Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
9.2 out of 10, Wonderful, (5 reviews)
"Very attentive and hospitable hosts. Beautiful property. Don't think twice, just book it."
United States
Eric
$86 nightly
The price is $96
Nov 11 - Nov 12
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)
"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.
$423 nightly
The price is $482
Nov 10 - Nov 11
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
Nov 10 - Nov 11
Total with taxes and fees
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
$344 nightly
The price is $392
Nov 10 - Nov 11
Total with taxes and fees
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.
$165 nightly
The price is $188
Nov 9 - Nov 10
Total with taxes and fees
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.
$400 nightly
The price is $456
Nov 9 - Nov 10
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.

7. 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.
$275 nightly
The price is $314
Nov 9 - Nov 10
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.

8. 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
$120 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
Cozy 1-bedroom hotel room, Hamilton - 318 Chenango
A two-story house with a porch, a covered front entrance, and a well-maintained lawn.

9. 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.
$212 nightly
The price is $240
Nov 17 - Nov 18
Total with taxes and fees
Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks
A house with a black front door, green shutters, and a small porch with potted plants.

10. 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.
$317 nightly
The price is $361
Nov 9 - Nov 10
Total with taxes and fees
Cooperstown - Walk everywhere! Cute Apartment. Steps away from HOF and Main St.
A deck with outdoor furniture and a covered table.

11. 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, (203 reviews)
"Great place and location."
United States
Matt M.
$187 nightly
The price is $213
Nov 15 - Nov 16
Total with taxes and fees
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.

12. 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.
$275 nightly
The price is $314
Nov 9 - Nov 10
Total with taxes and fees
1st Class Rentals Munson Manor VII at Watkins Avenue
A compact RV kitchen with a microwave, sink, and stove, a television mounted above the counter, and a bed with Halloween-themed bedding.

13. 1-bedroom recreational vehicle in lovely Smyrna with AC

1-bedroom recreational vehicle in lovely Smyrna with AC
Smyrna
$149 nightly
The price is $167
Nov 9 - Nov 10
Total with taxes and fees
1-bedroom recreational vehicle in lovely Smyrna with AC
A living room with a sofa, yellow armchairs, a coffee table, and a TV.

14. 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
$305 nightly
The price is $340
Nov 9 - Nov 10
Total with taxes and fees
The Barnhouse - Renovated Century-Old Barn , 2 Miles to Colgate
A modern kitchen with a central island, stainless steel appliances, and a wooden staircase.

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

The Away Game, A home run for baseball families
Portlandville
$359 nightly
The price is $409
Nov 15 - Nov 16
Total with taxes and fees
The Away Game, A home run for baseball families
A room with two beds, wooden walls, a window with curtains, and a nightstand with lamps.

16. Cozy 1BR hotel room, Hamilton - #340 Dekonawada

Cozy 1BR hotel room, Hamilton - #340 Dekonawada
Hamilton
$120 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
Cozy 1BR hotel room, Hamilton - #340 Dekonawada
A room with two beds, a nightstand with a lamp, and a window with blinds.

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

Cozy 1-bedroom hotel room, Hamilton - #350 Oneida
Hamilton
$120 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
Cozy 1-bedroom hotel room, Hamilton - #350 Oneida
A two-story house with a wooden staircase and a porch.

18. Cozy 1BR hotel room, Hamilton - #347 Onondaga

Cozy 1BR hotel room, Hamilton - #347 Onondaga
Hamilton
$120 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
Cozy 1BR hotel room, Hamilton - #347 Onondaga
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.
$120 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
Cozy 1BR hotel room, Hamilton - #335 Endawonnda
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.
$1,002 nightly
The price is $1,141
Nov 9 - Nov 10
Total with taxes and fees
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

An outdoor seating area with a stone fire feature, wicker furniture, and a building with large windows in the background.
Holiday Inn Express Oneonta by IHG

Holiday Inn Express Oneonta by IHG

Holiday Inn Express Oneonta by IHG
Southside

10/10 Excellent

Was there for 5 night stay while our son played at All Star Village. Hotel was extremely clean throughout and the staff was friendly and nice. It was a perfect stay!
United States
Robert
Reviewed August 15, 2022
Holiday Inn Express Oneonta by IHG

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 $408 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.