Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Winchester

4.95 out of 5 average rating, 124 reviews

Container Home GREAT Countryside Views COZY Stay

Singing Hills Cabin is the ultimate getaway for fresh air and an unbeatable view of the countryside. Enjoy morning coffee as the sun rises from the large front porch. This newly renovated container home is perfect for small families looking for an outdoor escape or for couples seeking a romantic getaway. It is located on a 40 acre hobby farm, so do not be surprised if you see cows and other wildlife during your stay! The best deer hunting, river access, and restaurants are located minutes away.

Jun 22 – 29

$86 per night
Guest favorite

Farm stay in Virginia

4.99 out of 5 average rating, 246 reviews

Log Cabin overlooking scenic Virginia Lake

This unique 1800’s log cabin is set on a bluff overlooking beautiful Virginia Lake with 80 acres of timber and water for you to explore. The cabin has many luxuries such as WiFi, smart TV, adjustable bed, luxury linens, bath robes, fireplace and a copper bathtub for two with all of the charm you would expect in an original cabin. Relax in the hammock, curl up with a book, soak in the tub, enjoy the fire pit, watch the wildlife, hike the trail , fish, kayak or do nothing at all. Relax and enjoy!

Sep 7 – 14

$155 per night
Guest favorite

Home in Pittsfield

4.83 out of 5 average rating, 201 reviews

Florence Guest House

This 1,200 sq. ft. PRIVATE BOOK is a 173 year old building that Abe Lincoln stayed in. Central A/C, Forced air heat, Two decks (one overlooking the Illinois River), burn pit, outside grill, fully equipped kitchen, screened in porch, ample parking, access to the Illinois River/ boat ramp near, tie up on Our Private Lots! NOTE: RECENTLY HAD Guests' wanting to "JUST GET AWAY" for A Time!!! WE'RE HERE, IF YOU NEED YOUR PRIVATE TIME ALONE, AS WELL!!! ***NEW KEURIG; BRING YOUR K-CUPS!!!***

Jun 20 – 27

$60 per night

Popular amenities for Pittsfield vacation rentals

Other great vacation rentals in Pittsfield

Guest favorite

Cabin in Carrollton

4.92 out of 5 average rating, 119 reviews

Graham Farm Cabin

Dec 2 – 9

$121 per night
Guest favorite

Home in Bowling Green

4.97 out of 5 average rating, 198 reviews

Peaceful Country Cottage

Sep 29 – Oct 6

$130 per night
Guest favorite

Home in Griggsville

4.88 out of 5 average rating, 76 reviews

Arrowhead Farmhouse, Spacious home, scenic views

Apr 6 – 13

$214 per night
Guest favorite

Home in Winchester

4.93 out of 5 average rating, 43 reviews

Winchester Guest Cottage

Dec 6 – 13

$80 per night
Guest favorite

Loft in Winchester

4.97 out of 5 average rating, 77 reviews

The Bike Flat

Jun 9 – 16

$80 per night
Guest favorite

Cabin in Hillview

5.0 out of 5 average rating, 29 reviews

The Hillview House on 2 Wooded Acres

Nov 1 – 8

$91 per night
Guest favorite

Home in Clarksville

4.94 out of 5 average rating, 50 reviews

Mighty Mississippi Riverview - St. Louis Area

Sep 30 – Oct 7

$128 per night
Guest favorite

Cottage in Pearl

4.98 out of 5 average rating, 66 reviews

Beautiful Secluded Home With a breathtaking view

May 16 – 23

$186 per night
Guest favorite

Home in White Hall

4.95 out of 5 average rating, 20 reviews

Cozy-Rose-Cottage

May 2 – 9

$77 per night
Guest favorite

Cabin in Camp Point

4.97 out of 5 average rating, 90 reviews

The Hunter's Cabin, a Rustic Retreat

Jan 8 – 15

$125 per night
Guest favorite

Cabin in Camp Point

4.99 out of 5 average rating, 76 reviews

Oakbrook Akers Lakeside Cabin Retreat

Aug 11 – 18

$120 per night
Guest favorite

Guesthouse in Jerseyville

4.99 out of 5 average rating, 77 reviews

Cozy cabin on farm near Jerseyville and Grafton IL

Sep 18 – 25

$119 per night

Destinations to explore

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