Pittsfield Vacation Rentals

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Check prices for these dates

Tonight
Jun 18 - Jun 19
Tomorrow
Jun 19 - Jun 20
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

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, (71)
"Fabulous"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
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, (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 ￥11,586
￥15,196 total
includes taxes & fees
Jun 20 - Jun 21
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, bed sheets

Idyllic Mt Sterling Retreat w/ Private Lake!

10.0 out of 10, Exceptional, (6)
"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!
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
Smart TV, books

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 ￥16,879
￥20,828 total
includes taxes & fees
Jun 23 - Jun 24
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)
"Loved staying at the yellow rose had plenty of room for family was such a nice place"
The price is ￥32,056
￥45,550 total
includes taxes & fees
Jun 19 - Jun 20
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, (52)
"Wonderful stay and even more wonderful host. Home away from home. "
The price is ￥26,038
￥29,673 total
includes taxes & fees
Jun 19 - Jun 20
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
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, (2)
"Clean and nice location"
Cozy 3 bedroom family friendly home in pike county IL
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
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, bed sheets

Idyllic Mt Sterling Retreat w/ Private Lake!

2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
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 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.