Search Condo Rentals in Western Shore of Maryland

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Compare 30 Condo Rentals in Western Shore of Maryland with updated reviews, rates, and availability.

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

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (68)
"The condo was just as pictured and advertised. Great location and clean and quiet. Will definitely be coming back here just as long as my Son and family are in Crofton"
Romantic Two Bedroom Condo

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (140)
"I currently live in this complex, and I rented this condo for my parents to come stay a few days while I recovered from surgery. Joe and Beth were extremely accommodating and kept communication with my parents while they stayed (but also didn't bug them!). I was thankful to have such an easy process for my older parents and they are already talking about coming back down again because they enjoyed their stay so much!"
Beautiful Condo - Water View Near City Dock

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (52)
"Chip's place is very well located on West Street. We stayed over Christmas and it was easy to walk to my sister's house on Spa View and super nice to be above the top-notch coffee and baked goods at Curate. The place is perfectly laid out for two people/couples to each have their own space and bathroom. "
Chic Condo w/ Balcony in the Heart of Annapolis!

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!

90 DAY MINIMUM STAY - Spacious Cyberpunk Themed Downtown Loft

10.0 out of 10, Exceptional, (8)
"I had a wonderful stay at this place! It is SUPER clean and close to lots of things; easy to get to where you want to go from there. I was staying in town for a conference, and it’s a 5-7 minute walk to the convention center. The owners have thought of everything-so many cute little touches in the loft. It’s a whole vibe in there! Great experience and I would definitely stay there again!"
90 DAY MINIMUM STAY - Spacious Cyberpunk Themed Downtown Loft

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"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

Available for CW 2025 Walk to Main Street from spacious waterfront Condo w Pool and Parking

10.0 out of 10, Exceptional, (14)
"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!"
Available for CW 2025 Walk to Main Street from spacious waterfront Condo w Pool and Parking

Downtown Loft & Close to EVERYTHING!

6.0 out of 10, (2)
"There was so much that was wrong with our stay. First, it was not the apt as shown in the pictures. The lighting was dreary —only one overhead light in the bedroom and living room. The front door didn’t lock and the rugs on the stairs and in the living room were disgustingly dirty. The walls were dingy and showed signs of being painted over in spots in a haphazard way. there were picture frames on the walls with no pictures and broken glass. There was a grimy feel to the whole place except the...
The price is AED 364
AED 959 total
includes taxes & fees
4 Mar - 5 Mar
Downtown Loft & Close to EVERYTHING!

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (6)
"Our unit was comfortable and clean with all the amenities. We loved the outside space overlooking the Bay Area. It was only a very short drive or 15 min walk to all the restaurants and shops. We will return!"
Waterfront 2-Bedroom Condo on Spa Creek

Chic Downtown Studio! 4 Min Walk to Waterfront!

2.0 out of 10, (2)
"We drove 10 hrs to take my father to an Orioles game to full fill his bucket list to find out after the game and checking into our condo someone was already in there staying because it was already booked out for the weekend. I had to call and talk to someone for over an hour to find out that they couldn’t help but tell me I should be getting a refund. They said I had to find my own stay somewhere else at 10:20pm. Closest place open was an hour away and had to drive there to check in. My father...
The price is AED 841
AED 1,582 total
includes taxes & fees
4 Mar - 5 Mar
Chic Downtown Studio! 4 Min Walk to Waterfront!

Spacious Home by the Water in Fells Point

10.0 out of 10, Exceptional, (5)
"Great location … close to harbor, restaurants and shops. Charming neighborhood … fun to just walk around. Apartment was spacious, well equipped and comfortable in every way. We had a couple of things we needed help with, and Shea, host, responded immediately and took care of the issue. We had a fabulous time because we were so comfortable with this place!"
Spacious Home by the Water in Fells Point

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. "
Downtown Annapolis Condo w/ Free Parking + Coffee

Quiet Fells Point Home Just off the Main Street

2.0 out of 10, (1)
Quiet Fells Point Home Just off the Main Street

Perfect Location: Fully Furnish Elegant One Bedroom Condo at the Harborview

Perfect Location: Fully Furnish Elegant One Bedroom Condo at the Harborview

Luxury Condo Penthouse in Owing mills/Pikesville

Luxury Condo Penthouse in Owing mills/Pikesville

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.

Inner Harbor Gem

Inner Harbor Gem

Comfy 1 Bedroom Condo- Peaceful area w/Parking Pad

9.4 out of 10, Exceptional, (11)
"This property is beautiful. I genuinely have no complaints other than the parking. The alley could be labeled better to find it and the space is super small, maybe even reserving a street spot for this property would be my only suggestion. Definitely would stay again!"
Comfy 1 Bedroom Condo- Peaceful area w/Parking Pad
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 Western Shore of Maryland

Fantastic 2 bedrooms apt. Harbor

4.0 star property
10.0 out of 10, Exceptional, (1)
"It was a nice place"
Fantastic 2 bedrooms apt. Harbor

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Spectacular Penthouse at 39 west.

4.0 star property
10.0 out of 10, Exceptional, (1)
The price is AED 750
AED 1,396 total
includes taxes & fees
16 Mar - 17 Mar
Spectacular Penthouse at 39 west.
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 Western Shore of Maryland cost?
Prepare to pay from AED 364 to AED 841 per night for condos in Western Shore of Maryland. No matter your budget, the perfect stay is a click away on Expedia. 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.
How many condos are there in Western Shore of Maryland?
Explore our 30 condos in Western Shore of Maryland and then select your favorite. Whether you’re off on a vacation with the whole fam or kicking back with your pals, with Expedia, your perfect stay is just clicks away.
Why book your condo in Western Shore of Maryland with Expedia?
Expedia makes it easy to find your dream condo in Western Shore of Maryland. After a luxury escape? Find your way to the filters to search for properties that have a 5-star rating. If you have a budget, choose how much you’re willing to spend and then browse our amazing options. We’ll help you find the right fit whatever your bank balance or plans.
How can I find cheap condos in Western Shore of Maryland?
An excellent way to get cheap condos in Western Shore of Maryland is with Expedia’s convenient filter tool. Fine-tune your search results by amenities, star rating and budget to land awesome rates in just a few keystrokes.