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Search results; Over 1,000 homes in Annapolis

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Top guest favourite

Home in Annapolis

Historic & sunny home steps from USNA/downtown

3 bedrooms, 5 beds, 2.5 private bathrooms

29 Nov – 4 Dec

$3,621 SGD for 5 nights

,

5.0 out of 5 average rating, 205 reviews

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Home in Annapolis

The 1845 Outpost

3 bedrooms, 3 king beds, 2 bathrooms

25–30 Oct

$3,456 SGD for 5 nights

Free cancellation

New place to stay

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Top guest favourite

Home in Annapolis

4BR Walk to USNA & Dock · Parking

4 bedrooms, 4 beds, 4 bathrooms

1–6 Oct

Free cancellation

5.0 out of 5 average rating, 18 reviews

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Home in Annapolis

The Melrose Retreat

4 bedrooms, 4 beds, 3.5 bathrooms

4–9 Oct

$1,863 SGD for 5 nights

New place to stay

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Guest favourite

Home in Annapolis

Charming Annapolis Townhome

2 bedrooms, 1.5 bathrooms

25–30 Oct

$1,614 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 68 reviews

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Flat in Annapolis

Annapolis Getaway | 2BR Sleeps 6 | Near USNA

3 bedrooms, 2 beds, 2 bathrooms

4–9 Oct

$1,348 SGD for 5 nights

New place to stay

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Guest suite in Annapolis

Annapolis Home 5 miles from Downtown Annapolis

4 bedrooms, 4 beds, 4 bathrooms

1–6 Oct

$6,545 SGD for 5 nights

New place to stay

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Guest favourite

Flat in Annapolis

Cozy Annapolis Basement APT

1 bedroom, 1 queen bed, 1 bathroom

4–9 Oct

$1,146 SGD for 5 nights

Free cancellation

4.91 out of 5 average rating, 53 reviews

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Top guest favourite

Guest house in Annapolis

Guesthouse on The Weems Creek

1 bedroom, 1 queen bed, 1 bathroom

1–6 Oct

$1,338 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 49 reviews

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Top guest favourite

Room in Annapolis

Guest Suite Getaway near Naval Academy Stadium

1 bed, 1 bathroom

1–6 Oct

$1,845 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 175 reviews

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Superhost

Home in Annapolis

Waterfront View of Severn, 6 Bedrooms, Sleeps 11

6 bedrooms, 7 beds, 3.5 bathrooms

11–16 Oct

$2,199 SGD for 5 nights

4.83 out of 5 average rating, 6 reviews

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Room in Annapolis

Cozy-Corner West Annapolis

1 double bed, 1 bathroom

2–7 Oct

$1,095 SGD for 5 nights

Free cancellation

New place to stay

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Top guest favourite

Guest house in Annapolis

Garden View, 1 Bedroom and a Loft.

2 bedrooms, 3 beds, 1 bathroom

17–22 Oct

$1,211 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 167 reviews

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Featured hotel

Hotel in Annapolis

Maryland Inn 2 double beds

1 bedroom, 1 double bed, 1 bathroom

31 Oct – 5 Nov

+$137 SGD Airbnb credit

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Guest favourite

Home in Arnold

Rachel's BnB

2 bedrooms, 3 beds, 1 bathroom

8–13 Nov

$894 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 155 reviews

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Guest favourite

Room in Annapolis

Osprey Room - Charming private room, Annapolis

1 queen bed, 1.5 bathrooms

8–13 Nov

$432 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 192 reviews

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Home in Annapolis

Beautiful 6BR home in Annapolis

6 bedrooms, 6 beds, 4 bathrooms

4–9 Oct

$2,802 SGD for 5 nights

Free cancellation

4.63 out of 5 average rating, 71 reviews

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Guest favourite

Guest suite in Annapolis

The Harness Creek Retreat

2 bedrooms, 2 beds, 1 bathroom

1–6 Oct

$2,606 SGD for 5 nights

5.0 out of 5 average rating, 5 reviews

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Guest favourite

Room in Annapolis

Blue Heron Room - Charming Private Room, Annapolis

1 queen bed, 3 bathrooms

25–30 Oct

$524 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 195 reviews