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Search results; Over 1,000 homes in Southwold

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Top guest favourite
Home in Southwold
New Home Sleeps 14, 6BR, BBQ, Games Room, Office
6 bedrooms, 8 beds, 3.5 private bathrooms
11–16 Oct
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4.97 out of 5 average rating, 159 reviews
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Cottage in Port Stanley
Look out over Port Stanley Main Beach
4 bedrooms, 4 beds, 3 bathrooms
5–10 Oct
4.78 out of 5 average rating, 120 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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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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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 Port Stanley
Timber & Tide Cottage | Steps to Beach & Downtown
3 bedrooms, 4 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Home in St. Thomas
Courthouse District Cozy Getaway
3 bedrooms, 4 beds, 1 bathroom
29 Oct – 3 Nov
4.92 out of 5 average rating, 48 reviews
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Guest favourite
Home in Port Stanley
Entire Home - 5 Luxury Suites in Mitchell Heights
5 bedrooms, 5 beds, 5 bathrooms
22–27 Nov
4.9 out of 5 average rating, 21 reviews
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Top guest favourite
Cottage in Port Stanley
The Sunbeam Cottage in the heart of P.S.!
2 bedrooms, 3 beds, 1 bathroom
23–28 Sept
4.92 out of 5 average rating, 60 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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Top guest favourite
Cottage in Port Stanley
Cute Cottage steps from the Main Beach
4 bedrooms, 6 beds, 1 bathroom
3–8 Oct
4.93 out of 5 average rating, 114 reviews
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Guest favourite
Home in Port Stanley
Port Stanley Getaway Hot tub Game room Big screen
5 bedrooms, 8 beds, 2.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 71 reviews
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Top guest favourite
Camper van/Motorhome in St. Thomas
Rollin' Recreation
2 bedrooms, 5 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 18 reviews
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Superhost
Cottage in Port Stanley
Rancho Relaxo - Sept/Oct dates still available!
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.79 out of 5 average rating, 53 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, 79 reviews
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Top guest favourite
Cottage in Port Stanley
Newly renovated cottage on large private beach
2 bedrooms, 3 beds, 1 bathroom
3–8 Oct
4.99 out of 5 average rating, 87 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
27 Sept – 2 Oct
4.76 out of 5 average rating, 46 reviews
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Treehouse in Port Stanley
Lakeview Treehouse Getaway
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.7 out of 5 average rating, 83 reviews
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Guest favourite
Cottage in Port Stanley
Fall ‘26 Winter ‘27 contact for special pricing!
3 bedrooms, 5 beds, 2 bathrooms
3–8 Nov
4.97 out of 5 average rating, 62 reviews