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Search results; 849 homes in Winchester

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Guest favourite
Tiny home in Winchester
Tiny House
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
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4.95 out of 5 average rating, 87 reviews
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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
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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
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Superhost
Home in Winchester
Lakeside Luxe | Lake + Pool Access
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Sept
4.79 out of 5 average rating, 28 reviews
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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
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Guest favourite
Home in Winchester
Lake House Dreams
4 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.9 out of 5 average rating, 10 reviews
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Top 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
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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
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Guest favourite
Home in Winchester
Location, location, location!
3 bedrooms, 10 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 24 reviews
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Superhost
Cottage in Winchester
Resort Cottage #9 Pet-Friendly & Marina Slip
4 bedrooms, 7 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Cottage in Winchester
Waterfront Cottage #7 PET & Wheelchair Friendly!
3 bedrooms, 6 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 15 reviews
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Superhost
Cottage in Winchester
Private Resort Waterside Pet Friendly Cottage #10
4 bedrooms, 8 beds, 3 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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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
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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
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Flat in Winchester
Just Around the Corner
2 bedrooms, 2 beds, 1 bathroom
23–28 Oct
4.83 out of 5 average rating, 69 reviews
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Guest favourite
Flat in Winchester
Clean Lines and Simple Comfort
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
4.97 out of 5 average rating, 39 reviews
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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
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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
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Guest favourite
Home in Winchester
Rare Flat Lot w/Beautiful Views, Dock, Hot Tub
4 bedrooms, 6 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 29 reviews