Pittsfield Vacation Rentals

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Vacation Rentals in Pittsfield

Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

10.0 out of 10, Exceptional, (53)
"This was my first time booking with Vrbo and Gary made it seamless. The space looks just like the photos. Gary was amazing for letting my family check in early so we could get ready for a family wedding. Thank you again Gary! Next time I am in the area, we will reach out to you! "
The price is CA $359
CA $612 total
includes taxes & fees
Jan 15 - Jan 16
Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14

Year-Round Renovated Lakefront Cottage & Pet Friendly!

9.8 out of 10, Exceptional, (183)
"Lovely home on Chautauqua Lake. Picture perfect fall weather, bonfires and fall foliage!"
Year-Round Renovated Lakefront Cottage & Pet Friendly!

Cozy 2 Bedroom Canal Front Cottage With Private Dock

9.6 out of 10, Exceptional, (35)
"Very nice getaway for late fall. Basically had the area to ourselves. Nice and quiet with plenty eateries still open."
The price is CA $142
CA $323 total
includes taxes & fees
Jan 9 - Jan 10
Cozy 2 Bedroom Canal Front Cottage With Private Dock

Beautiful Peek'n Peak Highlands Condo

10.0 out of 10, Exceptional, (91)
"We had an incredible time at Mark's place, everything went smoothly. The grandkids couldn't believe all the goodies and snacks in the baskets, the adults also enjoyed the beverages left. The kids took over the second floor and they thought they were in paradise. Can't wait for next year."
Beautiful Peek'n Peak Highlands Condo

Charming Resort in the Heart of Bemus Village on CHQ Lake

10.0 out of 10, Exceptional, (170)
"We’ve been coming to this lovely house for years and it is always clean & cozy! Plenty of room for our grown children & their families. Perfect again this year!!"
The price is CA $344
CA $697 total
includes taxes & fees
Jan 10 - Jan 11
Charming Resort in the Heart of Bemus Village on CHQ Lake

Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

10.0 out of 10, Exceptional, (89)
"Fantastic property!!! Clean, spacious, and inviting!! The girls and I enjoyed a beautiful weekend!! Thank you!!"
Secluded Chautauqua Lake House, private dock & beach, short stroll to town!

Pet Friendly home by the Stow Ferry

9.6 out of 10, Exceptional, (23)
"The place was overall comfortable, but left a little to be desired in expectation. It's the shoulder season and freezing at night. We didn't arrive until after dark and it was 53 inside. I was raised not to go to sleep with electric space heaters on, but that seemed to be the only working provision. The gas did not appear to be turned on"
The price is CA $143
CA $295 total
includes taxes & fees
Jan 31 - Feb 1
Pet Friendly home by the Stow Ferry

Beautiful Pet friendly cottage by the Stow Ferry

9.6 out of 10, Exceptional, (29)
"Super clean! Plenty of towels!!! We enjoyed our stay"
The price is CA $143
CA $300 total
includes taxes & fees
Jan 13 - Jan 14
Beautiful Pet friendly cottage by the Stow Ferry

8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit

9.8 out of 10, Exceptional, (64)
"Great stay, great location. We had a last minute trip to the Peak for some winter fun and this home was perfect. Plenty of room to spread out and enjoy yourself. Beds were comfortable, plenty of extra blankets and pillows, smart tvs in most bedrooms, plus a bathroom for each bedroom. Game room was enjoyable, especially the shuffleboard. Has most kitchen amenities you would need. Located at top of chair lift 8 and its a quick ride down to grab a bite to eat or a cocktail from the Suger Shack....
8409 PEEK N PEAK SLOPE SIDE SKI IN/OUT GOLF LIFT 8,Firepit

Prime Location! Ski-In&Ski-Out! Next to Ski Lift #8 & the Inn. 3Bed &3Full Bath.

10.0 out of 10, Exceptional, (59)
"2 night stay. Had a great time."
Prime Location! Ski-In&Ski-Out! Next to Ski Lift #8 & the Inn. 3Bed &3Full Bath.

Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard

9.6 out of 10, Exceptional, (80)
"I spent 3 October nights with my family including two kids, age 11 and 14. The leaves were beautiful and it was a very peaceful stay. We ate most meals in the house which had everything we needed in the kitchen. Bedrooms were comfortable. Great access to the lake where we were able to enjoy the northern lights. Cute enclosed porch where I could enjoy my morning coffee or a glass of wine at night. Would definitely stay again. "
Creek Side Cottage with Lake Views, Lake Access, Dock and Secluded Yard

Bemus Point Retreat ~ 3 Mi to Chautauqua Lake

9.6 out of 10, Exceptional, (14)
"It was very relaxing and a beautiful place. The sunset from the property was unbelievable!!"
Bemus Point Retreat ~ 3 Mi to Chautauqua Lake

Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

10.0 out of 10, Exceptional, (11)
"The home was very clean and cozy. Hosts were excellent. Great experience. "
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!

Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

8.4 out of 10, Very good, (8)
"Perfect little cabin in a great location. Good price and have no complaints. Thank you"
Lakefront Cozy Cottage with 1 bedroom in Charming Stow, NY

Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock

9.6 out of 10, Exceptional, (125)
"had everything that you needed great location had no problems great value for your money"
Chautauqua Lakefront Cottage - Low boat traffic bay- waterfront- new dock

Lakeside Retreat 4BR House |Kayak Adventure

9.4 out of 10, Exceptional, (12)
"Absolutely lovely place to stay! The setting was fabulous, the place was very clean and spacious. I will absolutely be back to stay next season! "
Lakeside Retreat 4BR House |Kayak Adventure

Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

10.0 out of 10, Exceptional, (227)
"Excellent"
Chalet on 250 acres, Private, 1 Mi from Chautauqua Institution / Lake

Cabin retreat in the heart of the Allegheny National Forest!

10.0 out of 10, Exceptional, (16)
"We had a great stay at the cabin. "
Cabin retreat in the heart of the Allegheny National Forest!

Peek'n Peak Clubhome - the Ultimate in Luxury Accommodations

10.0 out of 10, Exceptional, (57)
"Great place to stay, play golf and relax!"
Peek'n Peak Clubhome - the Ultimate in Luxury Accommodations

This is a timeshare condominium complex located on the northern end of Chautauqua Institution at 20 Elm Lane

This is a timeshare condominium complex located on the northern end of Chautauqua Institution at 20 Elm Lane
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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Other types of properties in Pittsfield you may be interested in

Charming Farmhouse on a working farm.

10.0 out of 10, Exceptional, (1)
"The only affordable option - It was perfect for our eclipse trip. Everything went smoothly. Nice people. Fun stay."
The price is CA $215
CA $279 total
includes taxes & fees
Jan 14 - Jan 15
Charming Farmhouse on a working farm.

Peek'n Peak Resort Trademark Collection by Wyndham

3.5 star property
8.6 out of 10, Excellent, (838)
"Lovely "
The price is CA $139
CA $193 total
includes taxes & fees
Jan 9 - Jan 10
Peek'n Peak Resort Trademark Collection by Wyndham

La Quinta Inn & Suites by Wyndham Jamestown

2.5 star property
8.4 out of 10, Very good, (1001)
"Nice room for the price. Worth the slightly longer drive from the interstate. Wish the property had a workout room though."
The price is CA $128
CA $145 total
includes taxes & fees
Jan 10 - Jan 11
La Quinta Inn & Suites by Wyndham Jamestown
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.

Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, you can find vacation rentals close to the most popular local attractions in Pittsfield, or you can go with a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Pittsfield has to offer?

Charming Resort in the Heart of Bemus Village on CHQ Lake: This vacation home rental outside of Pittsfield is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Pittsfield?

While you're exploring the area, Crescent Park and Chapman State Park are a couple of picturesque spots to get outside and enjoy nature. While here, Anders Run Natural Area and Cornplanter State Forest are other places worth a visit.

What are vacation rentals like in Pittsfield?

Vacation rentals are private properties you can reserve for a couple days or more in Pittsfield. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.