Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Fridge, microwave, oven, stovetop
Name: Hill Crest<br>Private Setting. Heated Pool. 4 Minutes to Dreams Park
Name: Hill Crest<br>Private Setting. Heated Pool. 4 Minutes to Dreams Park
9.8 out of 10, Exceptional, (18)
"Everything was great. Only 10 mins from Dreams Park. Great pool for the kids. Very clean and everything worked well. Highly recommend. "
United States
Sagar
Name: Hill Crest<br>Private Setting. Heated Pool. 4 Minutes to Dreams Park
Smart TV
Name: Hill Side<br>Country Setting. Heated Pool. 4 minutes to Dreams Park.
Name: Hill Side<br>Country Setting. Heated Pool. 4 minutes to Dreams Park.
9.8 out of 10, Exceptional, (22)
"The property was amazingly private and perfect for our stay in Cooperstown. The hosts were very helpful and responded quickly to our inquiries. I would definitely recommend this property for anyone travelling to Cooperstown. "
United States
Mike L.
Name: Hill Side<br>Country Setting. Heated Pool. 4 minutes to Dreams Park.
Property grounds
The Monarch - Private Setting, Heated Pool, 6 Bedroom, New Build. 6 min to CDP
The Monarch - Private Setting, Heated Pool, 6 Bedroom, New Build. 6 min to CDP
2.0 star property
10.0 out of 10, Exceptional, (7)
"Enjoyed our stay! Owners were great and a perfect location for Cooperstown Dream Park. "
United States
Emilie W.
The Monarch - Private Setting, Heated Pool, 6 Bedroom, New Build. 6 min to CDP
Exterior
Jeannies Dream Motel
Jeannies Dream Motel
2.0 star property
5.2 out of 10, (25)
"Perfect little spot to stay while working in the area! Great price and the room was exactly what we needed."
United States
Christian
$100 nightly
The price is $108
Oct 29 - Oct 30
Total with taxes and fees
Jeannies Dream Motel
Property grounds
Longview Cottage with views to compliment its name and close to cooperstown
Longview Cottage with views to compliment its name and close to cooperstown
9.8 out of 10, Exceptional, (225)
"Amazing place to stay lived up to its name for sure"
United States
Michael
Longview Cottage with views to compliment its name and close to cooperstown
Outdoor pool, a heated pool
Name: Three Gables <br>Private Setting. Heated Pool. 4 Minutes to Dreams Park.
Name: Three Gables <br>Private Setting. Heated Pool. 4 Minutes to Dreams Park.
10.0 out of 10, Exceptional, (22)
"The property was beautiful, and the hosts were very communicative. If you have to watch your kid play endless baseball there’s no better place to come back to rest and unwind."
United States
Anna C.
Name: Three Gables <br>Private Setting. Heated Pool. 4 Minutes to Dreams Park.
Outdoor dining
3 min. to Dreams Park, 33 ft. Long Heated Pool, Clean and Updated. Fun & Private
3 min. to Dreams Park, 33 ft. Long Heated Pool, Clean and Updated. Fun & Private
10.0 out of 10, Exceptional, (14)
"Extremely enjoyable stay and host is very nice"
United States
Sean P.
$2,739 nightly
The price is $3,122
Nov 17 - Nov 18
Total with taxes and fees
3 min. to Dreams Park, 33 ft. Long Heated Pool, Clean and Updated. Fun & Private
Interior
Toad Hall 1820s Historic Estate
Toad Hall 1820s Historic Estate
Toad Hall 1820s Historic Estate
Property grounds
Charming Full Bed & 2 Twin Bed cabin w/AC, Heat, WiFi in lovely Cooperstown,
Charming Full Bed & 2 Twin Bed cabin w/AC, Heat, WiFi in lovely Cooperstown,
10.0 out of 10, Exceptional, (13)
"Beautiful cabin and a great host "
United States
Dylan O.
Charming Full Bed & 2 Twin Bed cabin w/AC, Heat, WiFi in lovely Cooperstown,
Terrace/patio
Score a Home Run with Triple Play Hideaway – 2 Mins from Cooperstown Dreams Park
Score a Home Run with Triple Play Hideaway – 2 Mins from Cooperstown Dreams Park
10.0 out of 10, Exceptional, (21)
"The location is ideal for Dreams Park and it’s a great house."
United States
Aaron J.
Score a Home Run with Triple Play Hideaway – 2 Mins from Cooperstown Dreams Park
Terrace/patio
Cozy Cottage On The Susquehanna River
Cozy Cottage On The Susquehanna River
10.0 out of 10, Exceptional, (28)
"It was a great stay."
United States
Andrew L.
Cozy Cottage On The Susquehanna River
Outdoor dining
Cozy three bedroom cottage on Lake Canadarago
Cozy three bedroom cottage on Lake Canadarago
9.2 out of 10, Wonderful, (38)
"We were happy with our stay on the lake! There were plenty of options on site with two kayaks a canoe and a rowboat, plus a dock to help get on the water."
United States
Jason K.
Cozy three bedroom cottage on Lake Canadarago
Outdoor pool
Lovely 4 bedroom 3 bath farmhouse with pool, located in Cooperstown, NY
Lovely 4 bedroom 3 bath farmhouse with pool, located in Cooperstown, NY
9.8 out of 10, Exceptional, (18)
"Anita was awesome and the house was perfect for our family. Highlights include: less than 20 min from Dreams Park, kids loved the pool, nice to get away from the baseball chaos. We all loved living on a farm for 6 days, highly recommend this comfortable stay!"
United States
Justin P.
Lovely 4 bedroom 3 bath farmhouse with pool, located in Cooperstown, NY
Exterior
10min. to CDP -- "Resort-Like-Property" -- Heated Pool -- 6min. to Coop-Village
10min. to CDP -- "Resort-Like-Property" -- Heated Pool -- 6min. to Coop-Village
10.0 out of 10, Exceptional, (56)
"Beautiful property, recently updated, responsive host who gives great recommendations, heated pool, a perfect fall weekend!"
United States
Hillary S.
10min. to CDP -- "Resort-Like-Property" -- Heated Pool -- 6min. to Coop-Village
Dining
Destination, Overlooking Cooperstown, Large Grounds, 6.2 miles from Dreams Park.
Destination, Overlooking Cooperstown, Large Grounds, 6.2 miles from Dreams Park.
10.0 out of 10, Exceptional, (63)
"Great property "
United States
joseph
Destination, Overlooking Cooperstown, Large Grounds, 6.2 miles from Dreams Park.
Private kitchen
Lovely Private Setting
Lovely Private Setting
10.0 out of 10, Exceptional, (28)
"Property manager was very communicative and helped to make our stay a great experience "
United States
Gary M.
Lovely Private Setting
Property grounds
Beautiful Private Cooperstown Apartment Close To Dreams Park & All Attractions!
Beautiful Private Cooperstown Apartment Close To Dreams Park & All Attractions!
10.0 out of 10, Exceptional, (32)
"Perfect for what we needed. "
United States
Adam F.
Beautiful Private Cooperstown Apartment Close To Dreams Park & All Attractions!
Exterior
Apartment in Milford. Close to Dreams Park and National Baseball Hall of fame.
Apartment in Milford. Close to Dreams Park and National Baseball Hall of fame.
6.8 out of 10, (5)
"Positives: quiet little town, nice relaxing front porch, 5 min drive to Dreams Park baseball, plenty of towels and coffee supplies, owner was very responsive Negatives: up a steep set of stairs (we didn’t mind), laundry is outside around back and coin operated, kitchen is very minimal We would absolutely stay here again"
United States
Margaret D.
Apartment in Milford. Close to Dreams Park and National Baseball Hall of fame.
Property grounds
Grand Slam - Lake House Cooperstown Dreams Park
Grand Slam - Lake House Cooperstown Dreams Park
10.0 out of 10, Exceptional, (32)
"Perfect location to enjoy all that Cooperstown has to offer. We enjoyed spending hours at the lake on the dedicated dock in between baseball games at Dreams Park and dining downtown. Highly recommend!"
United States
Anthony G.
Grand Slam - Lake House Cooperstown Dreams Park
Outdoor dining
Sunrise Lodge at Mt. Waiontha: An Outdoor Experience
Sunrise Lodge at Mt. Waiontha: An Outdoor Experience
10.0 out of 10, Exceptional, (76)
"Stayed here while my son played at Cooperstown. Wonderful place and great host. "
United States
Cory F.
Sunrise Lodge at Mt. Waiontha: An Outdoor Experience
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 House

Lake House

10/10 Excellent
"very friendly staff room clean really nice setting in lake. also pet friendly. "
Wayne 1-night trip
Posted 13 hours ago
Lake House

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 $108 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.

Explore a world of travel with Expedia

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?

Name: Hill Crest
Private Setting. Heated Pool. 4 Minutes to Dreams Park : Visitors like this Pittsfield vacation home rental. It offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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.