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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 34 Apartments in Chesapeake Beach with updated reviews, rates, and availability.

The heart of St Michaels awaits.
Exterior

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (37)
"This flat/apartment is perfect, exactly as described. Located in the heart of town, convenient to all restaurants and shops. The flat beautifully updated and appointed, and spotlessly clean. We were extremely comfortable and will definitely return."
The heart of St Michaels awaits.
Guest Quarters at the Inn - 102
1 bedroom, iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 102

9.8 out of 10, Exceptional, (18)
"Close to many restaurants and activities "
Guest Quarters at the Inn - 102
Harbor View Suite
Fridge, microwave, coffee/tea maker, toaster

Harbor View Suite

10.0 out of 10, Exceptional, (22)
"Excellent!"
Harbor View Suite
Studio on the Bay.
Beach nearby, beach towels

Studio on the Bay.

10.0 out of 10, Exceptional, (18)
"The studio was amazing! The location was perfect and exactly what we needed . It also had some nice added amenities ( kayaks, jacuzzi ) we truly enjoyed our stay."
Studio on the Bay.
Cozy centrally located studio with WiFi and AC in delightful Port Republic, MD
Fridge, microwave, stovetop, coffee/tea maker

Cozy centrally located studio with WiFi and AC in delightful Port Republic, MD

Cozy centrally located studio with WiFi and AC in delightful Port Republic, MD
Guest quarters at the inn - 205
TV

Guest quarters at the inn - 205

9.4 out of 10, Exceptional, (12)
"Great stay"
Guest quarters at the inn - 205
Relax & Recharge in Our Family-Favorite Retreat
Exterior

Relax & Recharge in Our Family-Favorite Retreat

2.0 out of 10, (1)
"Was never able to actually stay here because the owner never provided check-in info. They didn't respond to messages on the app or calling their personal number directly, didn’t respond to Vrbo employees either when they tried to contact the owner. Had to get a hotel last-minute after giving them three hours past the scheduled check-in time to respond. Incredibly frustrating and inconvenient as I was looking for somewhere to stay with my infant daughter after our house was packed up as we're...
Relax & Recharge in Our Family-Favorite Retreat
Courtyard Studio at Bancroft Manor. Cozy Retreat!
Exterior

Courtyard Studio at Bancroft Manor. Cozy Retreat!

10.0 out of 10, Exceptional, (22)
"Needed a place to stay before I move to SC and this place/location was perfect! Great all around and great communication."
Courtyard Studio at Bancroft Manor. Cozy Retreat!
Bay View Studio Apartment
Outdoor spa tub

Bay View Studio Apartment

10.0 out of 10, Exceptional, (44)
"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 - 103
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 103

9.8 out of 10, Exceptional, (22)
"Wonderful place within walking distance of the beach and restaurants. Would definitely stay here again!"
Guest Quarters at the Inn - 103
Studio in Downtown – Walk to Everything!
Iron/ironing board, WiFi, bed sheets

Studio in Downtown – Walk to Everything!

10.0 out of 10, Exceptional, (19)
"Great central location. Spotless and comfortable-a great home base for being out and about in St. Michael's."
Studio in Downtown – Walk to Everything!
Water view studio. 20 minutes from Annapolis.
Property grounds

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.
Chesapeake Bayside Loft
Beach

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
Guest Quarters at the Inn - 101
Iron/ironing board, free WiFi, bed sheets

Guest Quarters at the Inn - 101

9.8 out of 10, Exceptional, (12)
"We had a great stay at the Guest Quarters. The place is very clean and has recently been updated. We lucked out and hit Fist Friday in North Beach and enjoyed live music and great food just a block away."
Guest Quarters at the Inn - 101
Apartment in Downtown – Walk to Everything!
Living area

Apartment in Downtown – Walk to Everything!

9.0 out of 10, Wonderful, (2)
"We loved the property and the location (can’t be beat!). We walked to shops, restaurants, and bars all over town. It also had convenient parking. The apartment was clean and had everything we needed for a short stay. "
Apartment in Downtown – Walk to Everything!
Guest quarters at the inn - 204
1 bedroom, iron/ironing board, free WiFi, bed sheets

Guest quarters at the inn - 204

9.8 out of 10, Exceptional, (14)
"My lady loved it. Would be a 10 out of 10 but the deck was not clean and ice bucket was dirty. "
Guest quarters at the inn - 204
New Loft w/South River view from treehouse deck!
Terrace/patio

New Loft w/South River view from treehouse deck!

10.0 out of 10, Exceptional, (21)
"Nice stay"
New Loft w/South River view from treehouse deck!
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Property grounds

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

9.8 out of 10, Exceptional, (17)
"Beautiful veiw Nice neighborhood Great location away from downtown but still close Excellent host"
HUGE DISCOUNTS FOR STAYS BY THE WEEK AND MONTH! 1ST CLASS AMEMITIES!
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
TV

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (29)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.
Luxury gourmet kitchen with backyard and parking at 1st floor Eastport apartment
Fridge, microwave, oven, stovetop

Luxury gourmet kitchen with backyard and parking at 1st floor Eastport apartment

10.0 out of 10, Exceptional, (4)
"My husband and I stayed here for his reunion weekend. The place was super-cute, very chic with a gorgeous gourmet kitchen we didn't take enough advantage of, very comfortable bed, and a great shower. The location was an easy 20 minute walk to Gate 1, and convenient to lots of Eastport restaurants, had parking, Nice yard with a place to sit outside. Really a fabulous stay! "
Luxury gourmet kitchen with backyard and parking at 1st floor Eastport apartment
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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Frequently asked questions

What's it like to stay at an apartment in Chesapeake Beach?
You’ll find 15 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?
Listed below are some of the favorite apartments in the area to choose from: The heart of St Michaels awaits.: Located in St. Michaels, 17.9 mi/28.7 km from the heart of Chesapeake Beach. Includes private balconies and fireplaces. Access to onsite laundry facilities is available on site. Relax & Recharge in Our Family-Favorite Retreat: Located 24.3 mi/39 km away in Lusby. Guest Quarters at the Inn - 102: Located in North Beach, 1 mi/1.7 km away. Includes free WiFi and private balconies. Access to a water park is available on site. Harbor View Suite: Located 18.1 mi/29.1 km away in St. Michaels. Amenities include free WiFi. Access to onsite laundry facilities is available on site.
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.