Pittsfield Holiday Rentals

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Check prices for these dates

Tonight
23 Jul - 24 Jul
Tomorrow
24 Jul - 25 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Holiday Rentals in Pittsfield

Eagle's Peak Cottage
Kitchen features a large island with sink and ample counter space, a dining table, and a seating area with a bench and chairs.

Eagle's Peak Cottage

8.2 out of 10, Very good, (10)
"Super cute cabin. Everything was clean and inviting. We would 100% stay here again. Great location, spacious indoor and deck with a beautiful view. "
The price is HK$495
HK$1,325 total
includes taxes & fees
4 Aug - 5 Aug
Eagle's Peak Cottage
Bemus Point Vacation Rental
Charming single-story house surrounded by a serene lawn and trees.

Bemus Point Vacation Rental

8.6 out of 10, Excellent, (105)
"Enjoyed the stay. Convenient and close to bemus and lake. Nice neighborhood. Would definitely stay again!"
Bemus Point Vacation Rental
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Relax by the serene lake with a picnic table and enjoy the scenic views of the bridge and boats.

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

10.0 out of 10, Exceptional, (101)
"We had a great time at this property. The location was convenient and the views were beautiful. It was a perfect winter escape."
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!
Cottage #7 - Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
Sit and enjoy the view from this cozy porch with a comfortable Adirondack chair.

Cottage #7 - Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

8.4 out of 10, Very good, (8)
"Perfect little cabin in a great location. Good price and have no complaints. Thank you"
Cottage #7 - Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY
Bemus Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
Relax in this serene outdoor seating area, complete with a pergola, dining table, and comfortable chairs.

Bemus Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock

9.6 out of 10, Exceptional, (130)
"Cute cottage with a perfect view. Everything we needed was supplied. We could eat inside or outside. Plenty of space. Lived it. "
Bemus Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock
Yogi's I love Lucy-themed 4-bed Home with A/C, Chautauqua Lake, Jamestown NY
Enjoy outdoor dining or relaxation on this deck with a table and two stools.

Yogi's I love Lucy-themed 4-bed Home with A/C, Chautauqua Lake, Jamestown NY

9.2 out of 10, Wonderful, (29)
"Great stay and great accommodations!"
Yogi's I love Lucy-themed 4-bed Home with A/C, Chautauqua Lake, Jamestown NY
Tiny House #1 - Lakefront, Spacious, & Modern "Tiny Home" with 2 bdrms & 1 bath
Guests can enjoy a peaceful lakeside retreat with a porch and outdoor seating.

Tiny House #1 - Lakefront, Spacious, & Modern "Tiny Home" with 2 bdrms & 1 bath

9.6 out of 10, Exceptional, (9)
"We had a great time and enjoyed the surroundings."
Tiny House #1 - Lakefront, Spacious, & Modern "Tiny Home" with 2 bdrms & 1 bath
Yogi Nature Stay #2 3 beds with spa shower, smart tv across the street from UPMC
Stunning historic building with a classical facade, surrounded by lush greenery and trees.

Yogi Nature Stay #2 3 beds with spa shower, smart tv across the street from UPMC

8.0 out of 10, Very good, (24)
"An enjoyable stay in a clean comfortable apartment "
Yogi Nature Stay #2 3 beds with spa shower, smart tv across the street from UPMC
The Refined Retreat
Relax in a stylish living space with a flat-screen TV, fireplace, and comfortable seating area.

The Refined Retreat

10.0 out of 10, Exceptional, (5)
The price is HK$1,060
HK$2,635 total
includes taxes & fees
13 Aug - 14 Aug
The Refined Retreat
Sweet Serenity in Bemus Point
Enjoy cooking in this well-equipped kitchen with a central island, stove, and convenient appliances.

Sweet Serenity in Bemus Point

10.0 out of 10, Exceptional, (12)
"Perfect location. Very nice property! Clean, comfortable and hosts were very gracious! "
Sweet Serenity in Bemus Point
Create your family memories at our nautical lakeside home!
Guests can enjoy serene views of the lake from the grassy area.

Create your family memories at our nautical lakeside home!

10.0 out of 10, Exceptional, (129)
"The property was lovely and very comfortable. It’s in a perfect location with plenty of restaurants and hiking nearby!"
Create your family memories at our nautical lakeside home!
Cottage #6 - Cute and airy 2 bedroom cottage right on Chautauqua Lake!
Relax in a serene bedroom with a bed, flat-screen TV, and large window.

Cottage #6 - Cute and airy 2 bedroom cottage right on Chautauqua Lake!

9.0 out of 10, Wonderful, (10)
"Had a great 2 night stay. Off season very quiet. "
Cottage #6 - Cute and airy 2 bedroom cottage right on Chautauqua Lake!
Charming 2-bedroom house in Tiona with sunset views and everything you need.
Enjoy a meal al fresco at this outdoor picnic table, set amidst a serene natural backdrop.

Charming 2-bedroom house in Tiona with sunset views and everything you need.

2.0 star property
10.0 out of 10, Exceptional, (4)
"A cute little house of the beaten path "
Charming 2-bedroom house in Tiona with sunset views and everything you need.
Beautiful Peek'n Peak Highlands Condo
Experience the charm of a historic building with a Tudor-style architecture, surrounded by mature trees in a serene setting.

Beautiful Peek'n Peak Highlands Condo

10.0 out of 10, Exceptional, (99)
"The house is amazing and great accommodations!"
Beautiful Peek'n Peak Highlands Condo
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14
Enjoy breathtaking views of the snowy landscape from this balcony.

Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

9.8 out of 10, Exceptional, (69)
"Great place just as described "
The price is HK$1,766
HK$3,548 total
includes taxes & fees
24 Jul - 25 Jul
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14
Peek'n Peak 2 Bedroom Condo, Ground Floor
Kitchen features a gas stove, microwave, and stainless steel sink with a dishwasher.

Peek'n Peak 2 Bedroom Condo, Ground Floor

10.0 out of 10, Exceptional, (74)
"Property was very nice and cozy. Well thought out we actually had everything we needed and wanted. Craig was very helpful and a class act! "
The price is HK$1,405
HK$2,830 total
includes taxes & fees
27 Jul - 28 Jul
Peek'n Peak 2 Bedroom Condo, Ground Floor
Bemus Point Retreat ~ 3 Mi to Chautauqua Lake
Relax in this inviting living room with a leather sofa, coffee table, and TV.

Bemus Point Retreat ~ 3 Mi to Chautauqua Lake

9.6 out of 10, Exceptional, (15)
"It was very relaxing and a beautiful place. The sunset from the property was unbelievable!!"
Bemus Point Retreat ~ 3 Mi to Chautauqua Lake
Lakeside Retreat 4BR House |Kayak Adventure
Enjoy a relaxing outdoor space with a deck, table, and chairs.

Lakeside Retreat 4BR House |Kayak Adventure

9.4 out of 10, Exceptional, (13)
"It was a veey nice peaceful stay."
Lakeside Retreat 4BR House |Kayak Adventure
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard
Cozy cabin with a gabled roof and covered porch, featuring a red door and a window with a forest view.

Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard

9.4 out of 10, Exceptional, (87)
"Wonderful stay"
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard
Cozy cabin in the Western part of the PA Wilds & the Allegheny Nat'l Forest
Situated in a wooded area, this cabin features a porch with wooden railings and a sloped roof.

Cozy cabin in the Western part of the PA Wilds & the Allegheny Nat'l Forest

9.8 out of 10, Exceptional, (103)
"This was our 2nd stay here, and already looking forward to coming back again. Great location, peaceful, well appointment, clean, fully stocked, cozy, quiet, fun for every age group"
Cozy cabin in the Western part of the PA Wilds & the Allegheny Nat'l Forest
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

10/10 Excellent
"My family of four adults enjoyed our stay very much. The restaurant's food was delicious! The amenities were excellent. We would definitely book here again. "
Anonymous traveller 1-night trip
Posted 1 day ago
Chautauqua Harbor Hotel - Jamestown

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?

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!: This holiday home rental outside of Pittsfield is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday 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 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.