Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

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 ￥4,283
￥20,444 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥7,139
￥23,614 total
includes taxes & fees
Apr 20 - Apr 21
Eagle's Peak Cottage
Fridge, microwave, oven, stovetop

Lovely King Ensuite bungalow

Lovely King Ensuite bungalow
Clarendon
10.0 out of 10, Exceptional, (1 review)
"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 ￥12,136
￥23,702 total
includes taxes & fees
Apr 27 - Apr 28
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 ￥13,564
￥18,420 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥13,326
￥29,601 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥14,119
￥26,309 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥10,708
￥25,815 total
includes taxes & fees
Apr 26 - Apr 27
Allegheny River House
Exterior

Firefly Suite

Firefly Suite
Warren
9.6 out of 10, Exceptional, (15 reviews)
"Clean, cozy, convenient to restaurants and shopping. "
United States
Diane F.
The price is ￥18,244
￥23,614 total
includes taxes & fees
Apr 20 - Apr 21
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, (14 reviews)
"Cute little place with all the amenities!"
United States
Heather V.
The price is ￥11,898
￥29,945 total
includes taxes & fees
Apr 20 - Apr 21
{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 ￥18,244
￥23,614 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥17,133
￥47,505 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥16,657
￥61,106 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 ￥12,533
￥24,517 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥18,244
￥23,614 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥15,705
￥25,198 total
includes taxes & fees
Apr 29 - Apr 30
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 ￥19,037
￥49,835 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥63,456
￥116,946 total
includes taxes & fees
Apr 21 - Apr 22
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 ￥37,526
￥88,833 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥20,703
￥39,343 total
includes taxes & fees
Apr 20 - Apr 21
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 ￥38,074
￥84,971 total
includes taxes & fees
May 3 - May 4
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.
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Top Pittsfield Hotel Reviews

Days Inn by Wyndham Warren

Days Inn by Wyndham Warren

6/10 Okay
"There was no coffee or breakfast like the advertisement showed."
Walter 2-night trip
Posted 2 days ago
Days Inn by Wyndham Warren

Find out more about Pittsfield

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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.