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Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Pittsfield vacation rentals

Fridge, microwave, oven, stovetop

⭐️Wildflower Country Cottage

⭐️Wildflower Country Cottage
Oxford
10.0 out of 10, Exceptional, (79 reviews)
"Divine Place!"
United States
Cynthia W.
The price is ￥23,802
￥38,035 total
includes taxes & fees
Jun 21 - Jun 22
⭐️Wildflower Country Cottage
Terrace/patio

Indulge in our Forest Retreat

Indulge in our Forest Retreat
Otego
The price is ￥17,577
￥23,715 total
includes taxes & fees
Jun 25 - Jun 26
Indulge in our Forest Retreat
1 bedroom, WiFi

Airstream on Turkey Hill *1* - Glamping in Ctown

Airstream on Turkey Hill *1* - Glamping in Ctown
Hartwick
10.0 out of 10, Exceptional, (4 reviews)
"Unique, fun stay in a nicely accommodated Air Stream!"
United States
Guido S.
The price is ￥20,158
￥54,600 total
includes taxes & fees
Jun 28 - Jun 29
Airstream on Turkey Hill *1* - Glamping in Ctown
Smart TV, fireplace, books

Spacious Private Guest Suite near Colgate

Spacious Private Guest Suite near Colgate
Earlville
9.8 out of 10, Exceptional, (15 reviews)
"Sweet houseTotally comfortable Delicious scones for breakfast Would return "
United States
Kirsten B.
The price is ￥40,315
￥56,893 total
includes taxes & fees
Jul 6 - Jul 7
Spacious Private Guest Suite near Colgate
Exterior

✨ Lakeside Reflections

✨ Lakeside Reflections
Oxford
10.0 out of 10, Exceptional, (17 reviews)
"Very quiet and beautiful"
United States
Robin T.
The price is ￥23,221
￥39,192 total
includes taxes & fees
Jun 25 - Jun 26
✨ Lakeside Reflections
Smart TV

The Barnhouse - Country Charm 2 miles from Colgate, renovated century-old barn

The Barnhouse - Country Charm 2 miles from Colgate, renovated century-old barn
Hamilton
10.0 out of 10, Exceptional, (24 reviews)
"Awesome property! Perfect for Colgate visits. Will be booking again for sure."
United States
Jeremy
The price is ￥25,195
￥47,725 total
includes taxes & fees
Jul 8 - Jul 9
The Barnhouse - Country Charm 2 miles from Colgate, renovated century-old barn
Exterior

Spacious and comfortable, king bed and double futon sofa, kitchen, near 7 Oaks

Spacious and comfortable, king bed and double futon sofa, kitchen, near 7 Oaks
Hamilton
10.0 out of 10, Exceptional, (65 reviews)
"The apartment was clean, comfortable and had everything we needed."
United States
david e.
The price is ￥27,285
￥42,481 total
includes taxes & fees
Jun 23 - Jun 24
Spacious and comfortable, king bed and double futon sofa, kitchen, near 7 Oaks
Exterior detail

Warm & Cozy Studio Cabin — Cooperstown, NY

Warm & Cozy Studio Cabin — Cooperstown, NY
Cooperstown
9.0 out of 10, Wonderful, (6 reviews)
"Plenty of space, was close to the area I needed to be for the weekend."
United States
Ashley W.
The price is ￥48,378
￥104,971 total
includes taxes & fees
Jun 21 - Jun 22
Warm & Cozy Studio Cabin — Cooperstown, NY
Exterior

Snowshoe Cabin across from Upper Lake Moraine and close to Colgate!

Snowshoe Cabin across from Upper Lake Moraine and close to Colgate!
Hamilton
10.0 out of 10, Exceptional, (1 review)
"This is a lovely little cabin. It was perfect for our trip. We saw a herd of sheep wandering outside. Thank you for a very nice stay!"
United States
Brian M.
The price is ￥27,866
￥66,609 total
includes taxes & fees
Jun 30 - Jul 1
Snowshoe Cabin across from Upper Lake Moraine and close to Colgate!
Living area

2 bedroom camper/trailer 3.5 miles from All Star Village on a very quiet road.

2 bedroom camper/trailer 3.5 miles from All Star Village on a very quiet road.
Oneonta
The price is ￥28,882
￥36,785 total
includes taxes & fees
Jul 7 - Jul 8
2 bedroom camper/trailer 3.5 miles from All Star Village on a very quiet road.
Interior

Romantic Vacation Rental with Lake Views near Cooperstown, New York

Romantic Vacation Rental with Lake Views near Cooperstown, New York
Richfield Springs
The price is ￥31,349
￥40,259 total
includes taxes & fees
Jun 21 - Jun 22
Romantic Vacation Rental with Lake Views near Cooperstown, New York
Exterior

Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool

Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool
Cooperstown
10.0 out of 10, Exceptional, (2 reviews)
"Was exactly what we were looking for in a short 2 night stay."
United States
Dustin G.
The price is ￥52,410
￥110,302 total
includes taxes & fees
Jun 21 - Jun 22
Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool
Outdoor dining

Private Cabin Near Cooperstown All Star Village - 14 Acres, Views & Guest House

Private Cabin Near Cooperstown All Star Village - 14 Acres, Views & Guest House
Franklin
The price is ￥60,364
￥96,201 total
includes taxes & fees
Jul 1 - Jul 2
Private Cabin Near Cooperstown All Star Village - 14 Acres, Views & Guest House
Property grounds

"Keep Life Simple" -Blue Door- Basement Apartment

"Keep Life Simple" -Blue Door- Basement Apartment
Cooperstown
9.0 out of 10, Wonderful, (29 reviews)
"A perfect place to stay if you're in town for Cooperstown tournaments or need a break from city life. Pet friendly, very quiet and serene with a beautiful backdrop of gardens, flowers and mountains. The wifi signal was strong and definitely the icing on the cake, in case you need to work remotely. Would definitely stay again."
United States
Grace O.
The price is ￥29,027
￥58,828 total
includes taxes & fees
Jun 22 - Jun 23
"Keep Life Simple" -Blue Door- Basement Apartment
Property grounds

Lake Cottage · Welcome Wine · 5 min Colgate

Lake Cottage · Welcome Wine · 5 min Colgate
Madison
10.0 out of 10, Exceptional, (1 review)
The price is ￥32,897
￥66,297 total
includes taxes & fees
Jun 21 - Jun 22
Lake Cottage · Welcome Wine · 5 min Colgate
Fridge, microwave, oven, stovetop

Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP

Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP
Hartwick
The price is ￥49,991
￥159,570 total
includes taxes & fees
Jun 24 - Jun 25
Parkside Manor*NEW* - Walk to Husky Park!8Mi.toCDP
Exterior

Lake Cottage · Two Decks · 2 Baths · 5 min Colgate, Lake Moraine Home #3 Near Colgate University

Lake Cottage · Two Decks · 2 Baths · 5 min Colgate, Lake Moraine Home #3 Near Colgate University
Hamilton
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful communication with the host and a perfect stay."
Canada
Sheryl
The price is ￥40,476
￥76,579 total
includes taxes & fees
Jun 22 - Jun 23
Lake Cottage · Two Decks · 2 Baths · 5 min Colgate, Lake Moraine Home #3 Near Colgate University
Property grounds

Score The perfect Summer Winter getaway: Lakeside retreat for your winning team

Score The perfect Summer Winter getaway: Lakeside retreat for your winning team
Maryland
The price is ￥42,895
￥118,942 total
includes taxes & fees
Jun 23 - Jun 24
Score The perfect Summer Winter getaway: Lakeside retreat for your winning team
Interior

*Oaks Creek Manor*ON the Creek*Sleep7*4.6Miles-HOF

*Oaks Creek Manor*ON the Creek*Sleep7*4.6Miles-HOF
Fly Creek
10.0 out of 10, Exceptional, (1 review)
The price is ￥50,797
￥113,427 total
includes taxes & fees
Jun 21 - Jun 22
*Oaks Creek Manor*ON the Creek*Sleep7*4.6Miles-HOF
Dining

The Octagon - Historic Charm Meets Modern Comfort

The Octagon - Historic Charm Meets Modern Comfort
Maryland
10.0 out of 10, Exceptional, (2 reviews)
"Great place highly recommend"
United States
Santiago L.
The price is ￥56,441
￥125,009 total
includes taxes & fees
Jun 24 - Jun 25
The Octagon - Historic Charm Meets Modern Comfort
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

Holiday Inn Express Oneonta by IHG

Holiday Inn Express Oneonta by IHG

10/10 Excellent
"Rooms were kept clean on a regular basis without ever having to ask for housekeeping. Staff was friendly and jolly. Rooms were air conditioned kept very cool to sleep comfy at night. Can’t get better than free breakfast. I will stay here again no doubt."
Giovanni 8-night trip
Posted less than an hour ago
Holiday Inn Express Oneonta by IHG

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:

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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?

Charming Cooperstown country house with views of Lake Otsego: Visitors like this Pittsfield vacation home rental. It is located in a rural location and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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.