Top Tours in Shady Side

Chesapeake Bay Small-Group Yacht Sailing Tour
Chesapeake Bay Small-Group Yacht Sailing Tour
10
Excellent
39 Reviews
5-Star Rating Recommendation
From
US $116Per Person
Reserve
Annapolis Historic Walking Tour: Harbor and Colonial Downtown
Annapolis Historic Walking Tour: Harbor and Colonial Downtown
10
Excellent
46 Reviews
5-Star Rating Recommendation
From
US $235Per Person
Reserve
Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
Tipsy History: The Happy Hour Historical Pub Crawl of Annapolis
10
Excellent
37 Reviews
5-Star Rating Recommendation
From
US $29Per Person
Reserve
Historic Annapolis Walking Tour - Small Group Guided Tour
Historic Annapolis Walking Tour - Small Group Guided Tour
10
Excellent
16 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Annapolis Colonial and Maritime History Walking Tour
Annapolis Colonial and Maritime History Walking Tour
10
Excellent
6 Reviews
5-Star Rating Recommendation
From
US $38Per Person
Reserve
Colonial Annapolis and Naval Academy Half Day Private Bus Tour
Colonial Annapolis and Naval Academy Half Day Private Bus Tour
10
Excellent
1 Reviews
5-Star Rating Recommendation
From
US $1,729Per Person
Reserve
Chesapeake Bay Private Themed and Special Event Cruise
Chesapeake Bay Private Themed and Special Event Cruise
10
Excellent
1 Reviews
5-Star Rating Recommendation
From
US $798Per Person
Reserve
Chesapeake Beach Guided Railway Trail Walk
Chesapeake Beach Guided Railway Trail Walk
10
Excellent
1 Reviews
5-Star Rating Recommendation
From
US $40Per Person
Reserve
Hidden History Pub Crawl of Historic Annapolis
Hidden History Pub Crawl of Historic Annapolis
10
Excellent
1 Reviews
5-Star Rating Recommendation
From
US $30Per Person
Reserve
Maryland 1-Hour Annapolis Ghost Walking Tour
Maryland 1-Hour Annapolis Ghost Walking Tour
9
Excellent
89 Reviews
5-Star Rating Recommendation
From
US $35Per Person
Reserve
Historic Annapolis Food Tour
Historic Annapolis Food Tour
9
Excellent
48 Reviews
5-Star Rating Recommendation
From
US $79Per Person
Reserve
The Original Walking Ghost Tour by Annapolis Ghost Tours
The Original Walking Ghost Tour by Annapolis Ghost Tours
9
Excellent
45 Reviews
5-Star Rating Recommendation
From
US $26Per Person
Reserve
Find A Tour In Shady Side

All Tours in Shady Side

Whether you love exploring landmarks or tasting local cuisine, you’ll find endless adventures here.

Most popular tours in Shady Side

See all 45+ Tours in Shady Side
See all 45+ Tours in Shady Side

Other tours in Shady Side

Outdoor Painting Activity with a Local Artist in Annapolis
Outdoor Painting Activity with a Local Artist in Annapolis
10
Excellent
7 Reviews
5-Star Rating Recommendation
From
US $120Per Person
Reserve
Annapolis Colonial and Maritime History Walking Tour
Annapolis Colonial and Maritime History Walking Tour
10
Excellent
6 Reviews
5-Star Rating Recommendation
From
US $39Per Person
Reserve
Urban Sketching and Painting Activity in Old Town Annapolis
Urban Sketching and Painting Activity in Old Town Annapolis
10
Excellent
1 Reviews
5-Star Rating Recommendation
From
US $120Per Person
Reserve
Ashes and Apparitions of Annapolis Ghost Tour
Ashes and Apparitions of Annapolis Ghost Tour
9
Excellent
89 Reviews
5-Star Rating Recommendation
From
US $25Per Person
Reserve
The Original Haunted Pub Crawl by Annapolis Ghost Tours
The Original Haunted Pub Crawl by Annapolis Ghost Tours
9
Excellent
22 Reviews
5-Star Rating Recommendation
From
US $31Per Person
Reserve
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
9
Excellent
13 Reviews
5-Star Rating Recommendation
From
US $28Per Person
Reserve
Chesapeake Beach: Sunset Cruise on the Bay
Chesapeake Beach: Sunset Cruise on the Bay
9
Excellent
12 Reviews
5-Star Rating Recommendation
From
US $139Per Person
Reserve
Chesapeake Bay Private Sailing Tour From Chesapeake Beach
Chesapeake Bay Private Sailing Tour From Chesapeake Beach
9
Excellent
7 Reviews
5-Star Rating Recommendation
From
US $735Per Person
Reserve
Amazing Annapolis Scavenger Hunt
Amazing Annapolis Scavenger Hunt
9
Excellent
7 Reviews
5-Star Rating Recommendation
From
US $20Per Person
Reserve
Annapolis Citywide Scavenger Hunt
Annapolis Citywide Scavenger Hunt
9
Excellent
7 Reviews
5-Star Rating Recommendation
From
US $20Per Person
Reserve
Chesapeake Beach Guided Walking Tour - The Cliffs
Chesapeake Beach Guided Walking Tour - The Cliffs
9
Excellent
6 Reviews
5-Star Rating Recommendation
From
US $41Per Person
Reserve
Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views
Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views
7
Good
18 Reviews
4-Star Rating Recommendation
From
US $15Per Person
Reserve
Show all 45+ Tours in Shady Side

Top-rated places to stay near Shady Side

Find the perfect place to stay in Shady Side with Varoom. Choose from a wide range of vacation rentals, cottages, condos, and private villas - many offering top amenities and great value.

Shady Side
Shady Side62+ Properties
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New
House
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
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like-icon9.4
Exceptional
(8 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Balcony/Terrace
    Balcony/Terrace
  • Kitchen
    Kitchen
More amenities
US $327/Night 7 Nights - US $2,290
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New
House
Otterspace at the beach
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 6 Guests 1399.31 ft²
  • EV Charge Station
    EV Charge Station
  • Parking
    Parking
More amenities
US $153/Night 7 Nights - US $1,071
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House
Sunset Cottage - West River Access and Views!
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like-icon10.0
Exceptional
(5 Reviews)
2 Bedrooms 3 Baths 6 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $576/Night 7 Nights - US $4,032
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House
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Map-icon
like-icon9.6
Exceptional
(7 Reviews)
3 Bedrooms 2 Baths 6 Guests
  • Oceanfront
    Oceanfront
  • Parking
    Parking
More amenities
US $303/Night 7 Nights - US $2,121
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House
Peaceful 2-bedroom/2-bathroom house with WiFi and AC in serene Shady Side
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like-icon10.0
Exceptional
(4 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Parking
    Parking
  • Kitchen
    Kitchen
More amenities
US $482/Night 7 Nights - US $3,372
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Cottage
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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like-icon9.8
Exceptional
(50 Reviews)
1 Bedroom 1 Bath 3 Guests
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $208/Night 7 Nights - US $1,458
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Apartment
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
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like-icon8.0
Excellent
(13 Reviews)
1 Bedroom 1 Bath 4 Guests 600 ft²
  • Parking
    Parking
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $307/Night 7 Nights - US $2,150
View Deal
House
Waterfront Home near Annapolis, MD
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like-icon10.0
Exceptional
(33 Reviews)
5 Bedrooms 7 Baths 10 Guests 4000 ft²
  • Private Pool
    Private Pool
  • Parking
    Parking
More amenities
US $2,077/Night 7 Nights - US $14,542
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House
West River Waterfront Escape with Boat Lift, Kayaks & Bay Views
Map-icon
like-icon10.0
Exceptional
(32 Reviews)
4 Bedrooms 3 Baths 8 Guests
  • Hot Tub
    Hot Tub
  • Parking
    Parking
More amenities
US $760/Night 7 Nights - US $5,317
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