Cottage holiday rentals in Milwaukee
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Top-rated cottage rentals in Milwaukee
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for cottage rentals in Milwaukee
Cottage rentals with a hot tub
Cottage in Williams Bay
4.99 out of 5 average rating, 89 reviewsClover Cottage in Williams Bay - Walk to Beach
2–9 Jan
Cottage in Fontana-on-Geneva Lake
4.98 out of 5 average rating, 94 reviews3bd 2ba cottage Abbey Springs on Lake Geneva
29 Oct – 5 Nov
Cottage in Lake Geneva
4.99 out of 5 average rating, 70 reviewsModern Cozy 2-bedroom cottage with Hot Tub
26 Mar – 2 Apr
Cottage in Racine
4.99 out of 5 average rating, 77 reviewsClementine Cottage
18–25 Apr
Pet-friendly cottage rentals
Cottage in Random Lake
4.86 out of 5 average rating, 42 reviewsPrivate 3 bedroom lake house
28 Jan – 4 Feb
Cottage in Lake Geneva
4.89 out of 5 average rating, 28 reviewsLinnwood Cottage walking distance to Lake Geneva
20–27 Feb
Cottage in Williams Bay
4.89 out of 5 average rating, 18 reviewsA vintage charming 2-bedroom cottage!
21–28 Mar
Cottage in Burlington
4.69 out of 5 average rating, 39 reviewsMint View Lakeside Cottage
17–24 Nov
Cottage in Lake Geneva
4.89 out of 5 average rating, 28 reviewsCOZY Cottage | 4 BEDS | Fenced yard
9–16 Aug
Cottage in Twin Lakes
5.0 out of 5 average rating, 56 reviews15 mins to Lk Geneva/ walk to town/ Fire Pit
16–23 Jun
Cottage in Williams Bay
4.96 out of 5 average rating, 45 reviews4 bedroom Williams Bay <1 mile Lake Geneva Beach
2–9 Jan
Cottage in Milwaukee
4.96 out of 5 average rating, 24 reviewsThe Snug Irish Cottage (King Bed)
28 May – 4 Jun
Private cottage rentals
Cottage in Williams Bay
4.99 out of 5 average rating, 80 reviewsPeaceful, serene cottage near Lake Geneva
18–25 Sept
Cottage in Mukwonago
5.0 out of 5 average rating, 13 reviewsCharming Phantom Lake Cottage
21–28 May
Cottage in Delafield
5.0 out of 5 average rating, 40 reviewsLake Country Guest Cottage
28 Aug – 4 Sept
Cottage in Lake Geneva
4.98 out of 5 average rating, 81 reviewsStylish Historic Cottage steps from lake&downtown
7–14 May
Cottage in Racine
4.91 out of 5 average rating, 95 reviewsHistoric cottage close to Lake Michigan
10–17 Jun
Cottage in Lake Geneva
4.96 out of 5 average rating, 68 reviewsClose to Town + Beach • Historic Pemberley Cottage
30 Nov – 7 Dec
Cottage in Lake Geneva
4.9 out of 5 average rating, 82 reviewsThe Peacock Cottage
18–25 Sept
Cottage in Wind Lake
4.61 out of 5 average rating, 18 reviewsA Place in the Sun 2 on Wind Lake
16–23 Feb
Destinations to explore
- Downtown Chicago Holiday rentals
- Madison Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Cottage rentals Chicago
- Cabin rentals Milwaukee
- Rentals with an EV charger Milwaukee
- Rentals with a hot tub Milwaukee
- Loft rentals Milwaukee
- Rentals with a firepit Milwaukee
- Flat rentals Milwaukee
- Rentals with a washing machine and dryer Milwaukee
- Smoking-friendly rentals Milwaukee
- Waterfront rentals Milwaukee
- Private suite rentals Milwaukee
- Rentals with beach access Milwaukee
- Mansion rentals Milwaukee
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- House rentals Milwaukee
- Rentals with pools Milwaukee
- Pet-friendly rentals Milwaukee
- Family-friendly rentals Milwaukee
- Fitness-friendly rentals Milwaukee
- Hotel rentals Milwaukee
- Rentals with breakfast Milwaukee
- Rentals with outdoor seating Milwaukee
- Rentals with lake access Milwaukee
- Apartment rentals Milwaukee
- Lakehouse rentals Milwaukee
- Monthly Rentals Milwaukee
- Rentals with a fireplace Milwaukee
- Cottage rentals Madison
- Cottage rentals Wisconsin
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