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Search results; Over 1,000 homes in Annapolis
Over 1,000 homes in Annapolis
Photo 1 of 25
Top guest favourite
Guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom
,
·
1 bed
,
·
1 private bathroom
17–22 Oct
17–22 Oct
$2,963 SGD
Show price breakdown
for 5 nights
$2,963 SGD for 5 nights
,
·
5.0 out of 5 average rating, 226 reviews
5.0 (226)
Photo 1 of 25
Top guest favourite
Guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,863 SGD
$1,176 SGD
Show price breakdown
for 5 nights
4.93 out of 5 average rating, 137 reviews
4.93 (137)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
,
·
3.5 bathrooms
3.5 bathrooms
20–25 Sept
20–25 Sept
$6,473 SGD
$2,593 SGD
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for 5 nights
4.91 out of 5 average rating, 92 reviews
4.91 (92)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
West street historic home
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$7,693 SGD
$6,768 SGD
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for 5 nights
Free cancellation
4.97 out of 5 average rating, 74 reviews
4.97 (74)
Photo 1 of 9
Top guest favourite
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Dec
4–9 Dec
$1,361 SGD
$1,168 SGD
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for 5 nights
Free cancellation
4.96 out of 5 average rating, 267 reviews
4.96 (267)
Photo 1 of 27
Top guest favourite
Guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
11–16 Oct
11–16 Oct
$2,492 SGD
$2,200 SGD
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for 5 nights
4.97 out of 5 average rating, 146 reviews
4.97 (146)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
3–8 Oct
3–8 Oct
$1,964 SGD
$1,680 SGD
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for 5 nights
Free cancellation
4.97 out of 5 average rating, 472 reviews
4.97 (472)
Photo 1 of 25
Top guest favourite
Guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms
3 bedrooms
,
·
3 single beds
3 single beds
,
·
1.5 bathrooms
1.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$4,097 SGD
$3,128 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 52 reviews
5.0 (52)
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3.5 bathrooms
3.5 bathrooms
30 Sept – 5 Oct
30 Sept – 5 Oct
$4,125 SGD
$2,459 SGD
Show price breakdown
for 5 nights
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
4–9 Oct
4–9 Oct
$2,679 SGD
$2,116 SGD
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for 5 nights
5.0 out of 5 average rating, 34 reviews
5.0 (34)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
3.5 bathrooms
3.5 bathrooms
20–25 Sept
20–25 Sept
$7,447 SGD
$5,916 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 147 reviews
5.0 (147)
Photo 1 of 15
Top guest favourite
Guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
3 bedrooms
,
·
2 bathrooms
2 bathrooms
25–30 Oct
25–30 Oct
$2,194 SGD
$1,867 SGD
Show price breakdown
for 5 nights
Free cancellation
4.94 out of 5 average rating, 35 reviews
4.94 (35)
Photo 1 of 29
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
30 Sept – 5 Oct
30 Sept – 5 Oct
$6,508 SGD
Show price breakdown
for 5 nights
$6,508 SGD for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 10
Top guest favourite
Guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
29 Oct – 3 Nov
29 Oct – 3 Nov
$1,271 SGD
Show price breakdown
for 5 nights
$1,271 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 228 reviews
4.96 (228)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
8–13 Nov
8–13 Nov
$2,106 SGD
$1,819 SGD
Show price breakdown
for 5 nights
Extended stay discount
Free cancellation
4.96 out of 5 average rating, 48 reviews
4.96 (48)
Photo 1 of 29
Home in Annapolis
Beautiful 6BR home in Annapolis
6 bedrooms
6 bedrooms
,
·
6 beds
6 beds
,
·
4 bathrooms
4 bathrooms
4–9 Oct
4–9 Oct
$2,793 SGD
Show price breakdown
for 5 nights
$2,793 SGD for 5 nights
Free cancellation
4.64 out of 5 average rating, 70 reviews
4.64 (70)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
Eastport Oasis
5 bedrooms
5 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Nov
1–6 Nov
$3,603 SGD
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for 5 nights
$3,603 SGD for 5 nights
4.97 out of 5 average rating, 64 reviews
4.97 (64)
Photo 1 of 12
Top guest favourite
Guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
3–8 Dec
3–8 Dec
$895 SGD
$780 SGD
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for 5 nights
Free cancellation
4.97 out of 5 average rating, 463 reviews
4.97 (463)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
26 Sept – 1 Oct
26 Sept – 1 Oct
$2,186 SGD
Show price breakdown
for 5 nights
$2,186 SGD for 5 nights
4.98 out of 5 average rating, 45 reviews
4.98 (45)
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