Pittsfield Vacation Rentals

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Our top choices for Pittsfield vacation rentals

Property grounds
✨ Lakeside Reflections

Cottage in Oxford

✨ Lakeside Reflections
10.0 out of 10, Exceptional, (17)
"My husband and I had a great time at Lakeside Reflections. It was super relaxing and had everything we needed. The weather was fabulous - got to go kayaking every day and just enjoy the wonderful view! "
United States
Heidi R.
$159 nightly
The price is $178
Dec 17 - Dec 18
Total with taxes and fees
✨ Lakeside Reflections
Property grounds
⭐️Wildflower Country Cottage

Cottage in Oxford

⭐️Wildflower Country Cottage
10.0 out of 10, Exceptional, (75)
"Cute place with lovely grounds. Very relaxing. We enjoyed our stay. "
United States
Danielle M.
$121 nightly
The price is $136
Dec 16 - Dec 17
Total with taxes and fees
⭐️Wildflower Country Cottage
Smart TV
The Barnhouse - Country Charm 2 miles from Colgate, renovated century-old barn

Vacation Home in Hamilton

The Barnhouse - Country Charm 2 miles from Colgate, renovated century-old barn
10.0 out of 10, Exceptional, (18)
"What a great place to stay near Colgate. Looking forwards to our next stay!"
United States
Todd S.
$254 nightly
The price is $284
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Barnhouse - Country Charm 2 miles from Colgate, renovated century-old barn
Outdoor dining
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area

Vacation Home in Cooperstown

Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
10.0 out of 10, Exceptional, (164)
"Loved the place, super clean, close to the locations we wanted to visit (hall of fame, few breweries, good restaurants, trails). "
United States
Hector F.
$205 nightly
The price is $234
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
Property grounds
Sunset Cottage #3, Lake Moraine Home #3 Near Colgate University

Vacation Home in Hamilton

Sunset Cottage #3, Lake Moraine Home #3 Near Colgate University
10.0 out of 10, Exceptional, (27)
"Great location close to Colgate. "
United States
Diane B.
$393 nightly
The price is $406
Dec 16 - Dec 17
Total with taxes and fees
Sunset Cottage #3, Lake Moraine Home #3 Near Colgate University
Cabin, Golf View | 1 bedroom, free WiFi
Stonegate Golf Cabins

Cabin in West Edmeston

Stonegate Golf Cabins
2.0 star property
$500 nightly
The price is $570
Dec 16 - Dec 17
Total with taxes and fees
Stonegate Golf Cabins
Exterior
Spacious and comfortable, king bed and double futon sofa, kitchen, near 7 Oaks

Apartment in Hamilton

Spacious and comfortable, king bed and double futon sofa, kitchen, near 7 Oaks
10.0 out of 10, Exceptional, (60)
"Perfect once again. Have stayed here several times and everything is perfect. "
United States
Rebecca J.
$233 nightly
The price is $260
Dec 16 - Dec 17
Total with taxes and fees
Spacious and comfortable, king bed and double futon sofa, kitchen, near 7 Oaks
Smart TV, books, printers
3 miles to B Ball, 5 min walk to Downtown! Stocked Kitchen, AC, WiFi, W/D

Apartment in Downtown Oneonta

3 miles to B Ball, 5 min walk to Downtown! Stocked Kitchen, AC, WiFi, W/D
9.4 out of 10, Exceptional, (3)
"The unit had everything we needed for our stay. Appreciated the nearby recommendations from Jeremy."
United States
Darren M.
$267 nightly
The price is $304
Dec 16 - Dec 17
Total with taxes and fees
3 miles to B Ball, 5 min walk to Downtown! Stocked Kitchen, AC, WiFi, W/D
Exterior
Coolis' Country Corner

Apartment in Richfield Springs

Coolis' Country Corner
10.0 out of 10, Exceptional, (155)
"We had a very nice stay!"
United States
Cynthia D.
$229 nightly
The price is $248
Dec 16 - Dec 17
Total with taxes and fees
Coolis' Country Corner
Fridge, microwave, oven, stovetop
Are you looking for the best place to stay? You found it!

Apartment in West End

Are you looking for the best place to stay? You found it!
9.6 out of 10, Exceptional, (26)
"The house was clean and we had everything we needed on our stay we loved the rain shower heads too"
United States
Michael
$223 nightly
The price is $254
Dec 16 - Dec 17
Total with taxes and fees
Are you looking for the best place to stay? You found it!
Exterior detail
1st Class Rentals - 3 Bedroom Apartment downtown Oneonta

Apartment in Downtown Oneonta

1st Class Rentals - 3 Bedroom Apartment downtown Oneonta
9.8 out of 10, Exceptional, (13)
"Great location. Less than 10 minutes from All Star Village and a 2 block walk to Main St. Dave is very responsive and a great host. "
United States
Dave D.
$205 nightly
The price is $234
Dec 16 - Dec 17
Total with taxes and fees
1st Class Rentals - 3 Bedroom Apartment downtown Oneonta
Property grounds
*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6

Vacation Home in Fly Creek

*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6
8.0 out of 10, Very Good, (4)
"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.
$389 nightly
The price is $443
Dec 16 - Dec 17
Total with taxes and fees
*Oaks Creek Cottage*ON the Creek*3bd 2bath Sleeps6
Exterior
1st Class Rentals Cooperstown New 3 Bedroom House

Vacation Home in Cooperstown

1st Class Rentals Cooperstown New 3 Bedroom House
3.5 star property
10.0 out of 10, Exceptional, (1)
"Fantastic place! Everything as advertised. "
United States
Douglas
$425 nightly
The price is $485
Dec 16 - Dec 17
Total with taxes and fees
1st Class Rentals Cooperstown New 3 Bedroom House
Exterior
Chic Mid-Century Apartment at Otego House

Apartment in Otego

Chic Mid-Century Apartment at Otego House
$326 nightly
The price is $372
Dec 16 - Dec 17
Total with taxes and fees
Chic Mid-Century Apartment at Otego House
Exterior
Vacation Like Gatsby on This Historic 500-Acre Fairy Tale Estate

Vacation Home in Gilbertsville

Vacation Like Gatsby on This Historic 500-Acre Fairy Tale Estate
9.2 out of 10, Wonderful, (36)
"Beautiful location"
United States
Anonymous traveler
$1,708 nightly
The price is $1,947
Dec 18 - Dec 19
Total with taxes and fees
Vacation Like Gatsby on This Historic 500-Acre Fairy Tale Estate
Fridge, microwave, oven, stovetop
Scenic CountryHouse on 122 acres

Vacation Home in South New Berlin

Scenic CountryHouse on 122 acres
10.0 out of 10, Exceptional, (1)
"Pulled in a 1am, slept and out again by 9am. Beds comfy, everyone had fresh linens, very clean. Only little worry was getting out of the parking area with trucks and trailers. The road isn’t busy, but people fly. "
United States
Jodi S.
$775 nightly
The price is $867
Dec 16 - Dec 17
Total with taxes and fees
Scenic CountryHouse on 122 acres
Fridge, microwave, oven, stovetop
Hamilton Home #4, Lake Moraine Home #4 Near Colgate University

Vacation Home in Hamilton

Hamilton Home #4, Lake Moraine Home #4 Near Colgate University
10.0 out of 10, Exceptional, (8)
"Clean, well appointed, beautiful views, and kayaks and paddle board were great! Would love to stay again!"
United States
Linda O.
$495 nightly
The price is $513
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hamilton Home #4, Lake Moraine Home #4 Near Colgate University
Fridge, microwave, oven, stovetop
Cozy Home Heart of the Village Near Golf & Colgate

Vacation Home in Hamilton

Cozy Home Heart of the Village Near Golf & Colgate
9.6 out of 10, Exceptional, (22)
"We were very happy with all aspects of our stay on the property."
United States
Christopher D.
$2,576 nightly
The price is $2,692
Dec 17 - Dec 18
Total with taxes and fees
Cozy Home Heart of the Village Near Golf & Colgate
Smart TV
Cozy Mountain Retreat – Quiet, Scenic, & 7 Miles to Cooperstown All-Star Village

Apartment in Oneonta

Cozy Mountain Retreat – Quiet, Scenic, & 7 Miles to Cooperstown All-Star Village
2.0 star property
$246 nightly
The price is $271
Dec 16 - Dec 17
Total with taxes and fees
Cozy Mountain Retreat – Quiet, Scenic, & 7 Miles to Cooperstown All-Star Village
Fridge, oven, stovetop, coffee/tea maker
CUTE & COZY TOO

Vacation Home in Hamilton

CUTE & COZY TOO
$396 nightly
The price is $444
Dec 16 - Dec 17
Total with taxes and fees
CUTE & COZY TOO
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

Best Western Cooperstown Inn & Suites

Best Western Cooperstown Inn & Suites

10/10 Excellent
"Clean comfortable most awesome bed and bath. I needed a good night’s sleep and this really helped as I couldn’t travel home because of the horrible weather! "
Melissa 1-night trip
Posted 5 days ago
Best Western Cooperstown Inn & Suites

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?

Longview Cottage with views to compliment its name and close to cooperstown: You might want to consider this vacation rental near Pittsfield, which is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a hot tub.

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.