Holiday Rentals in Pittsfield

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Holiday Rentals in Pittsfield

Waterfront Chautauqua Lake Home w/ Stunning Views

10.0 out of 10, Exceptional, (13)
"We were very pleased with the accommodations and would love to stay again in the future"
Waterfront Chautauqua Lake Home w/ Stunning Views

Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

10.0 out of 10, Exceptional, (12)
"Enjoyed our stay. Everything was as advertised. "
The price is €436
includes taxes & fees
3 May - 4 May
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

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

9.8 out of 10, Exceptional, (98)
"My wife and I were visiting the area to enjoy the fall foliage. The cabin was a wonderful place to stay. Good location to access the area. Abundant wildlife The cabin was clean and comfortable. The hosts did were responsive and friendly. Would stay there again."
Cozy cabin in the Western part of the PA Wilds & the Allegheny Nat'l Forest

Charming Resort in the Heart of Bemus Village on CHQ Lake

10.0 out of 10, Exceptional, (173)
"This property is very comfortable and roomy. It met our needs perfectly! I’d recommend it to anyone staying in Bemus!"
The price is €483
includes taxes & fees
3 May - 4 May
Charming Resort in the Heart of Bemus Village on CHQ Lake

Eagle's Peak Cottage

10.0 out of 10, Exceptional, (1)
"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 €160
includes taxes & fees
3 May - 4 May
Eagle's Peak Cottage

“Hickory Creek Haven” Creek-side Log Cabin

10.0 out of 10, Exceptional, (17)
"Wonderful, quaint, and cozy cabin settled along a lovely creek. All 8 of us plus our 2 dogs had a lovely time playing lots of games, hiking, and ping pong tournaments. House has plenty of heaters, towels, kitchen pots and pans. We truly enjoyed our stay!"
“Hickory Creek Haven” Creek-side Log Cabin

Bemus Point Vacation Rental

8.6 out of 10, Excellent, (103)
"Enjoyed the stay. Convenient and close to bemus and lake. Nice neighborhood. Would definitely stay again!"
Bemus Point Vacation Rental

Cottage #4 - Beautiful 3 Bedroom Lakefront Cottage - Fully Renovated in 2024!

2.0 star property
10.0 out of 10, Exceptional, (2)
"This was a fun location next to the Ferry with lakefront views. The home was nicely done and very clean. We had a concern which was responded to immediately. We made friends at the fire pit and would definitely stay here again. "
Cottage #4 - Beautiful 3 Bedroom Lakefront Cottage - Fully Renovated in 2024!

Cozy Cottage

9.0 out of 10, Wonderful, (21)
"This was the best short stay I have ever had so relaxing and such a beautiful area"
Cozy Cottage

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

9.6 out of 10, Exceptional, (124)
"had everything that you needed great location had no problems great value for your money"
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock

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

9.6 out of 10, Exceptional, (81)
"Everything was as described. Nice spot!"
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard

Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

10.0 out of 10, Exceptional, (231)
"Our family loves this Chalet. This was our fourth year in a row there! I highly recommend a stay there and you will not be disappointed! "
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

Spacious 5-bedroom house with AC, WiFi in charming Bemus Point

Spacious 5-bedroom house with AC, WiFi in charming Bemus Point

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

9.8 out of 10, Exceptional, (64)
"Property was great and had everything we needed. Great location."
The price is €429
includes taxes & fees
4 May - 5 May
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

Year-Round Renovated Lakefront Cottage & Pet Friendly!

9.8 out of 10, Exceptional, (183)
"Lovely home on Chautauqua Lake. Picture perfect fall weather, bonfires and fall foliage!"
Year-Round Renovated Lakefront Cottage & Pet Friendly!

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

The Refined Retreat

The price is €280
includes taxes & fees
4 May - 5 May
The Refined Retreat

Allegheny River House

9.2 out of 10, Wonderful, (7)
"The place was better than advertised.I had a great time. Steven was very receptive and handled any questions I had very quickly. I hope to have the opportunity to stay there again. "
The price is €155
includes taxes & fees
4 May - 5 May
Allegheny River House

Four Seasons Lodge - Ski In/Out - 5 Bdr. - Closest to Lift !

10.0 out of 10, Exceptional, (46)
"Very clean and well maintained"
Four Seasons Lodge - Ski In/Out - 5 Bdr. - Closest to Lift !

Creekside Cottage w/Lake access, Dock, Hot tub, Canoe/Kayaks

2.0 star property
9.6 out of 10, Exceptional, (5)
"The cottage was perfect for our getaway with friends. There was enough room for the 6 of us where we could all hang out together. The kids had their own space and we really enjoyed sitting on the deck by the water. The cottage was stocked with everything we needed.and more. Communication with the owner was great. Would definitely recommend staying here. "
Creekside Cottage w/Lake access, Dock, Hot tub, Canoe/Kayaks
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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Other types of properties in Pittsfield you may be interested in

La Quinta Inn & Suites by Wyndham Jamestown

3.0 star property
8.4 out of 10, Very good, (1002)
"I was very satisfied with the room, the quality of the property, the cleanliness and modern amenities"
The price is €85
includes taxes & fees
4 May - 5 May
La Quinta Inn & Suites by Wyndham Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 star property
9.6 out of 10, Exceptional, (1004)
"Great stay"
The price is €135
includes taxes & fees
6 May - 7 May
Chautauqua Harbor Hotel - Jamestown

Peek'n Peak Resort Trademark Collection by Wyndham

3.5 star property
8.6 out of 10, Excellent, (891)
"Very fun place to stay with the kids."
The price is €116
includes taxes & fees
15 May - 16 May
Peek'n Peak Resort Trademark Collection by Wyndham
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.

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?

Charming Resort in the Heart of Bemus Village on CHQ Lake: 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. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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, Cornplanter State Forest and Anders Run Natural Area 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.