Search Shady Side hotels

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check Shady Side hotel prices

Tomorrow night
This weekend
Next weekend

Filter by

Popular filters
Popular filters
Total price
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top hotels and accommodation in Shady Side

Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (60)
"Stayed here during wedding night. Host accommodated requests to make the night check in go smoothly. Property is amazing, the Star was everything we thought and more. Would absolutely stay again!"
The price is NZ$767
includes taxes & fees
28 May - 29 May
Waterfront Oasis of Annapolis Star
Front of property
Anchored Inn at Hidden Harbour Marina
2.5 star property
9.6 out of 10, Exceptional, (367)
"The location and the private balconies are excellent. It is a very peaceful and beautiful place"
The price is NZ$465
includes taxes & fees
23 May - 24 May
Anchored Inn at Hidden Harbour Marina
Beach nearby
Inn at Horn Point
3.0 star property
9.6 out of 10, Exceptional, (18)
"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...
The price is NZ$656
includes taxes & fees
28 May - 29 May
Inn at Horn Point
Save an average of 15% on thousands of hotels when you're signed in
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1044)
"Unique property, close to everything. Costly, but every hotel in the area is. "
The price is NZ$348
includes taxes & fees
9 Jun - 10 Jun
Graduate Annapolis
Desk, iron/ironing board, free cots/infant beds, free WiFi
Courtyard by Marriott Bowie
3.0 star property
9.4 out of 10, Exceptional, (643)
"Only issue was with low water pressure in the shower "
The price is NZ$295
includes taxes & fees
17 Jun - 18 Jun
Courtyard by Marriott Bowie
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (341)
"Beautiful property very kind staff and wonderful amenities..would highly recommend"
The price is NZ$477
includes taxes & fees
27 May - 28 May
The Inn at Chesapeake Bay Beach Club
25-inch TV with cable channels
TownePlace Suites Bowie Town Center
2.5 star property
9.2 out of 10, Wonderful, (461)
"Wasn’t bad only issue was the Wi-Fi wasn’t great "
The price is NZ$202
includes taxes & fees
9 Jun - 10 Jun
TownePlace Suites Bowie Town Center
Bar (on property)
Comfort Inn Conference Center
2.5 star property
9.0 out of 10, Wonderful, (1000)
"We had a very pleasant stay at Confort Inn Bowie!’ Very accommodating and fabulous breakfast included!!! We will be there again. "
The price is NZ$183
includes taxes & fees
16 Jun - 17 Jun
Comfort Inn Conference Center
Beach
Indulge or be still near Naval Academy/ Annapolis
9.0 out of 10, Wonderful, (8)
"Karen was absolutely wonderful! I had several questions and she responded within just a few moments. The place was immaculate, cozy it felt like it was a home away from home. Very close to anything you could possibly need and the view is absolutely breathtaking. The bed was so comfortable that I found out the type of mattress and I’ll be buying one. I highly recommend staying with Karen. I will certainly be booking again in the future. 5 Stars across the board!"
Indulge or be still near Naval Academy/ Annapolis
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1002)
"Parking lot A little dark at night. Front desk was very welcoming Bartender was stale. Not very welcoming at all. Over all place is nice. Would recommend "
The price is NZ$208
includes taxes & fees
28 May - 29 May
Crowne Plaza Annapolis, an IHG Hotel
Exterior
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
8.8 out of 10, Excellent, (731)
"Great improvement with the breakfast; we have stayed here before and it was so much better this time."
The price is NZ$189
includes taxes & fees
5 Jun - 6 Jun
Microtel Inn & Suites by Wyndham Gambrills
Room, 2 Queen Beds, Balcony
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (710)
"I like everything about this property!"
The price is NZ$447
includes taxes & fees
28 May - 29 May
Annapolis Waterfront Hotel, Autograph Collection
Property amenity
Staybridge Suites Washington DC East - Largo, an IHG Hotel
3.0 star property
8.8 out of 10, Excellent, (423)
"This is a great hotel on your way north or south. The room was spacious and came with a small kitchen which was nice to have. Breakfast was included - it wasn’t anything special but it was perfect if you are on the go in the morning. "
The price is NZ$258
includes taxes & fees
28 May - 29 May
Staybridge Suites Washington DC East - Largo, an IHG Hotel
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (621)
"We chose the property based on the cleanliness reviews after considering another property in the same area. We were not disappointed! The breakfast choices were plentiful with a different hot option each morning. "
The price is NZ$231
includes taxes & fees
29 May - 30 May
Sonesta ES Suites Annapolis
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1000)
"I was sadly visiting for a funeral and was there for a 4 nite stay. The staff was so kind and very helpful. The room was clean and comfortable. Perfect location to everything I needed. I will 100% stay at this double tree when I come back into town. "
The price is NZ$221
includes taxes & fees
28 May - 29 May
DoubleTree by Hilton Hotel Annapolis
Exterior
Courtyard by Marriott Annapolis
3.0 star property
8.6 out of 10, Excellent, (859)
"Marriott rarely disappoints. Good, well maintained, comfortable hotel with a nice courtyard with a fireplace, seating areas, etc. Large enough room, comfortable, clean."
The price is NZ$217
includes taxes & fees
26 May - 27 May
Courtyard by Marriott Annapolis
Suite, 1 Bedroom, Terrace | Living area
Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (849)
"Beds were super clean and comfortable. The stay was pleasant. The bartender on Thursday night was not very accommodating "
The price is NZ$259
includes taxes & fees
28 May - 29 May
Hilton Garden Inn Annapolis Downtown
Exterior
Lower Level Loft - Adorable Studio Apt. Near BWI
8.6 out of 10, Excellent, (4)
"Very nice for a short stay"
The price is NZ$196
includes taxes & fees
28 May - 29 May
Lower Level Loft - Adorable Studio Apt. Near BWI
Beach
Chesapeake Bayside Loft
8.6 out of 10, Excellent, (9)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
Chesapeake Bayside Loft
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board
Hilton Garden Inn Annapolis
3.0 star property
8.4 out of 10, Very good, (1000)
"The lighting in the room was not good, even with all lights on it felt dark. Only overhead was in foyer as you walk in. Unfortunately I had broken my foot the week before our trip and it had rained the weekend we stayed and though when you first walk in there was carpet to dry my crutches but due to the rain I wasn’t able to completely dry the bottom of them. The entire lobby to the elevator was tile where my crutches proceeded to slip a few times on the tile floor while heading to the elevator....
The price is NZ$205
includes taxes & fees
28 May - 29 May
Hilton Garden Inn Annapolis
Don't see what you're looking for?
See all available properties in Shady Side
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.

More cheap accommodation in Shady Side

Stay near top Shady Side attractions

Shady Side hotels information

Number of reviews
5,133
Accommodation
1,096 hotels
Lowest Price
NZ$121
Highest Price
NZ$447

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 Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD. See all available top hotels, or vacation rentals in Shady Side.

What are some of the best holiday rentals that Shady Side has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Shady Side offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind. See all 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 FedEx Field. Offers a snack bar/deli, a seasonal outdoor pool and buffet. DoubleTree by Hilton Hotel Largo/Washington DC 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 London Town and Maryland Quiet Waters Park 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.

Recent Reviews in Shady Side
Expedia verified reviews