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Search results; Over 1,000 places in Annapolis
Over 1,000 places in Annapolis
Guest favorite
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
1 king bed
May 30 – Jun 4
May 30 – Jun 4
$89
night
$89 per night
4.9 out of 5 average rating, 206 reviews
4.9 (206)
Guest favorite
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$140
night
$140 per night
4.96 out of 5 average rating, 213 reviews
4.96 (213)
Guest favorite
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
1 bed
Nov 18 – 23
Nov 18 – 23
$130
night
$130 per night
4.96 out of 5 average rating, 109 reviews
4.96 (109)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$147
night
$147 per night
4.94 out of 5 average rating, 312 reviews
4.94 (312)
Guest favorite
Guest favorite
Townhouse in Annapolis
1 Bedroom Apt - Walk to Downtown - With Parking
2 beds
2 beds
Apr 28 – May 3
Apr 28 – May 3
$130
$98
night
$98 per night, originally $130
4.94 out of 5 average rating, 50 reviews
4.94 (50)
Guest favorite
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$173
night
$173 per night
4.94 out of 5 average rating, 351 reviews
4.94 (351)
Guest favorite
Guest favorite
Guesthouse in Annapolis
RECENTLY RENOVATED Cottage Near Downtown Annapolis
1 king bed
1 king bed
Apr 22 – 27
Apr 22 – 27
$110
night
$110 per night
4.97 out of 5 average rating, 197 reviews
4.97 (197)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 21 – 26
Apr 21 – 26
$325
$290
night
$290 per night, originally $325
4.99 out of 5 average rating, 105 reviews
4.99 (105)
Guest favorite
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$250
$213
night
$213 per night, originally $250
4.96 out of 5 average rating, 102 reviews
4.96 (102)
Guest favorite
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
3 beds
3 beds
May 5 – 10
May 5 – 10
$177
night
$177 per night
4.94 out of 5 average rating, 287 reviews
4.94 (287)
Guest favorite
Guest favorite
Townhouse in Annapolis
Historic 3 Bedroom Downtown Annapolis Townhome
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
$399
$173
night
$173 per night, originally $399
4.97 out of 5 average rating, 99 reviews
4.97 (99)
Guest favorite
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
2 king beds
Apr 23 – 28
Apr 23 – 28
$177
night
$177 per night
4.96 out of 5 average rating, 332 reviews
4.96 (332)
Guest favorite
Guest favorite
Home in Annapolis
Elegant & Authentic Annapolis
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
$203
night
$203 per night
5.0 out of 5 average rating, 37 reviews
5.0 (37)
Guest favorite
Guest favorite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$195
night
$195 per night
4.98 out of 5 average rating, 64 reviews
4.98 (64)
Guest favorite
Guest favorite
Houseboat in Arnold
Boho Luxe Floating Tiny Home with 360 Views
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
$206
$185
night
$185 per night, originally $206
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
5 beds
May 19 – 24
May 19 – 24
$1,040
$458
night
$458 per night, originally $1,040
5.0 out of 5 average rating, 84 reviews
5.0 (84)
Superhost
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
6 beds
Apr 21 – 26
Apr 21 – 26
$900
night
$900 per night
New place to stay
New
Home in Annapolis
Nautical - and oh, so nice!
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
$326
night
$326 per night
New place to stay
New
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