Find hotels in Shady Side, MD from ฿2,557

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Our top choices for Shady Side hotels

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, (934)
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 on-site. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Centre after a quiet night's rest.
"It was very comfortable and clean"
United States
Maria
The price is ฿2,745
฿3,047 total
includes taxes & fees
3 Jan - 4 Jan 2026
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, (1001)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is ฿3,355
฿4,355 total
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
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, (1008)
Experience Art Deco style at this city centre Annapolis hotel, just minutes from the US Naval Academy. Enjoy regional cuisine at Kitchen on West St, unwind at the bar/lounge, or maintain your routine in the 24-hour fitness centre.
"Great value for stay with breakfast included "
United States
Aisling
The price is ฿2,499
฿2,848 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis Downtown
Hypo-allergenic bedding, desk, blackout curtains, 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, (1005)
Just 10 minutes from the US 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.
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is ฿3,003
฿3,424 total
includes taxes & fees
4 Jan - 5 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD
Lobby
Hampton Inn & Suites Glenarden/Washington DC

Hampton Inn & Suites Glenarden/Washington DC

Hampton Inn & Suites Glenarden/Washington DC
2.5 star property
Lanham
9.2 out of 10, Wonderful, (1010)
Located just 10 minutes from Northwest Stadium, this Lanham hotel offers a complimentary buffet breakfast daily. Enjoy free WiFi and parking while staying active in the fitness centre. NASA Visitor Centre is nearby, with Morgan Boulevard Station only 7 minutes away.
"Very clean, with friendly and professional staff. Would definitely stay here again!"
United States
Amanda
The price is ฿2,648
฿2,992 total
includes taxes & fees
3 Jan - 4 Jan 2026
Hampton Inn & Suites Glenarden/Washington DC
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
Situated just a short drive from the US 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 Harbour Centre.
"Wonderful stay. "
United States
Angela
The price is ฿2,650
฿3,021 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Annapolis
Exterior
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1007)
"Parking was safe and free. Staff from breakfast did good service although breakfast was the same for 3 days. Location was perfect."
Canada
Ermelita
The price is ฿2,243
฿2,557 total
includes taxes & fees
28 Dec - 29 Dec
Best Western Annapolis
Hypo-allergenic bedding, down duvets, 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 ฿2,347
฿2,676 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Annapolis
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 Centre and Queenstown Harbour 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 ฿2,682
฿2,977 total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Grasonville near Kent Island
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, (1002)
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.
"clean and comfy, friendly staff"
United States
Tamara
The price is ฿3,507
฿3,858 total
includes taxes & fees
16 Dec - 17 Dec
St Michaels Inn
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, (1000)
Wake up to a delicious buffet breakfast at this Annapolis hotel, just 5 minutes from the US Naval Academy. Enjoy complimentary WiFi and parking, plus a 24-hour fitness centre. Located within easy walking distance to restaurants and shops.
"Clean room and friendly staff! "
United States
Silvia
The price is ฿2,524
฿2,877 total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express & Suites Annapolis by IHG
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, (1011)
Located just 5 minutes from US Naval Academy, this hotel offers convenient access to Annapolis Harbour Centre and Westfield Annapolis Mall. Enjoy the 24-hour fitness centre, restaurant serving 3 meals daily, and garden. Guests particularly praise the helpful staff and prime location.
"Great place!"
United States
Tawnya
The price is ฿2,406
฿2,743 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel 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, (361)
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.
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is ฿3,786
฿4,164 total
includes taxes & fees
16 Dec - 17 Dec
Knapps Narrows Marina & Inn
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, (674)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Centre and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.
"Great view, good ambiance all around"
United States
Dianne
The price is ฿3,470
฿3,852 total
includes taxes & fees
21 Dec - 22 Dec
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, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is ฿4,521
฿6,145 total
includes taxes & fees
16 Dec - 17 Dec
Kent Island Resort
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, (1901)
Immerse in Maryland's maritime heritage at this historic hotel with a 24-hour fitness centre and garden terrace. Just a short walk from the US Naval Academy and colonial attractions, this hotel offers comfortable beds and exceptional service.
" Great place to stay!"
United States
Lewis
Historic Inns of 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, (1003)
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 Centre.
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is ฿2,632
฿2,921 total
includes taxes & fees
22 Dec - 23 Dec
Best Western Kent Narrows Inn
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1002)
Overlooking the bay in Grasonville, this hotel offers an indoor pool and fitness centre for active travellers. Explore nearby Chesapeake Bay Environmental Centre, then unwind with drinks at the bar. Rooms include microwaves and refrigerators for added convenience.
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
United States
Anthony
The price is ฿3,256
฿3,614 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1003)
Dive into comfort at this Annapolis hotel with a serene indoor pool, on-site restaurant, and bar. Just 10 minutes from the Naval Academy and steps from Westfield Mall, guests love the peaceful atmosphere, attentive staff, and clean rooms.
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is ฿3,596
฿4,100 total
includes taxes & fees
13 Jan - 14 Jan 2026
Crowne Plaza Annapolis by IHG
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (963)
Located minutes from US Naval Academy, this peaceful hotel offers spacious suites and complimentary breakfast. The outdoor pool provides relaxation after exploring nearby shopping centers, while friendly staff ensure a comfortable stay close to major highways.
"Clean, spacious, quiet, convenient location. I’d stay there again. "
United States
Michael
The price is ฿2,871
฿3,273 total
includes taxes & fees
4 Jan - 5 Jan 2026
Sonesta ES Suites Annapolis
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 savour its top-notch restaurants.
See properties

Captain Avery Museum

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

Top Shady Side Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
Paul 1-night trip
Posted 7 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"a very spotless room. The staff all of them very friendly and welcoming. I enjoyed a very clean room and the breakfast was fantastic. The girl kept the dining area well stocked and clean."
Kathie 1-night trip
Posted 11 days ago
Comfort Inn Conference Center

More cheap stays in Shady Side

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ฿2,243 per night from 28 Dec to 29 Dec
฿2,243
฿2,557 total
28 Dec - 29 Dec
includes taxes & fees
7.6/10 Good! (1,001 reviews)

Frequently asked questions

What's the best place to 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 traveller data. Two other choices for your visit to the area are DoubleTree by Hilton Hotel Largo/Washington DC and La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway. 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 room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.
What are some accommodation options 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 centre. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and Crowne Plaza Annapolis by IHG are two additional hotels that offer an on-site pool. View all hotels with pools in Shady Side.
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 13 hotels and other accommodation options 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 itinerary are Captain Avery Museum and Franklin Point State Park. Take a look at what more there is 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 temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Shady Side is 1307 mm.

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