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Search results; Over 1,000 homes in Southwold

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, 158 reviews
Top guest favourite
Flat in Port Stanley
Charming Village Loft Getaway
2 bedrooms, 2 queen beds, 1 bathroom
28 Sept – 4 Oct
5.0 out of 5 average rating, 98 reviews
Top guest favourite
Flat in St. Thomas
The Executive Hideaway: St Thomas Serenity
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.93 out of 5 average rating, 30 reviews
Top guest favourite
Cottage in Port Stanley
Timber & Tide Cottage | Steps to Beach & Downtown
3 bedrooms, 4 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in St. Thomas
Courthouse District Cozy Getaway
3 bedrooms, 4 beds, 1 bathroom
29 Oct – 3 Nov
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Home in Port Stanley
Tranquil Retreat in Charming Port Stanley
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
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, 119 reviews
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
Guest favourite
Home in St. Thomas
Groups: wedding parties, large families, business
5 bedrooms, 7 beds, 2.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 53 reviews
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
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
Top guest favourite
Home in Fingal
Port Talbot White House- With Pickleball Court!
6 bedrooms, 12 beds, 5 bathrooms
26–31 Oct
4.98 out of 5 average rating, 122 reviews
Guest favourite
Home in Port Stanley
Entire Home - 5 Luxury Suites in Mitchell Heights
5 bedrooms, 5 beds, 5 bathrooms
13–18 Sept
4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Port Stanley
Charming 2-bedroom home overlooking Lake Erie
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.86 out of 5 average rating, 76 reviews
Guest favourite
Holiday home in Port Stanley
4 of 5 Luxury Suites in Mitchell Heights Building
2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 34 reviews
Top guest favourite
Cottage in Port Stanley
Cute Cottage steps from the Main Beach
4 bedrooms, 6 beds, 1 bathroom
2–7 Oct
4.93 out of 5 average rating, 114 reviews
Top guest favourite
Home in Port Stanley
Dover Place Cottage Port Stanley
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 25 reviews
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
Guest favourite
Home in London
Modern*2026 Build*TV75”*Sleeps10*Patio*Laundry
4 bedrooms, 6 beds, 3.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 14 reviews