Pittsfield Travel Guide

Tourist Guide

15%+ off winter escapes close to home

Book a getaway and you can save on select hotels and homes.¹
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave Celoron NY
The price is NZ$289 per night from 27 May to 28 May
NZ$289
27 May - 28 May
includes taxes & fees
Stay at this business-friendly hotel in Celoron. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the pool and the helpful staff in their ...
9.6/10 Exceptional! (1,003 reviews)
Very attentive staff! Great hospitality.

Reviewed on 5 May 2026

Chautauqua Harbor Hotel - Jamestown
La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

3 out of 5
200 W 3rd St Jamestown NY
The price is NZ$171 per night from 11 May to 12 May
NZ$171
11 May - 12 May
includes taxes & fees
Stay at this business-friendly hotel in Jamestown. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,002 reviews)
Breakfast was excellent; staff were extremely courteous and helpful

Reviewed on 4 May 2026

La Quinta Inn & Suites by Wyndham Jamestown
DoubleTree by Hilton Jamestown

DoubleTree by Hilton Jamestown

4 out of 5
150 W 4th St Jamestown NY
Fully refundableReserve now, pay when you stay
The price is NZ$192 per night from 24 May to 25 May
NZ$192
24 May - 25 May
includes taxes & fees
Stay at this business-friendly hotel in Jamestown. Enjoy free parking, breakfast (surcharge) and room service. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (960 reviews)
Friendly, helpful staff day and evening, nice room, comfortable bed, walking distance to attractions, two restaurants and one bar in house, great security system, no one can get on the floors with rooms or into rooms without a digital guest card, parking garage next door is connected to hotel with ...

Reviewed on 3 May 2026

DoubleTree by Hilton Jamestown
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.
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 NY
Stay at this ski condo in Clymer. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Peek'n Peak Ski Resort and Wilderness Lodge are located ...
8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit
Eagle's Peak Cottage

Eagle's Peak Cottage

Pleasantville PA
Stay at this holiday home in West Hickory. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Allegheny River and Cornplanter State Forest ...
9/10 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!!

Reviewed on 28 Feb 2026

Eagle's Peak Cottage
Eagle's Peak Cozy Cabin

Eagle's Peak Cozy Cabin

Pleasantville PA
Stay at this cabin in West Hickory. Enjoy free Wi-Fi, patios and an in-room coffee maker. Popular attractions Allegheny River and Cornplanter State Forest are ...
8.6/10 Excellent! (17 reviews)
Perfect place to stay for everything I wanted to do, close proximity to Minister creek and the Allegheny National forest.Host is super nice and very responsive to all communication. Will definitely be staying again!

Reviewed on 24 Apr 2026

Eagle's Peak Cozy Cabin
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.