Shady Side Hotels from S$115

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17 Jul - 18 Jul
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Top 10 trending Shady Side hotels

1313 West Luxury Boutique Hotel
Stunning two-story home with a central entrance and beautifully manicured lawn.

1313 West Luxury Boutique Hotel

2.0 star property
The price is S$357
includes taxes & fees
21 Jul - 22 Jul
1313 West Luxury Boutique Hotel
Legacy Villa
Private kitchen

Legacy Villa

4.0 star property
The price is S$513
includes taxes & fees
31 Jul - 1 Aug
Legacy Villa
The Inn at Tacaro Estate
Stunning heritage building with a traditional brick façade, prominent statue, and charming shutters.

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"1940’s estate is maintained to remind you of those times. There was a “Speak-EZ” in the basement they had open Friday and Saturday evenings. My room was spacious and included a balcony. Huge front lawn with a pool and a view to the Bay. "
The price is S$493
includes taxes & fees
30 Jul - 31 Jul
The Inn at Tacaro Estate
86 State Circle - Luxury Boutique Hotel
Stroll through the charming streets, lined with historic architecture and vibrant autumn foliage.

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is S$358
includes taxes & fees
22 Jul - 23 Jul
86 State Circle - Luxury Boutique Hotel
George Brooks House B&B
Enjoy a relaxing stay in this two-story house with a spacious patio area and a swimming pool perfect for leisure activities.

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is S$343
includes taxes & fees
23 Jul - 24 Jul
George Brooks House B&B
Anchored Inn at Hidden Harbour Marina
Stunning hotel with a symmetrical facade and landscaped gardens.

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (440)
"The staff specifically Victoria was impeccable! "
The price is S$354
includes taxes & fees
20 Jul - 21 Jul
Anchored Inn at Hidden Harbour Marina
Rips Country Inn
Relax in a spacious room with a large bed, wooden headboard, and two bedside tables.

Rips Country Inn

2.5 star property
6.6 out of 10, (55)
"Not worth the money "
Rips Country Inn
Red Roof Inn Annapolis
Two single beds with white linens, a desk, and a television are featured in this hotel room.

Red Roof Inn Annapolis

2.0 star property
7.2 out of 10, Good, (360)
"Excellent check in staff. Old facility that needs remodeling. Dirty hallway carpet and dim lighting. Not the best bathroom amenities."
The price is S$117
includes taxes & fees
20 Jul - 21 Jul
Red Roof Inn Annapolis
Rod 'N' Reel Resort
Enjoy the serene waterfront view from this deck, featuring a picnic table and two Adirondack chairs.

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very good, (1002)
"Lovely place"
The price is S$294
includes taxes & fees
20 Jul - 21 Jul
Rod 'N' Reel Resort
Candlewood Suites Annapolis by IHG
Relax in a spacious room with a dining area, seating area, and desk, perfect for work and relaxation.

Candlewood Suites Annapolis by IHG

2.5 star property
8.8 out of 10, Excellent, (81)
"Great stay"
The price is S$128
includes taxes & fees
20 Jul - 21 Jul
Candlewood Suites Annapolis by IHG
Flag House Inn
Stunning two-story home with a charming porch and symmetrical facade, featuring a central entrance and evenly spaced windows.

Flag House Inn

3.5 star property
9.6 out of 10, Exceptional, (72)
"Delicious breakfast. Utilitarian room- perfectly acceptable but we expected a higher level given price point. "
The price is S$255
includes taxes & fees
22 Jul - 23 Jul
Flag House Inn
The Oaks Waterfront
Stately home with a central entrance and two wings, set amidst manicured lawns and shaded by trees.

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is S$583
includes taxes & fees
22 Jul - 23 Jul
The Oaks Waterfront
Executive Inn And Suites
Guests can park their vehicles in the on-site parking area.

Executive Inn And Suites

2.0 star property
7.2 out of 10, Good, (535)
"Clean rooms, excellent and accommodating staff met our expectations."
Executive Inn And Suites
Quality Inn
Relax in a comfortable seating area with a sofa and armchairs, and enjoy a view of the outside from the large window.

Quality Inn

2.5 star property
7.8 out of 10, Good, (789)
"full breakfast, comfortable bed and nice pillows"
The price is S$141
includes taxes & fees
17 Aug - 18 Aug
Quality Inn
Kent Island Resort
Surrounded by lush greenery and a serene lake, this historic property offers a picturesque setting with a spacious parking area and a circular driveway.

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (105)
"Welcoming and well-staffed property, in a lovely and tranquil setting. Staff was friendly and helpful. Restaurant/bar service and food were outstanding. Great quiet getaway weekend spot. "
The price is S$376
includes taxes & fees
4 Aug - 5 Aug
Kent Island Resort
Village Inn
Relax in a spacious room with a large bed, nightstand, and comfortable armchair.

Village Inn

2.0 star property
6.2 out of 10, (486)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is S$123
includes taxes & fees
20 Jul - 21 Jul
Village Inn
Residence Inn By Marriott Annapolis
Hotel exterior with outdoor seating areas and large windows.

Residence Inn By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (38)
"The hotel staff and accommodations were exceptional."
The price is S$197
includes taxes & fees
3 Aug - 4 Aug
Residence Inn By Marriott Annapolis
Wylder Tilghman Island
Relax by the serene pool surrounded by comfortable sun loungers and umbrellas, set in an and secure area.

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (52)
"Excellent stay. Very relaxing and great facilities."
The price is S$291
includes taxes & fees
11 Aug - 12 Aug
Wylder Tilghman Island
Historic Inns of Annapolis
Relax in the serene outdoor patio, surrounded by trees and equipped with comfortable seating and tables.

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1789)
"Great location close to bars, restaurants a s shops."
Historic Inns of Annapolis
Inn at Horn Point
Relax on the shore with two comfortable chairs and a small table, overlooking the calm waters and a picturesque pier.

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. "
The price is S$503
includes taxes & fees
4 Aug - 5 Aug
Inn at Horn Point
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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Learn more about Shady Side

Love dining, parks and museums? Get away to Shady Side!

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Top Shady Side Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"At the center of history "
Sung 3-night trip
Posted 3 days ago
Historic Inns of Annapolis

Frequently asked questions

What's the best place to stay in Shady Side?

Historic Inns of Annapolis, located 9.6 mi (15.4 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 La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and Comfort Inn Largo-Washington DC East. 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?

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Hotel located near Northwest Stadium. Provides a snack bar/deli, a seasonal outdoor pool and buffet. Comfort Inn Largo-Washington DC East and Country Inn & Suites by Radisson, Annapolis, MD 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 12 hotels and other accommodation options to choose from. Find out more about Shady Side.

What should I see while I'm in Shady Side?

Favourite places to visit include Shadyside Park, Captain Avery Museum and Franklin Point State Park. You'll also find Triton Beach and London Town in the area. 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.