Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Pittsfield

Exterior
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
Pittsfield
The price is HK$1,954
HK$2,739 total
includes taxes & fees
6 Dec - 7 Dec
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Private kitchen
3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat

2.0 star property
Chambersburg
The price is HK$835
HK$1,462 total
includes taxes & fees
8 Dec - 9 Dec
3-bedroom country home in Pike Co Il with AC and heat
Dining
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Jacksonville
10.0 out of 10, Exceptional, (15)
"This was the cutest and most relaxing a place I have ever stayed. We've so enjoyed our stay."
United States
Linda B.
The price is HK$771
HK$982 total
includes taxes & fees
8 Dec - 9 Dec
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Dining
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

Bluffs
10.0 out of 10, Exceptional, (58)
"Very nice property!! Loved being around the llamas. Will book again next time I’m in the area. "
United States
Michelle G.
The price is HK$1,394
HK$1,692 total
includes taxes & fees
7 Dec - 8 Dec
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Microwave, oven, stovetop
Dave’s River House

Dave’s River House

Mozier
The price is HK$876
HK$2,001 total
includes taxes & fees
14 Dec - 15 Dec
Dave’s River House
Interior
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Jacksonville
10.0 out of 10, Exceptional, (8)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
United States
James Z.
The price is HK$1,004
HK$1,229 total
includes taxes & fees
8 Dec - 9 Dec
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Property grounds
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area

Pleasant Hill
The price is HK$1,004
HK$1,452 total
includes taxes & fees
7 Dec - 8 Dec
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
5 bedrooms, desk, travel cot, free WiFi
The Yellow Rose Historic Home

The Yellow Rose Historic Home

Louisiana
9.8 out of 10, Exceptional, (12)
"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$1,716
HK$2,446 total
includes taxes & fees
7 Dec - 8 Dec
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
"We are on the road often & Eagles Nest is still our favorite. Been there twice. Will go again."
John 1-night trip
Posted 12 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
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • 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.