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Aug 29 - Aug 31
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Browse Select Pittsfield Cottages

Our top choices for Pittsfield cottages

⭐️Wildflower Country Cottage
Property grounds

⭐️Wildflower Country Cottage

10.0 out of 10, Exceptional, (69)
"It was an amazing stay. The cottage was cozy and warm very inviting. Will be heading back soon and amazing experience."
The price is CA $156
CA $267 total
includes taxes & fees
Sep 9 - Sep 10
⭐️Wildflower Country Cottage
Magical lakeside retreat with hot tub + dog friendly!
Exterior

Magical lakeside retreat with hot tub + dog friendly!

10.0 out of 10, Exceptional, (6)
"We really enjoyed this place, everything and more was provided to match the expected experience."
Magical lakeside retreat with hot tub + dog friendly!
BBQ Ready: Lakeside Milford Home w/ Paddleboat
Outdoor dining

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
Charming 2-bedroom cottage with AC, WiFi, 4 mi to Cooperstown Dreams Park
Smart TV, books

Charming 2-bedroom cottage with AC, WiFi, 4 mi to Cooperstown Dreams Park

10.0 out of 10, Exceptional, (1)
"The property was clean and was very convenient. We stayed at the Cooperstown Field of Dreams, and this was right down the same road a few miles. Our host was great with communicating and made the experience great. "
Charming 2-bedroom cottage with AC, WiFi, 4 mi to Cooperstown Dreams Park
Cooperstown/Oneonta Getaway! Cottage #2- Old World Village
Exterior

Cooperstown/Oneonta Getaway! Cottage #2- Old World Village

9.8 out of 10, Exceptional, (27)
"Excellent place to stay"
Cooperstown/Oneonta Getaway! Cottage #2- Old World Village
Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool
Exterior

Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool

The price is CA $276
CA $697 total
includes taxes & fees
Sep 2 - Sep 3
Feather & Fern @ Cooperstown Lodge 3 to CDP + Pool
Cooperstown/Oneonta Getaway! Cottage #1- Old World Village
Exterior

Cooperstown/Oneonta Getaway! Cottage #1- Old World Village

9.8 out of 10, Exceptional, (34)
"We enjoyed our stay at this unique location. Great proximity to Oneonta and Cooperstown."
Cooperstown/Oneonta Getaway! Cottage #1- Old World Village
Charming Village Cottage
Exterior

Charming Village Cottage

10.0 out of 10, Exceptional, (12)
"This cottage was so beautifully decorated. It felt like home. Truly upgrades in bedding, towels, fixtures… it did not feel like an outside stay. Sarah, the property manager was so attentive and responsive as was the Host. "
Charming Village Cottage
Pvt Lake...Fish, Swim and Kayak (surrounded by nature)
Exterior

Pvt Lake...Fish, Swim and Kayak (surrounded by nature)

10.0 out of 10, Exceptional, (27)
"Nice & cozy cabin in a very peaceful area right next to the lake . My wife & I had a great time . "
Pvt Lake...Fish, Swim and Kayak (surrounded by nature)
✨ Lakeside Reflections
Property grounds

✨ Lakeside Reflections

10.0 out of 10, Exceptional, (15)
"Quiet and relaxing, super clean, kind host, delightful experience, I actually texted the link to friend to rent!"
The price is CA $207
CA $349 total
includes taxes & fees
Aug 27 - Aug 28
✨ Lakeside Reflections
Rustic Bainbridge Retreat w/ Spacious Yard!
Exterior

Rustic Bainbridge Retreat w/ Spacious Yard!

10.0 out of 10, Exceptional, (2)
"Very nice place. Amazing views, was a very vacation-like home. "
Rustic Bainbridge Retreat w/ Spacious Yard!
Breezy Meadow Two 2 of 2,custom built cottage, under a mile from CDP
Outdoor dining

Breezy Meadow Two 2 of 2,custom built cottage, under a mile from CDP

9.8 out of 10, Exceptional, (12)
"Breezy meadow was the perfect place for your Dreams Park stay! It’s so convenient being minute’s from the field and most restaurants! The hosts are so welcoming. Very clean. Perfect for a family of 3 or 4!"
Breezy Meadow Two 2 of 2,custom built cottage, under a mile from CDP
StarField Cottage...The Perfect Cooperstown Dreams Park Getaway!
Exterior

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!
Camp Runamuk, great location just 1/2 hour from West Branch Delaware river
Property grounds

Camp Runamuk, great location just 1/2 hour from West Branch Delaware river

10.0 out of 10, Exceptional, (1)
"We absolutely loved our stay at this charming cabin! The property was very clean and the bed was one of the most comfortable we’ve slept in. Lonnie and his wife were exceptional hosts, going above and beyond to ensure our comfort. Their hospitality made us feel right at home. We can’t wait to return in the future!""
Camp Runamuk, great location just 1/2 hour from West Branch Delaware river
Cooperstown Dreams Park, All Star Village & Hall of Fame cottage rental.
Exterior

Cooperstown Dreams Park, All Star Village & Hall of Fame cottage rental.

10.0 out of 10, Exceptional, (56)
"Great place, great scenery."
Cooperstown Dreams Park, All Star Village & Hall of Fame cottage rental.
Mountain Top Country Hideaway: 48 Acres, Fire Pit!
House (2 Bedrooms) | Front of property

Mountain Top Country Hideaway: 48 Acres, Fire Pit!

3.0 star property
Mountain Top Country Hideaway: 48 Acres, Fire Pit!
Liten Stuga Guest Cottage
Terrace/patio

Liten Stuga Guest Cottage

Liten Stuga Guest Cottage
5 Mi to Cooperstown All Star Village: Otego Home
House (3 Bedrooms) | Interior

5 Mi to Cooperstown All Star Village: Otego Home

3.0 star property
5 Mi to Cooperstown All Star Village: Otego Home
Cooperstown/Oneonta Getaway! Cottage #3- Old World Village
Exterior

Cooperstown/Oneonta Getaway! Cottage #3- Old World Village

10.0 out of 10, Exceptional, (35)
"Loved the wooded grounds and the cottage was perfect for us. I would definitely stay here again. "
Cooperstown/Oneonta Getaway! Cottage #3- Old World Village
Fly Creek Historic Home By Cooperstown!
House (3 Bedrooms) | Interior

Fly Creek Historic Home By Cooperstown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay. The house has plenty of space to spread out and has everything you need. Easy commute to Cooperstown. Would definitely stay there again. "
Fly Creek Historic Home By 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.
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Top Pittsfield Hotel Reviews

Lake House

Lake House

10/10 Excellent
"Outside of the parking during Friday and Saturday nights due to concerts, our stay was excellent. "
Edoardo 5-night trip
Posted 19 hours ago
Lake House