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Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Pittsfield vacation rentals

A cozy room with a wooden door, a small table with chairs, a patterned rug, and a black couch.

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 CA $71
CA $142 total
includes taxes & fees
Oct 27 - Oct 28
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)
"Ample living space for 2 families and tons of stuff for the non-baseball playing siblings along for the ride!Nice and clean and Very well stocked to accommodate."
United States
Stephen M.
The price is CA $281
CA $733 total
includes taxes & fees
Nov 3 - Nov 4
Cooperstown All Star Village, or Cooperstown Dreams Park or Oneonta area
A modern kitchen with wooden cabinets, a central island with stools, a microwave, and a large window providing a view of the outdoors.

3. Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP

Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP
Hartwick
10.0 out of 10, Exceptional, (1 review)
"Clean & very convenient to Cooperstown Dreams Park. Linens being included was a huge plus! Family friendly yard & in house activities. Would rebook this house."
United States
Christina M.
The price is CA $268
CA $901 total
includes taxes & fees
Oct 22 - Oct 23
Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP
A bedroom with two beds, a window, a shelf with books, and a desk with a lamp.

4. 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 CA $203
CA $574 total
includes taxes & fees
Nov 3 - Nov 4
Deck, Large Yard! Country Home in Mount Vision
A hallway with white walls, a wooden staircase, and a chandelier.

5. *NEW*Hops House-Sleeps10-8Mi.toCDP&15Mi.toASV

*NEW*Hops House-Sleeps10-8Mi.toCDP&15Mi.toASV
Hartwick
10.0 out of 10, Exceptional, (2 reviews)
"Location and house filled all our needs "
United States
Richard M.
The price is CA $212
CA $690 total
includes taxes & fees
Oct 22 - Oct 23
*NEW*Hops House-Sleeps10-8Mi.toCDP&15Mi.toASV
A narrow stone staircase leading to a door, flanked by walls with climbing plants and potted plants.

6. 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)
"Pizza place next door is awesome! Great location"
United States
robert L.
The price is CA $238
CA $306 total
includes taxes & fees
Oct 26 - Oct 27
1st Class Rentals Munson Manor VI at Chestnut 2nd Floor
A deck with outdoor furniture and a covered table.

7. 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, (199 reviews)
"Great place and location."
United States
Matt M.
The price is CA $280
CA $361 total
includes taxes & fees
Nov 21 - Nov 22
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
A room with a grey sofa, a wooden table with a lamp, a white chair, and a wooden desk. There is a white door with a stained glass window, and an air conditioning unit on the wall.

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

Deck, Large Yard! Country Home in Mount Vision
Mount Vision
The price is CA $145
CA $569 total
includes taxes & fees
Nov 3 - Nov 4
Deck, Large Yard! Country Home in Mount Vision
A wooden staircase with white railings leading to a second floor.

9. 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 CA $930
CA $1,060 total
includes taxes & fees
Oct 25 - Oct 26
1st Class Rentals The Thurman Munson House
A grassy area with wooden chairs and a table, surrounded by trees and a river.

10. *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 CA $281
CA $733 total
includes taxes & fees
Nov 3 - Nov 4
*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6
Two wooden crates stacked against a wall, one with a 'NY' logo and the other with a 'BILLS' logo.

11. *Oaks Creek Manor*ON the Creek*Sleep7*4.6Miles-HOF

*Oaks Creek Manor*ON the Creek*Sleep7*4.6Miles-HOF
Fly Creek
10.0 out of 10, Exceptional, (4 reviews)
"This is an historic home with beautiful details and quirks that only older homes will have. It is a perfect location between Downtown Cooperstown and Cooperstown Dreams Park, which made it great for our baseball family. There is a lovely yard with a fire pit and a beautiful creek for fishing or just enjoying the view. The owners were very communicable and made sure to do everything to make our stay comfortable."
United States
Kristina M.
The price is CA $212
CA $687 total
includes taxes & fees
Nov 1 - Nov 2
*Oaks Creek Manor*ON the Creek*Sleep7*4.6Miles-HOF
A two-story red building with a balcony, surrounded by trees and a grassy yard.

12. Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool

Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool
Cooperstown
10.0 out of 10, Exceptional, (3 reviews)
"Was exactly what we were looking for in a short 2 night stay."
United States
Dustin G.
The price is CA $212
CA $643 total
includes taxes & fees
Oct 22 - Oct 23
Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool
A living room with a sofa, yellow armchairs, a coffee table, and a TV.

13. 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 CA $252
CA $482 total
includes taxes & fees
Nov 3 - Nov 4
The Barnhouse - Renovated Century-Old Barn , 2 Miles to Colgate
A modern living room with a large sofa, a flat-screen TV, and a bookshelf.

14. Turtle Cove*ON Oaks Creek!*Fish&Swim!

Turtle Cove*ON Oaks Creek!*Fish&Swim!
Fly Creek
10.0 out of 10, Exceptional, (2 reviews)
"The house was very clean, everything we needed was provided. It was a perfect house for our week long stay for our week in. Cooperstown. I would definitely recommend staying here! "
United States
Beth O.
The price is CA $281
CA $779 total
includes taxes & fees
Nov 3 - Nov 4
Turtle Cove*ON Oaks Creek!*Fish&Swim!
A two-story house with a porch, a covered front entrance, and a well-maintained lawn.

15. 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 CA $229
CA $359 total
includes taxes & fees
Oct 27 - Oct 28
Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks
A modern living room with a sofa, a coffee table, and a TV. There is a ceiling fan and a window with blinds.

16. *Fly Creek Manor*3.7Mi to HOF*4Bedrooms2Ba/Sleep10

*Fly Creek Manor*3.7Mi to HOF*4Bedrooms2Ba/Sleep10
Fly Creek
10.0 out of 10, Exceptional, (5 reviews)
"Perfect pet friendly host for our Cooperstown Village experience. We had a great week!"
United States
Tom H.
*Fly Creek Manor*3.7Mi to HOF*4Bedrooms2Ba/Sleep10
A spacious living room with a fireplace, a large bay window, and a wooden floor.

17. 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 CA $351
CA $458 total
includes taxes & fees
Nov 1 - Nov 2
1st Class Rentals Munson Manor VII at Watkins Avenue
A room with two beds, a nightstand with a lamp, a window with curtains, and a wall-mounted air conditioner.

18. 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 CA $167
CA $207 total
includes taxes & fees
Nov 3 - Nov 4
Cozy 1-bedroom hotel room, Hamilton - 318 Chenango
A deck with outdoor furniture and a covered table.

19. 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 CA $600
CA $683 total
includes taxes & fees
Oct 25 - Oct 26
1st Class Rentals Cooperstown New 3 Bedroom House
A swimming pool with lounge chairs and umbrellas, surrounded by a fenced yard with a house in the background.

20. 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 CA $395
CA $1,526 total
includes taxes & fees
Oct 25 - Oct 26
Private Pool Oasis - heated Memorial day to Labor day/ Minutes from Dreams Park
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

Best Western Cooperstown Inn & Suites

Best Western Cooperstown Inn & Suites

8/10 Good
"Front desk staff so helpful and pleasant to work with. Two gentlemen!"
Jamie 1-night trip
Posted 1 hour ago
Best Western Cooperstown Inn & Suites

Find out more about Pittsfield

Everything you need to know about Pittsfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pittsfield vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield vacation rentals we have selected for you start as low as CA $362 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsfield rentals

At Expedia, we put the best Pittsfield vacation 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 vacation.

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 vacation rental in Pittsfield?

Yes, we give you a choice of vacation rentals near top points of interest in Pittsfield, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Pittsfield?

Cooperstown Dreams Park and Baseball Hall of Fame are 3 miles away!: Visitors like this Pittsfield vacation home rental. It offers a balcony, a garden, and a barbecue grill 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 vacation with amenities like 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 larger area.

What are vacation rentals like in Pittsfield?

Vacation rentals are private properties you can stay in for a couple days or more in Pittsfield. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family gatherings.