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Search results; Over 1,000 homes in Annapolis

Top guest favourite

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

Studio, 1 bed, 1 private bathroom

1–6 Aug

,

4.98 out of 5 average rating, 161 reviews

Top guest favourite

Home in Annapolis

CJ's Cottage

2 bedrooms, 3 beds, 2 bathrooms

15–20 Aug

$1,864 SGD for 5 nights

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4.96 out of 5 average rating, 75 reviews

Guest favourite

Home in Arnold

Rachel's BnB

2 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$1,040 SGD for 5 nights

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Free cancellation

4.91 out of 5 average rating, 138 reviews

Top guest favourite

Home in Annapolis

Cozy Stay in Downtown Naptown

3 bedrooms, 2 bathrooms

10–15 Aug

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4.94 out of 5 average rating, 31 reviews

Guest favourite

Room in Annapolis

Blue Heron Room - Charming Private Room, Annapolis

1 queen bed, 3 bathrooms

15–20 Aug

$414 SGD for 5 nights

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4.95 out of 5 average rating, 182 reviews

Top guest favourite

Home in Annapolis

2Bd Water View, w/Beach near Downtown Annapolis

2 bedrooms, 3 beds, 1 bathroom

22–27 Aug

$1,986 SGD for 5 nights

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5.0 out of 5 average rating, 15 reviews

Guest favourite

Room in Annapolis

Osprey Room - Charming private room, Annapolis

1 queen bed, 1.5 bathrooms

16–21 Aug

$375 SGD for 5 nights

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4.93 out of 5 average rating, 181 reviews

Guest favourite

Flat in Annapolis

Private Annapolis Inlaw Apartment

1 bedroom, 1 king bed, 1 bathroom

10–15 Aug

$826 SGD for 5 nights

4.89 out of 5 average rating, 365 reviews

Guest favourite

Townhouse in Annapolis

Historic Row Home in Downtown Annapolis

2 bedrooms, 6 beds, 2 bathrooms

10–15 Aug

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4.95 out of 5 average rating, 22 reviews

Guest favourite

Home in Annapolis

Stay Retro Naptown

4 bedrooms, 4 queen beds, 2 bathrooms

15–20 Sept

$1,809 SGD for 5 nights

4.95 out of 5 average rating, 80 reviews

Top guest favourite

Guest suite in Annapolis

Charming Detached Studio w/ easy walk to Downtown.

1 bedroom, 1 queen bed, 1 bathroom

1–6 Aug

$1,391 SGD for 5 nights

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4.96 out of 5 average rating, 224 reviews

Guest favourite

Home in Annapolis

Firepit + Basement Lounge + Putt Green | Sleeps 12

4 bedrooms, 6 beds, 2.5 bathrooms

10–15 Aug

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4.96 out of 5 average rating, 24 reviews

Guest favourite

Home in Annapolis

Peaceful Pet-Friendly Stay | Near USNA & Beaches

3 bedrooms, 5 beds, 2.5 bathrooms

1–6 Aug

$1,900 SGD for 5 nights

4.9 out of 5 average rating, 21 reviews

Superhost

Home in Annapolis

*NEW* Pristine, Upscale, Walkable to Town/Stadium

3 bedrooms, 4 beds, 3.5 bathrooms

29 Sept – 4 Oct

$4,833 SGD for 5 nights

New place to stay

Guest favourite

Home in Annapolis

Historic Row Home | Hot Tub - 1 Block from Gate 1!

3 bedrooms, 6 beds, 2.5 bathrooms

10–15 Aug

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4.94 out of 5 average rating, 31 reviews

Guest favourite

Guest suite in Annapolis

Quaint 2BR Naptown Hidden Gem<1 Mile-Navy Stadium

2 bedrooms, 4 beds, 1 bathroom

10–15 Aug

Extended stay discount

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4.91 out of 5 average rating, 57 reviews

Top guest favourite

Home in Annapolis

Annapolis Cottage at Bay Ridge, Renovated

3 bedrooms, 5 beds, 2 bathrooms

10–15 Aug

$2,777 SGD for 5 nights

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4.98 out of 5 average rating, 66 reviews

Guest favourite

Home in Annapolis

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

3 bedrooms, 4 beds, 1 bathroom

16–21 Aug

$2,800 SGD for 5 nights

4.97 out of 5 average rating, 98 reviews

Guest favourite

Home in Annapolis

Marymont Cottage

3 bedrooms, 3 beds, 2 bathrooms

11–16 Aug

$2,739 SGD for 5 nights

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5.0 out of 5 average rating, 28 reviews