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Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Pittsfield holiday homes

A window with a view of a snowy landscape and bare trees.

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 NZ$319
includes taxes & fees
10 Nov - 11 Nov
Charming Farmhouse on a working farm.
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.

2. Eagle's Peak Cottage

Eagle's Peak Cottage
Pleasantville
9.2 out of 10, Wonderful, (54 reviews)
"I loved the property, such a great location for all the local hikes and such."
United States
Jacqueline N.
The price is NZ$232
includes taxes & fees
5 Nov - 6 Nov
Eagle's Peak Cottage
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)
"The property was very nice, It was just the right size for five adults to stay two nights. We were visiting family nearby and it was easy to travel into Warren for activities and shopping. We plan on returning someday for another visit, thanks."
United States
Brian H.
The price is NZ$455
includes taxes & fees
9 Nov - 10 Nov
River view getaway
A living room with a sectional sofa, a coffee table, and a TV.

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

Charming 2-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 NZ$979
includes taxes & fees
5 Nov - 6 Nov
Charming 2-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
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
10.0 out of 10, Exceptional, (12 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 NZ$378
includes taxes & fees
8 Nov - 9 Nov
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 NZ$603
includes taxes & fees
11 Nov - 12 Nov
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 NZ$271
includes taxes & fees
18 Nov - 19 Nov
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 NZ$1,142
includes taxes & fees
8 Nov - 9 Nov
Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
A spacious kitchen with a central island, a dining area with a wooden table, and a view of a body of water through large sliding doors.

9. Welcoming 2-bedroom home on the shores of Lake Chautauqua

Welcoming 2-bedroom home on the shores of Lake Chautauqua
Lakewood
The price is NZ$426
includes taxes & fees
18 Nov - 19 Nov
Welcoming 2-bedroom home on the shores of Lake Chautauqua
A large, two-story house with a prominent porch and a sign indicating it is a resort.

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, (226 reviews)
"A beautiful hotel in a great location."
United States
Elizabeth N.
The price is NZ$919
includes taxes & fees
17 Nov - 18 Nov
Charming Resort in the Heart of Bemus Village on CHQ Lake
A single-story house with a front porch, a small garden, and a driveway.

11. 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 NZ$845
includes taxes & fees
5 Nov - 6 Nov
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
A landscaped garden with a pathway leading to a building with a green roof.

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

Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
Bemus Point
10.0 out of 10, Exceptional, (44 reviews)
"Great place to stay!"
United States
RupczykNC U.
The price is NZ$829
includes taxes & fees
17 Nov - 18 Nov
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
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, (13 reviews)
"Love the property. Will definitely stay there again. "
United States
Melissa J.
The price is NZ$897
includes taxes & fees
5 Nov - 6 Nov
Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
A large, historic building with a symmetrical facade, multiple windows, and a central entrance with steps.

14. 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, (38 reviews)
"Perfect location, great house, and host very easy to work with"
United States
Wendy D.
The price is NZ$925
includes taxes & fees
17 Nov - 18 Nov
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
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

Hampton Inn & Suites Jamestown

Hampton Inn & Suites Jamestown

10/10 Excellent
"Breakfast staff was terrific and helpful!"
Mary 1-night trip
Posted 4 hours ago
Hampton Inn & Suites Jamestown

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
444
Accommodation
129 Holiday Homes
Lowest Price
NZ$232
Highest Price
NZ$1,142