Anchored Inn at Hidden Harbor 3.7 km from Shady Side
Hotel in Deale MD
9.2
Excellent
From $227
From $227
Info Categories
Dog Friendly Hotel

Hotel with Swimming Pool

Outdoor Pool  

Small Hotel

Show more
 
The Inn at Tacaro Estate 5.1 km from Shady Side
Bed & Breakfast in Deale MD
8.4
Very Good
Info Categories
Dog Friendly Bed & Breakfast

Bed & Breakfast with Swimming Pool

Small Bed & Breakfast

Show more
 
Pool Vibes At Vanishing Run 5.9 km from Shady Side
Vacation Home in Lothian MD
10
Excellent
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

Show more
 
Bay Poolhouse 6.8 km from Shady Side
Vacation Home in Annapolis MD
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Private Pool    Outdoor Pool  

Vacation Home with Parking

Show more
 
Updated North Beach Cottage Pet Friendly! 7.1 km from Shady Side
Vacation Home in Deale MD
9.3
Excellent
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Show more
 
The Morning Watch 8.4 km from Shady Side
Vacation Home in Annapolis MD
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Private Pool    Outdoor Pool  

Show more
 
Waterfront 5BR on Kent Island with Private Pool and Firepit 8.6 km from Shady Side
Vacation Home in Stevensville MD
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Vacation Home with Free Wi-Fi

Show more
 
Waterside with it All 8.8 km from Shady Side
Vacation Home in Annapolis MD
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Private Pool    Outdoor Pool  

Show more
 
Oasis by the Bay - Waterfront Heated Pool Hot Tub 8.8 km from Shady Side
Vacation Home in Annapolis MD
10
Excellent
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool  

Vacation Home with Free Wi-Fi

Show more
 
Saved by the Bay 10.1 km from Shady Side
Vacation Home in Cox Creek Acres MD
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Vacation Home with Free Wi-Fi

Show more
 
Annapolis Boat Life - Overnight Stays 10.4 km from Shady Side
Boat in Annapolis MD
9.0
Excellent
Info Categories
Dog Friendly Boat

Boat with Swimming Pool

Private Pool  

Boat with Parking

Show more
 
The Westin Annapolis 10.5 km from Shady Side
Hotel in Annapolis MD
8.5
Very Good
From $227
From $227
Info Categories
Hotel with Swimming Pool

Indoor Pool  

Indoor Pool  

Dog Friendly Hotel

Luxury Hotel

Show more
 
Sonesta ES Suites Annapolis 10.5 km from Shady Side
Hotel in Annapolis MD
8.1
Very Good
From $125
From $125
Info Categories
Dog Friendly Hotel

Hotel with Swimming Pool

Outdoor Pool  

Family Friendly Hotel

Show more
 
Hilton Garden Inn Annapolis 10.7 km from Shady Side
Hotel in Annapolis MD
7.9
Good
From $126
From $126
Info Categories
Hotel with Swimming Pool

Outdoor Pool  

Outdoor Pool  

Dog Friendly Hotel

Family Friendly Hotel

Show more
 
Hampton Inn & Suites Annapolis 10.7 km from Shady Side
Hotel in Annapolis MD
7.2
Good
From $135
From $135
Info Categories
Hotel with Swimming Pool

Outdoor Pool  

Outdoor Pool  

Dog Friendly Hotel

Family Friendly Hotel

Show more
 
Best Western Annapolis 11.0 km from Shady Side
Hotel in Annapolis MD
7.3
Good
From $102
From $102
Info Categories
Hotel with Swimming Pool

Outdoor Pool  

Dog Friendly Hotel

Business Hotel

Show more
 
DoubleTree by Hilton Hotel Annapolis 11.1 km from Shady Side
Hotel in Annapolis MD
8.0
Very Good
From $134
From $134
Info Categories
Hotel with Swimming Pool

Outdoor Pool  

Dog Friendly Hotel

Hotel Taking Steps Towards Sustainability

Show more
 
Country Inn & Suites by Radisson, Annapolis, MD 11.4 km from Shady Side
Hotel in Annapolis MD
8.4
Very Good
From $108
From $108
Info Categories
Hotel with Swimming Pool

Indoor Pool  

Indoor Pool  

Dog Friendly Hotel

Family Friendly Hotel

Show more
 
Tilghman Island Inn 11.7 km from Shady Side
Hotel in Tilghman Island MD
9.1
Excellent
From $223
From $223
Info Categories
Dog Friendly Hotel

Hotel with Swimming Pool

Outdoor Pool  

Hotel with Parking

Show more
 
Clearview 11.9 km from Shady Side
Vacation Home in Tilghman Island MD
Info Categories
Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Vacation Home with Free Wi-Fi

Show more
 
*Additional taxes or fees may apply. Please check the final price before completing your booking.
Categories:
  •     Pool (76)
  •     Dog Friendly (76)
  •     Outdoor Pool (38)
  •     Indoor Pool (13)
  •     Private Pool (11)
  •     Heated Pool (4)
  •     Parking (52)
  •     Free Wi-Fi (26)
  •     Gym (24)
  •     Accessible (24)
  •     3 Star (22)
  •     Family (19)
  •     Business (19)
  •     Honeymoon (17)
  •     Sustainability Journey (12)
  •     Luxury (7)
  •     4 Star (7)
  •     EV charging stations (6)
  •     Small (5)
  •     Golf (4)
  •     Adult Only (3)
  •     Romantic (3)
  •     Spa (3)
  •     Rooms with Jacuzzi / Hot-Tub (2)
  •     Rooms with Fireplace (2)
  •     5 Star (1)
  •     Tennis (1)
  •     Cheap (1)
  •     Yoga (1)
×
Checkin
×
Categories
2
Map
× Home About Press Categories Blog Hotel Awards Travelmyth GPT Contact Terms & Conditions Privacy Policy Cookies Policy FAQ