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

Search results; Over 1,000 homes in Annapolis

Top guest favourite

Guest house in Annapolis

Garden View, a spacious 1 bedroom with loft.

2 bedrooms, 3 beds, 1 private bathroom

30 Jul – 4 Aug

$1,389 SGD for 5 nights

,

4.99 out of 5 average rating, 160 reviews

Guest favourite

Room in Annapolis

Blue Heron Room - Charming Private Room, Annapolis

1 queen bed

26–31 Jul

$441 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 180 reviews

Guest favourite

Room in Annapolis

Sandpiper Room - Charming private room, Annapolis

1 queen bed

24–29 Jul

$492 SGD for 5 nights

Pay $0 today

Free cancellation

4.93 out of 5 average rating, 179 reviews

Top guest favourite

Room in Annapolis

Lovely Private Master Bedroom

1 queen bed

4–9 Jul

$1,107 SGD for 5 nights

4.98 out of 5 average rating, 246 reviews

Top guest favourite

Home in Annapolis

CJ's Cottage

2 bedrooms, 3 beds

11–16 Jul

$1,869 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 69 reviews

Top guest favourite

Loft in Annapolis

Step Out to Main Street From a Chic Loft

1 bedroom, 2 beds

10–15 Aug

$1,218 SGD for 5 nights

4.92 out of 5 average rating, 1121 reviews

Top guest favourite

Home in Stevensville

Waterfront | Swim Spa + Sauna + Beach + Game Room

4 bedrooms, 6 beds

30 Aug – 4 Sept

$5,387 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Guest favourite

Home in Annapolis

1 Block to USNA Stadium: Modern Annapolis Home!

2 bedrooms, 3 beds

12–17 Jul

$1,908 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Guest favourite

Home in Annapolis

Cute bungalow blocks to Stadium

2 bedrooms, 3 beds

18–23 Jul

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 71 reviews

Guest favourite

Home in Annapolis

8 Bells Bungalow - Cozy, Stylish, Prime Location

3 bedrooms, 4 beds

22–27 Jul

$1,931 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

1 queen bed

9–14 Jul

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 154 reviews

Top guest favourite

Flat in Annapolis

Stylish Apt in DTA w/porch&parking

2 bedrooms, 1 queen bed

16–21 Jul

Pay $0 today

Free cancellation

4.92 out of 5 average rating, 72 reviews

Top guest favourite

Flat in Annapolis

Upscale Condo In Annapolis w/Private Parking

2 bedrooms, 3 beds

5–10 Jul

4.96 out of 5 average rating, 28 reviews

Top guest favourite

Home in Annapolis

Stay Retro Naptown

4 bedrooms, 4 queen beds

24–29 Jul

4.95 out of 5 average rating, 79 reviews

Top guest favourite

Room in Annapolis

Private Waterfront Treetop Suite, Rooftop Patio

1 queen bed

6–11 Jul

$1,229 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 127 reviews

Top guest favourite

Flat in Annapolis

Serene Hideaway

1 bedroom, 2 beds

5–10 Jul

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Home in Annapolis

Cozy Stay in Downtown Naptown

3 bedrooms

5–10 Jul

Pay $0 today

Free cancellation

4.93 out of 5 average rating, 27 reviews

Top guest favourite

Rooms in Annapolis

Rooms at Garden House next to USNA & Harbor

2 bedrooms, 4 beds

5–10 Jul

$1,183 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 256 reviews

Top guest favourite

Guest house in Annapolis

Eastport Gem ~ Walk to Downtown Annapolis

1 bedroom, 2 beds

10–15 Jul

$2,035 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 90 reviews