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Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Pittsfield holiday rentals

A small, dark-colored cabin with a porch and lights, surrounded by a grassy field and trees.

1. Welcoming 1-bedroom cabin in charming New Berlin perfect for getaway

Welcoming 1-bedroom cabin in charming New Berlin perfect for getaway
New Berlin
10.0 out of 10, Exceptional, (3 reviews)
"Very attentive and hospitable hosts. Beautiful property. Don't think twice, just book it."
United States
Eric
The price is AU$143
includes taxes & fees
2 Dec - 3 Dec
Welcoming 1-bedroom cabin in charming New Berlin perfect for getaway
A sunroom with large windows, a round table, and two chairs.

2. Cooperstown All Star Village, or Cooperstown Dreams Park or Oneonta area

Cooperstown All Star Village, or Cooperstown Dreams Park or Oneonta area
Mt Vision
10.0 out of 10, Exceptional, (86 reviews)
"While visiting Cooperstown for Baseball Hall of Fame induction ceremony we stayed at Abel’s Acres. The house was huge, clean, comfortable and the perfect setting for relaxing in evenings! Giant kitchen equipped with everything needed for cooking. Quiet area for enjoying nature and star gazing. Perfect place for family gatherings."
United States
Carolyn D.
The price is AU$694
includes taxes & fees
3 Nov - 4 Nov
Cooperstown All Star Village, or Cooperstown Dreams Park or Oneonta area
A spacious living area with a wooden ceiling, a sectional sofa, a dining table with chairs, and a wood-burning stove.

3. Deck, Large Yard! Country Home in Mount Vision

Deck, Large Yard! Country Home in Mount Vision
3.0 star property
Mount Vision
The price is AU$581
includes taxes & fees
2 Nov - 3 Nov
Deck, Large Yard! Country Home in Mount Vision
A spacious living area with a wooden ceiling, a sectional sofa, a dining table with chairs, and a wood-burning stove.

4. Deck, Large Yard! Country Home in Mount Vision

Deck, Large Yard! Country Home in Mount Vision
Mount Vision
The price is AU$537
includes taxes & fees
2 Nov - 3 Nov
Deck, Large Yard! Country Home in Mount Vision
A narrow stone staircase leading to a door, flanked by walls with climbing plants and potted plants.

5. 1st Class Rentals Munson Manor VI at Chestnut 2nd Floor

1st Class Rentals Munson Manor VI at Chestnut 2nd Floor
West End
9.6 out of 10, Exceptional, (30 reviews)
"We really enjoyed our stay! Very roomy and comfortable. The host communication was super! The apartment is about 3 minutes from ASV. Perfect location! There are steps-this is an upstairs apartment. You can tell the host has put a lot of thought into making guests as comfortable as possible. Highly recommended!"
United States
Mary H.
The price is AU$275
includes taxes & fees
2 Nov - 3 Nov
1st Class Rentals Munson Manor VI at Chestnut 2nd Floor
A grassy area with wooden chairs and a table, surrounded by trees and a river.

6. *Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6

*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6
Fly Creek
9.0 out of 10, Wonderful, (7 reviews)
"Oaks Creek Cottage met all our needs and expectations.the rooms were spacious and cozy. We loved the fire pit by the creek and enjoyed a sunny afternoon with drinks and books to read.The location was within a few miles of all our activities.We recommend the cottage. "
United States
Leila K.
The price is AU$639
includes taxes & fees
2 Nov - 3 Nov
*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6
A compact RV kitchen with a microwave, sink, and stove, a television mounted above the counter, and a bed with Halloween-themed bedding.

7. 1-bedroom recreational vehicle in lovely Smyrna with AC

1-bedroom recreational vehicle in lovely Smyrna with AC
Smyrna
The price is AU$204
includes taxes & fees
2 Nov - 3 Nov
1-bedroom recreational vehicle in lovely Smyrna with AC
A wooden staircase with white railings leading to a second floor.

8. 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 review)
"The house was well maintained, clean, convenient and newly renovated. A great experience. "
United States
JEFF
The price is AU$1,068
includes taxes & fees
2 Nov - 3 Nov
1st Class Rentals The Thurman Munson House
A deck with outdoor furniture and a covered table.

9. Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area

Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
Cooperstown
9.8 out of 10, Exceptional, (202 reviews)
"Great place and location."
United States
Matt M.
The price is AU$364
includes taxes & fees
8 Nov - 9 Nov
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
A spacious living room with a fireplace, a large bay window, and a wooden floor.

10. 1st Class Rentals Munson Manor VII at Watkins Avenue

1st Class Rentals Munson Manor VII at Watkins Avenue
Downtown Oneonta
9.2 out of 10, Wonderful, (20 reviews)
"Lots of space, great location for all star village and yummy restaurants (simply Thai was delish) and easy parking! "
United States
Nicole H.
The price is AU$448
includes taxes & fees
2 Nov - 3 Nov
1st Class Rentals Munson Manor VII at Watkins Avenue
A house with a black front door, green shutters, and a small porch with potted plants.

11. Cooperstown - Walk everywhere! Cute Apartment. Steps away from HOF and Main St.

Cooperstown - Walk everywhere! Cute Apartment. Steps away from HOF and Main St.
Cooperstown
9.8 out of 10, Exceptional, (83 reviews)
"Wonderful stay! Host was amazing. Thank you!"
United States
Deanna W.
The price is AU$522
includes taxes & fees
3 Nov - 4 Nov
Cooperstown - Walk everywhere! Cute Apartment. Steps away from HOF and Main St.
A modern kitchen with a central island, stainless steel appliances, and a wooden staircase.

12. The Away Game, A home run for baseball families

The Away Game, A home run for baseball families
Portlandville
The price is AU$586
includes taxes & fees
8 Nov - 9 Nov
The Away Game, A home run for baseball families
A staircase with white railings and wooden steps leading to a second floor.

13. 1st Class Rentals The Thurman Munson House

1st Class Rentals The Thurman Munson House
Cooperstown
10.0 out of 10, Exceptional, (69 reviews)
"Awesome quaint home"
United States
Kim B.
The price is AU$440
includes taxes & fees
2 Nov - 3 Nov
1st Class Rentals The Thurman Munson House
A two-story house with a porch, a covered front entrance, and a well-maintained lawn.

14. Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks

Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks
Hamilton
10.0 out of 10, Exceptional, (70 reviews)
"Great place"
United States
Dorothy M.
The price is AU$346
includes taxes & fees
4 Nov - 5 Nov
Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks
A swimming pool with lounge chairs and umbrellas, surrounded by a fenced yard with a house in the background.

15. Private Pool Oasis - heated Memorial day to Labor day/ Minutes from Dreams Park

Private Pool Oasis - heated Memorial day to Labor day/ Minutes from Dreams Park
Cooperstown
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful stay for our time in Cooperstown. Pool was great for kids. 8 min drive to town and 10 to dreams park"
United States
Maureen R.
The price is AU$1,597
includes taxes & fees
2 Nov - 3 Nov
Private Pool Oasis - heated Memorial day to Labor day/ Minutes from Dreams Park
A room with two beds, a nightstand with a lamp, a window with curtains, and a wall-mounted air conditioner.

16. Cozy 1-bedroom hotel room, Hamilton - 318 Chenango

Cozy 1-bedroom hotel room, Hamilton - 318 Chenango
Hamilton
9.4 out of 10, Exceptional, (3 reviews)
"The room was very clean. No bad smell at all. Staff was very nice. Good price. Excellent services. I will recommend it."
United States
Mercedes
The price is AU$176
includes taxes & fees
2 Nov - 3 Nov
Cozy 1-bedroom hotel room, Hamilton - 318 Chenango
A living room with a sofa, yellow armchairs, a coffee table, and a TV.

17. The Barnhouse - Renovated Century-Old Barn , 2 Miles to Colgate

The Barnhouse - Renovated Century-Old Barn , 2 Miles to Colgate
Hamilton
10.0 out of 10, Exceptional, (33 reviews)
"Excellent property great location and very clean"
United States
Barri
The price is AU$491
includes taxes & fees
2 Nov - 3 Nov
The Barnhouse - Renovated Century-Old Barn , 2 Miles to Colgate
A deck with outdoor furniture and a covered table.

18. 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 review)
"Fantastic place! Everything as advertised. "
United States
Douglas
The price is AU$689
includes taxes & fees
6 Nov - 7 Nov
1st Class Rentals Cooperstown New 3 Bedroom House
A single-story building with a porch, two doors, and a small sign.

19. Cozy 1BR hotel room, Hamilton - #335 Endawonnda

Cozy 1BR hotel room, Hamilton - #335 Endawonnda
Hamilton
10.0 out of 10, Exceptional, (1 review)
"Love this entire property! Look forward to returning!"
United States
Kelly D.
The price is AU$187
includes taxes & fees
8 Nov - 9 Nov
Cozy 1BR hotel room, Hamilton - #335 Endawonnda
A room with two beds, a nightstand with a lamp, and a window with blinds.

20. Cozy 1-bedroom hotel room, Hamilton - #350 Oneida

Cozy 1-bedroom hotel room, Hamilton - #350 Oneida
Hamilton
The price is AU$176
includes taxes & fees
2 Nov - 3 Nov
Cozy 1-bedroom hotel room, Hamilton - #350 Oneida
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

The Inn at Cooperstown

The Inn at Cooperstown

10/10 Excellent
"Lovely Inn right in town. Friendly staff."
Kelly 1-night trip
Posted 2 hours ago
The Inn at Cooperstown

Find out more about Pittsfield

Everything you need to know about Pittsfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pittsfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield holiday rentals we have selected for you start as low as AU$364 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pittsfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 are some of the best holiday rentals that Pittsfield has to offer?

Cooperstown Dreams Park and Baseball Hall of Fame are 3 miles away!: This holiday home rental outside of Pittsfield offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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. Cooperstown All Star Village Fields and State University of New York-Oneonta 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.