Hotels in Shady Side
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The Wildset
The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (413)
9.8/10
Exceptional
(413)
- Experience downtown St. Michaels with free breakfast, WiFi, and marina views.
The price is $179
$179
$219 total
includes taxes & fees
Jan 8 - Jan 9
Flag House Inn
Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (85)
9.4/10
Exceptional
(85)
- Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $182
$182
$207 total
includes taxes & fees
Jan 11 - Jan 12
Parsonage Inn
Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (130)
9.2/10
Wonderful
(130)
- Stay in a charming B&B in St. Michaels, with free breakfast and nearby trails.
The price is $149
$149
$164 total
includes taxes & fees
Jan 8 - Jan 9
The Westin Annapolis
The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
- Luxurious spa escape near U.S. Naval Academy with attentive service.
The price is $127
$127
$144 total
includes taxes & fees
Jan 8 - Jan 9
George Brooks House B&B
George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (66)
8.8/10
Excellent
(66)
- Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $170
$170
$187 total
includes taxes & fees
Jan 8 - Jan 9
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34)
9.8/10
Exceptional
(34)
- Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.
The price is $206
$206
$234 total
includes taxes & fees
Jan 11 - Jan 12
Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (473)
9.4/10
Exceptional
(473)
The price is $149
$149
$170 total
includes taxes & fees
Jan 11 - Jan 12
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1019)
8.8/10
Excellent
(1019)
- Central location near shopping malls, with a relaxing indoor pool and welcoming staff.
The price is $106
$106
$121 total
includes taxes & fees
Feb 4 - Feb 5
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District
10.0 out of 10, Exceptional, (3)
10/10
Exceptional
(3)
- Discover historic Annapolis from this boutique hotel near the U.S. Naval Academy.
The price is $295
$295
$336 total
includes taxes & fees
Jan 11 - Jan 12
Knapps Narrows Marina & Inn
Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (364)
9.4/10
Exceptional
(364)
- Enjoy Chesapeake Bay marina views with kayaking and seasonal outdoor pool.
The price is $100
$100
$110 total
includes taxes & fees
Jan 8 - Jan 9
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1011)
8.2/10
Very Good
(1011)
- Enjoy Naval Academy access and seasonal outdoor swim in Maryland's historic capital.
The price is $89
$89
$102 total
includes taxes & fees
Jan 13 - Jan 14
Rips Country Inn
Rips Country Inn
2.5 star property
Bowie
6.6 out of 10, (60)
6.6/10
(60)
- Gateway to Fort Meade with homestyle dining and cozy accommodations nearby.
The Inn at Tacaro Estate
The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
9.4/10
Exceptional
(11)
- Vineyard retreat with seasonal pool and hot tub in tranquil Tracys Landing.
The price is $322
$322
$367 total
includes taxes & fees
Feb 4 - Feb 5
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1911)
9.0/10
Wonderful
(1911)
- Downtown charm steps from the U.S. Naval Academy in historic Annapolis.
The price is $139
$139
$193 total
includes taxes & fees
Jan 8 - Jan 9
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1006)
8.6/10
Excellent
(1006)
- Contemporary hotel near U.S. Naval Academy with fitness center and garden.
The price is $83
$83
$94 total
includes taxes & fees
Jan 11 - Jan 12
Inn at Perry Cabin
Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (373)
9.6/10
Exceptional
(373)
- Classic Chesapeake Bay escape with marina, spa, and waterfront dining options.
The price is $513
$513
$564 total
includes taxes & fees
Jan 15 - Jan 16
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1000)
9.0/10
Wonderful
(1000)
- Country Inn and Suites provides peaceful stays near Annapolis attractions.
The price is $98
$98
$112 total
includes taxes & fees
Jan 13 - Jan 14
The Tilghman Island Inn
The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121)
9.6/10
Exceptional
(121)
- Immerse in serenity along Chesapeake Bay with stunning water views and island charm.
The price is $200
$200
$220 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1009)
8.6/10
Excellent
(1009)
- Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.
The price is $91
$91
$104 total
includes taxes & fees
Jan 11 - Jan 12
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (896)
8.8/10
Excellent
(896)
- Savor the harbor views and rooftop terrace in walkable downtown Annapolis.
The price is $219
$219
$250 total
includes taxes & fees
Jan 11 - Jan 12
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.
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
Pet friendly
Family friendly
Cottage
Top landmarks in Shady Side
Shadyside Park
Shadyside Park is 0.4 mi (0.6 km) from central Shady Side, why not stop by during your stay. Our travelers also like this walkable area for its port and restaurants.If you like Shadyside Park, you'll love Maryland Quiet Waters Park and Ellen O. Moyer Nature Park at Back Creek, both just a short drive away.
Captain Avery Museum
Captain Avery Museum is 0.5 mi (0.8 km) from central Shady Side, why not stop by during your stay. Why not take a stroll along the port and watch the sunset while you're here? If you want to experience more of the culture Shady Side has to offer, head to Shadyside Park, Franklin Point State Park, and Triton Beach.
Check out reviews of Shady Side hotels guests love
DoubleTree by Hilton Hotel Largo/Washington DC
10/10 Excellent
"Room was spotless staff were amazing "
Residence Inn by Marriott Upper Marlboro Joint Base Andrews
10/10 Excellent
"Everything was wonderful!!"
Country Inn & Suites by Radisson, Annapolis, MD
10/10 Excellent
"No hot water for the entire first night. Had plans for the night but could not take shower. Not a good experience. Other than that, everything was fine."
Comfort Inn Conference Center
10/10 Excellent
"Clean room. Nice staff. "
Holiday Inn Express I-95 Capitol Beltway-Largo by IHG
10/10 Excellent
"Clean room, Awesome Breakfast!!! Breakfast staff excellent service! "
The Westin Annapolis
10/10 Excellent
"We were able to get there an hour early and our room was ready and the staff were great!"
Crowne Plaza Annapolis by IHG
10/10 Excellent
"Amazing staff and breakfast was delicious. "
Comfort Inn Largo-Washington DC East
10/10 Excellent
"Yes"
Historic Inns of Annapolis
10/10 Excellent
"Staff was exceptionally friendly & helpful. Room clean & tastefully appointed. Location was perfectly situated in the old town & near antique stores, Main Street & the harbor. Great getaway!"
Frequently asked questions
What hotels do travelers like in Shady Side?
Can I book a refundable hotel in Shady Side?
If you need the flexibility to change your plans to Shady Side, most properties provide refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Shady Side if I want a vacation rental instead of a hotel?
If you want to find a good alternative to a hotel, browse our selection of 11 vacation homes.
What will the weather in Shady Side be like during my vacation?
The warmest months in Shady Side are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 40°F. The rainiest months are July and August.
Why should I book my Shady Side accommodation with Hotels.com?
There are plenty of reasons to book your Shady Side travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.