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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, 145 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
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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, 53 reviews
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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
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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Top 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, 115 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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Guest favourite
Home in Brewster
Stunning Renovated Home Near Chatham & Beaches
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Oct
4.95 out of 5 average rating, 19 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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Top guest favourite
Home in Chatham
The Osprey Nest - Beach house with stunning views
2 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 178 reviews
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Home in Orleans
Private Lakefront Retreat
3 bedrooms, 4 beds, 2 bathrooms
2–9 Jan
4.93 out of 5 average rating, 59 reviews
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Apartment in Brewster
Cute Waterfront Condo: Pool, Hot Tub & Patio
1 bedroom, 5 beds, 2 bathrooms
1–6 Oct
4.47 out of 5 average rating, 19 reviews
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Top guest favourite
Apartment in Brewster
Ocean Edge Resort/Pool access/2bedroom-2bath Condo
2 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 105 reviews
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Top guest favourite
Home in Brewster
The Brewster Pearl Brewster 3 bed 2 bath
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 30 reviews
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Guest favourite
Home in Chatham
2 House Compound, Huge Yard, Game Room, Kayaks
5 bedrooms, 7 beds, 5 bathrooms
12–17 Oct
4.95 out of 5 average rating, 77 reviews
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Top guest favourite
Home in Brewster
4BR/3B | Walk2Pond | Screened Porch | FireTbl | AC
4 bedrooms, 7 beds, 3 bathrooms
24–29 Oct
4.93 out of 5 average rating, 165 reviews
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Guest house in Orleans
Charming Cape Cottage~Walk to Town~Outdoor Shower
1 bedroom, 1 double bed, 1 bathroom
1–6 Oct
4.75 out of 5 average rating, 4 reviews