Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Annapolis
Check in / Check out
Any week
Guests
Add guests
Filters
0
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
Show map
Search results; Over 1,000 homes in Annapolis
Over 1,000 homes in Annapolis
Guest favourite
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom
,
·
2 beds
,
·
1 private bathroom
25–30 Oct
25–30 Oct
$1,280 SGD
Show price breakdown
for 5 nights
$1,280 SGD for 5 nights
,
·
4.96 out of 5 average rating, 240 reviews
4.96 (240)
Top guest favourite
Guest favourite
Flat in Annapolis
Perfect Eastport location
4.98 out of 5 average rating, 142 reviews
4.98 (142)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,966 SGD
Show price breakdown
for 5 nights
$1,966 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
4.97 out of 5 average rating, 454 reviews
4.97 (454)
,
·
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
9–14 Nov
9–14 Nov
$808 SGD
Show price breakdown
for 5 nights
$808 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
4.96 out of 5 average rating, 255 reviews
4.96 (255)
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$1,212 SGD
Show price breakdown
for 5 nights
$1,212 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
4.97 out of 5 average rating, 72 reviews
4.97 (72)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
28 Jul – 2 Aug
28 Jul – 2 Aug
$2,175 SGD
$1,593 SGD
Show price breakdown
for 5 nights
Top guest favourite
Guest favourite
Home in Annapolis
Downtown Home/ Central Location
5.0 out of 5 average rating, 35 reviews
5.0 (35)
,
·
2 bedrooms
2 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,659 SGD
Show price breakdown
for 5 nights
$2,659 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews
4.93 (179)
,
·
1 queen bed
1 queen bed
,
·
1.5 bathrooms
1.5 bathrooms
24–29 Jul
24–29 Jul
$492 SGD
Show price breakdown
for 5 nights
$492 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews
4.93 (179)
,
·
1 queen bed
1 queen bed
,
·
1.5 bathrooms
1.5 bathrooms
9–14 Jul
9–14 Jul
$518 SGD
Show price breakdown
for 5 nights
$518 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
5.0 out of 5 average rating, 47 reviews
5.0 (47)
,
·
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Jul
13–18 Jul
$2,477 SGD
Show price breakdown
for 5 nights
$2,477 SGD for 5 nights
Guest favourite
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 180 reviews
4.95 (180)
,
·
1 queen bed
1 queen bed
,
·
3 bathrooms
3 bathrooms
26–31 Jul
26–31 Jul
$440 SGD
Show price breakdown
for 5 nights
$440 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 72 reviews
4.92 (72)
,
·
2 bedrooms
2 bedrooms
,
·
1 bed
1 bed
,
·
1.5 bathrooms
1.5 bathrooms
16–21 Jul
16–21 Jul
$1,796 SGD
$1,610 SGD
Show price breakdown
for 5 nights
Free cancellation
Guest favourite
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
4.86 out of 5 average rating, 122 reviews
4.86 (122)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,146 SGD
$1,791 SGD
Show price breakdown
for 5 nights
Free cancellation
Guest favourite
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 358 reviews
4.89 (358)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
27 Jul – 1 Aug
27 Jul – 1 Aug
$789 SGD
Show price breakdown
for 5 nights
$789 SGD for 5 nights
Guest favourite
Guest favourite
Home in Annapolis
Marymont Cottage
5.0 out of 5 average rating, 28 reviews
5.0 (28)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
6–11 Jul
6–11 Jul
$2,743 SGD
Show price breakdown
for 5 nights
$2,743 SGD for 5 nights
Free cancellation
Guest favourite
Guest favourite
Flat in Annapolis
Annapolis 4 Steps to Harbor Backs to Gate 1
4.96 out of 5 average rating, 27 reviews
4.96 (27)
,
·
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$904 SGD
Show price breakdown
for 5 nights
$904 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4.94 out of 5 average rating, 200 reviews
4.94 (200)
,
·
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$3,215 SGD
$2,400 SGD
Show price breakdown
for 5 nights
Free cancellation
Guest favourite
Guest favourite
Home in Annapolis
Cozy Cottage
4.96 out of 5 average rating, 25 reviews
4.96 (25)
,
·
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,661 SGD
Show price breakdown
for 5 nights
$1,661 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 57 reviews
4.98 (57)
,
·
2 bedrooms
2 bedrooms
,
·
1.5 bathrooms
1.5 bathrooms
13–18 Jul
13–18 Jul
$2,780 SGD
$2,050 SGD
Show price breakdown
for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Guest suite in Annapolis
Restful guest suite, scent-free, step-free
5.0 out of 5 average rating, 36 reviews
5.0 (36)
,
·
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
7–12 Jul
7–12 Jul
$1,971 SGD
$1,683 SGD
Show price breakdown
for 5 nights
Free cancellation
1
2
3
4
…
15