Pittsfield Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Pittsfield

Jeannies Dream Motel
Exterior

Jeannies Dream Motel

2.0 star property
5.8 out of 10, (21)
"Perfect little spot to stay while working in the area! Great price and the room was exactly what we needed."
The price is ￥10,192
￥14,734 total
includes taxes & fees
Sep 12 - Sep 13
Jeannies Dream Motel
Located in Oneonta & Minutes from Cooperstown -- Perfect for Baseball Season!
Fridge, microwave, oven, stovetop

Located in Oneonta & Minutes from Cooperstown -- Perfect for Baseball Season!

9.8 out of 10, Exceptional, (30)
"Great property, and great host!"
Located in Oneonta & Minutes from Cooperstown -- Perfect for Baseball Season!
Charming Campsite in Hartwick, NY few miles from Cooperstown & area attractions
Outdoor dining

Charming Campsite in Hartwick, NY few miles from Cooperstown & area attractions

The price is ￥19,247
￥25,317 total
includes taxes & fees
Sep 5 - Sep 6
Charming Campsite in Hartwick, NY few miles from Cooperstown & area attractions
Longview Cottage with views to compliment its name and close to cooperstown
Property grounds

Longview Cottage with views to compliment its name and close to cooperstown

9.8 out of 10, Exceptional, (221)
"Amazing place to stay lived up to its name for sure"
Longview Cottage with views to compliment its name and close to cooperstown
Sunrise Lodge at Mt. Waiontha: An Outdoor Experience
Outdoor dining

Sunrise Lodge at Mt. Waiontha: An Outdoor Experience

10.0 out of 10, Exceptional, (74)
"We stayed here for a few days while our son competed at Cooperstown and it was a great location and space for our family."
Sunrise Lodge at Mt. Waiontha: An Outdoor Experience
Lakefront Home With Island View
Exterior

Lakefront Home With Island View

10.0 out of 10, Exceptional, (52)
"The cottage was excellent - clean, well appointed, with a beautiful view. "
Lakefront Home With Island View
Tiny house, loft bedroom, near the river, Cooperstown and Baseball hall of fame
2 bedrooms, iron/ironing board, WiFi, bed sheets

Tiny house, loft bedroom, near the river, Cooperstown and Baseball hall of fame

10.0 out of 10, Exceptional, (37)
"The location of the property is perfect for a trip to Cooperstown. We also drove up to the Adirondacks, which was a little over an hour, but still close enough if you're exploring the southern part of the park. Plenty of room to play catch with our dog and overall very comfortable. "
Tiny house, loft bedroom, near the river, Cooperstown and Baseball hall of fame
Cooperstown Dreams Park and Baseball Hall of Fame are 3 miles away!
Interior

Cooperstown Dreams Park and Baseball Hall of Fame are 3 miles away!

10.0 out of 10, Exceptional, (39)
"Stayed for baseball tournament. Easy to get to and beautiful location."
Cooperstown Dreams Park and Baseball Hall of Fame are 3 miles away!
StarField Cottage...The Perfect Cooperstown Dreams Park Getaway!
Dining

StarField Cottage...The Perfect Cooperstown Dreams Park Getaway!

9.8 out of 10, Exceptional, (79)
"The host and his dog, Shoog, are very friendly and helpful! The cottage was clean and well stocked. Cottage is close Cooperstown and the area is very nice."
StarField Cottage...The Perfect Cooperstown Dreams Park Getaway!
Cozy studio with WiFi in charming Cooperstown
Exterior

Cozy studio with WiFi in charming Cooperstown

8.8 out of 10, Excellent, (3)
"Beautiful property. Cozy unit, bigger than it looks from the pictures."
Cozy studio with WiFi in charming Cooperstown
Breweries! Cross the road to Northway Brewing or stroll to Brewery Ommegang.
Beach

Breweries! Cross the road to Northway Brewing or stroll to Brewery Ommegang.

10.0 out of 10, Exceptional, (61)
"Have stayed here before with some family friends, and will continue to rent it every year. Plenty of personal space, but large group space as well. This house is perfect, and great location in cooperstown. "
Breweries! Cross the road to Northway Brewing or stroll to Brewery Ommegang.
Cozy Cottage On The Susquehanna River
Terrace/patio

Cozy Cottage On The Susquehanna River

10.0 out of 10, Exceptional, (27)
"We really enjoyed our stay! Great location and a Beautiful home with a great view! Everything was perfect!"
Cozy Cottage On The Susquehanna River
Timber Lodge- New Lake House near Cooperstown, NY
4 bedrooms, free WiFi, bed sheets

Timber Lodge- New Lake House near Cooperstown, NY

10.0 out of 10, Exceptional, (28)
"Highly recommend. It's a beautiful house and we had a great stay!"
Timber Lodge- New Lake House near Cooperstown, NY
A Lakeview Paradise
Fridge, microwave, oven, dishwasher

A Lakeview Paradise

10.0 out of 10, Exceptional, (44)
"We came for our son’s baseball tournament at Dreams Park. The location of this property was great in terms of ease to get to everything. Place was spacious and comfortable and welcome basket was a nice added touch!"
A Lakeview Paradise
Lakefront Serenity in the Catskills near All Star Village
Terrace/patio

Lakefront Serenity in the Catskills near All Star Village

10.0 out of 10, Exceptional, (22)
"This my family’s second Memorial Day weekend in this house. We gather to play games and spend quality time together and this house is perfect for that. The weather was rainy so we couldn’t enjoy water activities on the pond but we still had a wonderful long weekend. We also love the proximity to Delhi and Cooperstown. "
Lakefront Serenity in the Catskills near All Star Village
Quiet 2-bedroom country cabin with scenic views 3 miles from Norwich NY.
Interior

Quiet 2-bedroom country cabin with scenic views 3 miles from Norwich NY.

10.0 out of 10, Exceptional, (3)
"Very nice the host was excellent!"
Quiet 2-bedroom country cabin with scenic views 3 miles from Norwich NY.
Cozy three bedroom cottage on Lake Canadarago
Outdoor dining

Cozy three bedroom cottage on Lake Canadarago

9.2 out of 10, Wonderful, (37)
"Clean, nice access to the lake."
Cozy three bedroom cottage on Lake Canadarago
BBQ Ready: Lakeside Milford Home w/ Paddleboat
Interior

BBQ Ready: Lakeside Milford Home w/ Paddleboat

9.8 out of 10, Exceptional, (36)
"This was my 5th stay. The host is a wonderful person, the property is amazing, its kid friendly, truely a rare gem. You wont be disappointed no matter what time of year you go!"
BBQ Ready: Lakeside Milford Home w/ Paddleboat
Cooperstown - Walk everywhere! Cute Apartment. Steps away from HOF and Main St.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (72)
"Great amenities for our week in Cooperstown!"
Cooperstown - Walk everywhere! Cute Apartment. Steps away from HOF and Main St.
Goodyear Lake waterfront home sleeps 13. Near Dreams Park, Cooperstown.
Exterior

Goodyear Lake waterfront home sleeps 13. Near Dreams Park, Cooperstown.

10.0 out of 10, Exceptional, (3)
"The house was great! Very clean, quiet, right on the lake with an amazing view. We loved the game room and the bunk room was awesome."
Goodyear Lake waterfront home sleeps 13. Near Dreams Park, Cooperstown.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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?

Sunrise Lodge at Mt. Waiontha: An Outdoor Experience: Visitors like this Pittsfield vacation home rental. It is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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.