Pittsfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Pittsfield vacation rentals

1 bedroom, free WiFi, bed sheets

Eagle's Peak Cozy Cabin

Eagle's Peak Cozy Cabin
Pleasantville
8.4 out of 10, Very Good, (16 reviews)
"Cute cabin would stay again"
United States
Angee K.
The price is ￥6,430
￥22,840 total
includes taxes & fees
Apr 29 - Apr 30
Eagle's Peak Cozy Cabin
Fridge, microwave, oven, stovetop

Eagle's Peak Cottage

Eagle's Peak Cottage
Pleasantville
9.0 out of 10, Wonderful, (24 reviews)
"Was a great couple months during winter. Had what we needed. Was cozy and the wildlife around was great to watch daily. Would book again. On negative temperature nights it got a little chilly but was sufficient. Driveway during snow was tough but all in all very happy with Eagles Peak Cottage!!"
United States
Rick
The price is ￥7,173
￥23,728 total
includes taxes & fees
Apr 29 - Apr 30
Eagle's Peak Cottage
Fridge, microwave, oven, stovetop

Lovely King Ensuite bungalow

Lovely King Ensuite bungalow
Clarendon
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great, comfortable and clean. The massage chair was exceptional. Upstairs bedroom should have a pony wall by stairs for safety"
United States
Kelly B.
The price is ￥12,146
￥23,722 total
includes taxes & fees
Apr 28 - Apr 29
Lovely King Ensuite bungalow
Exterior

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, (15 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 ￥13,575
￥18,435 total
includes taxes & fees
Apr 23 - Apr 24
Charming 2-bedroom apartment in peaceful Warren with AC
Fridge, microwave, oven, stovetop

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 ￥13,337
￥29,625 total
includes taxes & fees
Apr 29 - Apr 30
Spacious 2 bedroom apartment
1 bedroom, iron/ironing board, free WiFi, bed sheets

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)
"The location in downtown Corry was the most appealing aspect of the apartment. Having grown up in Corry, the central location brought back so many good memories of our formative years."
United States
Sandy C.
The price is ￥14,131
￥26,331 total
includes taxes & fees
Apr 23 - Apr 24
Sleeps 5 Fully Equipped Apartment Near Golf Courses
TV

Allegheny River House

Allegheny River House
Tidioute
9.2 out of 10, Wonderful, (10 reviews)
"Fantastic as always "
United States
Andrew F.
The price is ￥10,717
￥25,837 total
includes taxes & fees
Apr 26 - Apr 27
Allegheny River House
Exterior

Firefly Suite

Firefly Suite
Warren
9.8 out of 10, Exceptional, (16 reviews)
"Clean, cozy, convenient to restaurants and shopping. "
United States
Diane F.
The price is ￥18,259
￥23,633 total
includes taxes & fees
Apr 23 - Apr 24
Firefly Suite
Interior

{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, (15 reviews)
"Cute little place with all the amenities!"
United States
Heather V.
The price is ￥11,908
￥29,801 total
includes taxes & fees
Apr 23 - Apr 24
{LUXE Lil Tio} Downtown Retreat - 5 Min Walk To River Access w/ Firepit & Grill
Smart TV

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 ￥18,259
￥23,633 total
includes taxes & fees
Apr 23 - Apr 24
Stowaway Suites on the Avenue: Mt Laurel Suite
Property grounds

Cozy Lake Retreat + Firepit + Near Chautauqua

Cozy Lake Retreat + Firepit + Near Chautauqua
Ashville
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful view of the lake. Very nice little house and quiet. "
United States
Joelyn G.
The price is ￥17,216
￥47,735 total
includes taxes & fees
Apr 23 - Apr 24
Cozy Lake Retreat + Firepit + Near Chautauqua
TV

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

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Warren
10.0 out of 10, Exceptional, (1 review)
"House was beautiful and well maintained, very welcoming. The host was easy to communicate with and checked in to see if we needed anything or had any issues. Would absolutely book again in the future! "
United States
Jill M.
The price is ￥16,671
￥61,157 total
includes taxes & fees
May 4 - May 5
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Interior

Sleeps 4 Fully Equipped Apartment Near Golf Courses

Sleeps 4 Fully Equipped Apartment Near Golf Courses
Corry
8.6 out of 10, Excellent, (8 reviews)
"This was the perfect place to stay! It was easy to find and Holly was super pleasant and responded super quickly with any questions we had! :)"
United States
Autumn M.
The price is ￥12,543
￥24,536 total
includes taxes & fees
May 21 - May 22
Sleeps 4 Fully Equipped Apartment Near Golf Courses
3 bedrooms, WiFi

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 ￥18,259
￥23,633 total
includes taxes & fees
Apr 23 - Apr 24
Allegheny Suite
Exterior detail

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 ￥15,718
￥25,219 total
includes taxes & fees
Apr 28 - Apr 29
Stay in our immaculate newly remodeled and cozy home in Old Order Amish country
Smart TV, fireplace, books

The Refined Retreat

The Refined Retreat
Celoron
9.6 out of 10, Exceptional, (15 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is ￥19,052
￥49,876 total
includes taxes & fees
May 5 - May 6
The Refined Retreat
Dining

Meadow View at Chautauqua Lake • 1.5 Acres • Sleeps 10

Meadow View at Chautauqua Lake • 1.5 Acres • Sleeps 10
Bemus Point
The price is ￥63,508
￥117,042 total
includes taxes & fees
Apr 23 - Apr 24
Meadow View at Chautauqua Lake • 1.5 Acres • Sleeps 10
Smart TV, fireplace, DVD player, foosball

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, (93 reviews)
"Best location at Peek n’ Peak "
United States
Steve A.
The price is ￥40,889
￥93,941 total
includes taxes & fees
Apr 23 - Apr 24
8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit
Smart TV, fireplace, books

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 ￥23,022
￥42,603 total
includes taxes & fees
May 5 - May 6
River view getaway
Outdoor dining

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)
"We enjoyed our stay! "
United States
Andrew B.
The price is ￥34,294
￥79,658 total
includes taxes & fees
May 5 - May 6
Charming Resort in the Heart of Bemus Village on CHQ Lake
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

10/10 Excellent
"Great place md beautiful view!"
burton 1-night trip
Posted 10 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:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

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?

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!: This vacation home rental outside of Pittsfield is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation 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 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.