Pittsfield Vacation Rentals

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Check prices for these dates

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Aug 11 - Aug 12
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Aug 12 - Aug 13
This weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Pittsfield

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, (77)
"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 ￥37,098
￥51,999 total
includes taxes & fees
Aug 13 - Aug 14
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
Dining

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

10.0 out of 10, Exceptional, (9)
"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 ￥14,626
￥18,633 total
includes taxes & fees
Aug 13 - Aug 14
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Buckhorn Barndo &Nature Retreat-near SiloamSprings
Fridge, microwave, oven, stovetop

Buckhorn Barndo &Nature Retreat-near SiloamSprings

Buckhorn Barndo &Nature Retreat-near SiloamSprings
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 ￥19,058
￥23,329 total
includes taxes & fees
Aug 13 - Aug 14
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
The Yellow Rose Historic Home
5 bedrooms, desk, travel crib, 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 ￥32,577
￥46,438 total
includes taxes & fees
Aug 13 - Aug 14
The Yellow Rose Historic Home
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 ￥26,460
￥31,957 total
includes taxes & fees
Aug 13 - Aug 14
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
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)
"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!
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
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!
House (4 Bedrooms) | Interior

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
House (1 Bedroom) | 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 ￥14,774
￥43,997 total
includes taxes & fees
Sep 1 - Sep 2
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

River's Edge Motel

River's Edge Motel

10/10 Excellent
"Friendly staff and helpful. The room was clean and spacious. It’s a little bit dated but overall nice view and a great staff. We would stay again when in the area. "
Alexis 1-night trip
Posted 2 days ago
River's Edge Motel

Frequently asked questions

Are there vacation rentals in Pittsfield?

Yes, you can find vacation rentals near top points of interest in Pittsfield, or you can go with a secluded option if you want a relaxing place to stay. Pittsfield is known for its cafes and entertainment choices. Make sure you have time to check out the breweries and theaters during your trip.

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

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Visitors like this Pittsfield vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Pittsfield?

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

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 larger area.

What are vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can book for several days or longer in Pittsfield. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family gatherings.