Hotels in Shady Side
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The Wildset
The WildsetDowntown St. Michaels
9.8 out of 10, Exceptional, (413)
- Experience downtown St. Michaels with free breakfast, WiFi, and marina views.
The price is $189
$230 total
includes taxes & fees
Jan 11 - Jan 12
Flag House Inn
Flag House InnHistoric District
9.4 out of 10, Exceptional, (85)
- Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $182
$207 total
includes taxes & fees
Jan 11 - Jan 12
Parsonage Inn
Parsonage InnDowntown St. Michaels
9.2 out of 10, Wonderful, (130)
- Stay in a charming B&B in St. Michaels, with free breakfast and nearby trails.
The price is $149
$164 total
includes taxes & fees
Jan 12 - Jan 13
The Westin Annapolis
The Westin AnnapolisAnnapolis
8.6 out of 10, Excellent, (1000)
- Luxurious spa escape near U.S. Naval Academy with attentive service.
The price is $127
$144 total
includes taxes & fees
Jan 11 - Jan 12
George Brooks House B&B
George Brooks House B&BSt. Michaels
8.8 out of 10, Excellent, (66)
- Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $170
$187 total
includes taxes & fees
Jan 12 - Jan 13
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
9.8 out of 10, Exceptional, (34)
- Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.
The price is $206
$234 total
includes taxes & fees
Jan 11 - Jan 12
Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour MarinaDeale
9.4 out of 10, Exceptional, (473)
The price is $149
$170 total
includes taxes & fees
Jan 11 - Jan 12
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHGAnnapolis
8.8 out of 10, Excellent, (1019)
- Central location near shopping malls, with a relaxing indoor pool and welcoming staff.
The price is $106
$121 total
includes taxes & fees
Feb 6 - Feb 7
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique HotelHistoric District
10.0 out of 10, Exceptional, (3)
- Discover historic Annapolis from this boutique hotel near the U.S. Naval Academy.
The price is $295
$336 total
includes taxes & fees
Jan 11 - Jan 12
Knapps Narrows Marina & Inn
Knapps Narrows Marina & InnTilghman
9.4 out of 10, Exceptional, (364)
- Enjoy Chesapeake Bay marina views with kayaking and seasonal outdoor pool.
The price is $100
$110 total
includes taxes & fees
Jan 9 - Jan 10
Hampton Inn & Suites Annapolis
Hampton Inn & Suites AnnapolisAnnapolis
8.2 out of 10, Very Good, (1011)
- Enjoy Naval Academy access and seasonal outdoor swim in Maryland's historic capital.
The price is $89
$102 total
includes taxes & fees
Jan 14 - Jan 15
Rips Country Inn
Rips Country InnBowie
6.6 out of 10, (60)
- Gateway to Fort Meade with homestyle dining and cozy accommodations nearby.
The Inn at Tacaro Estate
The Inn at Tacaro EstateTracys Landing
9.4 out of 10, Exceptional, (11)
- Vineyard retreat with seasonal pool and hot tub in tranquil Tracys Landing.
The price is $322
$367 total
includes taxes & fees
Feb 4 - Feb 5
Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
9.0 out of 10, Wonderful, (1885)
- Downtown charm steps from the U.S. Naval Academy in historic Annapolis.
The price is $139
$193 total
includes taxes & fees
Jan 11 - Jan 12
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel AnnapolisAnnapolis
8.6 out of 10, Excellent, (1001)
- Contemporary hotel near U.S. Naval Academy with fitness center and garden.
The price is $75
$85 total
includes taxes & fees
Feb 8 - Feb 9
Inn at Perry Cabin
Inn at Perry CabinDowntown St. Michaels
9.6 out of 10, Exceptional, (373)
- Classic Chesapeake Bay escape with marina, spa, and waterfront dining options.
The price is $513
$564 total
includes taxes & fees
Jan 15 - Jan 16
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MDAnnapolis
9.0 out of 10, Wonderful, (1000)
- Country Inn and Suites provides peaceful stays near Annapolis attractions.
The price is $98
$112 total
includes taxes & fees
Jan 14 - Jan 15
The Tilghman Island Inn
The Tilghman Island InnTilghman
9.6 out of 10, Exceptional, (121)
- Immerse in serenity along Chesapeake Bay with stunning water views and island charm.
The price is $200
$220 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis DowntownAnnapolis
8.6 out of 10, Excellent, (1009)
- Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.
The price is $90
$102 total
includes taxes & fees
Feb 8 - Feb 9
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph CollectionHistoric District
8.8 out of 10, Excellent, (896)
- Savor the harbor views and rooftop terrace in walkable downtown Annapolis.
The price is $203
$232 total
includes taxes & fees
Jan 18 - Jan 19
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Go beyond your typical stay in Shady Side
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Comfort Inn Largo-Washington DC East
10/10 Excellent
