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Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (1 review)
"Very attentive and hospitable hosts. Beautiful property. Don't think twice, just book it."
United States
Eric
$75 nightly
The price is $84
Sep 25 - Sep 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, (84 reviews)
"This is a great property! Everything was as described in the listing. We thought it was even better. Plenty of room and very welcoming. We felt like it was home. Our host was very accommodating."
United States
Susan W.
$457 nightly
The price is $521
Oct 8 - Oct 9
Total with taxes and fees
Cooperstown All Star Village, or Cooperstown Dreams Park or Oneonta area
A hallway with white walls, a wooden staircase, and a chandelier.

3. *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.
$543 nightly
The price is $619
Sep 27 - Sep 28
Total with taxes and fees
*NEW*Hops House-Sleeps10-8Mi.toCDP&15Mi.toASV
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.
$800 nightly
The price is $912
Sep 27 - Sep 28
Total with taxes and fees
Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP
A compact kitchen with a wooden countertop, a sink, and a small dining area with a hanging rope swing.

5. Airstream on Turkey Hill *1* - Glamping in Ctown

Airstream on Turkey Hill *1* - Glamping in Ctown
Hartwick
8.8 out of 10, Excellent, (5 reviews)
"Unique, fun stay in a nicely accommodated Air Stream!"
United States
Guido S.
$268 nightly
The price is $306
Sep 27 - Sep 28
Total with taxes and fees
Airstream on Turkey Hill *1* - Glamping in Ctown
A compact kitchenette with a wooden countertop, two stainless steel sinks, and a hanging plant.

6. Airstream at Turkey Hill *2* Glamping in CTown!

Airstream at Turkey Hill *2* Glamping in CTown!
Hartwick
10.0 out of 10, Exceptional, (3 reviews)
"It was a pleasure to stay in the Airstream with absolute quiet and peaceful surrounding. Never slept better. Samantha responded immediately to requests. Loved it."
United States
Rochelle H.
$268 nightly
The price is $306
Sep 27 - Sep 28
Total with taxes and fees
Airstream at Turkey Hill *2* Glamping in CTown!
A narrow stone staircase leading to a door, flanked by walls with climbing plants and potted plants.

7. 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, (29 reviews)
"Pizza place next door is awesome! Great location"
United States
robert L.
$193 nightly
The price is $220
Sep 27 - Sep 28
Total with taxes and fees
1st Class Rentals Munson Manor VI at Chestnut 2nd Floor
A two-story red building with a balcony, surrounded by trees and a grassy yard.

8. 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.
$360 nightly
The price is $410
Sep 27 - Sep 28
Total with taxes and fees
Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool
A modern living room with a large sofa, a flat-screen TV, and a bookshelf.

9. 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.
$486 nightly
The price is $554
Oct 1 - Oct 2
Total with taxes and fees
Turtle Cove*ON Oaks Creek!*Fish&Swim!
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
8.8 out of 10, Excellent, (6 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.
$457 nightly
The price is $521
Sep 28 - Sep 29
Total with taxes and fees
*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6
A staircase with white railings and wooden steps leading to a second floor.

11. 1st Class Rentals The Thurman Munson House

1st Class Rentals The Thurman Munson House
Cooperstown
10.0 out of 10, Exceptional, (63 reviews)
"Awesome quaint home"
United States
Kim B.
$285 nightly
The price is $325
Sep 27 - Sep 28
Total with taxes and fees
1st Class Rentals The Thurman Munson House
A compact kitchen with wooden cabinets, a white refrigerator, a microwave, and a dining area with a table and chairs.

12. Dreams Park/All Star Getaway! Cottage #3- Old World Village

Dreams Park/All Star Getaway! Cottage #3- Old World Village
Maryland
10.0 out of 10, Exceptional, (40 reviews)
"Very comfortable stay"
United States
Christine R.
$201 nightly
The price is $229
Oct 1 - Oct 2
Total with taxes and fees
Dreams Park/All Star Getaway! Cottage #3- Old World Village
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a ceiling fan.

13. Pine Hollow Hideout: Access to Canadarago Lake

Pine Hollow Hideout: Access to Canadarago Lake
Richfield Springs
$462 nightly
The price is $527
Sep 27 - Sep 28
Total with taxes and fees
Pine Hollow Hideout: Access to Canadarago Lake
A deck with outdoor furniture and a covered table.

14. 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, (194 reviews)
"This was a beautiful place to stay. Only minutes from the heart of Cooperstown. Highly recommended!"
United States
Kevin M.
$171 nightly
The price is $195
Oct 3 - Oct 4
Total with taxes and fees
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
A living room with a sofa, yellow armchairs, a coffee table, and a TV.

15. 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, (32 reviews)
$307 nightly
The price is $342
Sep 28 - Sep 29
Total with taxes and fees
The Barnhouse - Renovated Century-Old Barn , 2 Miles to Colgate
A two-story house with a porch, a covered front entrance, and a well-maintained lawn.

16. 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, (68 reviews)
"Great place"
United States
Dorothy M.
$227 nightly
The price is $257
Sep 28 - Sep 29
Total with taxes and fees
Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks
A red barn on a grassy hill with a pond in the foreground.

17. Unique Farm Stay -Close to Colgate University, Hamilton College, Bouckville

Unique Farm Stay -Close to Colgate University, Hamilton College, Bouckville
Hubbardsville
10.0 out of 10, Exceptional, (1 review)
"We thoroughly enjoyed our stay."
United States
Suzann F.
$406 nightly
The price is $459
Oct 2 - Oct 3
Total with taxes and fees
Unique Farm Stay -Close to Colgate University, Hamilton College, Bouckville
A swimming pool with lounge chairs and umbrellas, surrounded by a fenced yard with a house in the background.

18. 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)
"This is a Cooperstown gem! Sandra is a great host and very responsive. As for the property, a great location and short ride from Dreams Park and downtown Cooperstown. Plenty of space for a few families and the adjacent cottage was an added bonus that let us spread out a little more. Can't forget the pool out back and the woods all around. Highly recommend to all looking!"
United States
Thomas F.
$988 nightly
The price is $1,005
Sep 28 - Sep 29
Total with taxes and fees
Private Pool Oasis - heated Memorial day to Labor day/ Minutes from Dreams Park
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
$425 nightly
The price is $485
Sep 27 - Sep 28
Total with taxes and fees
1st Class Rentals Cooperstown New 3 Bedroom 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

Lake View Motel

Lake View Motel

8/10 Good
"The property is closing for renovations at the end of the season. I understood this when booking the property so I expected some issues. It was a bit dilapidated but you do not renovate a perfect property. Therefore I have NO complaints. The view was awesome. The staff was fabulous (esp. Doreen in reservations and Willis at the front desk). I hope to visit again once renovations are completed."
Mary 1-night trip
Posted 4 hours ago
Lake View Motel

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 $84 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. Unadilla Motocross and Cooperstown All Star Village Fields 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.