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Top 10 Shady Side hotels and places to stay

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is ฿13,392
฿14,732 total
includes taxes & fees
3 Aug - 4 Aug
The Oaks Waterfront
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"Great spot to be close to town for a modest price. "
The price is ฿3,776
฿4,153 total
includes taxes & fees
3 Aug - 4 Aug
St Michaels Inn
The Wildset
Premium Room | 1 bedroom, Frette Italian sheets, premium bedding, iron/ironing board

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (345)
"The room was lovely - comfortable beds, it bathroom, nice toiletries. It’s quiet yet right in the center of town so you can walk to all the shops and restaurants. "
The price is ฿6,390
฿7,742 total
includes taxes & fees
18 Aug - 19 Aug
The Wildset
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (355)
"Beautiful place to stay."
The price is ฿19,986
฿24,184 total
includes taxes & fees
28 Aug - 29 Aug
Inn at Perry Cabin
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is ฿6,840
฿7,524 total
includes taxes & fees
27 Aug - 28 Aug
Parsonage Inn
George Brooks House B&B
Exterior

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 ฿7,878
฿8,666 total
includes taxes & fees
7 Aug - 8 Aug
George Brooks House B&B
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (796)
"Conveniently located with overall great value."
The price is ฿3,278
฿3,638 total
includes taxes & fees
3 Aug - 4 Aug
Quality Inn
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (971)
"Friendly staff, nice environment"
The price is ฿5,211
฿5,784 total
includes taxes & fees
19 Aug - 20 Aug
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
The price is ฿5,219
฿5,794 total
includes taxes & fees
20 Aug - 21 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is ฿3,248
฿3,605 total
includes taxes & fees
7 Aug - 8 Aug
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (601)
"Great place to stay. "
The price is ฿5,252
฿5,830 total
includes taxes & fees
27 Aug - 28 Aug
Hyatt Place Kent Narrows & Marina
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (337)
"This is a wonderful place "
The price is ฿7,132
฿7,845 total
includes taxes & fees
3 Aug - 4 Aug
Knapps Narrows Marina & Inn
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (56)
"Good service and good options to enjoy the stays. "
The price is ฿5,544
฿7,524 total
includes taxes & fees
18 Aug - 19 Aug
Wylder Tilghman Island
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (98)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
The price is ฿7,294
฿8,024 total
includes taxes & fees
11 Aug - 12 Aug
The Tilghman Island Inn
Kent Island Resort
Aerial view

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 ฿6,453
฿8,394 total
includes taxes & fees
4 Aug - 5 Aug
Kent Island Resort
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is ฿6,709
฿8,279 total
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
Rod 'N' Reel Resort
Superior Studio Suite | Balcony

Rod 'N' Reel Resort

4.0 star property
8.4 out of 10, Very good, (1001)
"Great place to stay."
The price is ฿4,931
฿6,122 total
includes taxes & fees
7 Aug - 8 Aug
Rod 'N' Reel Resort
Inn at Horn Point
Beach nearby

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 ฿11,146
฿12,706 total
includes taxes & fees
4 Aug - 5 Aug
Inn at Horn Point
Village Inn
TV

Village Inn

2.0 star property
6.2 out of 10, (490)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is ฿2,893
฿3,298 total
includes taxes & fees
4 Aug - 5 Aug
Village Inn
Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (847)
"Front desk staff was very friendly and helpful."
The price is ฿7,137
฿8,136 total
includes taxes & fees
10 Aug - 11 Aug
Annapolis Waterfront Hotel, Autograph Collection
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!

See all hotels in Shady Side

Top Shady Side Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Great place to stay. This is the only hotel I stay at when I’m in the area for work."
Wesley 2-night trip
Posted 1 day ago
Hilton Garden Inn Kent Island Marina

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. Offers 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 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?

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.