Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Pittsfield holiday rentals

Exterior

Cabin in Pittsfield

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
2.0 star property
The price is HK$1,958
HK$2,744 total
includes taxes & fees
21 Jan - 22 Jan
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Dining

Cabin in Jacksonville

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
10.0 out of 10, Exceptional, (15 reviews)
"Always a nice place to stay."
United States
Pete D.
The price is HK$772
HK$983 total
includes taxes & fees
26 Jan - 27 Jan
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Property grounds

Cabin in Mozier

Dave’s River House
The price is HK$877
HK$2,012 total
includes taxes & fees
26 Jan - 27 Jan
Dave’s River House
Exterior

Holiday Home in Bluffs

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
10.0 out of 10, Exceptional, (58 reviews)
"Beautiful place, highly recommend "
United States
Anthony S.
The price is HK$1,396
HK$1,695 total
includes taxes & fees
20 Jan - 21 Jan
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Interior

Holiday Home in Pleasant Hill

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
The price is HK$1,006
HK$1,454 total
includes taxes & fees
20 Jan - 21 Jan
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Exterior

Cabin in Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
10.0 out of 10, Exceptional, (8 reviews)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
United States
James Z.
The price is HK$1,006
HK$1,231 total
includes taxes & fees
26 Jan - 27 Jan
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Interior

Holiday Home in Louisiana

The Yellow Rose Historic Home
9.8 out of 10, Exceptional, (12 reviews)
"We are 7 sisters aged 50-76. We had a wonderful stay at the Yellow Rose. This beautiful old home had rooms and beds for all of us. Would definitely stay here again"
United States
Ellen B.
The price is HK$1,719
HK$2,451 total
includes taxes & fees
20 Jan - 21 Jan
The Yellow Rose Historic Home
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

The Eagles Nest Inn

The Eagles Nest Inn

10/10 Excellent
"Room was spacious and clean. Had a great stay. The restaurant was delicious. "
James 2-night trip
Posted 3 days ago
The Eagles Nest Inn

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
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  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

Frequently asked questions

Are there holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. Pittsfield is known for its cafés and entertainment choices. Make sure you have time to check out the breweries and theatres during your trip.

What are some of the best holiday rentals that Pittsfield has to offer?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This highly rated holiday home rental in Pittsfield is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What can I see and do in Pittsfield?

Cultural attractions include John Greene Shastid House and Pike County Historic Museum, whereas King Park is one spot to enjoy nature. Old Orchard Country Club and Clarksville Riverfront Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for families.