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Top 10 trending Shady Side hotels

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, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is P23,690
P26,060 total
includes taxes & fees
Aug 11 - Aug 12
The Oaks Waterfront
St Michaels Inn
Stately building with a covered entrance and porch, set amidst a well-manicured lawn.

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 P6,679
P7,347 total
includes taxes & fees
Aug 4 - Aug 5
St Michaels Inn
The Wildset
Relax in a spacious room with a large bed and sliding glass door leading to a balcony with a view.

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 P11,350
P13,752 total
includes taxes & fees
Aug 18 - Aug 19
The Wildset
Inn at Perry Cabin
Enjoy a romantic meal for two in our serene outdoor dining area, surrounded by a tranquil pool.

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (355)
"Beautiful place to stay."
The price is P35,501
P42,957 total
includes taxes & fees
Aug 28 - Aug 29
Inn at Perry Cabin
Parsonage Inn
Experience the charm of this historic bed and breakfast, featuring a traditional gabled roof and wrap-around 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 P12,035
P13,239 total
includes taxes & fees
Aug 13 - Aug 14
Parsonage Inn
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 P13,936
P15,329 total
includes taxes & fees
Aug 11 - Aug 12
George Brooks House B&B
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, (796)
"Conveniently located with overall great value."
The price is P5,791
P6,428 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn
Hilton Garden Inn Kent Island Marina
Relax on the outdoor terrace with a view of the marina, surrounded by wicker furniture and beautiful flowers.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (971)
"Friendly staff, nice environment"
The price is P9,218
P10,231 total
includes taxes & fees
Aug 19 - Aug 20
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Welcome to the Holiday Inn Express, where guests can check in and enjoy a convenient stay.

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 P8,235
P9,140 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
Two single beds with white linens and dark wood headboard, flat-screen TV, and a dresser with drawers.

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 P5,769
P6,403 total
includes taxes & fees
Aug 7 - Aug 8
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Relax by the fire pit in this scenic waterfront seating area, overlooking the marina with boats docked.

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (601)
"Great place to stay. "
The price is P9,156
P10,163 total
includes taxes & fees
Aug 11 - Aug 12
Hyatt Place Kent Narrows & Marina
Knapps Narrows Marina & Inn
Boats dock at the marina, surrounded by lush greenery and a building with a sloping roof.

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (337)
"This is a wonderful place "
The price is P12,617
P13,878 total
includes taxes & fees
Aug 5 - Aug 6
Knapps Narrows Marina & Inn
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, (56)
"Good service and good options to enjoy the stays. "
The price is P9,807
P13,310 total
includes taxes & fees
Aug 18 - Aug 19
Wylder Tilghman Island
The Tilghman Island Inn
Enjoy al fresco dining with a view of the water and a warm fire pit.

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 P12,903
P14,194 total
includes taxes & fees
Aug 12 - Aug 13
The Tilghman Island 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 P10,652
P13,977 total
includes taxes & fees
Aug 4 - Aug 5
Kent Island Resort
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

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 P11,805
P14,568 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
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
8.4 out of 10, Very Good, (1002)
"Great place to stay."
The price is P8,723
P10,829 total
includes taxes & fees
Aug 3 - Aug 4
Rod 'N' Reel Resort
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 P19,716
P22,476 total
includes taxes & fees
Aug 11 - Aug 12
Inn at Horn Point
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, (490)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is P5,118
P5,834 total
includes taxes & fees
Aug 3 - Aug 4
Village Inn
Annapolis Waterfront Hotel, Autograph Collection
Relax in this serene room with a large bed, a comfortable armchair, and a floor lamp, offering a view of the nearby water.

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 P12,677
P14,452 total
includes taxes & fees
Aug 10 - Aug 11
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 out, parks, and museums? Get away to Shady Side!

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Top Shady Side Hotel Reviews

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

10/10 Excellent
"Great stay ! Great location with almost anything you can eat nearby! And lots of stores to do slight shopping at. Would say that you’d have to find things to do activity wise but overall excellent location. "
Anyia 4-night trip
Posted 2 days ago
Microtel Inn & Suites by Wyndham Gambrills

Frequently asked questions

Where is the best place for a 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 traveler data. Two other choices for your trip 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 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?

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 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 13 hotels and other accommodations to choose from. Find out more about Shady Side.

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

Favorite 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. 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.