Search Condos Rentals in Shady Side from CA $282

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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Shady Side condo rentals

A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

1. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is CA $320
CA $759 total
includes taxes & fees
Nov 30 - Dec 1
Upscale Condo in Annapolis w/Private Parking
A living room with a dining table, two sofas, a coffee table, and a patterned rug.

2. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
The price is CA $282
CA $760 total
includes taxes & fees
Nov 8 - Nov 9
Chapel Gate 3BR Steps to City Dock & Naval Academy
A living room with a fireplace, a television mounted above it displaying an airplane, and a glass coffee table.

3. Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.

Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay!"
United States
Michaell M.
The price is CA $399
CA $920 total
includes taxes & fees
Nov 10 - Nov 11
Luxury Annapolis condo, fully remodeled, rooftop pool & marina, free parking, 0.3 mi to downtown. Perfect for Navy games, Academy visits, or a waterfront getaway.
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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Learn more about Shady Side

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

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

Top reviews in Shady Side

A modern kitchen with a large island, bar stools, and a wine rack.
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale

10/10 Excellent

G
Canada
Valerie
Reviewed July 27, 2026
Anchored Inn at Hidden Harbour Marina

Frequently Asked Questions

How much do condos in Shady Side cost?

Condos in Shady Side range from CA $282 to CA $399 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.

What is there to do in Shady Side near my condo?

The best travel accessory is a well-planned to-do list. Shadyside Park is a great place to kick off your adventures in Shady Side.

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