Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Eagle's Peak Cottage

8.4 out of 10, Very good, (7)
"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 NZ$232
includes taxes & fees
9 July - 10 July
Eagle's Peak Cottage

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

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

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

9.0 out of 10, Wonderful, (27)
"Neat house. As advertised. Would stay again."
Yogi's I love Lucy-themed 4-bed Home with A/C, Chautauqua Lake, Jamestown NY

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

8.0 out of 10, Very good, (24)
"The neighborhood was less than safe feeling and the neighbor across the street didn’t help any"
Yogi Nature Stay #2 3 beds with spa shower, smart tv across the street from UPMC

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!

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

Beautiful Peek'n Peak Highlands Condo

10.0 out of 10, Exceptional, (98)
"The house is amazing and great accommodations!"
Beautiful Peek'n Peak Highlands Condo

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!

The Refined Retreat

10.0 out of 10, Exceptional, (2)
"Cozy. beautiful home next to the lake on a quiet street. The host has thought of everything. Lots of extras! Host is very responsive and helpful. Will definitely book again."
The price is NZ$507
includes taxes & fees
3 Aug - 4 Aug
The Refined Retreat

Cozy ski and golf condo at Peek n Peak

9.2 out of 10, Wonderful, (33)
"Nice location "
Cozy ski and golf condo at Peek n Peak

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

9.8 out of 10, Exceptional, (102)
"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

Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA

10.0 out of 10, Exceptional, (5)
"Accommodations and setting were wonderful, owners, cabin, and property are top notch!"
The price is NZ$344
includes taxes & fees
9 July - 10 July
Poland Hill Hideaway, located in the beautiful woods surrounding Tionesta, PA

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

9.8 out of 10, Exceptional, (64)
"Great place just as described "
The price is NZ$746
includes taxes & fees
9 July - 10 July
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

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

9.6 out of 10, Exceptional, (84)
"Everything was as described. Nice spot!"
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard

4BR Lakeside Bliss| Kayak Adventure!

9.4 out of 10, Exceptional, (13)
"Absolutely lovely place to stay! The setting was fabulous, the place was very clean and spacious. I will absolutely be back to stay next season! "
4BR Lakeside Bliss| Kayak Adventure!

3 Bedroom Cottage on the Shores of Chautauqua Lake

10.0 out of 10, Exceptional, (134)
"Comfortable house situated on shore of Lake Chautauqua with great views."
3 Bedroom Cottage on the Shores of Chautauqua Lake

Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!

9.8 out of 10, Exceptional, (102)
"Very clean, well stocked property! Close to town w/shops, restaurants,etc within walking distance. "
Chautauqua Lake Front Property - Short Walk to the Village of Bemus Point!

Chautauqua Lake area 2 bedroom cottage

10.0 out of 10, Exceptional, (32)
"Very nice would absolutely stay again"
Chautauqua Lake area 2 bedroom cottage
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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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?

Eagle's Peak Cottage: This holiday home rental outside of Pittsfield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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, Allegheny River and Buckaloons Recreation Area 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.