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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 12 Condo Rentals in Shady Side with updated reviews, rates, and availability.

Romantic Two Bedroom Condo
Fridge, microwave, oven, stovetop

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (71)
"Nice little two bedroom with everything you need. Food is conveniently close. If simple is what you are looking for this fits."
Romantic Two Bedroom Condo
Downtown Annapolis Condo w/ Free Parking + Coffee
Property grounds

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (19)
"Great condominium at a great location. Reserved parking. We were impressed with the owners’ approach—a lot of very nice small details. Beautifully decorated. "
The price is SAR 409
SAR 1,138 total
includes taxes & fees
29 Apr - 30 Apr
Downtown Annapolis Condo w/ Free Parking + Coffee
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, (269)
"This property is just steps from Main Street. It was the perfect location for exploring town and enjoying all that Annapolis had to offer during the holiday season. "
Annapolis Condominium in the heart of the historic center
Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking
Point of interest

Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking

10.0 out of 10, Exceptional, (15)
"The property was outstanding in proximity to the USNA and downtown Annapolis. We were able to walk to a fabulous bakery and good restaurants. The apartment was well appointed. The King-sized bed was exceptionally comfortable. We will return to this location!"
Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking
Beautiful Condo - Water View Near City Dock
Outdoor dining

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (142)
"Joe was super kind and generous - my wife and I were delayed a bit in getting there and Joe went out of his way to offer us help and support that he didn't need to do. Greatly appreciated and his place was outstanding as well. Semper fi,Dave"
Beautiful Condo - Water View Near City Dock
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
Pool

Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!

10.0 out of 10, Exceptional, (9)
"We enjoyed our visit with our son at USNA. Easy walk to DTA and great restaurants in Eastport. View from rooftop was spectacular!! Beds were comfortable."
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
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, (55)
"We have stayed in this building 3 times, and the location and the set up of the units are excellent. The complex is safe, quiet and is in a great location. It also is very accessible for handicap and having a secure parking spot is advantageous. "
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, (9)
"I recently stayed at the USNA Getaway in Annapolis, MD, and it was fantastic! The location is perfect, right near the Naval Academy and downtown Annapolis. The property is immaculate and beautifully furnished, with a cozy living area, fully equipped kitchen, and a lovely outdoor patio. The bedroom was spacious and super comfortable. The host was incredibly responsive and made sure I had everything I needed. Check-in and check-out were smooth and easy. I highly recommend the USNA Getaway for...
Water-view condo with rooftop pool & balcony - minutes from downtown
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our 5th trip to North Beach and our 4th time at a condo in Southwinds, and we have never been disappointed. Jenn and Mike, our hosts this time, provided all the information we needed to feel comfortable in their home. We found it exactly as pictured. NB has 5 good restaurants within walking distance and at least 2 more within a 5 minute drive. The boardwalk is great for walking at anytime of day. The new library is a jewel with special sections for all ages and a “makers” room. Teens...
Unbelievable beach views for 6
Kent Island Waterfront Cottage
Beach

Kent Island Waterfront Cottage

9.4 out of 10, Exceptional, (8)
"My husband and I stayed here for a quick weekend getaway to celebrate our anniversary. We appreciated the host being able to accommodate us an earlier check in and later check out time to maximize our short time away. They only charged us a small fee. The place was clean. So clean that I didn't feel I needed to wipe anything down, which is usually the case when we go to other places. The view was stunning and we had nice weather. We loved being able to walk out onto the dock as well as sit out...
Kent Island Waterfront Cottage
Waterfront 2-Bedroom Condo on Spa Creek
Interior

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (7)
"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
Delightful little Historic District gem - for the antique lover and history buff.
Fridge, microwave, oven, stovetop

Delightful little Historic District gem - for the antique lover and history buff.

9.0 out of 10, Wonderful, (4)
"Excellent location for all things USNA and downtown Annapolis. We walked everywhere. The second bedroom was a little warm but it was unseasonably hot while we were there. There is a K cup coffeemaker but you’ll need to bring everything to enjoy a cup. Would definitely stay again!"
Delightful little Historic District gem - for the antique lover and history buff.
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
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
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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Other property types in Shady Side

Washington Plaza Hotel
Exterior

Washington Plaza Hotel

4.0 star property
8.8 out of 10, Excellent, (4222)
"The receptionists were all wonderful!!!"
The price is SAR 409
SAR 474 total
includes taxes & fees
20 Apr - 21 Apr
Washington Plaza Hotel
Hotel Nell - Union Market
Reception

Hotel Nell - Union Market

3.0 star property
8.2 out of 10, Very Good, (574)
"Liked it"
The price is SAR 484
SAR 561 total
includes taxes & fees
2 May - 3 May
Hotel Nell - Union Market
Generator Hotel Washington DC
Terrace/patio

Generator Hotel Washington DC

3.0 star property
8.0 out of 10, Very Good, (1187)
"Fun, funky spot. Not luxury, if that’s what you’re looking for. But definitely a great place. Excellent staff, delicious cafe and bar onsite. Just don’t get the room directly above the bar on a Friday night if you plan on sleeping, ha!"
The price is SAR 439
SAR 618 total
includes taxes & fees
20 Apr - 21 Apr
Generator Hotel Washington DC
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.

Frequently asked questions

How much do condos in Shady Side cost?
Condos in Shady Side range from SAR 409 to SAR 409 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?
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