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Search results; Over 1,000 homes in Woolland

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Cottage in Woolland
Family cottage Spacious garden Aug available
3 bedrooms, 6 beds, 1 shared bathroom
1–6 Nov, Individual host
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4.73 out of 5 average rating, 45 reviews
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Top guest favourite
Barn in Woolland
Mount Pleasant Barn in Woolland, North Dorset
Individual host
10–15 Oct
5.0 out of 5 average rating, 33 reviews
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Cabin in Blandford Forum
Trappers
Business host
19–24 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Room in Hilton
The Old School at Hilton (Room 1)
Individual host
29 Sept – 4 Oct
4.97 out of 5 average rating, 254 reviews
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Top guest favourite
Guest house in Child Okeford
Cosy Countryside 2-Bedroom Guest House
Individual host
29 Sept – 4 Oct
4.98 out of 5 average rating, 143 reviews
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Guest favourite
Home in Winterborne Houghton
Dorset Country Home- 6 Bed - Hot Tub
Business host
4–9 Oct
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Cottage in Tolpuddle
The Hideaway, Tolpuddle
Individual host
15–20 Oct
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Cottage in Milton Abbas
Luxury Cottage | Sleeps 8 | Jurassic Coast
Individual host
28 Sept – 3 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Shepherd’s hut in Milton Abbas
Shepherds Hut in Milton Abbas
Individual host
4–9 Oct
4.98 out of 5 average rating, 139 reviews
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Guest favourite
Home in Winterborne Stickland
Cute cob cottage - own garden
Individual host
20–25 Sept
4.92 out of 5 average rating, 51 reviews
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Top guest favourite
Cottage in Dorset
No1. The Courtyard, Clyffe House
Individual host
30 Oct – 4 Nov
5.0 out of 5 average rating, 102 reviews
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Top guest favourite
Bungalow in Dorset
The Covey - 1 Bedroom Annex with Country Views
Individual host
26–31 Oct
4.97 out of 5 average rating, 172 reviews
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Top guest favourite
Cottage in Okeford Fitzpaine
The Garden House Okeford Fitzpaine Dorset
Individual host
4–9 Oct
4.97 out of 5 average rating, 424 reviews
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Top guest favourite
Guest house in Pulham
Old Smokey
Individual host
29 Sept – 4 Oct
4.99 out of 5 average rating, 129 reviews
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Top guest favourite
Home in Dorset
Delightful one bed accommodation near Sherborne
Individual host
21–26 Sept
4.95 out of 5 average rating, 247 reviews
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Top guest favourite
Home in Cheselbourne
Rose Cottage - romantic, cosy, country home
Individual host
22–27 Sept
4.93 out of 5 average rating, 15 reviews
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Top guest favourite
Cottage in Dorset
Cute Button Cottage, a Most Magical Place.
Individual host
20–25 Sept
5.0 out of 5 average rating, 35 reviews
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Guest favourite
Home in Dorset
Luxury House on private estate. Hot tub & Playbarn
Business host
20–25 Sept
4.97 out of 5 average rating, 60 reviews
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Top guest favourite
Cottage in Henley Dorchester
New Luxury Hot Tub August 2026 Shepherds Cottage
Business host
12–17 Oct
4.93 out of 5 average rating, 414 reviews