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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

$1,970 SGD for 5 nights

,

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

$954 SGD for 5 nights

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

$3,648 SGD for 5 nights

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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

Extended stay discount

5.0 out of 5 average rating, 43 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

$16,075 SGD for 5 nights

4.95 out of 5 average rating, 59 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

Home in Orleans

Walk to Lake + Fire Pit | Near Nauset + Sleeps 10

3 bedrooms, 6 beds, 2 bathrooms

1–6 Oct

Extended stay discount

4.99 out of 5 average rating, 115 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

$6,185 SGD for 5 nights

4.98 out of 5 average rating, 42 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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Top guest favourite

Flat in Brewster

A walk in the park

1 bedroom, 1 queen bed, 1 bathroom

4–9 Nov

$861 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 84 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

$2,673 SGD for 7 nights

4.97 out of 5 average rating, 35 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

Villa in Cape Cod

Cape Cod Villa retreat, venue, film & bachelorette

5 bedrooms, 9 beds, 2 bathrooms

11–16 Oct

$6,343 SGD for 5 nights

4.98 out of 5 average rating, 135 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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Guest favourite

Home in Orleans

Luxury 7 BR, 4 BA w/Unique 60 ft Swimming Pool

7 bedrooms, 13 beds, 4 bathrooms

1–6 Oct

4.95 out of 5 average rating, 21 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

3–8 Nov

Extended stay discount

Free cancellation

5.0 out of 5 average rating, 12 reviews

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Featured hotel

Hotel in Yarmouth

Blue Lobster Inn, Select

1 bedroom, 1 king bed, 1 bathroom

1–6 Oct

$768 SGD for 5 nights

+$115 SGD Airbnb credit

4.88 out of 5 average rating, 48 reviews

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Top guest favourite

Room in Orleans

Noor's Nook

1 bed, 1 bathroom

1–6 Oct

$1,307 SGD for 5 nights

4.97 out of 5 average rating, 34 reviews

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Guest favourite

Home in Eastham

Charming Waterfront Escape Along the Cove

2 bedrooms, 3 beds, 1 bathroom

19–24 Oct

$1,799 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews