Holiday Rentals in Pittsfield

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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 €164
includes taxes & fees
13 Nov - 14 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, (19 reviews)
"Very nice place to stay "
United States
Kaleigh M.
The price is €142
includes taxes & fees
26 Nov - 27 Nov
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, (37 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 €89
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom apartment in peaceful Warren with AC
A multi-story building with a courtyard, featuring a parking area and a small outdoor seating area.

4. Firefly Suite

Firefly Suite
Warren
9.6 out of 10, Exceptional, (26 reviews)
"Very clean, excellent location, walk to nearby shops and restaurants."
United States
James H.
The price is €145
includes taxes & fees
13 Nov - 14 Nov
Firefly Suite
A spacious kitchen with a large island, wooden cabinets, and a stone accent wall.

5. 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 €366
includes taxes & fees
13 Nov - 14 Nov
Tidioute Riverfront Chalet - Pet Friendly - Across from Game Lands
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 €167
includes taxes & fees
15 Nov - 16 Nov
Quaint 2 bedroom apartment. 5 minute walk to down town Close to local bike trail
A kitchen with wooden cabinets, a black countertop, a ceiling fan, and a pendant light.

7. Lovely King Ensuite bungalow

Lovely King Ensuite bungalow
Clarendon
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and comfortable - it was the perfect setting for my cousin and me to visit and then each have our own space when the day was done. Definitely recommend!"
United States
Leslie R.
The price is €150
includes taxes & fees
21 Nov - 22 Nov
Lovely King Ensuite bungalow
A garden area with a round table and two blue chairs, surrounded by various flowering plants.

8. 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 €138
includes taxes & fees
14 Nov - 15 Nov
Charming 1-bedroom apartment in fantastic Warren with AC
A room with a four-poster bed, two bedside lamps, a small table with a lamp, and a mirror on the wall.

9. 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 €146
includes taxes & fees
14 Nov - 15 Nov
Allegheny Suite
A bedroom with a bed, a chandelier, and a window with curtains.

10. 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 €143
includes taxes & fees
30 Nov - 1 Dec
Sleeps 5 Fully Equipped Apartment Near Golf Courses
A living room with a wooden floor, two sofas, a table, and a fireplace.

11. 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 €146
includes taxes & fees
14 Nov - 15 Nov
Stowaway Suites on the Avenue: Mt Laurel Suite
Living area

12. 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 €146
includes taxes & fees
13 Nov - 14 Nov
Homestead Suite
A compact kitchen with white cabinetry, a stove, a sink, and a refrigerator.

13. 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 €163
includes taxes & fees
30 Nov - 1 Dec
Spacious 2 bedroom apartment
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 €227
includes taxes & fees
16 Nov - 17 Nov
River view getaway
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.

15. 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 €115
includes taxes & fees
15 Nov - 16 Nov
Eagle's Peak Cottage
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 €501
includes taxes & fees
13 Nov - 14 Nov
Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
A rustic log cabin with a stone facade, outdoor seating, and a welcoming entrance.

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

“Hickory Creek Haven” Creek-side Log Cabin
Tionesta
10.0 out of 10, Exceptional, (40 reviews)
"Beth has truly thought of everything! Wonderful place to stay. Our kids especially loved the creek."
United States
Brett G.
The price is €260
includes taxes & fees
16 Nov - 17 Nov
“Hickory Creek Haven” Creek-side Log Cabin
A wooden interior with a dining area, a sofa, and a staircase.

18. 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 €215
includes taxes & fees
16 Nov - 17 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.

19. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (28 reviews)
"Thoroughly enjoyed another stay at this lovely place. Clean and comfortable with every comfort of home. We're already looking forward to our next visit."
United States
Mary A.
The price is €299
includes taxes & fees
15 Nov - 16 Nov
The Refined Retreat
A kitchen with a wooden countertop, a basket, jars, and a paper towel dispenser.

20. 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 €146
includes taxes & fees
30 Nov - 1 Dec
Executive Apartment 1 Bedroom Excellent Location
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, apart-hotels, 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 €89 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.