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Search results; Over 1,000 homes in South Orleans

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Top guest favourite
Flat in South Orleans
Walk to private beach, spacious peaceful apartment
1 bedroom, 2 beds, 1 private bathroom
1–6 Oct
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4.93 out of 5 average rating, 144 reviews
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Guest favourite
Home in Orleans
Spacious Cottage near Pleasant Bay
2 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.81 out of 5 average rating, 99 reviews
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Home in Orleans
Classic Cape House 5M to Nauset Beach
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
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Guest favourite
Home in Orleans
Pond-Front Home w/ Water Views!
5 bedrooms, 6 beds, 3.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 43 reviews
Photo 1 of 29
Top guest favourite
Villa in Orleans
Charming Private Villa with Private Pool
6 bedrooms, 14 beds, 5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 59 reviews
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Guest favourite
Home in Orleans
Charming Retreat with AC, Fire Pit, Game Room!
3 bedrooms, 4 beds, 2 bathrooms
6–11 May
4.88 out of 5 average rating, 8 reviews
Photo 1 of 29
Guest favourite
Home in Orleans
Walk to Lake + Fire Pit | Near Nauset + Sleeps 10
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.99 out of 5 average rating, 114 reviews
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Top guest favourite
Home in Orleans
1850 Orleans Antique Home with Path to Arey’s Pond
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 52 reviews
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Top guest favourite
Flat in Brewster
A walk in the park
1 bedroom, 1 queen bed, 1 bathroom
4–9 Nov
4.99 out of 5 average rating, 84 reviews
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Guest favourite
Home in Brewster
Stunning Renovated Home Near Chatham & Beaches
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 18 reviews
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Guest favourite
Home in Orleans
Orleans Pleasant Bay CulDeSac 4BR 2BA
4 bedrooms, 8 beds, 2 bathrooms
3–10 Oct
4.97 out of 5 average rating, 35 reviews
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Guest favourite
Home in Orleans
Charming Family-Friendly, 3+ Bedroom, Farmhouse
4 bedrooms, 7 beds, 2 bathrooms
19–24 Oct
4.98 out of 5 average rating, 42 reviews
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Top guest favourite
Home in Harwich
Dog Friendly | Close to Beaches | Fenced In Yard
3 bedrooms, 3 beds, 1 bathroom
10–15 Oct
5.0 out of 5 average rating, 12 reviews
Photo 1 of 29
Guest favourite
Home in Orleans
Antique Cottage with Path to Arey’s Pond
1 bedroom, 1 king bed, 1 bathroom
6–11 Oct
4.94 out of 5 average rating, 33 reviews
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Guest favourite
Guest house in Orleans
Crystal lake getaway
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.73 out of 5 average rating, 15 reviews
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Top guest favourite
Room in Orleans
Noor's Nook
1 bed, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 34 reviews
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Top guest favourite
Villa in Cape Cod
Cape Cod Villa retreat, venue, film & bachelorette
5 bedrooms, 9 beds, 2 bathrooms
11–16 Oct
4.98 out of 5 average rating, 135 reviews
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Top guest favourite
Home in Brewster
Cheerful and spacious 3BR, indoor fireplace
4 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
4.97 out of 5 average rating, 60 reviews
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Guest favourite
Cottage in Orleans
Joy Cottage: a/c, EV charger, outdoor shower
2 bedrooms, 3 beds, 1 bathroom
8–13 Oct
4.96 out of 5 average rating, 26 reviews