Find hotels in Shady Side, MD from ₩118,572

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Our top choices for Shady Side hotels

Front of property
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1001)
Experience serene stays at this peaceful inn with seasonal outdoor pool and garden terrace. Located conveniently near Saint Michaels Village and Classic Motor Museum, guests appreciate the helpful staff, clean rooms, and complimentary breakfast, WiFi, and parking.
"Good value and close to downtown."
United States
John
The price is ₩145,297
₩159,830 total
includes taxes & fees
Jan 11 - Jan 12
St Michaels Inn
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (947)
Discover tranquility on Kent Island with beautiful bay views and a seasonal outdoor pool. This hotel sits right on a bike trail with rentals available onsite. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Center after a quiet night's rest.
"It was very comfortable and clean"
United States
Maria
The price is ₩125,679
₩139,504 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Annapolis East-Kent Island by IHG
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1008)
"Yes, everything was spot on. Do come and stay at the Rod and Reel for any special occassion. You will be glad you can."
United States
Alfred
The price is ₩131,508
₩174,866 total
includes taxes & fees
Jan 11 - Jan 12
Rod 'N' Reel Resort
Exterior
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1005)
"Great hospitality and breakfast was good…"
United States
Martha
The price is ₩104,010
₩118,572 total
includes taxes & fees
Jan 10 - Jan 11
Best Western Annapolis
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
Experience Art Deco style at this downtown Annapolis hotel, just minutes from the U.S. Naval Academy. Enjoy regional cuisine at Kitchen on West St, unwind at the bar/lounge, or maintain your routine in the 24-hour fitness center.
"Great value for stay with breakfast included "
United States
Aisling
The price is ₩133,018
₩151,641 total
includes taxes & fees
Jan 25 - Jan 26
Hilton Garden Inn Annapolis Downtown
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1005)
Located just 5 minutes from U.S. Naval Academy, this hotel offers convenient access to Annapolis Harbor Center and Westfield Annapolis Mall. Enjoy the 24-hour fitness center, restaurant serving 3 meals daily, and garden. Guests particularly praise the helpful staff and prime location.
"Great stay "
United States
Jose Miguel
The price is ₩119,641
₩136,390 total
includes taxes & fees
Jan 11 - Jan 12
DoubleTree by Hilton Hotel Annapolis
Dinner served, American cuisine
Comfort Inn Conference Center

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1003)
Just steps from Prince George's Stadium, this tranquil retreat offers free breakfast, WiFi and parking. Guests love the quiet atmosphere and convenient location near shopping and dining options. The 24-hour fitness center and American cuisine at Chessies Chesapeake Grill complete your relaxing stay.
"The staff was amazing , very friendly. Rooms were very clean."
United States
Victoria
The price is ₩141,570
₩159,974 total
includes taxes & fees
Feb 2 - Feb 3
Comfort Inn Conference Center
Hypo-allergenic bedding, down comforters, in-room safe, desk
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is ₩114,412
₩130,429 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Garden Inn Annapolis
Hypo-allergenic bedding, desk, blackout drapes, iron/ironing board
Country Inn & Suites by Radisson, Annapolis, MD

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, (1006)
Just 10 minutes from the U.S. Naval Academy, this serene hotel offers free parking and WiFi. Unwind in the indoor pool and hot tub after exploring nearby Westfield Annapolis Mall and local restaurants. Guests consistently praise the peaceful atmosphere and attentive staff.
"Breakfast menu was great! Pool and hot tub were nice!"
United States
Terrence
The price is ₩139,721
₩159,283 total
includes taxes & fees
Jan 8 - Jan 9
Country Inn & Suites by Radisson, Annapolis, MD
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1003)
This tranquil hotel offers a serene retreat with comfortable beds and stylish Trophy Room for dinner. Explore local attractions using free bike rentals, or unwind at the bar after a workout in the 24-hour fitness center.
"Pleasant staff. Good location to walk to restaurants, shops. "
United States
Beth
The price is ₩212,037
₩241,722 total
includes taxes & fees
Jan 12 - Jan 13
Graduate by Hilton Annapolis
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1908)
Immerse in Maryland's maritime heritage at this historic hotel with a 24-hour fitness center and garden terrace. Just a short walk from the U.S. Naval Academy and colonial attractions, this hotel offers comfortable beds and exceptional service.
" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1003)
Wake up to a delicious buffet breakfast at this Annapolis hotel, just 5 minutes from the U.S. Naval Academy. Enjoy complimentary WiFi and parking, plus a 24-hour fitness center. Located within easy walking distance to restaurants and shops.
"Clean room and friendly staff! "
United States
Silvia
The price is ₩115,567
₩131,746 total
includes taxes & fees
Jan 10 - Jan 11
Holiday Inn Express & Suites Annapolis by IHG
Premium bedding, pillowtop beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1010)
Located within a 10-minute drive of U.S. Naval Academy, this hotel offers a seasonal outdoor pool and fitness center. Guests praise the helpful staff and free breakfast. Annapolis Harbor Center Shopping Center is nearby for all your needs.
"Appreciated that it was in a quiet area. Great hospitality! Will stay again when visiting Maryland."
United States
robin
The price is ₩129,117
₩147,194 total
includes taxes & fees
Jan 12 - Jan 13
Hampton Inn & Suites Annapolis
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1004)
Ideally located near restaurants and walking trails, this Grasonville getaway offers superior rooms with spectacular sunset views over the water. Enjoy the indoor pool, hot tub, and sauna after exploring nearby Chesapeake Bay Environmental Center.
"Nice place "
United States
Tucker T
The price is ₩120,508
₩133,764 total
includes taxes & fees
Jan 11 - Jan 12
Best Western Kent Narrows Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
This Grasonville hotel provides a peaceful environment with a seasonal outdoor pool and complimentary breakfast, WiFi, and parking. Located near Chesapeake Bay Environmental Center and Queenstown Harbor Golf Links for easy exploration.
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ₩121,562
₩134,933 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Grasonville near Kent Island
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (693)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Center and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is ₩167,572
₩186,006 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is ₩184,825
₩255,888 total
includes taxes & fees
Jan 6 - Jan 7
Kent Island Resort
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1004)
Situated just a short drive from the U.S. Naval Academy, this hotel offers American cuisine at The Bistro. Guests praise the peaceful atmosphere, helpful staff, and clean rooms. Free WiFi and parking enhance your stay near Annapolis Harbor Center.
"We keep coming back to the hotel with every visit to Annapolis. "
United States
Catherine
The price is ₩121,346
₩138,335 total
includes taxes & fees
Jan 25 - Jan 26
Courtyard by Marriott Annapolis
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
Discover peaceful luxury in Annapolis with a full-service spa offering massages and facials. After enjoying Captain's Daughter restaurant, take a refreshing dip in the indoor pool or maintain your workout routine at the 24-hour fitness center.
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is ₩200,798
₩228,910 total
includes taxes & fees
Jan 6 - Jan 7
The Westin Annapolis
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (364)
Discover serenity on the water at this Tilghman hotel with marina access, seasonal outdoor pool, and complimentary kayaking adventures. Comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your Chesapeake Bay getaway.
"nice clean room staff very nice would stay again "
United States
mario
The price is ₩144,459
₩158,905 total
includes taxes & fees
Jan 6 - Jan 7
Knapps Narrows Marina & Inn
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.
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Stay near popular Shady Side attractions

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
See properties

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
See properties

Top Shady Side Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Amazing staff and breakfast was delicious. "
jennifer 1-night trip
Posted 3 days ago
Crowne Plaza Annapolis by IHG

More cheap stays in Shady Side

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ₩104,010 per night from Jan 10 to Jan 11
₩104,010
₩118,572 total
Jan 10 - Jan 11
includes taxes & fees
7.6/10 Good! (1,005 reviews)

Frequently asked questions

Where is the best place for a stay in Shady Side?
DoubleTree by Hilton Hotel Annapolis, located 9.8 mi (15.8 km) from the heart of Shady Side, is a top choice for your stay based on our traveler data. Two other choices for your trip to the area are DoubleTree by Hilton Hotel Largo/Washington DC and Historic Inns of Annapolis. See all available top hotels, or vacation rentals in Shady Side.
If I need to cancel my hotel reservation in Shady Side, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.
Where can I learn more about changing or cancelling my trip to Shady Side?
To find more details about updating your trip to Shady Side or cancelling it, click here.
Where is the best hotel to stay near Shadyside Park?
Anchored Inn at Hidden Harbour Marina is one of the top choices for your stay based on our traveler data, and this hotel offers an outdoor pool and free parking. It's located 4.8 mi (7.7 km) from Shadyside Park.
What about the best place to stay near Captain Avery Museum?
One of the top choices for your stay is Anchored Inn at Hidden Harbour Marina, located 5 mi (8.1 km) from Captain Avery Museum, and this hotel offers an outdoor pool and free parking.
What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Offers free self parking, an indoor pool, and a 24-hour fitness center. Crowne Plaza Annapolis by IHG and La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway are two additional hotels that offer an onsite pool. View all hotels with pools in Shady Side.
What's the best place to stay near Ronald Reagan Washington National Airport (DCA)?
Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.
What is staying in Shady Side like?
Visitors can enjoy all that Shady Side has to offer including the shopping, restaurants, and parks. Tourists can also enjoy so much more including its museums. In Shady Side, there are 14 hotels and other accommodations to choose from. Find out more about Shady Side.
What should I see while I'm in Shady Side?
Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay, and Shadyside Park. A couple of additional sights to add to your agenda are Franklin Point State Park and Captain Avery Museum. Check out what more to see and do in Expedia's Shady Side guide.
What's the weather like in Shady Side?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches.