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Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Pittsfield holiday 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 NZ$319
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.
The price is NZ$275
includes taxes & fees
15 Nov - 16 Nov
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 NZ$192
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom apartment in peaceful Warren with AC
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.

4. Eagle's Peak Cottage

Eagle's Peak Cottage
Pleasantville
9.2 out of 10, Wonderful, (54 reviews)
"I loved the property, such a great location for all the local hikes and such."
United States
Jacqueline N.
The price is NZ$232
includes taxes & fees
5 Nov - 6 Nov
Eagle's Peak Cottage
A compact kitchen with white cabinetry, a stove, a sink, and a refrigerator.

5. 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 NZ$317
includes taxes & fees
5 Nov - 6 Nov
Spacious 2 bedroom apartment
A living room with a grey sectional sofa, a wooden coffee table, and a patterned rug.

6. 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 NZ$339
includes taxes & fees
22 Nov - 23 Nov
Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail
A bedroom with a bed, a desk, a chair, a TV, and a storage unit.

7. 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 NZ$258
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom apartment in fantastic Warren with AC
A bedroom with a bed, a chandelier, and a window with curtains.

8. 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 NZ$281
includes taxes & fees
9 Nov - 10 Nov
Sleeps 5 Fully Equipped Apartment Near Golf Courses
A spacious kitchen with a large island, wooden cabinets, and a stone accent wall.

9. 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 NZ$693
includes taxes & fees
5 Nov - 6 Nov
Tidioute Riverfront Chalet - Pet Friendly - Across from Game Lands
A multi-story building with a courtyard, featuring a parking area and a small outdoor seating area.

10. Firefly Suite

Firefly Suite
Warren
9.6 out of 10, Exceptional, (25 reviews)
"Very nice property. Convenient location. Host was very good with communication. Would recommend to others."
United States
Bonnie
The price is NZ$283
includes taxes & fees
7 Nov - 8 Nov
Firefly Suite
Living area

11. 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 NZ$283
includes taxes & fees
5 Nov - 6 Nov
Homestead Suite
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 NZ$283
includes taxes & fees
5 Nov - 6 Nov
Stowaway Suites on the Avenue: Mt Laurel Suite
A room with a four-poster bed, two bedside lamps, a small table with a lamp, and a mirror on the wall.

13. 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 NZ$285
includes taxes & fees
5 Nov - 6 Nov
Allegheny Suite
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 NZ$455
includes taxes & fees
9 Nov - 10 Nov
River view getaway
A living room with a sectional sofa, a coffee table, and a TV.

15. 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 NZ$979
includes taxes & fees
5 Nov - 6 Nov
Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
A room with a striped sofa, a wooden side table with a lamp, and a white dresser.

16. 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 NZ$285
includes taxes & fees
1 Dec - 2 Dec
Executive Apartment 1 Bedroom Excellent Location
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 NZ$378
includes taxes & fees
8 Nov - 9 Nov
Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.
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.

18. 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 NZ$603
includes taxes & fees
11 Nov - 12 Nov
The Refined Retreat
A deck with four Adirondack chairs, a fire pit, and a view of a forested area.

19. Quiet Escape, Peaceful Lake Glimpses

Quiet Escape, Peaceful Lake Glimpses
Ashville
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful location! We enjoyed the peaceful quiet time."
United States
Anonymous traveller
The price is NZ$600
includes taxes & fees
9 Nov - 10 Nov
Quiet Escape, Peaceful Lake Glimpses
A view from a window overlooking a calm lake surrounded by trees, with a wooden deck in the foreground.

20. Charming 3-bedroom cottage in Russell with AC, WiFi. Enjoy your stay

Charming 3-bedroom cottage in Russell with AC, WiFi. Enjoy your stay
Russell
10.0 out of 10, Exceptional, (8 reviews)
"The back deck is wonderful. Relaxing and peaceful. Good place to stay"
United States
deborah k.
The price is NZ$719
includes taxes & fees
5 Nov - 6 Nov
Charming 3-bedroom cottage in Russell with AC, WiFi. Enjoy your stay
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

Hampton Inn & Suites Jamestown

Hampton Inn & Suites Jamestown

10/10 Excellent
"Breakfast staff was terrific and helpful!"
Mary 1-night trip
Posted 5 hours ago
Hampton Inn & Suites Jamestown

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$232 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.

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.