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Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Pittsfield holiday rentals

A room with a brick fireplace, wooden flooring, a dining table with a patterned tablecloth, and a dark wooden cabinet.

1. Charming Farmhouse on a working farm.

Charming Farmhouse on a working farm.
Pittsfield
7.8 out of 10, Good, (6 reviews)
"Everything was great and I enjoyed my stay."
United States
Justin S.
The price is HK$1,059
HK$1,414 total
includes taxes & fees
10 Nov - 11 Nov
Charming Farmhouse on a working farm.
A cozy living room with a wooden sofa, a dining table, and a view of a snowy landscape through large sliding glass doors.

2. Allegheny River House

Allegheny River House
Tidioute
9.4 out of 10, Exceptional, (18 reviews)
"Very nice place to stay "
United States
Kaleigh M.
Allegheny River House
A street view with two-story brick buildings, one with a storefront and another with a library sign.

3. Charming 2-bedroom apartment in peaceful Warren with AC

Charming 2-bedroom apartment in peaceful Warren with AC
Warren
9.6 out of 10, Exceptional, (35 reviews)
"What an amazing find! The apartment is so spacious, well equipped and right in the center of the cutest downtown area. We loved our stay!"
United States
Jacklyn
The price is HK$671
HK$844 total
includes taxes & fees
2 Nov - 3 Nov
Charming 2-bedroom apartment in peaceful Warren with AC
A living room with a grey sectional sofa, a wooden coffee table, and a patterned rug.

4. 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, (26 reviews)
"This place was so nice to stay at and very clean. Quiet neighborhood with on street parking that was always close and available. We will definitely stay here again! "
United States
Eric S.
The price is HK$745
HK$1,501 total
includes taxes & fees
2 Nov - 3 Nov
Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail
A multi-story building with a courtyard, featuring a parking area and a small outdoor seating area.

5. Firefly Suite

Firefly Suite
Warren
9.8 out of 10, Exceptional, (24 reviews)
"Very nice property. Convenient location. Host was very good with communication. Would recommend to others."
United States
Bonnie
The price is HK$1,036
HK$1,249 total
includes taxes & fees
2 Nov - 3 Nov
Firefly Suite
A garden area with a round table and two blue chairs, surrounded by various flowering plants.

6. Charming 1-bedroom apartment in fantastic Warren with AC

Charming 1-bedroom apartment in fantastic Warren with AC
Warren
8.8 out of 10, Excellent, (6 reviews)
"The apartment was wonderful. Very clean and convenient "
United States
Maura W.
The price is HK$784
HK$1,187 total
includes taxes & fees
14 Nov - 15 Nov
Charming 1-bedroom apartment in fantastic Warren with AC
A compact kitchen with white cabinetry, a stove, a sink, and a refrigerator.

7. Spacious 2 bedroom apartment

Spacious 2 bedroom apartment
Warren
8.8 out of 10, Excellent, (5 reviews)
"Easy check in process. Owner was very helpful and responsive. Location was clean and ready for my stay. Apartment was located in a great location. Easy walk to downtown Warren. "
United States
John S.
The price is HK$659
HK$1,406 total
includes taxes & fees
2 Nov - 3 Nov
Spacious 2 bedroom apartment
A spacious kitchen with wooden cabinets, a marble countertop, and a large island. There is a dining area with a bench and chairs, and a ceiling fan.

8. Eagle's Peak Cottage

Eagle's Peak Cottage
Pleasantville
9.2 out of 10, Wonderful, (53 reviews)
"I loved the property, such a great location for all the local hikes and such."
United States
Jacqueline N.
The price is HK$282
HK$1,023 total
includes taxes & fees
2 Nov - 3 Nov
Eagle's Peak Cottage
Living area

9. Homestead Suite

Homestead Suite
Warren
10.0 out of 10, Exceptional, (1 review)
"The owners were very responsive, clean, comfortable, and exactly as shown. Would stay there again."
United States
julia o.
The price is HK$1,036
HK$1,249 total
includes taxes & fees
2 Nov - 3 Nov
Homestead Suite
A room with a four-poster bed, two bedside lamps, a small table with a lamp, and a mirror on the wall.

10. Allegheny Suite

Allegheny Suite
Warren
9.6 out of 10, Exceptional, (37 reviews)
"Nice apartment within walking distance to great restaurants. Clean and comfortable. Coffee, tea and snacks thoughtful addition."
United States
Teresa
The price is HK$1,036
HK$1,249 total
includes taxes & fees
2 Nov - 3 Nov
Allegheny Suite
A spacious kitchen with a large island, wooden cabinets, and a stone accent wall.

11. Tidioute Riverfront Chalet - Pet Friendly - Across from Game Lands

Tidioute Riverfront Chalet - Pet Friendly - Across from Game Lands
Tidioute
10.0 out of 10, Exceptional, (3 reviews)
"Awesome four season location. The host was responsive and accommodating. It was a new listing and was up to date with current appliances, furniture, and decor. I would definitely rent again and recommend to all!"
United States
Brandon C.
The price is HK$1,530
HK$3,099 total
includes taxes & fees
2 Nov - 3 Nov
Tidioute Riverfront Chalet - Pet Friendly - Across from Game Lands
A living room with a wooden floor, two sofas, a table, and a fireplace.

12. Stowaway Suites on the Avenue: Mt Laurel Suite

Stowaway Suites on the Avenue: Mt Laurel Suite
Warren
9.2 out of 10, Wonderful, (13 reviews)
"Great place, nice to be in downtown."
United States
James R.
The price is HK$1,036
HK$1,249 total
includes taxes & fees
2 Nov - 3 Nov
Stowaway Suites on the Avenue: Mt Laurel Suite
A bedroom with a bed, a chandelier, and a window with curtains.

13. Sleeps 5 Fully Equipped Apartment Near Golf Courses

Sleeps 5 Fully Equipped Apartment Near Golf Courses
Corry
9.6 out of 10, Exceptional, (32 reviews)
"Great location, Holly was awesome!"
United States
James
The price is HK$698
HK$1,234 total
includes taxes & fees
2 Nov - 3 Nov
Sleeps 5 Fully Equipped Apartment Near Golf Courses
A living room with two grey sofas, a coffee table, and a patterned rug.

14. River view getaway

River view getaway
Warren
9.8 out of 10, Exceptional, (51 reviews)
"The property was very nice, It was just the right size for five adults to stay two nights. We were visiting family nearby and it was easy to travel into Warren for activities and shopping. We plan on returning someday for another visit, thanks."
United States
Brian H.
The price is HK$1,138
HK$2,005 total
includes taxes & fees
9 Nov - 10 Nov
River view getaway
A modern living room with a fireplace, a flat-screen TV, a dining area with a table and chairs, and a kitchen with wooden cabinets and a refrigerator.

15. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (27 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is HK$981
HK$2,719 total
includes taxes & fees
2 Nov - 3 Nov
The Refined Retreat
A living room with a sectional sofa, a coffee table, and a TV.

16. Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Warren
9.8 out of 10, Exceptional, (6 reviews)
"I did not stay there but my employees liked it"
United States
Bill S.
The price is HK$692
HK$4,366 total
includes taxes & fees
3 Nov - 4 Nov
Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
A wooden interior with a dining area, a sofa, and a staircase.

17. Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.

Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.
Tionesta
10.0 out of 10, Exceptional, (12 reviews)
"Overall, worth the stay. Host is friendly and fast to get back to you if you have any issues. Rooms were comfortable and clean. "
United States
Kcass 0.
The price is HK$792
HK$1,701 total
includes taxes & fees
16 Nov - 17 Nov
Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.
A kitchen with a wooden countertop, a basket, jars, and a paper towel dispenser.

18. Executive Apartment 1 Bedroom Excellent Location

Executive Apartment 1 Bedroom Excellent Location
Corry
9.6 out of 10, Exceptional, (18 reviews)
"So convenient and huge! Had everything we needed! Loved the keyless entry!"
United States
Nancy A.
The price is HK$659
HK$1,132 total
includes taxes & fees
3 Nov - 4 Nov
Executive Apartment 1 Bedroom Excellent Location
A rustic log cabin with a stone facade, outdoor seating, and a welcoming entrance.

19. “Hickory Creek Haven” Creek-side Log Cabin

“Hickory Creek Haven” Creek-side Log Cabin
Tionesta
10.0 out of 10, Exceptional, (39 reviews)
"Beth has truly thought of everything! Wonderful place to stay. Our kids especially loved the creek."
United States
Brett G.
The price is HK$1,765
HK$3,063 total
includes taxes & fees
16 Nov - 17 Nov
“Hickory Creek Haven” Creek-side Log Cabin
A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

20. Premier St Elmo Unit w Large Balcony over Park

Premier St Elmo Unit w Large Balcony over Park
Chautauqua
10.0 out of 10, Exceptional, (3 reviews)
"Great property, very clean and in great condition. Very accommodating hosts, excellent and prompt communication."
United States
Leonid T.
The price is HK$846
HK$1,654 total
includes taxes & fees
2 Nov - 3 Nov
Premier St Elmo Unit w Large Balcony over Park
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

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

8/10 Good
"ok, place to stay"
GEORGE 1-night trip
Posted 4 hours ago
Chautauqua Harbor Hotel - Jamestown

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pittsfield!

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?

Beautiful Pet friendly cottage by the Stow Ferry: 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. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Pittsfield?

While you're exploring the area, Allegheny River and Karen Bonnell Memorial Park 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.