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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Pittsfield vacation homes

A room with a brick fireplace, wooden flooring, a dining table with a patterned tablecloth, and a dark wooden cabinet.

1. Charming Farmhouse on a working farm.

Charming Farmhouse on a working farm.
Pittsfield
7.8 out of 10, Good, (6 reviews)
"Everything was great and I enjoyed my stay."
United States
Justin S.
The price is AED 496
AED 697 total
includes taxes & fees
4 Oct - 5 Oct
Charming Farmhouse on a working farm.
A living room with a sectional sofa, a coffee table, and a TV.

2. Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes

Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
Warren
9.8 out of 10, Exceptional, (6 reviews)
"I did not stay there but my employees liked it"
United States
Bill S.
The price is AED 334
AED 1,581 total
includes taxes & fees
5 Oct - 6 Oct
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
A living room with two grey sofas, a coffee table, and a patterned rug.

3. River view getaway

River view getaway
Warren
9.8 out of 10, Exceptional, (51 reviews)
"It was a great place to stay!"
United States
Lindsey F.
The price is AED 479
AED 919 total
includes taxes & fees
4 Oct - 5 Oct
River view getaway
A spacious kitchen with wooden cabinets, a marble countertop, and a large island. There is a dining area with a bench and chairs, and a ceiling fan.

4. Eagle's Peak Cottage

Eagle's Peak Cottage
Pleasantville
9.2 out of 10, Wonderful, (50 reviews)
"I loved the property, such a great location for all the local hikes and such."
United States
Jacqueline N.
The price is AED 132
AED 510 total
includes taxes & fees
8 Oct - 9 Oct
Eagle's Peak Cottage
A wooden interior with a dining area, a sofa, and a staircase.

5. Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.

Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.
Tionesta
9.8 out of 10, Exceptional, (9 reviews)
"Overall, worth the stay. Host is friendly and fast to get back to you if you have any issues. Rooms were comfortable and clean. "
United States
Kcass 0.
The price is AED 327
AED 783 total
includes taxes & fees
5 Oct - 6 Oct
Waterfront Campfires With a Relaxing Creek View. Trout View Cottage near ANF.
A modern living room with a fireplace, a flat-screen TV, a dining area with a table and chairs, and a kitchen with wooden cabinets and a refrigerator.

6. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (27 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is AED 459
AED 1,340 total
includes taxes & fees
4 Oct - 5 Oct
The Refined Retreat
A house with a porch, surrounded by trees and grass.

7. Tionesta LO a Rustic Cabin that sleeps 6!

Tionesta LO a Rustic Cabin that sleeps 6!
Tionesta
10.0 out of 10, Exceptional, (1 review)
"The cabin was great, close by to all the things we love about the area. If you're looking for a quiet, lovely rustic mountain setting, this is your rental!! We will definitely rent again!"
United States
Sharon B.
The price is AED 436
AED 562 total
includes taxes & fees
4 Oct - 5 Oct
Tionesta LO a Rustic Cabin that sleeps 6!
A modern kitchen with a central island, pendant lighting, and a view into the dining area.

8. Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites

Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
Ashville
10.0 out of 10, Exceptional, (2 reviews)
"This was a beautiful house!! Very clean and had everything we needed and more! The hosts were very helpful and communicated very quickly! I highly recommend staying in this house!"
United States
Janson D.
The price is AED 984
AED 2,763 total
includes taxes & fees
11 Oct - 12 Oct
Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
A modern kitchen with white cabinets, stainless steel appliances, and a window providing natural light.

9. Family & pet friendly home with yard - 5 minutes from Chautauqua Lake!

Family & pet friendly home with yard - 5 minutes from Chautauqua Lake!
Jamestown
9.8 out of 10, Exceptional, (14 reviews)
"Great communication with the host and a good location that was quiet and relaxing."
United States
Nathan R.
The price is AED 643
AED 1,307 total
includes taxes & fees
16 Oct - 17 Oct
Family & pet friendly home with yard - 5 minutes from Chautauqua Lake!
A lakeside patio with outdoor seating, a dock, and boats.

10. Charming Resort in the Heart of Bemus Village on CHQ Lake

Charming Resort in the Heart of Bemus Village on CHQ Lake
Bemus Point
10.0 out of 10, Exceptional, (224 reviews)
"A beautiful hotel in a great location."
United States
Elizabeth N.
The price is AED 793
AED 1,901 total
includes taxes & fees
4 Oct - 5 Oct
Charming Resort in the Heart of Bemus Village on CHQ Lake
An outdoor seating area with tables and chairs, overlooking a body of water with boats and a sunset in the background.

11. Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms

Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
Bemus Point
9.8 out of 10, Exceptional, (37 reviews)
"Bet nice house. Lots of room to spread out plus a nice bonus room upstairs. "
United States
John W.
The price is AED 661
AED 2,042 total
includes taxes & fees
4 Oct - 5 Oct
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
A single-story house with a front porch, a small garden, and a driveway.

12. 20 Park-Walk to Everything CHQ-Pets OK-Free Bikes

20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
Chautauqua
10.0 out of 10, Exceptional, (8 reviews)
"Great property. Tiffany thought of everything. It was all so welcoming and new. Would definitely stay here again. "
United States
Jennifer L.
The price is AED 725
AED 1,650 total
includes taxes & fees
4 Oct - 5 Oct
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
A two-story house with a front porch, a well-maintained lawn, and a large flowering shrub.

13. Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake

Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
Ellery
10.0 out of 10, Exceptional, (12 reviews)
"Love the property. Will definitely stay there again. "
United States
Melissa J.
The price is AED 993
AED 2,134 total
includes taxes & fees
4 Oct - 5 Oct
Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
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

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

10/10 Excellent
"We had a wonderful stay at the Chautauqua Harbor Hotel. The views of the water are absolutely gorgeous, and the entire property is exceptionally clean and well-kept. The staff was welcoming, and the atmosphere was so relaxing. We can’t wait to come back!"
Helen 1-night trip
Posted 8 hours ago
Chautauqua Harbor Hotel - Jamestown