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Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Pittsfield holiday 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
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great and I enjoyed my stay."
United States
Justin S.
The price is AU$267
includes taxes & fees
1 Sept - 2 Sept
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
9.6 out of 10, Exceptional, (5 reviews)
"House was beautiful and well maintained, very welcoming. The host was easy to communicate with and checked in to see if we needed anything or had any issues. Would absolutely book again in the future! "
United States
Jill M.
The price is AU$531
includes taxes & fees
21 Sept - 22 Sept
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, (50 reviews)
"It was a great place to stay!"
United States
Lindsey F.
The price is AU$376
includes taxes & fees
30 Aug - 31 Aug
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, (37 reviews)
"This cottage is nicely situated for easy access to the Allegheny National Forest while offering all the amenities of home. I intend to stay here again the next time I'm in the area."
United States
David H.
The price is AU$226
includes taxes & fees
1 Sept - 2 Sept
Eagle's Peak Cottage
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.

5. The Refined Retreat

The Refined Retreat
Celoron
9.8 out of 10, Exceptional, (23 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is AU$437
includes taxes & fees
30 Aug - 31 Aug
The Refined Retreat
A modern kitchen with a central island, pendant lighting, and a view into the dining area.

6. 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 AU$909
includes taxes & fees
24 Aug - 25 Aug
Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
A campfire with four Adirondack chairs around it, set in a forested area with a picnic table in the background.

7. Quiet Escape, Peaceful Lake Glimpses

Quiet Escape, Peaceful Lake Glimpses
Ashville
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful view of the lake. Very nice little house and quiet. "
United States
Joelyn G.
The price is AU$563
includes taxes & fees
25 Aug - 26 Aug
Quiet Escape, Peaceful Lake Glimpses
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.
The price is AU$218
includes taxes & fees
23 Aug - 24 Aug
Tionesta LO a Rustic Cabin that sleeps 6!
An outdoor seating area with tables and chairs, overlooking a body of water with boats and a sunset in the background.

9. 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 AU$991
includes taxes & fees
2 Sept - 3 Sept
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms

10. Cozy 2-bedroom bungalow in gorgeous Jamestown with AC

Cozy 2-bedroom bungalow in gorgeous Jamestown with AC
Jamestown
The price is AU$438
includes taxes & fees
2 Sept - 3 Sept
Cozy 2-bedroom bungalow in gorgeous Jamestown with AC
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
"Close to everything we wanted to do. So we could just walk around. They need more parking but unfortunately it's in downtown Jamestown so property are limited."
Marcia 2-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Jamestown

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
157
Accommodation
126 Holiday Homes
Lowest Price
AU$226
Highest Price
AU$991