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Search results; Over 1,000 homes in Orleans

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Top guest favourite
Home in Orleans
Orleans, MA Luxury Getaway
4 bedrooms, 5 beds, 4.5 bathrooms
27 Sept – 2 Oct
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4.95 out of 5 average rating, 39 reviews
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Guest favourite
Cottage in Orleans
Nauset Heights Cottage- 5 minute walk to beach!
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.98 out of 5 average rating, 81 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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Guest house in Orleans
Charming Cape Cottage~Walk to Town~Outdoor Shower
1 bedroom, 1 double bed, 1 bathroom
22–27 Sept
4.67 out of 5 average rating, 3 reviews
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Home in Orleans
Luxury - Orleans Getaway Perfect for Large Groups
5 bedrooms, 8 beds, 4.5 bathrooms
4–9 Oct
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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
26 Sept – 1 Oct
4.96 out of 5 average rating, 52 reviews
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Top guest favourite
Home in Orleans
Peaceful Nauset Beach Sanctuary
3 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 38 reviews
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Top guest favourite
Cottage in Orleans
Cozy Condo/Cottage on Cove, Walk to Town
2 bedrooms, 2 queen beds, 1.5 bathrooms
26–31 Aug
4.97 out of 5 average rating, 104 reviews
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Guest favourite
Home in Orleans
7 bedrooms all ensuite, hot tub, pets welcome
7 bedrooms, 7 beds, 8 bathrooms
19–26 Jun
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Guest house in Orleans
Rock Harbor Hideaway
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 44 reviews
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Guest favourite
Home in Orleans
Spacious Cottage near Pleasant Bay
2 bedrooms, 5 beds, 2 bathrooms
30 Sept – 5 Oct
4.81 out of 5 average rating, 99 reviews
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Home in Orleans
Orleans "Hydrangea House" Cape Cottage
5 bedrooms, 7 beds, 3.5 bathrooms
1–8 Jan
4.8 out of 5 average rating, 20 reviews
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Guest favourite
Home in Orleans
Walk to Lake + Fire Pit | Near Nauset + Sleeps 10
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.99 out of 5 average rating, 114 reviews
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Guest favourite
Home in Orleans
Luxury 7 BR, 4 BA w/Unique 60 ft Swimming Pool
7 bedrooms, 13 beds, 4 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 21 reviews
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Top guest favourite
Home in Orleans
Luxury September Retreat w Pool -Near Nauset Beach
4 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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Home in Eastham
Ambergris Gables & Owl's Nest Cottage
5 bedrooms, 8 beds, 4 bathrooms
28 Sept – 5 Oct
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Guest favourite
Cottage in Orleans
East Orleans Family Estate with Water Views
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
4.92 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Eastham
Renovated with WATER VIEWS of Orleans Town Cove
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Orleans
Steps to Rock Harbor | AC, Deck, Outdoor Shower
2 bedrooms, 3 beds, 1 bathroom
3–8 Oct
5.0 out of 5 average rating, 47 reviews