Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Shady Side
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Europe
Europe
Italy
Italy
Caribbean
Caribbean
Mexico
Mexico
South America
South America
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Gift cards
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Rooms
Countryside
Amazing pools
Vineyards
Lake
Amazing views
Beach
Chef's kitchens
Trending
Play
Cabins
Farms
Bed & breakfasts
Lakefront
New
Beachfront
Design
Tiny homes
Skiing
Grand pianos
Golfing
Camping
Mansions
Surfing
National parks
Filters
, 1 filter applied
1
Display total before taxes
Show map
Search results; 185 places in Shady Side
185 places in Shady Side
Apartment in Deale
Chesapeake Bayside Bungalow
4 beds
4 beds
Mar 19 – 24
Mar 19 – 24
$143
night
$143 per night
4.52 out of 5 average rating, 54 reviews
4.52 (54)
Superhost
Superhost
Apartment in North Beach
Cheery 1st Level of Beach House -Walk Everywhere!!
5 beds
5 beds
Mar 19 – 24
Mar 19 – 24
$156
night
$156 per night
4.73 out of 5 average rating, 60 reviews
4.73 (60)
Guest favorite
Guest favorite
Apartment in North Beach
Bayside Oasis of Southern Maryland
1 king bed
1 king bed
Mar 21 – 26
Mar 21 – 26
$126
night
$126 per night
4.97 out of 5 average rating, 100 reviews
4.97 (100)
Apartment in Davidsonville
Aspen Woods
1 king bed
1 king bed
May 1 – 6
May 1 – 6
$150
night
$150 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Apartment in Annapolis
Bayside Retreat
1 bed
1 bed
Mar 20 – 25
Mar 20 – 25
$154
night
$154 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Apartment in Edgewater
Pet Friendly Garden Apartment Near Annapolis
1 queen bed
1 queen bed
Apr 10 – 15
Apr 10 – 15
$99
night
$99 per night
4.92 out of 5 average rating, 398 reviews
4.92 (398)
Guest favorite
Guest favorite
Apartment in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
2 beds
2 beds
Mar 23 – 28
Mar 23 – 28
$115
$102
night
$102 per night, originally $115
4.92 out of 5 average rating, 438 reviews
4.92 (438)
Guest favorite
Guest favorite
Apartment in Deale
Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
2 beds
2 beds
Apr 15 – 20
Apr 15 – 20
$179
night
$179 per night
4.91 out of 5 average rating, 614 reviews
4.91 (614)
Guest favorite
Guest favorite
Apartment in Stevensville
Boutique by the Bay
1 queen bed
1 queen bed
Mar 19 – 24
Mar 19 – 24
$175
night
$175 per night
4.97 out of 5 average rating, 239 reviews
4.97 (239)
Guest favorite
Guest favorite
Apartment in Annapolis
Hillsmere Hideaway
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$132
night
$132 per night
4.93 out of 5 average rating, 30 reviews
4.93 (30)
Apartment in Annapolis
Gracie's Garden in Annapolis
1 queen bed
1 queen bed
Mar 19 – 24
Mar 19 – 24
$95
night
$95 per night
4.91 out of 5 average rating, 11 reviews
4.91 (11)
Apartment in Stevensville
Heron Roost
2 beds
2 beds
May 5 – 10
May 5 – 10
$195
night
$195 per night
Superhost
Superhost
Apartment in Annapolis
Annapolis Charmer! 2BR Bright BSMT APT 3 mi to DT
2 beds
2 beds
Mar 19 – 24
Mar 19 – 24
$153
night
$153 per night
4.89 out of 5 average rating, 19 reviews
4.89 (19)
Guest favorite
Guest favorite
Apartment in Upper Marlboro
Stylish Fun! Game & Theater Room, Gym, Pool
5 beds
5 beds
Apr 5 – 10
Apr 5 – 10
$172
night
$172 per night
4.98 out of 5 average rating, 55 reviews
4.98 (55)
Guest favorite
Guest favorite
Apartment in Port Republic
Serenity Suite on Chesapeake Bay
2 beds
2 beds
Apr 7 – 12
Apr 7 – 12
$110
night
$110 per night
4.96 out of 5 average rating, 169 reviews
4.96 (169)
Guest favorite
Guest favorite
Apartment in Saint Michaels
Blue Crab Lodge
3 beds
3 beds
Mar 24 – 29
Mar 24 – 29
$310
$239
night
$239 per night, originally $310
4.95 out of 5 average rating, 21 reviews
4.95 (21)
Apartment in Pasadena
Relaxing Waterfront Apartment!
4 beds
4 beds
Mar 20 – 25
Mar 20 – 25
$277
night
$277 per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Apartment in Fulton
Family Vacation Home Base
3 beds
3 beds
Apr 7 – 12
Apr 7 – 12
$99
$79
night
$79 per night, originally $99
New place to stay
New
1
2
3
4
…
11