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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 25 Apartments in Chesapeake Beach with updated reviews, rates, and availability.

Bay View Studio Apartment
Property grounds

Bay View Studio Apartment

10.0 out of 10, Exceptional, (42)
"Lovely property, larger than I expected, hot tub on the waterfront was wonderful. We will certainly be back. "
Bay View Studio Apartment
Guest quarters at the inn - 205
Exterior

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"The property was not only as described, but better than described, honestly words don’t do it justice. It was exactly what my best friend and I needed to get ready for a friends wedding, and have a comfortable place to stay for the weekend. We loved the classy decor, full length, mirror, soaking tub, and the big thank you for the welcome tray of snacks! The location is perfect, a block from the water, close to bars and restaurants, while being in a quiet neighborhood, and it’s proximity to...
Guest quarters at the inn - 205
Warm their heart with a valentine getaway!

Warm their heart with a valentine getaway!

Warm their heart with a valentine getaway!
Chesapeake Bayside Loft
Room

Chesapeake Bayside Loft

8.0 out of 10, Very Good, (12)
"Great property, needs some TLC in areas to really make this be an amazing property...overall it's very clean, soft beds and has a fantastic 2 min walk to the bay for coffee or a beer/ wine...quiet neighborhood, easy access...I think the owner is really miss out on the opportunity to make this home a must rent ..back yard needs some love, lights, fire pit, corn hole etc...overall, great stay, compared to DTA this is excellent "
Chesapeake Bayside Loft
Harbor View Suite
View of harbor 1/2 block from suite.

Harbor View Suite

10.0 out of 10, Exceptional, (19)
"Excellent!"
Harbor View Suite
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Terrace/patio

Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!

10.0 out of 10, Exceptional, (27)
"Well decorated and comfortable stay. Very quiet and great place to sit and enjoy the sunrise/sunset."
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
Cozy 1st Level Beach House - Walk Everywhere

Cozy 1st Level Beach House - Walk Everywhere

2.0 star property
The price is AED 415
AED 1,568 total
includes taxes & fees
18 Feb - 19 Feb
Cozy 1st Level Beach House - Walk Everywhere
Studio on the Bay.
Beach

Studio on the Bay.

10.0 out of 10, Exceptional, (17)
"What a beautiful little gem hidden on the shores of Calvert beach. The description of the house was perfect and drew our attention when booking. In reality, it was even nicer. Can’t say enough how impressed we were. The house was decorated tastefully, and had everything we needed for a few day stay. Thank you for thinking of the small details that make you feel like you are at home. Location is everything. It is so close to the beach. The area is gorgeous. We took multiple trips to local parks...
Studio on the Bay.
New Loft w/South River view from treehouse deck!

New Loft w/South River view from treehouse deck!

10.0 out of 10, Exceptional, (21)
"The loft was very clean and modern inside. We enjoyed having our meals on the deck, with a nice calming view of South River. The owner was very flexible (e.g. check-in time) and easy to communicate with. Beware that the kitchenette is small (not much room to cook if that matters to you). I personally would prefer having a firmer mattress, but others may disagree."
New Loft w/South River view from treehouse deck!
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Enjoy outstanding sunrises and sunsets!

HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!

9.8 out of 10, Exceptional, (16)
"What a beautiful and welcoming property! Tons of wildlife activity to view and great water views. Amenities were great. Really appreciate everything! Lovely host!"
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Charming Beach House Top Floor - Walk Everywhere!

Charming Beach House Top Floor - Walk Everywhere!

2.0 star property
The price is AED 415
AED 1,568 total
includes taxes & fees
18 Feb - 19 Feb
Charming Beach House Top Floor - Walk Everywhere!
Guest Quarters at the Inn - 103
Exterior

Guest Quarters at the Inn - 103

9.8 out of 10, Exceptional, (22)
"Loved front porch"
Guest Quarters at the Inn - 103
Water view studio. 20 minutes from Annapolis.
Room

Water view studio. 20 minutes from Annapolis.

10.0 out of 10, Exceptional, (1)
"Perfect for a couple weekend getaway! We were in town for sail boat demos for the weekend and found this newly renovated studio apartment above the owners garage bright and clean. With a short walk down to the beach, the beautiful sunrises will take your breath away! A must see. Will return again! Thanks Rob and Suzanne"
Water view studio. 20 minutes from Annapolis.
Guest Quarters at the Inn - 101
Exterior

Guest Quarters at the Inn - 101

9.8 out of 10, Exceptional, (12)
"This property is right in the Main Street running through Chesapeake Beach and North Beach. It's close to the beaches, restaurants, and close to all of the local attractions. The room itself was large, clean, and comfortable, and the building was both quiet, secure, and well kept. We'll definitely be back!"
Guest Quarters at the Inn - 101
Guest Quarters at the Inn - 102
Exterior

Guest Quarters at the Inn - 102

9.8 out of 10, Exceptional, (18)
"I came to North Beach for a friend’s wedding near by. The Guest Quarters was a cute place and very welcoming. The instructions provided were clear and easy to enter into the building and room. The location is in a great spot - easy walk to the cute shops and to the beach. I would stay there again! "
Guest Quarters at the Inn - 102
Guest quarters at the inn - 204
Exterior

Guest quarters at the inn - 204

9.8 out of 10, Exceptional, (13)
"Loved the place! Plenty of room. Hubby and I snuggled in the comfy robes most of the time! Only thing I’d recommend is WiFi for tvs so visitors can log on to their personal streaming apps. "
Guest quarters at the inn - 204
Available for CW 2025 Eastport apartment with gourmet kitchen, backyard and parking
Welcome to the gathering space at Eden on Adams.

Available for CW 2025 Eastport apartment with gourmet kitchen, backyard and parking

10.0 out of 10, Exceptional, (4)
"Nicely appointed and updated. Easy check in and out. "
Available for CW 2025 Eastport apartment with gourmet kitchen, backyard and parking
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual

Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual

Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
Home away from home
Bathroom

Home away from home

Home away from home
Cozy 1-bedroom apartment in brilliant Cheltenham with WiFi, AC
Dining

Cozy 1-bedroom apartment in brilliant Cheltenham with WiFi, AC

Cozy 1-bedroom apartment in brilliant Cheltenham with WiFi, AC
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 Chesapeake Beach

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Property grounds

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (75)
"Great house. Had everything you need for a vacation rental. Had great views, watched ducks and eagles. Got sharks teeth from beach. Definitely recommend to ones seeking Bayfront getaway."
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Family Beach House: Spacious Deck, Grill & Views
Miscellaneous

Family Beach House: Spacious Deck, Grill & Views

9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is AED 632
AED 1,611 total
includes taxes & fees
10 Mar - 11 Mar
Family Beach House: Spacious Deck, Grill & Views
Cozy Cottage with access to and partially obstructed views of the bay.
Exterior

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
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

What's it like to stay at an apartment in Chesapeake Beach?
You’ll find 19 accommodations in Chesapeake Beach. Though there aren’t many apartments, we can help you locate accommodations with similar amenities. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also filter by similar property types like vacation homes, condos, or guest houses. Why not visit the spas and take time to enjoy the beaches while you’re in this relaxing area?
How do you know if an apartment is a good option for you?
An apartment is often more spacious than a traditional hotel room and comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples looking for something with a more local feel.
What's the top apartment for my stay in Chesapeake Beach?
Here are some of the more popular apartments in the area to choose from: Bay View Studio Apartment: Located 18.9 mi/30.5 km away in Annapolis. Free WiFi, private patios, and fireplaces are included. A water park and a hot tub are on site. Warm their heart with a valentine getaway!: It’s situated in St. Michaels, 17.9 mi/28.8 km from Chesapeake Beach.
What will the weather be like during my trip to Chesapeake Beach?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Chesapeake Beach. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Chesapeake Beach is 52 inches.
What should I see and do in Chesapeake Beach?
Chesapeake Beach is known for its beaches and spas. Cultural attractions include Chesapeake Beach Railway Museum and Bruce Gabrielson’s Surf Art Gallery and Museum, whereas Breezy Point Beach is one spot to enjoy nature. Chesapeake Beach Water Park and Rod n Reel Charter Fishing are other places to visit while you’re in town.
What's the best way to get to and around Chesapeake Beach?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Easton, MD (ESN-Easton - Newnam), which is located 26.5 mi (42.7 km) from the city center. Otherwise, look for flights into College Park, MD (CGS), which is 28.8 mi (46.3 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.