Search Condo Rentals in Western Shore of Maryland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month

Compare 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, (67)
"Extended family in town for holidays and perfect place to use for extra space!"
Romantic Two Bedroom Condo

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (139)
"We came up for the bowl game in Annapolis and this place offered a great place to stay near downtown and access to anywhere! The condo offered a clean comfortable place with all you need so close. "
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!

Eastport Condo in Building with Rooftop 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."
Eastport Condo in Building with Rooftop 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, (4)
"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 SAR 371
SAR 944 total
includes taxes & fees
2 Mar - 3 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 SAR 859
SAR 1,603 total
includes taxes & fees
3 Feb - 4 Feb
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, (17)
"I had such a wonderful time in Annapolis celebrating Thanksgiving week with college friends. The location is perfect for anyone that wants to explore Annapolis. The condo was exactly as described, but what was so wonderful were the personal touches. I cannot wait to book this condo again. If I could give 11 stars I would."
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.
Don't see what you're looking for?
See all available properties in Western Shore of Maryland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Western Shore of Maryland

Baltimore executive Furnished rentals

4.0 star property
8.0 out of 10, Very Good, (2)
"I highly recommend this property if you’re visiting the Baltimore area. Very spacious for myself, my husband and our 4 kids. Lorraine checked in on us every other day and Mr. Derrick made sure everything was in order upon our arrival."
The price is SAR 1,222
SAR 1,923 total
includes taxes & fees
2 Mar - 3 Mar
Baltimore executive Furnished rentals

⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

9.6 out of 10, Exceptional, (21)
"Couldn't ask for a better location for walking to The Bank. Parking pass good on game days. Had no problem parking right out front. Excellent communication with host and house was very nicely appointed! Stairs wider and safer than most in Pigtown"
⭐️Luxury Modern Home⭐️ Walk to Ravens Stadium, Orioles Park, Horse Shoe Casino

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.
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 to per night for condos in Western Shore of Maryland. No matter your budget, you’ll find the perfect stay 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?
Western Shore of Maryland has condos to pick from. Enter your destination and dates and organize your next escape today.
Why book your condo in Western Shore of Maryland with Expedia?
Booking a condo in Western Shore of Maryland is as simple as clicking on your travel dates and choosing an option that suits your style. Looking for something upscale or budget friendly, or a stay that also features a pool and a hot tub? Use Expedia’s search filters to further narrow your search results and find the ideal fit.
How can I find cheap condos in Western Shore of Maryland?
The quickest way to uncover cheap condos in Western Shore of Maryland is with Expedia’s handy filter tool. Narrow your search results by budget, star rating and amenities to nab awesome bargains in a couple of clicks.