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In two weeks
10 Oct - 12 Oct
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21 Nov - 23 Nov
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16 Jan - 18 Jan

Condo Rentals in Shady Side

Waterfront condo. Completely renovated. Walk to Kent Island's best places
TV, fireplace

Waterfront condo. Completely renovated. Walk to Kent Island's best places

Waterfront condo. Completely renovated. Walk to Kent Island's best places
Romantic Two Bedroom Condo
Fridge, microwave, oven, stovetop

Romantic Two Bedroom Condo

9.8 out of 10, Exceptional, (87)
"The accommodations met and even exceeded my expectations! Location was perfect with restaurants and grocery shopping nearby while still located in a quiet area! Communication with the host was great and the place was super clean! Would stay here again if in the area!"
Romantic Two Bedroom Condo
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, (284)
"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
New Downtown Annapolis Condo With Free Parking
Property grounds

New Downtown Annapolis Condo With Free Parking

10.0 out of 10, Exceptional, (30)
"Clean, modern apartment walking distance from all of Annapolis harbor and restaurants. "
The price is AED 547
AED 1,361 total
includes taxes & fees
30 Sep - 1 Oct
New Downtown Annapolis Condo With Free Parking
Beautiful Condo - Water View Near City Dock
Outdoor pool

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (147)
"Clean, quiet, and very close to both downtown and Eastport restaurants."
Beautiful Condo - Water View Near City Dock
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Pool

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

10.0 out of 10, Exceptional, (21)
"Can’t have a better location near everything in Eastport and Main St Annapolis!"
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Waterfront 2-Bedroom Condo on Spa Creek
Smart TV

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (9)
"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
Kent Island Waterfront Cottage
Fridge, microwave, oven, stovetop

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was unbelievable stay with fantastic sunrise and moon rise on the day of the eclipse"
Unbelievable beach views for 6
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, (59)
"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!
3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown.
Dining

3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown.

3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown.
3-bedroom condo in charming Bowie with AC
TV, fireplace

3-bedroom condo in charming Bowie with AC

2.0 star property
3-bedroom condo in charming Bowie with AC
Charming 2-bedroom condo in brilliant Bowie with AC
Property grounds

Charming 2-bedroom condo in brilliant Bowie with AC

2.0 star property
Charming 2-bedroom condo in brilliant Bowie with AC
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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Top Shady Side Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Clean room. Professional staff"
William 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG

Frequently asked questions

How much do condos in Shady Side cost?
Condos in Shady Side range from AED 1,361 to AED 1,361 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.