House holiday rentals in Winnebago County
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Top-rated house rentals in Winnebago County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Winnebago County
House rentals with a pool
Home in Milton
4.85 out of 5 average rating, 184 reviewsTree Top House with mini indoor pool and sauna
16–23 Apr
Home in Delavan
5.0 out of 5 average rating, 13 reviewsLake Days ~ Family friendly & dogs welcome
29 Dec – 5 Jan
Home in Janesville
5.0 out of 5 average rating, 64 reviewsFamily Home w/Deck, Yard, Dock on Rock River!
14–21 Aug
Home in Oregon
5.0 out of 5 average rating, 20 reviewsRock River Relaxation Home
3–10 Mar
Home in Oregon
4.9 out of 5 average rating, 10 reviewsRock River Getaway!
14–21 Oct
Home in Rockford
5.0 out of 5 average rating, 8 reviewsYour Friendly Neighborhood Airbnb
25 Sept – 2 Oct
Home in Freeport
Mid Century Pool House
27 Sept – 4 Oct
Weekly house rentals
Home in Rockford
5.0 out of 5 average rating, 31 reviewsNEW! Adults Only Riverfront home with "Red Room"
30 Dec – 6 Jan
Home in Cherry Valley
5.0 out of 5 average rating, 28 reviewsCozy house in Cherry Valley
17–24 Apr
Home in Rockford
4.98 out of 5 average rating, 47 reviewsComfy 3-bedroom home backed by a forest preserve
6–13 Oct
Home in Roscoe
5.0 out of 5 average rating, 22 reviewsS & H Farm & Charm
8–15 Aug
Home in Rockton
5.0 out of 5 average rating, 40 reviewsThe River House in Historic Rockton Illinois
13–20 Nov
Home in Rockford
4.97 out of 5 average rating, 29 reviewsDowntown Fun, 2 Doors from River
4–11 Sept
Home in Rockford
5.0 out of 5 average rating, 26 reviewsBishop's House on the Rock
16–23 Sept
Home in Rockford
4.94 out of 5 average rating, 69 reviewsHistorical Riverfront Mansion: Serenity+Location
28 Dec – 4 Jan
Private house rentals
Home in Machesney Park
4.89 out of 5 average rating, 35 reviewsSpacious. Wi-fi. Near Sports Arenas. Arcades!
28 Dec – 4 Jan
Home in Machesney Park
4.86 out of 5 average rating, 22 reviewsFenced in backyard with firepit; foosball & office
24–31 Dec
Home in Rockford
5.0 out of 5 average rating, 17 reviewsSleeps 22|Hot Tub|GameRoom|Theater|Gym|Lake Views
3–10 Apr
Home in Rockford
4.5 out of 5 average rating, 10 reviewsThe Schwartz River House
25 Jul – 1 Aug
Home in Rockford
4.88 out of 5 average rating, 24 reviewsPets welcome /King bed /Fence yard
3–10 Nov
Home in Rockford
4.75 out of 5 average rating, 4 reviewsUptown Loft
11–18 Jan
Home in Cherry Valley
5.0 out of 5 average rating, 22 reviewsUpper apartment in the heart of Cherry Valley!
10–17 Apr
Home in Rockford
5.0 out of 5 average rating, 5 reviewsRockford’s Enchanted Cottage
24 Nov – 1 Dec
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