Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Holiday Rentals in Pittsfield

Our top choices for Pittsfield holiday rentals

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Terrace/patio

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

9.8 out of 10, Exceptional, (78)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Exterior

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is HK$1,957
HK$2,685 total
includes taxes & fees
6 Sept - 7 Sept
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
West Central Lodging
BBQ/picnic Area

West Central Lodging

2.5 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful time - very quiet country location, the manager is friendly but not invasive. First time I have heard a whippoorwill sing in many years. "
West Central Lodging
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Fridge, microwave, oven, stovetop

Buckhorn Barndo &Nature Retreat-near SiloamSprings

Buckhorn Barndo &Nature Retreat-near SiloamSprings
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Dining

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

10.0 out of 10, Exceptional, (10)
"Very nice and cozy cabin in the middle of a cornfield. This place is close to town but completely isolated. We sat on the front porch and enjoyed our morning coffee in almost complete silence. Not sure if this is the place for everyone, but it was perfect for us."
The price is HK$772
HK$983 total
includes taxes & fees
31 Aug - 1 Sept
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Dining

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (55)
"We enjoyed our stay at this beautiful country home. "
The price is HK$1,399
HK$1,657 total
includes taxes & fees
1 Sept - 2 Sept
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Interior

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

10.0 out of 10, Exceptional, (7)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
The price is HK$1,005
HK$1,231 total
includes taxes & fees
6 Sept - 7 Sept
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
The Yellow Rose Historic Home
5 bedrooms, desk, travel cot, free WiFi

The Yellow Rose Historic Home

10.0 out of 10, Exceptional, (11)
"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"
The price is HK$1,719
HK$2,450 total
includes taxes & fees
28 Aug - 29 Aug
The Yellow Rose Historic Home
Spacious 6-bedroom house in rural Versailles with many amenities included.
Exterior

Spacious 6-bedroom house in rural Versailles with many amenities included.

10.0 out of 10, Exceptional, (1)
"We stayed for our Mendota FFA Chapter Officer Retreat. It was very accommodating for our group of nine high school students and two adult chaperones. The house itself is a bit chopped up, but has a lot of charm and many unique decor elements. The bar/kitchen was very unique. We utilized both outdoor grill and firepit area to prepare evening meals. The pool table in the basement was a big hit with the boys. Air fresheners were a little overpowering. "
Spacious 6-bedroom house in rural Versailles with many amenities included.
Exotic Animal Farm Stay in Illinois: Tour, Explore
Fridge, microwave, stovetop, coffee/tea maker

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, bed sheets

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (7)
"Wonder!! House and lake amazing! Kitchen well stocked with everything one would need! So many outside adventures! We had a wonderful time. Thank you. "
Idyllic Mt Sterling Retreat w/ Private Lake!
Country Retreat in the heart of Pike County Illinois
Interior

Country Retreat in the heart of Pike County Illinois

Country Retreat in the heart of Pike County Illinois
Cozy 3 bedroom family friendly home in pike county IL
Exterior

Cozy 3 bedroom family friendly home in pike county IL

10.0 out of 10, Exceptional, (3)
"Clean and nice location"
Cozy 3 bedroom family friendly home in pike county IL
Idyllic Mt Sterling Retreat w/ Private Lake!
Interior

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
Exotic Animal Farm Stay in Illinois: Tour, Explore
Interior

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore
Waterfront cottage in Calhoun County, IL
Property grounds

Waterfront cottage in Calhoun County, IL

The price is HK$779
HK$2,321 total
includes taxes & fees
6 Sept - 7 Sept
Waterfront cottage in Calhoun County, IL
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

Find out more about Pittsfield

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 Pike County Historic Museum and John Greene Shastid House, whereas King Park is one spot to enjoy nature. Old Orchard Country Club and The Eagle's Nest Winery 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.