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Search results; Over 1,000 homes in Annapolis

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Top guest favourite

Home in Annapolis

Marymont Cottage

3 bedrooms, 3 beds, 2 private bathrooms

26–31 Oct

$2,656 SGD for 5 nights

,

5.0 out of 5 average rating, 32 reviews

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Home in Annapolis

Charming & Elegant in historic downtown Annapolis

4 bedrooms, 8 beds

12–17 Oct

$6,019 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 13 reviews

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Flat in Annapolis

Annapolis Getaway | 2BR Sleeps 6 | Near USNA

3 bedrooms, 2 beds

4–9 Oct

$1,348 SGD for 5 nights

New place to stay

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Home in Annapolis

The Melrose Retreat

4 bedrooms, 4 beds

4–9 Oct

$1,863 SGD for 5 nights

New place to stay

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Top guest favourite

Flat in Annapolis

Charming, Chic Downtown Annapolis Apartment #1

1 bedroom, 1 bed

4–9 Oct

$1,892 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 126 reviews

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Top guest favourite

Home in Annapolis

Walk to Navy Stadium & Shops. No cleaning fee!

3 bedrooms, 4 beds

1–6 Oct

$3,008 SGD for 5 nights

5.0 out of 5 average rating, 37 reviews

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Top guest favourite

Home in Annapolis

Cozy Stay in Downtown Naptown

3 bedrooms

25–30 Oct

$1,840 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 36 reviews

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Top guest favourite

Cottage in Annapolis

Wonderful Cottage Nestled On Chesapeake Bay

3 bedrooms, 5 beds

26–31 Oct

$2,184 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 46 reviews

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Top guest favourite

Home in Annapolis

The Red Door Cottage - Pet-Friendly!

2 bedrooms, 2 beds

16–21 Nov

$1,721 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 43 reviews

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Guest suite in Annapolis

Annapolis Home 5 miles from Downtown Annapolis

4 bedrooms, 4 beds

1–6 Oct

$6,528 SGD for 5 nights

New place to stay

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Guest favourite

Home in Annapolis

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

3 bedrooms, 5 beds

1–6 Oct

Extended stay discount

4.96 out of 5 average rating, 26 reviews

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Top guest favourite

Home in Annapolis

The Midship Quarters

3 bedrooms, 3 single beds

4–9 Oct

$3,414 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 53 reviews

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Top guest favourite

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

2 bedrooms, 2 king beds

3–8 Oct

$1,677 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 473 reviews

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Guest favourite

Home in Annapolis

Charming Annapolis Townhome

2 bedrooms

25–30 Oct

$1,614 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 68 reviews

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Guest favourite

Home in Annapolis

The Lighthouse: Walk to stadium, downtown, West St

4 bedrooms, 6 beds

4–9 Oct

Extended stay discount

Free cancellation

4.96 out of 5 average rating, 48 reviews

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Top guest favourite

Guest house in Annapolis

Coastal Waterfront 1 Bedroom Cottage

1 bedroom, 1 bed

17–22 Oct

$2,972 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 226 reviews

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Home in Annapolis

The 1845 Outpost

3 bedrooms, 3 king beds

25–30 Oct

$3,456 SGD for 5 nights

Free cancellation

New place to stay

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Home in Annapolis

The Harness Creek House

6 bedrooms, 6 beds

1–6 Oct

$13,021 SGD for 5 nights

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Guest favourite

Home in Annapolis

The Navy House-Walk or Shuttle Downtown! 3 bd

3 bedrooms, 4 beds

4–9 Oct

$2,627 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 206 reviews