filters

Search results; 539 homes in Annapolis

Photo 1 of 17
Home in Robinson
Country Retreat
3 bedrooms, 3 queen beds, 1.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 16
Top guest favourite
Home in Oblong
The Lakeview House
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 27 reviews
Photo 1 of 20
Superhost
Home in Oblong
Cozy on Range Street
3 bedrooms, 5 beds, 1 bathroom
22–27 Nov
Photo 1 of 19
Guest favourite
Home in Oblong
The Farm House
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
4.89 out of 5 average rating, 45 reviews
Photo 1 of 29
Top guest favourite
Home in Casey
Miss Honey’s Cottage
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.96 out of 5 average rating, 47 reviews
Photo 1 of 29
Top guest favourite
Cabin in Robinson
Rustic Guest House Cabin in a Secluded Setting
2 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 154 reviews
Photo 1 of 18
Superhost
Home in Greenup
Private Arcade + Bar Lounge | Giant bed | Sleeps 9
2 bedrooms, 8 beds, 2 bathrooms
24–29 Sept
New place to stay
Photo 1 of 12
Superhost
Home in Robinson
Quiet home near a park in Robinson, Illinois
3 bedrooms, 3 double beds, 1 bathroom
30 Sept – 5 Oct
Photo 1 of 29
Top guest favourite
Cabin in Casey
Cabin by the Creek‼️🏡🎣🦌
3 bedrooms, 4 beds, 1 bathroom
24–29 Sept
4.98 out of 5 average rating, 142 reviews
Photo 1 of 18
Top guest favourite
Home in Greenup
Cozy Corner 1 Mile from I-70
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.94 out of 5 average rating, 359 reviews
Photo 1 of 29
Top guest favourite
Bungalow in Greenup
Craftsman Bungalow Guest House
2 bedrooms, 4 beds, 1 bathroom
22–27 Sept
4.99 out of 5 average rating, 189 reviews
Photo 1 of 8
Guest favourite
Cabin in Martinsville
Rustic Cabin in Wooded Setting - The Oaks
6 beds, 1 bathroom
19–24 Sept
4.97 out of 5 average rating, 38 reviews
Photo 1 of 16
Top guest favourite
Home in Marshall
Charming Country Home
3 bedrooms, 5 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 22 reviews
Photo 1 of 17
Guest favourite
Home in Oblong
Cozy on Adams St in Oblong
2 beds, 1 bathroom
18–23 Sept
4.9 out of 5 average rating, 30 reviews
Photo 1 of 24
Superhost
Resort in Robinson
Updated Resort, Scenic Quail Creek/Pool/Pond/Golf
1 bedroom, 2 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 7 reviews
Photo 1 of 22
Guest favourite
Cabin in Martinsville
Built New 2025 - Our Neck of the Woods
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 13 reviews
Photo 1 of 29
Top guest favourite
Home in Greenup
Pine Lodge
2 bedrooms, 4 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 58 reviews
Photo 1 of 12
Guest favourite
Home in Casey
KZ Cozy Inn
1 bedroom, 3 beds, 1 bathroom
21–26 Sept
4.85 out of 5 average rating, 94 reviews