Pittsfield Holiday Rentals

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Check prices for these dates

Tonight
9 Jul - 10 Jul
Tomorrow
10 Jul - 11 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Pittsfield

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Relax by the serene fountain and enjoy the pool area with lounge chairs and potted plants.

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

9.8 out of 10, Exceptional, (73)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Relax on the porch with two comfortable chairs, surrounded by a deck and beautiful flower beds.

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2.0 star property
The price is HK$1,971
HK$2,776 total
includes taxes & fees
13 Jul - 14 Jul
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
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Stroll through the vibrant public square, surrounded by shops, restaurants, and lush greenery.

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

10.0 out of 10, Exceptional, (8)
"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$777
HK$982 total
includes taxes & fees
13 Jul - 14 Jul
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Enjoy cooking in this well-equipped kitchen with a central island and bar stools.

Buckhorn Barndo &Nature Retreat-near SiloamSprings

Buckhorn Barndo &Nature Retreat-near SiloamSprings
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Enjoy cooking in this well-equipped kitchen with a large island, microwave, oven, and refrigerator.

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10.0 out of 10, Exceptional, (54)
"We enjoyed our stay at this beautiful country home. "
The price is HK$1,406
HK$1,610 total
includes taxes & fees
11 Jul - 12 Jul
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Staircase leads to an upper level in a rustic cabin setting.

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

10.0 out of 10, Exceptional, (5)
"Absolutely loved our stay! Comfortable and cozy! Felt like we were staying in the Ingalls little house, but with modern conveniences. It really was a hidden gem! Can’t recommend enough! My only feedback is that the master bed wasn’t super comfy. Great stay and great host"
The price is HK$1,013
HK$1,232 total
includes taxes & fees
13 Jul - 14 Jul
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
The Yellow Rose Historic Home
Classic bedroom with a four-poster bed, dresser, and large mirror.

The Yellow Rose Historic Home

10.0 out of 10, Exceptional, (11)
"Loved staying at the yellow rose had plenty of room for family was such a nice place"
The price is HK$1,731
HK$2,460 total
includes taxes & fees
15 Jul - 16 Jul
The Yellow Rose Historic Home
Idyllic Mt Sterling Retreat w/ Private Lake!
Stunning hallway with framed artwork and a staircase leading to a cozy bedroom.

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (7)
"It was a delightful stay - games on the patio, corn hole on the desk, swimming, fishing, walks, and sitting around the fire. Also, we greatly appreciated the ample fridge and freezer space."
Idyllic Mt Sterling Retreat w/ Private Lake!
Exotic Animal Farm Stay in Illinois: Tour, Explore
Enjoy cooking in this well-equipped kitchen with a wooden countertop, stainless steel sink, and white stove.

Exotic Animal Farm Stay in Illinois: Tour, Explore

Exotic Animal Farm Stay in Illinois: Tour, Explore
Cozy 3 bedroom family friendly home in pike county IL
Attached to a charming home, this garage offers ample space for a vehicle and additional storage.

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
Spacious 6-bedroom house in wonderful Versailles with AC
Exterior

Spacious 6-bedroom house in wonderful Versailles with AC

Spacious 6-bedroom house in wonderful Versailles with AC
Idyllic Mt Sterling Retreat w/ Private Lake!
Stylish hallway with a door leading to a cozy room, adorned with framed artwork and a wooden railing.

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
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
Exotic Animal Farm Stay in Illinois: Tour, Explore
Kitchen with wooden countertop, stainless steel sink, and white stove, offering ample space for cooking and dining.

Exotic Animal Farm Stay in Illinois: Tour, Explore

3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore
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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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.

How many holiday rentals are there in Pittsfield?

Choose from 3 Expedia holiday rentals in Pittsfield for a memorable 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 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.