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Search results; Over 1,000 places in Annapolis
Over 1,000 places in Annapolis
Home in Annapolis
Quaint in the Heart of Annapolis
2 queen beds
2 queen beds
Apr 1 – 6
Apr 1 – 6
$177
$160
night
$160 per night, originally $177
New place to stay
New
Guest favorite
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 1 – 6
Apr 1 – 6
$299
night
$299 per night
4.99 out of 5 average rating, 102 reviews
4.99 (102)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 2 – 7
Apr 2 – 7
$199
$168
night
$168 per night, originally $199
4.94 out of 5 average rating, 308 reviews
4.94 (308)
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, 103 reviews
4.96 (103)
Guest favorite
Guest favorite
Houseboat in Arnold
Boho Luxe Floating Tiny Home with 360 Views
1 queen bed
1 queen bed
Apr 7 – 12
Apr 7 – 12
$232
$209
night
$209 per night, originally $232
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Guest favorite
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
5 beds
Apr 7 – 12
Apr 7 – 12
$328
$294
night
$294 per night, originally $328
5.0 out of 5 average rating, 82 reviews
5.0 (82)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
1 king bed
Apr 7 – 12
Apr 7 – 12
$89
night
$89 per night
4.9 out of 5 average rating, 202 reviews
4.9 (202)
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, 645 reviews
4.82 (645)
Guest favorite
Guest favorite
451
Reviews
4.96
Rating
6
Years hosting
Room in Annapolis
Stay with Jennifer
Stay with Jennifer
Hosting for 6 years
,
·
Hosting for 6 years
Chesapeake Mornings
Apr 21 – 26
Apr 21 – 26
$54
night
$54 per night
4.96 out of 5 average rating, 451 reviews
4.96 (451)
Guest favorite
Guest favorite
Apartment in Annapolis
Eastport Bungalow
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$117
night
$117 per night
4.92 out of 5 average rating, 59 reviews
4.92 (59)
Guest favorite
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
2 beds
Apr 6 – 11
Apr 6 – 11
$102
night
$102 per night
4.96 out of 5 average rating, 560 reviews
4.96 (560)
Guest favorite
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
2 beds
Apr 10 – 15
Apr 10 – 15
$140
night
$140 per night
4.96 out of 5 average rating, 208 reviews
4.96 (208)
Guest favorite
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$244
$208
night
$208 per night, originally $244
4.94 out of 5 average rating, 284 reviews
4.94 (284)
Guest favorite
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
2 beds
Apr 12 – 17
Apr 12 – 17
$186
night
$186 per night
4.94 out of 5 average rating, 349 reviews
4.94 (349)
Guest favorite
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
2 king beds
Apr 7 – 12
Apr 7 – 12
$169
night
$169 per night
4.96 out of 5 average rating, 328 reviews
4.96 (328)
Superhost
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
$875
night
$875 per night
New place to stay
New
Guest favorite
Guest favorite
Houseboat in Annapolis
Condo Houseboat
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
$519
night
$519 per night
4.98 out of 5 average rating, 110 reviews
4.98 (110)
Guest favorite
Guest favorite
Home in Annapolis
Elegant & Authentic Annapolis
1 queen bed
1 queen bed
Apr 7 – 12
Apr 7 – 12
$200
night
$200 per night
5.0 out of 5 average rating, 36 reviews
5.0 (36)
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