Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Pittsfield

Terrace/patio
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
9.8 out of 10, Exceptional, (80)
"We had the best time staying here. My family of 20 stayed for 3 days and this place was perfect for our trip. The house was large enough to accommodate everyone comfortably and we had everything we needed. The pool area is awesome - everyone had an amazing time from the 2 year old to my 70 year old dad. A great place for kids. Communication was great and the owners were friendly and very helpful. Hope to come back again some day! "
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Exterior
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
2.0 star property
The price is HK$1,953
HK$2,722 total
includes taxes & fees
16 Oct - 17 Oct
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
BBQ/picnic Area
West Central Lodging
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
Dining
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
10.0 out of 10, Exceptional, (14)
"Wonderfully peaceful with a little wildlife added for fun. "
The price is HK$770
HK$981 total
includes taxes & fees
16 Oct - 17 Oct
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!
10.0 out of 10, Exceptional, (58)
"Our stay at the Llama Fun Guest House was incredible! We got to tour the grounds and meet the llamas and then relaxed in the very spacious and clean house! Kris and Terry were very welcoming and we felt right at home there. We will definitely be back!"
The price is HK$1,393
HK$1,650 total
includes taxes & fees
15 Oct - 16 Oct
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Interior
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
10.0 out of 10, Exceptional, (8)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
The price is HK$1,004
HK$1,228 total
includes taxes & fees
15 Oct - 16 Oct
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
5 bedrooms, desk, travel cot, free WiFi
The Yellow Rose Historic Home
The Yellow Rose Historic Home
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"
The price is HK$1,715
HK$2,406 total
includes taxes & fees
27 Oct - 28 Oct
The Yellow Rose Historic Home
Interior
Country Retreat in the heart of Pike County Illinois
Country Retreat in the heart of Pike County Illinois
Country Retreat in the heart of Pike County Illinois
Microwave, oven, stovetop
Dave’s River House
Dave’s River House
The price is HK$778
HK$1,795 total
includes taxes & fees
21 Oct - 22 Oct
Dave’s River House
Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
Idyllic Mt Sterling Retreat w/ Private Lake!
2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
Interior
Exotic Animal Farm Stay in Illinois: Tour, Explore
Exotic Animal Farm Stay in Illinois: Tour, Explore
3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore
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
The price is HK$903
HK$1,287 total
includes taxes & fees
26 Oct - 27 Oct
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
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

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

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

10/10 Excellent
"Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house. "
kelly w. 4-night trip
Posted 8 days ago
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

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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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 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.