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Pittsfield Vacation Rentals

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 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
$90 nightly
The price is $101
Oct 25 - Oct 26
Total with taxes and fees
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.
$457 nightly
The price is $521
Oct 27 - Oct 28
Total with taxes and fees
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
$358 nightly
The price is $408
Oct 25 - Oct 26
Total with taxes and fees
Deck, Large Yard! Country Home in Mount Vision
A modern kitchen with wooden cabinets, a central island with stools, a microwave, and a large window providing a view of the outdoors.

4. 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.
$624 nightly
The price is $711
Oct 25 - Oct 26
Total with taxes and fees
Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP
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.
$426 nightly
The price is $486
Oct 25 - Oct 26
Total with taxes and fees
*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.
$170 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
1st Class Rentals Munson Manor VI at Chestnut 2nd Floor
A room with a wooden ceiling, a large window, a dining table with chairs, and a wood-burning stove.

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

Deck, Large Yard! Country Home in Mount Vision
Mount Vision
$353 nightly
The price is $402
Oct 25 - Oct 26
Total with taxes and fees
Deck, Large Yard! Country Home in Mount Vision
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
$659 nightly
The price is $751
Oct 25 - Oct 26
Total with taxes and fees
1st Class Rentals The Thurman Munson House
A room with two beds, a nightstand with a lamp, a window with curtains, and a wall-mounted air conditioner.

9. 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
$132 nightly
The price is $140
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-bedroom hotel room, Hamilton - 318 Chenango
A deck with outdoor furniture and a covered table.

10. 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, (200 reviews)
"Great place and location."
United States
Matt M.
$227 nightly
The price is $259
Oct 25 - Oct 26
Total with taxes and fees
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
A two-story house with a porch, a covered front entrance, and a well-maintained lawn.

11. 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.
$227 nightly
The price is $257
Oct 26 - Oct 27
Total with taxes and fees
Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks
A living room with a sofa, yellow armchairs, a coffee table, and a TV.

12. 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
$307 nightly
The price is $342
Oct 25 - Oct 26
Total with taxes and fees
The Barnhouse - Renovated Century-Old Barn , 2 Miles to Colgate
A grassy area with wooden chairs and a table, surrounded by trees and a river.

13. *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.
$454 nightly
The price is $518
Oct 25 - Oct 26
Total with taxes and fees
*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6
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.
$483 nightly
The price is $551
Oct 25 - Oct 26
Total with taxes and fees
Turtle Cove*ON Oaks Creek!*Fish&Swim!
Two wooden crates stacked against a wall, one with a 'NY' logo and the other with a 'BILLS' logo.

15. *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.
$429 nightly
The price is $489
Nov 1 - Nov 2
Total with taxes and fees
*Oaks Creek Manor*ON the Creek*Sleep7*4.6Miles-HOF
A wooden deck with two chairs, a table, and an open book, overlooking a forested landscape.

16. Private Cabin Near Cooperstown All Star Village - 14 Acres, Views & Guest House

Private Cabin Near Cooperstown All Star Village - 14 Acres, Views & Guest House
Franklin
10.0 out of 10, Exceptional, (1 review)
"Clean house and host was in contact to make sure we had all we needed. Place was all set up for pets. Stayed with our son and daughter in law for a family weekend. It is up the mountain some. It does have a steeper driveway. Son and daughter in law enjoyed the screened in balcony to watch sunrise over the mountain in the morning."
United States
Denise W.
$474 nightly
The price is $522
Oct 27 - Oct 28
Total with taxes and fees
Private Cabin Near Cooperstown All Star Village - 14 Acres, Views & Guest House
A living room with a dining table, sofa, and a flat-screen TV mounted on the wall.

17. Hawthorne Suite at The Grove on Lake Moraine

Hawthorne Suite at The Grove on Lake Moraine
Hamilton
$329 nightly
The price is $349
Oct 25 - Oct 26
Total with taxes and fees
Hawthorne Suite at The Grove on Lake Moraine
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
$425 nightly
The price is $485
Oct 25 - Oct 26
Total with taxes and fees
1st Class Rentals Cooperstown New 3 Bedroom House
A wooden deck leading to a house with a view of the lake, kayaks, and a red umbrella.

19. 5 Min to Colgate, Sleeps 8, Welcome Wine

5 Min to Colgate, Sleeps 8, Welcome Wine
Hamilton
10.0 out of 10, Exceptional, (10 reviews)
"Christian was a wonderful host and we enjoyed our visit. Great location and wonderful view of the lake."
United States
Eileen B.
$372 nightly
The price is $385
Nov 16 - Nov 17
Total with taxes and fees
5 Min to Colgate, Sleeps 8, Welcome Wine
A spacious living area with a white sofa, wooden flooring, and a staircase leading to an upper level.

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

The Away Game, A home run for baseball families
Portlandville
$387 nightly
The price is $441
Oct 31 - Nov 1
Total with taxes and fees
The Away Game, A home run for baseball families
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 Railroad Inn

The Railroad Inn

10/10 Excellent
"We rented a suite with a loft, and it was perfect for our family. Clean comfortable, charming hotel. Easy walking distance to the Baseball Museum and downtown shops, pretty country, charming town. Would recommend the Railway Inn to anybody."
Kathy 2-night trip
Posted 6 hours ago
The Railroad Inn

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pittsfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $259 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.