Default HTG hotel image

Holiday Homes in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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
8.6 out of 10, Excellent, (4 reviews)
"Everything was great and I enjoyed my stay."
United States
Justin S.
The price is €166
includes taxes & fees
15 Sept - 16 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
9.8 out of 10, Exceptional, (6 reviews)
"I did not stay there but my employees liked it"
United States
Bill S.
The price is €342
includes taxes & fees
14 Sept - 15 Sept
Charming 3-Bedroom Vacation Retreat Near Historical Downtown & Nature Escapes
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
9.0 out of 10, Wonderful, (43 reviews)
"I loved the property, such a great location for all the local hikes and such."
United States
Jacqueline N.
The price is €128
includes taxes & fees
14 Sept - 15 Sept
Eagle's Peak Cottage
A living room with two grey sofas, a coffee table, and a patterned rug.

4. 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 €231
includes taxes & fees
4 Oct - 5 Oct
River view getaway
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 €210
includes taxes & fees
14 Sept - 15 Sept
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, (25 reviews)
" wonderful place to stay "
United States
Christopher R.
The price is €306
includes taxes & fees
14 Sept - 15 Sept
The Refined Retreat
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 €318
includes taxes & fees
14 Sept - 15 Sept
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 €136
includes taxes & fees
14 Sept - 15 Sept
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 €568
includes taxes & fees
14 Sept - 15 Sept
Modern Farmhouse | Firepit | Stocked Trout Stream | 2 Suites
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, (219 reviews)
"A beautiful hotel in a great location."
United States
Elizabeth N.
The price is €463
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 €492
includes taxes & fees
1 Oct - 2 Oct
Renovated Home in Heart of Bemus Point, Large Yard-Fire Pit- 3-4 Bedrooms
A two-story house with a front porch, a well-maintained lawn, and a large flowering shrub.

12. 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, (11 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.

13. 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 living room with a sofa set, a lamp, and two windows with patterned curtains.

14. Warren Wilderness - A Unique Architectural Gem Near the Allegheny River and Kinzua Dam

Warren Wilderness - A Unique Architectural Gem Near the Allegheny River and Kinzua Dam
Warren
The price is €1,043
includes taxes & fees
12 Oct - 13 Oct
Warren Wilderness - A Unique Architectural Gem Near the Allegheny River and Kinzua Dam
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

DoubleTree by Hilton Jamestown

DoubleTree by Hilton Jamestown

10/10 Excellent
"Wonderful staff! Front desk and bar staff were great - chock full of advice on how best to enjoy what Jamestown has to offer."
Robin 1-night trip
Posted 5 hours ago
DoubleTree by Hilton Jamestown

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
412
Accommodation
123 Holiday Homes
Lowest Price
€128
Highest Price
€568