We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Annapolis

Photo 1 of 29

Guest favourite

Home in Cape St. Claire

Country House on the Bay

5 bedrooms, 10 beds, 3 private bathrooms

1–6 Oct

$1,465 SGD for 5 nights

,

4.9 out of 5 average rating, 231 reviews

Photo 1 of 29

Home in Annapolis

Charming & Elegant in historic downtown Annapolis

4 bedrooms, 8 beds, 3 bathrooms

12–17 Oct

$6,019 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 13 reviews

Photo 1 of 21

Top guest favourite

Home in Annapolis

Walk to Navy Stadium & Shops. No cleaning fee!

3 bedrooms, 4 beds, 2.5 bathrooms

1–6 Oct

$3,008 SGD for 5 nights

5.0 out of 5 average rating, 37 reviews

Photo 1 of 12

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

Photo 1 of 18

Top guest favourite

Flat in Annapolis

Charming, Chic Downtown Annapolis Apartment #1

1 bedroom, 1 bed, 1 bathroom

4–9 Oct

$1,892 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 126 reviews

Photo 1 of 29

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

Photo 1 of 29

Guest favourite

Home in Annapolis

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

3 bedrooms, 5 beds, 3.5 bathrooms

1–6 Oct

Extended stay discount

4.96 out of 5 average rating, 26 reviews

Photo 1 of 29

Guest favourite

Home in Annapolis

Across from stadium - walk to downtown Annapolis!

4 bedrooms, 4 beds, 3 bathrooms

4–9 Oct

$2,298 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 136 reviews

Photo 1 of 26

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

Photo 1 of 15

Top guest favourite

Home in Annapolis

Cozy Stay in Downtown Naptown

3 bedrooms, 2 bathrooms

25–30 Oct

$1,840 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 36 reviews

Photo 1 of 9

Top guest favourite

Home in Annapolis

Historic Downtown in-law suite

1 bedroom, 2 beds, 1 bathroom

4–9 Dec

$1,172 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 268 reviews

Photo 1 of 29

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

Photo 1 of 29

Top guest favourite

Home in Annapolis

The General's House-Spacious Home w/Pool & Hot Tub

4 bedrooms, 7 beds, 4 bathrooms

1–6 Oct

$4,360 SGD for 5 nights

4.96 out of 5 average rating, 46 reviews

Photo 1 of 29

Guest favourite

Home in Annapolis

The Navy House-Walk or Shuttle Downtown! 3 bd

3 bedrooms, 4 beds, 2.5 bathrooms

4–9 Oct

$2,627 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 206 reviews

Photo 1 of 29

Top guest favourite

Cottage in Annapolis

Wonderful Cottage Nestled On Chesapeake Bay

3 bedrooms, 5 beds, 2.5 bathrooms

26–31 Oct

$2,184 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 46 reviews

Photo 1 of 29

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

Photo 1 of 29

Home in Annapolis

The Harness Creek House

6 bedrooms, 6 beds, 5 bathrooms

1–6 Oct

$13,021 SGD for 5 nights

Photo 1 of 29

Top guest favourite

Guest house in Annapolis

Coastal Waterfront 1 Bedroom Cottage

1 bedroom, 1 bed, 1 bathroom

17–22 Oct

$2,972 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 226 reviews

Photo 1 of 13

Top guest favourite

Flat in Annapolis

The Sail Loft

3 bedrooms, 4 beds, 2 bathrooms

4–9 Oct

$2,699 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 44 reviews