Shady Side Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Shady Side hotels

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is P23,284
P25,612 total
includes taxes & fees
Jul 10 - Jul 11
The Oaks Waterfront

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 P6,863
P7,549 total
includes taxes & fees
Jul 17 - Jul 18
St Michaels Inn

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (333)
"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 P11,174
P13,539 total
includes taxes & fees
Jul 22 - Jul 23
The Wildset

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (353)
"Grounds are beautiful. Staff very friendly and attentive "
The price is P35,255
P42,659 total
includes taxes & fees
Jul 13 - Jul 14
Inn at Perry Cabin

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is P14,654
P16,120 total
includes taxes & fees
Aug 7 - Aug 8
Parsonage Inn

George Brooks House B&B

3.0 star property
8.6 out of 10, Excellent, (60)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is P13,696
P15,066 total
includes taxes & fees
Jul 24 - Jul 25
George Brooks House B&B

Quality Inn

2.5 star property
7.8 out of 10, Good, (784)
"full breakfast, comfortable bed and nice pillows"
The price is P5,613
P6,230 total
includes taxes & fees
Aug 3 - Aug 4
Quality Inn

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (956)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
The price is P8,626
P9,575 total
includes taxes & fees
Jul 20 - Jul 21
Hilton Garden Inn Kent Island Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (867)
"Great place"
The price is P6,304
P6,998 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"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 P7,125
P7,909 total
includes taxes & fees
Aug 3 - Aug 4
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (576)
"Great place to stay. "
The price is P8,576
P9,519 total
includes taxes & fees
Aug 4 - Aug 5
Hyatt Place Kent Narrows & Marina

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (334)
"Extremely clean, wonderful place "
The price is P12,400
P13,640 total
includes taxes & fees
Jul 15 - Jul 16
Knapps Narrows Marina & Inn

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (49)
"Excellent stay. Very relaxing and great facilities."
The price is P10,205
P13,493 total
includes taxes & fees
Jul 17 - Jul 18
Wylder Tilghman Island

The Tilghman Island Inn

3.5 star property
9.6 out of 10, Exceptional, (95)
"What a great surprise! A great Inn "
The price is P14,091
P15,500 total
includes taxes & fees
Jul 15 - Jul 16
The Tilghman Island Inn

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (104)
"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 P13,725
P17,485 total
includes taxes & fees
Jul 22 - Jul 23
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (400)
"Staff was very polite and friendly. "
The price is P12,189
P14,972 total
includes taxes & fees
Jul 22 - Jul 23
The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very Good, (1000)
"The new renovations are gorgeous and we look forward to returning when everything is up and running! It will be a spectacular resort. "
The price is P10,602
P12,895 total
includes taxes & fees
Jul 14 - Jul 15
Rod 'N' Reel Resort

Inn at Horn Point

3.0 star property
9.4 out of 10, Exceptional, (19)
"This B&B was centrally located, clean,safe and quiet. However, even though I knew there would be no breakfast, I thought that like most B&B’s there would be the possibility of coffee or tea in the morning. There was no one home to welcome us or give information about nearby restaurants, etc. Why take the reservation if you can’t provide the amenities most B&B’s feature?"
The price is P19,941
P22,733 total
includes taxes & fees
Aug 6 - Aug 7
Inn at Horn Point

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 P4,756
P5,422 total
includes taxes & fees
Jul 15 - Jul 16
Village Inn

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (837)
"Front desk staff was very friendly and helpful."
The price is P13,138
P14,978 total
includes taxes & fees
Aug 4 - Aug 5
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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Shady Side

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

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. Provides a snack bar/deli, a seasonal outdoor pool, and buffet. Comfort Inn Largo-Washington DC East and Sonesta ES Suites Annapolis 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 12 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 London Town and Maryland Quiet Waters Park 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.