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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cabin in Winchester/ presque isle
Lily Pad Lodge w/ Golf Cart, Kayaks, & Game Room!
4 bedrooms, 5 beds, 2 private bathrooms
16–21 Sept
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4.98 out of 5 average rating, 56 reviews
Top guest favourite
Cabin in Winchester
The Northwoods At It's Finest!
3 bedrooms, 6 beds, 2 bathrooms
15–22 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Winchester
Sticks and Stones on the Lake
4 bedrooms, 5 beds, 3.5 bathrooms
18–23 Sept
4.96 out of 5 average rating, 50 reviews
Guest favourite
Home in Winchester
Turtle Cove
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Presque Isle
Cozy Lakefront Cabin on Turtle Chain + Huge Yard!
4 bedrooms, 6 beds, 2 bathrooms
15–22 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Presque Isle
Moose Tracks Lodge on North Turtle Lake
5 bedrooms, 6 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Cabin in Winchester
Cozy Northwoods Cabin Getaway!
4 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
4.87 out of 5 average rating, 68 reviews
Superhost
Home in Presque Isle
Dancing Loon Hideaway at Turtle Lake
4 bedrooms, 9 beds, 3 bathrooms
13–18 Oct
4.75 out of 5 average rating, 12 reviews
Top guest favourite
Cabin in Winchester
ON Water Lodge! 5 Beds!
4 bedrooms, 5 beds, 2 bathrooms
2–7 Nov
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Cabin in Presque Isle
Dock Hollands
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 3 Oct
4.95 out of 5 average rating, 44 reviews
Superhost
Cabin in Winchester
Lakefront Resort | Sleeps 18 | 5 Rooms
5 bedrooms, 11 beds, 6 bathrooms
27 Sept – 2 Oct
4.83 out of 5 average rating, 6 reviews
Guest favourite
Cabin in Winchester
Winchester Headquarters! Direct trail access!
3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Sept
4.97 out of 5 average rating, 31 reviews
Guest favourite
Island in Presque Isle
Dog-friendly home on private island w/boat landing
4 bedrooms, 9 beds, 3.5 bathrooms
17–24 Sept
4.9 out of 5 average rating, 20 reviews
Home in Presque Isle
Lakeside Gem: Panoramic Views & Private Beach
4 bedrooms, 7 beds, 2.5 bathrooms
4–9 Oct
4.54 out of 5 average rating, 37 reviews
Guest favourite
Home in Presque Isle
North Woods Escape
5 bedrooms, 7 beds, 3 bathrooms
26–31 Oct
4.78 out of 5 average rating, 49 reviews
Guest favourite
Home in Manitowish Waters
Stone Lake View – Dock, Sauna & Bunkhouse
4 bedrooms, 11 beds, 2.5 bathrooms
5–10 Oct
4.86 out of 5 average rating, 14 reviews
Guest favourite
Cabin in Winchester
Northwoods Lake Cabin | Sleeps 6 | Dock & Boats
1 bedroom, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 20 reviews
Top guest favourite
Home in Manitowish Waters
Waterfront modified A-frame on chain of 10 lakes
3 bedrooms, 9 beds, 2 bathrooms
12–17 Oct
4.99 out of 5 average rating, 76 reviews
Top guest favourite
Cabin in Mercer
Trailside Retreat w/ Sauna+Game Room+Dog Friendly
2 bedrooms, 4 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 50 reviews