Find the best vacation rental

ACCOMMODATION TYPES

Save Up To 78%

Airbnb, Vacation rentals and hotel deals in Shady Side, MD

7.9 (298 reviews)
Hampton Inn & Suites Annapolis
Hotel · 2 Guests · 1 Bedroom
$109 /night
View deal
9.8 (10 reviews)
New! Stylish downtown home w/awesome outdoor area!
Holiday home · 2 Guests · 1 Bedroom
$193 /night*
View deal
9.0 (541 reviews)
Comfort Inn Conference Center Bowie
Hotel · 2 Guests · 1 Bedroom
$102 /night
View deal
10 (57 reviews)
West Annapolis Waterfront Stay with Views, Dock & Boat
Cottage · 2 Guests · 1 Bedroom
$206 /night*
View deal
10 (73 reviews)
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Apartment · 2 Guests · 1 Bedroom
$150 /night*
View deal
8.8 (620 reviews)
Crowne Plaza Annapolis, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$114 /night
View deal
Rod 'N' Reel Resort
Resort · 2 Guests · 1 Bedroom
$185 /night
View deal
6.1 (150 reviews)
Village Inn
Motel · 2 Guests · 1 Bedroom
$91 /night
View deal
10 (7 reviews)
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Holiday home · 2 Guests · 1 Bedroom
$135 /night*
View deal
9.1 (323 reviews)
Annapolis Waterfront Hotel, Autograph Collection
Hotel · 2 Guests · 1 Bedroom
$218 /night
View deal
10 (15 reviews)
Private Cottage on gated estate
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
View deal
9.8 (34 reviews)
Lovely Family Home Just Minutes From Annapolis
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
View deal
8.8 (589 reviews)
Country Inn & Suites by Radisson, Annapolis, MD
Hotel · 2 Guests · 1 Bedroom
$105 /night
View deal
7.8 (276 reviews)
Holiday Inn Express Hotel & Suites Annapolis, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$98 /night
View deal
9.0 (1024 reviews)
SpringHill Suites by Marriott Annapolis
Hotel · 2 Guests · 1 Bedroom
$139 /night
View deal
Homestyle Studio Suites
Hotel · 2 Guests · 1 Bedroom
$90 /night
View deal
9.4 (136 reviews)
Anchored Inn at Hidden Harbor
Hotel · 2 Guests · 1 Bedroom
$115 /night
View deal
9.8 (7 reviews)
Modern Coastal Retreat
Holiday home · 2 Guests · 1 Bedroom
$100 /night*
View deal
10 (10 reviews)
Charming Downtown 3rd Floor 1 Bedroom Apt
Apartment · 2 Guests · 1 Bedroom
$175 /night*
View deal
8.9 (1085 reviews)
Historic Inns of Annapolis
Hotel · 2 Guests · 1 Bedroom
$149 /night
View deal

Airbnb, Vacation House with Air Conditioning in Shady Side, MD

Moore space
Holiday home · 2 Guests · 1 Bedroom
$210 /night
View deal
Mini Suite
B & B · 2 Guests · 1 Bedroom
$421 /night
View deal
How Does The Amenity Info Looks Like at Shady Side, MD?
Best Amenities in Shady Side, MD
+
There are in total of 15 rental amenities in Shady Side, shown above with the property numbers. In Shady Side, 721 rentals offer Internet or Wifi, 694 rentals offer Air Conditioning, 661 rentals offer No Smoking. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pool.
Which Price Range Is Considered As A Good Deal in Shady Side, MD Area?
Vacation House & Apartment Rental Price Information in Shady Side, MD
+
The graph shows the percentages of vacation homes in each price bucket. Shady Side has the largest percentage (22.74%) of homes in $500+ price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What Are The Most Liked Rental Accommodations in Shady Side, MD?
Rental Property Types in Shady Side, MD
+
In Shady Side, 59.60% of listings are House, which is the most popular accommodation out of 21 total accommodation types. Avg price per night for House is around $413. And the most searched amenities for House accommodation is Hot Tub.The least popular accommodation in Shady Side is Chalet rentals
How Many Rental Accommodations Are Pets Friendly in Shady Side, MD?
Pets Allowed vs Not Allowed in Shady Side, MD
+
24.11% of vacation homes in Shady Side are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
Which Airports Should I Choose To Get To Shady Side, MD?
Airports Options in Shady Side, MD
+

2 airport(s) close to Shady Side are:

Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Shady Side, MD

10 (161 reviews)
Charming Historic Annapolis Home With Two Off-street Parking Places!
Holiday home · 2 Guests · 1 Bedroom
$600 /night*
View deal
Brazilian Artsy Townhome with great location and outdoor amenities!
Holiday home · 2 Guests · 1 Bedroom
$400 /night*
View deal
10 (12 reviews)
Historic District Charm with two mid-size or smaller parking spots!
Holiday home · 2 Guests · 1 Bedroom
$300 /night*
View deal

Airbnb, Vacation Cottage with Fireplace, and Other Rental Options in Shady Side, MD

9.4 (112 reviews)
Eastern Shore Getaway Near St. Michaels
Cottage · 2 Guests · 1 Bedroom
$300 /night*
View deal
10 (43 reviews)
Firefly Cottage, discounted holiday fun, USNA, community beach, HOT TUB, and EV
Cottage · 2 Guests · 1 Bedroom
$225 /night*
View deal
9.4 (42 reviews)
'Newer Cottage Incredibly and Comfortably Furnished.'
Cottage · 2 Guests · 1 Bedroom
$255 /night*
View deal
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers