304 places in Chester

Guest favorite
Guesthouse in Steeleville
RockCastle Retreat
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 14 reviews
Guest favorite
Treehouse in Perryville
TreeLoft at BaseCamp
1 king bed
Aug 4 – 9
5.0 out of 5 average rating, 510 reviews
Guest favorite
Cabin in Steeleville
Cabin By The Woods -Country Living at it's Best!
7 beds
Apr 21 – 26
4.98 out of 5 average rating, 62 reviews
Guest favorite
Cabin in Perryville
Escape At Eagle View
Apr 21 – 26
5.0 out of 5 average rating, 25 reviews
Superhost
Home in Ste. Genevieve
Elegant 3BR in the Heart of Historic Ste Genevieve
6 beds
Apr 20 – 25
New place to stay
Guest favorite
Farm stay in Perryville
Kirn's Hummingbird Haven
1 queen bed
Apr 20 – 25
5.0 out of 5 average rating, 54 reviews
Guest favorite
Loft in Perryville
June Bug’s Loft **NO CLEANING FEE**
1 king bed
Jun 2 – 7
4.92 out of 5 average rating, 336 reviews
Guest favorite
Home in Sparta
Remote, with a ton of wildlife!
3 beds
May 1 – 6
4.94 out of 5 average rating, 18 reviews
Guest favorite
Home in Perryville
Brewer House
3 beds
Apr 22 – 27
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Ste. Genevieve
3 bedroom home in downtown historic Ste Genevieve
3 beds
Apr 28 – May 3
4.9 out of 5 average rating, 77 reviews
Guest favorite
Home in Ava
JGB’s Farm and Getaway
6 beds
Apr 25 – 30
4.93 out of 5 average rating, 69 reviews
Guest favorite
Cabin in Ste. Genevieve
Sassafras Creek Cabin
4 beds
Apr 20 – 25
4.97 out of 5 average rating, 155 reviews
Guest favorite
Loft in Perryville
Downtown Loft Amazing Bath Tub & Shower
1 king bed
Apr 26 – May 1
4.97 out of 5 average rating, 267 reviews
Home in Ste. Genevieve
The Clapsaddle House
6 beds
Apr 20 – 25
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Ste. Genevieve
"Little Brick House" (Hael House built in 1865)
3 beds
May 19 – 24
4.97 out of 5 average rating, 95 reviews
Guest favorite
Cabin in Saint Mary
Arrowhead Lodge - Pool/WiFi/Secluded/1 Hr from StL
7 beds
Apr 25 – 30
5.0 out of 5 average rating, 20 reviews
Guest favorite
Cabin in Ste. Genevieve
Honey Hideaways
1 queen bed
May 5 – 10
4.97 out of 5 average rating, 71 reviews
Guest favorite
Home in Ste. Genevieve
Secluded Private Cabin with Pool, hot tub, firepla
12 beds
Apr 20 – 25
5.0 out of 5 average rating, 63 reviews