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Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 €173
includes taxes & fees
29 Oct - 30 Oct
Charming Farmhouse on a working farm.
A living room with two grey sofas, a coffee table, and a patterned rug.

2. 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 €240
includes taxes & fees
9 Nov - 10 Nov
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.

3. Eagle's Peak Cottage

Eagle's Peak Cottage
Pleasantville
9.2 out of 10, Wonderful, (53 reviews)
"I loved the property, such a great location for all the local hikes and such."
United States
Jacqueline N.
The price is €151
includes taxes & fees
3 Nov - 4 Nov
Eagle's Peak Cottage
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.
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
9.8 out of 10, Exceptional, (10 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 €201
includes taxes & fees
15 Nov - 16 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 €329
includes taxes & fees
5 Nov - 6 Nov
The Refined Retreat
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.

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

Welcoming 2-bedroom home on the shores of Lake Chautauqua
Lakewood
The price is €228
includes taxes & fees
11 Nov - 12 Nov
Welcoming 2-bedroom home on the shores of Lake Chautauqua
A house with a porch, surrounded by trees and grass.

8. 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.
Tionesta LO a Rustic Cabin that sleeps 6!
A modern kitchen with a central island, pendant lighting, and a view into the dining area.

9. 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 €581
includes taxes & fees
29 Oct - 30 Oct
Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
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 €465
includes taxes & fees
29 Oct - 30 Oct
Charming Resort in the Heart of Bemus Village on CHQ Lake
A two-story house with a front porch, a well-maintained lawn, and a large flowering shrub.

11. 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.
Bemus-HOT TUB-Fire Pit-Pets OK-1 Block to Lake
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.
20 Park-Walk to Everything CHQ-Pets OK-Free Bikes
A landscaped garden with a pathway leading to a building with a green roof.

13. 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 €448
includes taxes & fees
11 Nov - 12 Nov
Quaint historic home in the heart of Bemus Point Village- a stroll to the water!
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 €490
includes taxes & fees
30 Oct - 31 Oct
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

La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

8/10 Good
"The location was great - 5 minute walk to Desi & Lucy Museum and to some restaurants. Unfortunately the room we were in in third floor was right above the street. WiFi was ok and we had to tell front desk the toilet ran continuously."
Jeann 2-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Jamestown

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
441
Accommodation
129 Holiday Homes
Lowest Price
€151
Highest Price
€581