Search Holiday Rentals in Pittsfield

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Pittsfield holiday rentals

Exterior
1st Class Rentals Cooperstown New 3 Bedroom House

1st Class Rentals Cooperstown New 3 Bedroom House

1st Class Rentals Cooperstown New 3 Bedroom House
3.5 star property
Cooperstown
10.0 out of 10, Exceptional, (1)
"Fantastic place! Everything as advertised. "
United States
Douglas
The price is 11.184.300 ₫
12.750.102 ₫ total
includes taxes & fees
29 Dec - 30 Dec
1st Class Rentals Cooperstown New 3 Bedroom House
Exterior
Jeannies Dream Motel

Jeannies Dream Motel

Jeannies Dream Motel
2.0 star property
West Winfield
5.2 out of 10, (25)
"Perfect little spot to stay while working in the area! Great price and the room was exactly what we needed."
United States
Christian
The price is 1.811.620 ₫
2.618.979 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Jeannies Dream Motel
Cabin, Golf View | 1 bedroom, free WiFi
Stonegate Golf Cabins

Stonegate Golf Cabins

Stonegate Golf Cabins
2.0 star property
West Edmeston
The price is 13.158.000 ₫
15.000.120 ₫ total
includes taxes & fees
27 Dec - 28 Dec
Stonegate Golf Cabins
House, 5 Bedrooms, Patio | Interior
1st Class Rentals The Thurman Munson House

1st Class Rentals The Thurman Munson House

1st Class Rentals The Thurman Munson House
3.5 star property
Cooperstown
10.0 out of 10, Exceptional, (1)
"The house was well maintained, clean, convenient and newly renovated. A great experience. "
United States
JEFF
The price is 17.342.244 ₫
19.770.158 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
1st Class Rentals The Thurman Munson House
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

Hampton Inn Oneonta

Hampton Inn Oneonta

10/10 Excellent
"Clean room, pleasant staff, good breakfast "
Jennifer 1-night trip
Posted 1 day ago
Hampton Inn Oneonta

Frequently asked questions

Can I find a holiday rental 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 can I see and do in Pittsfield?

While exploring the area, visit family-friendly sights like National Baseball Hall of Fame, or get outside and enjoy nature at Cooperstown Dreams Park. Unadilla Motocross and Cooperstown All Star Village Fields are a couple of places you'll find in the wider area.

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 feature extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family getaway.