stowaway Suites on the Avenue: Mt Laurel Suite

Stowaway Suites on the Avenue: Mt Laurel Suite
Warren
9.0 out of 10, Wonderful, (12 reviews)
"Great place, nice to be in downtown."
United States
James R.
The price is AU$213
includes taxes & fees
3 Mar - 4 Mar
Stowaway Suites on the Avenue: Mt Laurel Suite

Sleeps 5 Fully Equipped Apartment Near Golf Courses

Sleeps 5 Fully Equipped Apartment Near Golf Courses
Corry
9.4 out of 10, Exceptional, (26 reviews)
"Lovely sunny place. Loved your high ceilings, front window, lace curtains, comfortable seating. Very accommodating. Thank you! "
United States
Leonard M.
The price is AU$238
includes taxes & fees
22 Feb - 23 Feb
Sleeps 5 Fully Equipped Apartment Near Golf Courses

Spacious 2 bedroom apartment

Spacious 2 bedroom apartment
Warren
8.6 out of 10, Excellent, (4 reviews)
"Cherry was an excellent host and responded promptly. The apartment was very clean, well decorated, and comfortable. It had everything we needed. The beds were very comfortable and we slept well. It was in a quiet and safe neighborhood with free parking on the street. We stayed a week to visit with family and friends. We would definitely book here again!"
United States
Teresa B.
The price is AU$266
includes taxes & fees
20 Feb - 21 Feb
Spacious 2 bedroom apartment

Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake
Bemus Point
10.0 out of 10, Exceptional, (199 reviews)
"This home was gorgeous. It had everything we needed and check in and check out were a breeze!! Thank you, Rick and Debra, for a wonderful stay!!"
United States
Valerie H.
The price is AU$691
includes taxes & fees
22 Feb - 23 Feb
Charming Resort in the Heart of Bemus Village on CHQ Lake

Firefly Suite

Firefly Suite
Warren
9.8 out of 10, Exceptional, (13 reviews)
"Clean, cozy, convenient to restaurants and shopping. "
United States
Diane F.
The price is AU$213
includes taxes & fees
27 Feb - 28 Feb
Firefly Suite

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Chautauqua
10.0 out of 10, Exceptional, (5 reviews)
"It was a very clean house with spacious areas including a full apartment upstairs. It was one of the better places we have ever stayed at as far as accommodations go. Highly recommended! Thank you."
United Kingdom
Bill T.
The price is AU$568
includes taxes & fees
22 Feb - 23 Feb
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

Eagle's Peak Cottage

Eagle's Peak Cottage
Pleasantville
9.0 out of 10, Wonderful, (23 reviews)
"Everything was great - including communication with the owner. Would absolutely recommend this place to anyone wanting to getaway!! "
United States
Connie H.
The price is AU$207
includes taxes & fees
2 Mar - 3 Mar
Eagle's Peak Cottage

Allegheny River House

Allegheny River House
Tidioute
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful view, pet friendly area, peaceful setting. Host communication was excellent in correcting some check in difficulties."
United States
Cindy I.
The price is AU$233
includes taxes & fees
22 Feb - 23 Feb
Allegheny River House

The Refined Retreat

The Refined Retreat
Celoron
10.0 out of 10, Exceptional, (14 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is AU$424
includes taxes & fees
22 Feb - 23 Feb
The Refined Retreat

Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake

Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
Ellery
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house, decorated nicely, great accommodations with special touches that made the stay so nice!"
United States
Deanna L.
The price is AU$743
includes taxes & fees
22 Feb - 23 Feb
Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake

8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit

8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit
Clymer
9.8 out of 10, Exceptional, (87 reviews)
"Great stay! "
United States
Bob T.
8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Warren
The price is AU$513
includes taxes & fees
25 Feb - 26 Feb
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Allegheny Suite

Allegheny Suite
Warren
9.8 out of 10, Exceptional, (29 reviews)
"Very comfortable. Would stay here again."
United States
Katherine R.
The price is AU$213
includes taxes & fees
3 Mar - 4 Mar
Allegheny Suite

{LUXE Lil Tio} Downtown Retreat - 5 Min Walk To River Access w/ Firepit & Grill

{LUXE Lil Tio} Downtown Retreat - 5 Min Walk To River Access w/ Firepit & Grill
Tionesta
10.0 out of 10, Exceptional, (14 reviews)
"Cute little place with all the amenities!"
United States
Heather V.
The price is AU$268
includes taxes & fees
12 Mar - 13 Mar
{LUXE Lil Tio} Downtown Retreat - 5 Min Walk To River Access w/ Firepit & Grill

Stay in our immaculate newly remodeled and cozy home in Old Order Amish country

Stay in our immaculate newly remodeled and cozy home in Old Order Amish country
Spartansburg
The price is AU$278
includes taxes & fees
4 Mar - 5 Mar
Stay in our immaculate newly remodeled and cozy home in Old Order Amish country
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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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 favourite 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 depend 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 AU$573 per night. Entering your travel dates in the search wizard might find you 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.

What are some of the best holiday rentals that Pittsfield has to offer?

Peaceful Lakefront Cottage - Completely Renovated - Available Year Round!: This holiday home rental outside of Pittsfield is located on a lake, and has a fireplace, a patio 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. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Pittsfield?

While you're exploring the area, Warren County Historical Society and Allegheny River are a couple of picturesque spots to get outside and enjoy nature. While here, Anders Run Natural Area and Cornplanter State Forest are other places worth a visit.

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 provide amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for small groups.