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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
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for 5 nights
$2,963 SGD for 5 nights
,
·
5.0 out of 5 average rating, 226 reviews
5.0 (226)
Photo 1 of 20
Top guest favourite
Guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$1,040 SGD
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for 5 nights
$1,040 SGD for 5 nights
4.92 out of 5 average rating, 1141 reviews
4.92 (1141)
Photo 1 of 17
Guest favourite
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
8–13 Nov
8–13 Nov
$987 SGD
$896 SGD
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for 5 nights
Free cancellation
4.9 out of 5 average rating, 153 reviews
4.9 (153)
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, 266 reviews
4.96 (266)
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
$1,692 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 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
$6,507 SGD
$2,757 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
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
$2,329 SGD
$1,953 SGD
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for 5 nights
4.98 out of 5 average rating, 54 reviews
4.98 (54)
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
$4,126 SGD
$2,459 SGD
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for 5 nights
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$1,181 SGD
$1,034 SGD
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for 5 nights
4.99 out of 5 average rating, 167 reviews
4.99 (167)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
2 bedrooms
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
$2,096 SGD
$1,157 SGD
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for 5 nights
4.97 out of 5 average rating, 68 reviews
4.97 (68)
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 29
Superhost
Superhost
Home in Annapolis
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
5 bathrooms
5 bathrooms
20–25 Sept
20–25 Sept
$6,701 SGD
$4,155 SGD
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for 5 nights
4.86 out of 5 average rating, 22 reviews
4.86 (22)
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
$2,170 SGD
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for 5 nights
$2,170 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 45 reviews
4.98 (45)
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
19–24 Sept
19–24 Sept
$6,512 SGD
Show price breakdown
for 5 nights
$6,512 SGD for 5 nights
New place to stay
New
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
The General's House-Spacious Home w/Pool & Hot Tub
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
4 bathrooms
4 bathrooms
28 Sept – 3 Oct
28 Sept – 3 Oct
$5,356 SGD
$4,455 SGD
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for 5 nights
4.96 out of 5 average rating, 46 reviews
4.96 (46)
Photo 1 of 19
Top guest favourite
Guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
2 beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
$1,324 SGD
$1,147 SGD
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for 5 nights
4.96 out of 5 average rating, 179 reviews
4.96 (179)
Photo 1 of 29
Home in Severn
Jo’s Luxury Retreat
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
4–9 Oct
4–9 Oct
$1,579 SGD
$1,310 SGD
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for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
20–25 Sept
20–25 Sept
$3,154 SGD
$1,749 SGD
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for 5 nights
4.94 out of 5 average rating, 33 reviews
4.94 (33)
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
$4,103 SGD
$3,185 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 52 reviews
5.0 (52)
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