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Search results; Over 1,000 homes in Tilghman Island

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Top guest favourite

Home in Tilghman Island

Panoramic water views

2 bedrooms, 2 beds, 1 private bathroom

19–24 Oct

$2,203 SGD for 5 nights

,

4.95 out of 5 average rating, 43 reviews

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Top guest favourite

Home in Tilghman Island

The Getaway

3 bedrooms, 3 beds, 2 bathrooms

28 Sept – 3 Oct

Free cancellation

5.0 out of 5 average rating, 34 reviews

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Guest favourite

Home in Tilghman Island

Charming Tilghman Island Cottage | Pets Welcome

3 bedrooms, 4 beds, 2.5 bathrooms

4–9 Oct

$2,917 SGD for 5 nights

5.0 out of 5 average rating, 39 reviews

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Guest favourite

Home in Tilghman Island

Tranquility on Tilghman Island – Wide Water Views

5 bedrooms, 8 beds, 4.5 bathrooms

12–17 Oct

$6,031 SGD for 5 nights

4.96 out of 5 average rating, 46 reviews

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Guest favourite

Home in Tilghman Island

Tilghman Island Retreat By Knapps Narrows!

2 bedrooms, 3 beds, 2 bathrooms

21–26 Sept

$1,784 SGD for 5 nights

4.95 out of 5 average rating, 22 reviews

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Top guest favourite

Guest suite in Tilghman Island

Black Walnut Cove Retreat, Tilghman Island

1 bedroom, 4 beds, 1 bathroom

20–25 Sept

$1,019 SGD for 5 nights

4.97 out of 5 average rating, 181 reviews

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Guest favourite

Home in Tilghman Island

Pet-Friendly Summer Retreat on Tilghman

3 bedrooms, 4 beds, 2 bathrooms

20–25 Sept

$2,203 SGD for 5 nights

4.81 out of 5 average rating, 16 reviews

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Guest favourite

Home in Tilghman Island

Tilghman Retreat: A house on the Chesapeake Bay.

3 bedrooms, 4 beds, 2 bathrooms

21–26 Sept

4.94 out of 5 average rating, 54 reviews

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Superhost

Home in Tilghman Island

Bayfront Escape Tilghman Island | Sunset Views

3 bedrooms, 3 queen beds, 2 bathrooms

25–30 Oct

$3,424 SGD for 5 nights

4.84 out of 5 average rating, 19 reviews

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Guest favourite

Home in Sherwood

Chesapeake Mansion-heated pool 30acre waterfront

8 bedrooms, 11 beds, 11 bathrooms

5–10 Oct

4.99 out of 5 average rating, 80 reviews

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Home in Tilghman Island

Sunsets on Skipjack

3 bedrooms, 3 queen beds, 2 bathrooms

23–28 Sept

$2,109 SGD for 5 nights

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Superhost

Home in Tilghman Island

Waterfront Bliss | an ESVR property

4 bedrooms, 6 beds, 3 bathrooms

17–22 Sept

$4,970 SGD for 5 nights

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Superhost

Home in Tilghman Island

Charming 2 Bedroom Cottage on Tilghman Island

2 bedrooms, 3 beds, 2 bathrooms

20–25 Sept

$2,523 SGD for 5 nights

4.73 out of 5 average rating, 15 reviews

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Guest favourite

Home in Tilghman Island

Tilghman Island Cottage – Pets Welcome!

3 bedrooms, 3 beds, 2 bathrooms

20–25 Sept

$2,626 SGD for 5 nights

4.88 out of 5 average rating, 17 reviews

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Featured hotel

Hotel in St. Michaels

Standard double room

1 bedroom, 2 double beds, 1 bathroom

20–25 Sept

$712 SGD for 5 nights

+$106 SGD Airbnb credit

New place to stay

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Guest favourite

Home in Shady Side

Waterfront Coastal Retreat w/ Beach Access

3 bedrooms, 1 bathroom

28 Sept – 3 Oct

$783 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 13 reviews

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Top guest favourite

Home in Sherwood

Time Stands Still, While Memories Are Made.

6 bedrooms, 8 beds, 4.5 bathrooms

4–9 Oct

$7,176 SGD for 5 nights

4.97 out of 5 average rating, 35 reviews

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Guest favourite

Home in Sherwood

Punch Point boasts a sandy beach w/ pool and pier

5 bedrooms, 5 beds, 4.5 bathrooms

16–21 Sept

$6,806 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

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Top guest favourite

Home in Cambridge

Relaxing Retreat on the Hudson

5 bedrooms, 5 beds, 2 bathrooms

4–9 Oct

4.96 out of 5 average rating, 81 reviews