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Search results; Over 1,000 homes in Southwold

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Top guest favourite
Home in Southwold
Nature Lover's Luxury Paradise
4 bedrooms, 5 beds, 3.5 private bathrooms
5–10 Oct
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4.97 out of 5 average rating, 216 reviews
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Top guest favourite
Cabin in Port Stanley
Port Stanley Spruce Ridge Retreat
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Cottage in Fingal
Private Lake Front Chalet- With Pickleball Court!
3 bedrooms, 7 beds, 3 bathrooms
20–25 Sept
4.96 out of 5 average rating, 93 reviews
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Cottage in Port Stanley
isolated, 1800s built cottage, lake view w/ sauna!
3 bedrooms, 6 beds, 1 bathroom
27 Sept – 2 Oct
4.85 out of 5 average rating, 78 reviews
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Top guest favourite
Cabin in Rodney
Maple Lane Luxury Cabin
1 bedroom, 4 beds, WC
19–24 Oct
4.99 out of 5 average rating, 154 reviews
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Superhost
Cottage in Port Stanley
Rancho Relaxo - September dates now available!
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.79 out of 5 average rating, 53 reviews
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Top guest favourite
Cottage in Port Stanley
Timber & Tide Cottage | Steps to Beach & Downtown
3 bedrooms, 4 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Rooms in Southwold
Nature's Oasis Retreat: Dreamer's Oasis
2 bedrooms, 2 beds, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 81 reviews
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Top guest favourite
Cottage in Port Stanley
Fall and Winter in Port Stanley
1 bedroom, 1 queen bed, 1 bathroom
23–28 Sept
4.97 out of 5 average rating, 67 reviews
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Superhost
Holiday home in Port Stanley
5 of 5 Luxury Suites in Mitchell Heights Building
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.76 out of 5 average rating, 45 reviews
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Top guest favourite
Cabin in Iona Station
Waterfront Cabin In The Woods
2 bedrooms, 4 king beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 53 reviews
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Guest favourite
Flat in Port Stanley
A great place for some awesome port time.
1 bedroom, 1 bed, 1 bathroom
30 Sept – 5 Oct
4.88 out of 5 average rating, 16 reviews
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Top guest favourite
Chalet in Port Stanley
The Sunset Chalet is in a Quiet neighbourhood.
2 bedrooms, 2 double beds, 1 bathroom
19–24 Sept
4.85 out of 5 average rating, 225 reviews
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Cabin in Appin
Cabin 1 at Silver Dove
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.63 out of 5 average rating, 8 reviews
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Treehouse in Port Stanley
Lakeview Treehouse Getaway
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
4.7 out of 5 average rating, 83 reviews
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Top guest favourite
Tiny home in Iona Station
Waterfront Cabin Hideaway: Nature’s Perfect Escape
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 70 reviews
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Guest house in St. Thomas
Our Loft Lounge
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in St. Thomas
Yudi’s Cozy Retreat
1 bedroom, 2 beds, No bathroom
21–26 Sept
4.92 out of 5 average rating, 39 reviews
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Guest favourite
Home in Central Elgin
Dick & Bernie's Kokomo's, Port Stanley Ont.
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.92 out of 5 average rating, 13 reviews