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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
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Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Condo Rentals in Shady Side

Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (274)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center
Romantic Two Bedroom Condo
Fridge, microwave, oven, stovetop

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (76)
"Very good "
Romantic Two Bedroom Condo
Beautiful Condo - Water View Near City Dock
Outdoor dining

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (145)
"This is our second time at this property and it is just perfect for us. Quiet, great location, comfortable, great host!!!!"
Beautiful Condo - Water View Near City Dock
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (6)
"It was unbelievable stay with fantastic sunrise and moon rise on the day of the eclipse"
Unbelievable beach views for 6
Modern condo in the heart of DTA with garage parking!
Smart TV, books

Modern condo in the heart of DTA with garage parking!

10.0 out of 10, Exceptional, (1)
"Excellent condo. Very comfy, spacious, clean, and has a beautiful view from the balcony. We loved our morning coffee and talks on the balcony! "
Modern condo in the heart of DTA with garage parking!
Kent Island Waterfront Cottage
Beach

Kent Island Waterfront Cottage

9.4 out of 10, Exceptional, (8)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
Downtown Annapolis Condo w/ Free Parking + Coffee
Property grounds

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (24)
"Very nice location and nice apartment!"
Downtown Annapolis Condo w/ Free Parking + Coffee
Chic Condo w/ Balcony in the Heart of Annapolis!
Interior

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (57)
"This cute condo is as pictured; charming and clean. Nice bathrooms. Comfortable beds. Great location. Loved the parking ease as well. Host was very receptive and flexible with my arrival/departure times.Would highly recommend and would stay here again."
Chic Condo w/ Balcony in the Heart of Annapolis!
Water-view condo with rooftop pool & balcony - minutes from downtown
TV

Water-view condo with rooftop pool & balcony - minutes from downtown

9.2 out of 10, Wonderful, (10)
"We loved our stay and will definitely return! Close to USNA and lots of restaurants. We enjoyed the pool and the place was clean and comfortable . Can’t wait to return!"
Water-view condo with rooftop pool & balcony - minutes from downtown
Waterfront 2-Bedroom Condo on Spa Creek
Smart TV

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (8)
"This is a great location. Walking distance to everything. Near all the sailing clubs! Property manager was the best we have ever experienced."
Waterfront 2-Bedroom Condo on Spa Creek
Waterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location with Parking
Pool

Waterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location with Parking

10.0 out of 10, Exceptional, (16)
"Absolutely perfect. Wonderful location. Beautiful property. Great staff made the weekend easy. "
Waterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location with Parking
Unique 2-Bedroom Condo in Renovated Church Parish House
Point of interest

Unique 2-Bedroom Condo in Renovated Church Parish House

Unique 2-Bedroom Condo in Renovated Church Parish House
Modern Serenity in Upper Marlboro - Luxe 2-Bed Condo with Alluring Amenities
Fridge, microwave, oven, stovetop

Modern Serenity in Upper Marlboro - Luxe 2-Bed Condo with Alluring Amenities

Modern Serenity in Upper Marlboro - Luxe 2-Bed Condo with Alluring Amenities
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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Frequently asked questions

How much do condos in Shady Side cost?
Condos in Shady Side range from to per night. This will give you lots of room for the entire family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your condo in Shady Side with Expedia?
We think that vacations shouldn't be difficult, so if you're looking for condos at an affordable rate, Expedia can help. Stick to the budget and go for something small and affordable, or book 5-star accommodations and really spoil your crew. Our search filters make it a breeze to secure a property in Shady Side that checks your boxes.
How can I find cheap condos in Shady Side?
Expedia can help you narrow down your search for cheap condos in Shady Side. To find a fantastic stay in a few quick keystrokes, use the filter tool to refine your search by star rating, budget and amenities.