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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
Jul 7 – 12
Jul 7 – 12
$89
night
$89 per night
4.9 out of 5 average rating, 206 reviews
4.9 (206)
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
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$141
night
$141 per night
4.96 out of 5 average rating, 213 reviews
4.96 (213)
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
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, 104 reviews
4.99 (104)
Superhost
Superhost
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
2 queen beds
2 queen beds
Jul 21 – 26
Jul 21 – 26
$119
night
$119 per night
4.82 out of 5 average rating, 655 reviews
4.82 (655)
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, 108 reviews
4.96 (108)
Guest favorite
Guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 queen bed
1 queen bed
Jun 18 – 23
Jun 18 – 23
$169
night
$169 per night
4.91 out of 5 average rating, 916 reviews
4.91 (916)
Guest favorite
Guest favorite
Home in Annapolis
Adorable 1 bedroom apartment in downtown Annapolis
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$129
night
$129 per night
4.87 out of 5 average rating, 46 reviews
4.87 (46)
Guest favorite
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
2 beds
Apr 28 – May 3
Apr 28 – May 3
$99
night
$99 per night
4.96 out of 5 average rating, 563 reviews
4.96 (563)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
$146
night
$146 per night
4.94 out of 5 average rating, 312 reviews
4.94 (312)
Home in Annapolis
Quaint in the Heart of Annapolis
Apr 28 – May 3
Apr 28 – May 3
$165
night
$165 per night
New place to stay
New
Guest favorite
Guest favorite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 beds
3 beds
Apr 28 – May 3
Apr 28 – May 3
$263
$199
night
$199 per night, originally $263
4.96 out of 5 average rating, 50 reviews
4.96 (50)
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
$238
night
$238 per night
4.96 out of 5 average rating, 101 reviews
4.96 (101)
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
Home in Annapolis
New Hotel Chic
2 beds
2 beds
Jun 9 – 14
Jun 9 – 14
$240
night
$240 per night
4.95 out of 5 average rating, 344 reviews
4.95 (344)
Guest favorite
Guest favorite
Home in Annapolis
Nautical Luxe Retreat! 6 Guests • 3 BDR • 2 Baths
3 beds
3 beds
Apr 28 – May 3
Apr 28 – May 3
$239
night
$239 per night
5.0 out of 5 average rating, 24 reviews
5.0 (24)
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)
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