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Pittsfield Vacation Rentals

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Check prices for these dates

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

Our top choices for Pittsfield vacation rentals

A window with a view of a snowy landscape and bare trees.

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 ￥21,271
￥28,405 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is ￥10,635
￥24,303 total
includes taxes & fees
Nov 2 - Nov 3
Allegheny River House
A living room with a dark brown leather sofa, a glass coffee table, and a matching armchair. There is a wooden side table with a lamp, a framed picture on the wall, and a door in the background.

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 ￥13,471
￥16,958 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥14,968
￥30,154 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥20,798
￥25,090 total
includes taxes & fees
Nov 2 - Nov 3
Firefly Suite
A bedroom with a bed, a desk, a chair, a TV, and a storage unit.

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 ￥14,322
￥22,274 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥13,235
￥28,230 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥5,672
￥20,543 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥20,798
￥25,090 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥20,798
￥25,090 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥30,724
￥62,247 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥20,798
￥25,090 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥14,023
￥24,794 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥22,846
￥40,274 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥19,695
￥54,615 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥13,897
￥87,690 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥15,914
￥34,161 total
includes taxes & fees
Nov 16 - Nov 17
Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.
A room with a striped sofa, a wooden side table with a lamp, and a white dresser.

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 ￥13,235
￥22,734 total
includes taxes & fees
Nov 3 - Nov 4
Executive Apartment 1 Bedroom Excellent Location
A rustic log cabin with a stone facade, outdoor seating, and a welcoming entrance.

19. Secluded Nature Escape w/ Firepit Under the Stars! Family and Friends Reconnect!

Secluded Nature Escape w/ Firepit Under the Stars! Family and Friends Reconnect!
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 ￥23,965
￥47,766 total
includes taxes & fees
Nov 3 - Nov 4
Secluded Nature Escape w/ Firepit Under the Stars! Family and Friends Reconnect!
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 ￥16,994
￥33,212 total
includes taxes & fees
Nov 2 - Nov 3
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 3 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 vacation rentals in Pittsfield?

Yes, you can find vacation rentals close to the most popular local attractions in Pittsfield, or you can go with a more secluded option if you're looking for a relaxing stay.

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

Beautiful Pet friendly cottage by the Stow Ferry: This vacation home rental outside of Pittsfield is located on a lake and has a patio, a garden, and a barbecue grill 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 vacation rentals like in Pittsfield?

Vacation rentals are private properties you can reserve for a couple days or more in Pittsfield. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.