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Pittsfield Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Pittsfield vacation rentals

Terrace/patio

1. Indulge in our Forest Retreat

Indulge in our Forest Retreat
Otego
$129 nightly
The price is $147
Aug 10 - Aug 11
Total with taxes and fees
Indulge in our Forest Retreat
Smart TV

2. 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, (27 reviews)
"Awesome property! Perfect for Colgate visits. Will be booking again for sure."
United States
Jeremy
$225 nightly
The price is $254
Aug 12 - Aug 13
Total with taxes and fees
The Barnhouse - Country Charm 2 miles from Colgate, renovated century-old barn
Exterior

3. 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, (65 reviews)
"Great place"
United States
Dorothy M.
$228 nightly
The price is $257
Sep 9 - Sep 10
Total with taxes and fees
Spacious and comfy, king bed, double futon sofa, kitchen, near Colgate, 7 Oaks
Smart TV, fireplace, books

4. Spacious Private Guest Suite near Colgate

Spacious Private Guest Suite near Colgate
Earlville
9.8 out of 10, Exceptional, (16 reviews)
"Very nice place and 5 min from Colgate. Owner very easy to communicate with and responsive. "
United States
Ursula B.
$272 nightly
The price is $307
Aug 16 - Aug 17
Total with taxes and fees
Spacious Private Guest Suite near Colgate
Interior

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, (28 reviews)
"Pizza place next door is awesome! Great location"
United States
robert L.
$193 nightly
The price is $220
Aug 23 - Aug 24
Total with taxes and fees
1st Class Rentals Munson Manor VI at Chestnut 2nd Floor
Coffee/tea maker, fridge, microwave, oven

6. ⭐️Wildflower Country Cottage

⭐️Wildflower Country Cottage
Oxford
10.0 out of 10, Exceptional, (83 reviews)
"I stayed with my daughter and it was lovely. Lots of beautiful wildlife in the fields around the home. It is peaceful and quiet yet an easy drive into town. Will definitely stay again"
United States
Luis
$216 nightly
The price is $242
Aug 10 - Aug 11
Total with taxes and fees
⭐️Wildflower Country Cottage
Exterior detail

7. 1st Class Rentals - 3 Bedroom Apartment downtown Oneonta

1st Class Rentals - 3 Bedroom Apartment downtown Oneonta
Downtown Oneonta
9.8 out of 10, Exceptional, (13 reviews)
"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.
$170 nightly
The price is $194
Aug 23 - Aug 24
Total with taxes and fees
1st Class Rentals - 3 Bedroom Apartment downtown Oneonta
Exterior

8. ✨ Lakeside Reflections

✨ Lakeside Reflections
Oxford
9.8 out of 10, Exceptional, (18 reviews)
"Very quiet and beautiful"
United States
Robin T.
$273 nightly
The price is $306
Aug 18 - Aug 19
Total with taxes and fees
✨ Lakeside Reflections
Terrace/patio

9. 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, (186 reviews)
"Great place and location."
United States
Matt M.
$204 nightly
The price is $233
Sep 4 - Sep 5
Total with taxes and fees
Cooperstown Hall of Fame, Dreams Park Baseball, Ommegang #1 Location in the area
Exterior

10. 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.
$416 nightly
The price is $470
Sep 9 - Sep 10
Total with taxes and fees
Snowshoe Cabin across from Upper Lake Moraine and close to Colgate!
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

11. 5 min to Colgate, Pet Friendly, Sleeps 6

5 min to Colgate, Pet Friendly, Sleeps 6
Madison
10.0 out of 10, Exceptional, (1 review)
$364 nightly
The price is $370
Sep 1 - Sep 2
Total with taxes and fees
5 min to Colgate, Pet Friendly, Sleeps 6
Interior

12. 1st Class Rentals The Thurman Munson House

1st Class Rentals The Thurman Munson House
Cooperstown
10.0 out of 10, Exceptional, (56 reviews)
"The house was immaculate, bedrooms were spacious. Bathrooms were beautiful. Loved the house and will definitely stay there again if we happen to be out that way. "
United States
Amanda L.
$285 nightly
The price is $325
Aug 30 - Aug 31
Total with taxes and fees
1st Class Rentals The Thurman Munson House
Exterior detail

13. Warm & Cozy Studio Cabin — Cooperstown, NY

Warm & Cozy Studio Cabin — Cooperstown, NY
Cooperstown
9.4 out of 10, Exceptional, (9 reviews)
"Plenty of space, was close to the area I needed to be for the weekend."
United States
Ashley W.
$571 nightly
The price is $651
Aug 11 - Aug 12
Total with taxes and fees
Warm & Cozy Studio Cabin — Cooperstown, NY
Outdoor dining

14. 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
$374 nightly
The price is $412
Aug 29 - Aug 30
Total with taxes and fees
Private Cabin Near Cooperstown All Star Village - 14 Acres, Views & Guest House
Smart TV

15. Secluded Lodge on 56 Acres Firepit • Creek

Secluded Lodge on 56 Acres Firepit • Creek
Schenevus
10.0 out of 10, Exceptional, (1 review)
"Fabulous stay! Such a beautiful home perfect for our family. Communication was always super quick and so helpful. Would definitely stay here again!"
United States
Susan A.
Secluded Lodge on 56 Acres Firepit • Creek
Coffee/tea maker, fridge, microwave, oven

16. 5 Min to Colgate, Sleeps 6, Kayaks, Fire Pit

5 Min to Colgate, Sleeps 6, Kayaks, Fire Pit
Hamilton
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful communication with the host and a perfect stay."
Canada
Sheryl
$552 nightly
The price is $574
Aug 11 - Aug 12
Total with taxes and fees
5 Min to Colgate, Sleeps 6, Kayaks, Fire Pit
Interior

17. Game Room, Sauna, 5 Min to Colgate, Sleeps 8

Game Room, Sauna, 5 Min to Colgate, Sleeps 8
Madison
10.0 out of 10, Exceptional, (4 reviews)
"The beauty we experienced & the layout worked beautifully for us"
United States
Patti P.
$558 nightly
The price is $579
Aug 11 - Aug 12
Total with taxes and fees
Game Room, Sauna, 5 Min to Colgate, Sleeps 8
Exterior

18. 5 Min to Colgate, Sleeps 8, Welcome Wine

5 Min to Colgate, Sleeps 8, Welcome Wine
Hamilton
10.0 out of 10, Exceptional, (9 reviews)
"Christian was a wonderful host and we enjoyed our visit. Great location and wonderful view of the lake."
United States
Eileen B.
$579 nightly
The price is $602
Aug 11 - Aug 12
Total with taxes and fees
5 Min to Colgate, Sleeps 8, Welcome Wine
Property grounds

19. 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
8.0 out of 10, Very Good, (1 review)
"The house is under going multiple improvements. None of which effect staying in the house. There are window units in every room for a/c. The WIFI available is subpar so working remotely was near impossible and even streaming a show on the living room tv proved to be difficult. Towels and bedding were adequate. We did not use the stovetop or microwave/ toaster oven combo but they seemed in operating order. Only having one bathroom can be difficult but something we were prepared for already. Only...
United States
Matthew M.
$688 nightly
The price is $784
Sep 9 - Sep 10
Total with taxes and fees
Score The perfect Summer Winter getaway: Lakeside retreat for your winning team
Outdoor dining

20. 5 Min to Colgate, Sleeps 8, Game Room, Sauna

5 Min to Colgate, Sleeps 8, Game Room, Sauna
Madison
10.0 out of 10, Exceptional, (5 reviews)
"This was the PERFECT place for us to stay as we attended a Reunion at Colgate University. Very cute house right on Lake Moraine. Comfortable with all amenities included. Would happily stay here again!"
United States
Patti L.
$533 nightly
The price is $553
Aug 11 - Aug 12
Total with taxes and fees
5 Min to Colgate, Sleeps 8, Game Room, Sauna
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

Bayside Inn & Marina

Bayside Inn & Marina

10/10 Excellent
"We greatly enjoyed our stay at the Bayside Inn. The room was bright and clean. The bed was one of the most comfortable hotel beds of my experience. The location was perfect for the Glimmerglass Festival one mile away. We will be booking a stay next year for sure! I have one suggestion for the owners. Parking was a little difficult without lines. Since the property slopes down toward the lake it is important that cars don't take more space that they need or spaces get eliminated."
Dianne 1-night trip
Posted 1 hour ago
Bayside Inn & Marina

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 $325 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?

Longview Cottage with views to compliment its name and close to cooperstown: Visitors like this Pittsfield vacation home rental. It 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 Gilbert Lake State 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.