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Search results; 849 homes in Winchester

Top guest favourite
Home in Winchester
Best Views on Lake, TIki Hut, Boat Rental + More
5 bedrooms, 8 beds, 4 private bathrooms
8–13 Aug
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4.98 out of 5 average rating, 112 reviews
Top guest favourite
Home in Winchester
The Hangout on Heath Lane
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 68 reviews
Guest favourite
Home in Winchester
Lakeside Retreat Marina/Pool, Golf Cart, Game Room
4 bedrooms, 6 beds, 3.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 67 reviews
Guest favourite
Home in Winchester
Huge lakefront retreat w/ views, dock, decks & bar
5 bedrooms, 10 beds, 5.5 bathrooms
2–7 Sept
4.93 out of 5 average rating, 28 reviews
Guest favourite
Tiny home in Winchester
Tiny House
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 87 reviews
Top guest favourite
Home in Winchester
Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 91 reviews
Guest favourite
Flat in Winchester
Winchester's Premier Downtown Loft! Near The Lake!
2 bedrooms, 2 king beds, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 93 reviews
Guest favourite
Home in Winchester
Barefoot Bungalow Bright airy lakeside home
4 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
4.89 out of 5 average rating, 28 reviews
Superhost
Home in Winchester
Lakeside Luxe | Lake + Pool Access
4 bedrooms, 5 beds, 2.5 bathrooms
2–7 Sept
4.79 out of 5 average rating, 28 reviews
Guest favourite
Home in Winchester
Barefoot Retreat w/kayaks/SUP/Game Room/Pool
3 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Winchester
Lake Lane Landing Enjoy fall on the lake !
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Winchester
Lakeshore Modern- steps to water
5 bedrooms, 8 beds, 5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Winchester
Lake Days at Twin Creeks Pool, Golf Cart, Marina
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Winchester
Unbeatable Charm & Convenience On The Square!
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 73 reviews
Top guest favourite
Home in Winchester
Latitude Adjustment - Lake Cottage
3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 111 reviews
Guest favourite
Home in Winchester
Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath
4 bedrooms, 4 beds, 4 bathrooms
15–20 Sept
4.92 out of 5 average rating, 48 reviews
Guest favourite
Home in Winchester
Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc
4 bedrooms, 6 beds, 3 bathrooms
13–18 Sept
4.99 out of 5 average rating, 91 reviews
Guest favourite
Home in Winchester
The Bourbon Embassy at Twin Creeks
4 bedrooms, 6 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Winchester
On Water w/ Private Dock, Entire Home, sleeps 14
5 bedrooms, 9 beds, 4.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 59 reviews