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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Oyster Condo Rentals

Perfect Cozy Vacation Rental on the Eastern Shore
Relax in this inviting living space with a sofa, table, and ceiling fan.

Perfect Cozy Vacation Rental on the Eastern Shore

8.2 out of 10, Very good, (26)
"Dated and not modern, clean but not a getaway or vacation rental, stove and oven dirty, only a few dishwater items available. "
Perfect Cozy Vacation Rental on the Eastern Shore
Delmarva - Brand new condo in downtown Cape Charles!
Relax on the balcony with a chair and enjoy the view.

Delmarva - Brand new condo in downtown Cape Charles!

Delmarva - Brand new condo in downtown Cape Charles!
Bayside Getaways Oyster Oasis | Chesapeake Properties
Relax in this stylish living room with a sofa, coffee table, and wicker chair.

Bayside Getaways Oyster Oasis | Chesapeake Properties

10.0 out of 10, Exceptional, (2)
"Clean, nicely decorated, comfortable bed, and excellent location. "
Bayside Getaways Oyster Oasis | Chesapeake Properties
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits
Guests can enjoy the beach with umbrellas and calm waters surrounded by lush greenery and a rocky breakwater.

Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits

10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay. The townhouse was welcoming in every way. The furniture and beds were comfortable and the property was very clean. I enjoyed the Bay Creek location with access to pools and a private beach."
Rendezvous at the Bay, Resort Condo in charming Cape Charles. Relaxation awaits
Above it All | Chesapeake Properties
Relax in this stylish living room with a striped armchair and sofa set, glass coffee table, and framed artwork.

Above it All | Chesapeake Properties

9.6 out of 10, Exceptional, (25)
"We had a lovely stay. Location was excellent and the condo was the perfect size. The roof deck was perfect for the sunset view."
Above it All | Chesapeake Properties
Princess Anne - Brand new condo in downtown Cape Charles!
Enjoy breathtaking views of the waterfront from this spacious rooftop terrace, featuring comfortable outdoor seating and a stylish railing.

Princess Anne - Brand new condo in downtown Cape Charles!

10.0 out of 10, Exceptional, (1)
"Fantastic condo in a great location! Property manager was helpful and easy to communicate with. Property/location were accurately described.Condo was within a short walk to beach, restaurants, coffee, and ice cream."
Princess Anne - Brand new condo in downtown Cape Charles!
Maryland - Brand new condo in Downtown Cape Charles!
Enjoy breathtaking harbor views from this rooftop terrace with a seating area and stunning cityscape.

Maryland - Brand new condo in Downtown Cape Charles!

Maryland - Brand new condo in Downtown Cape Charles!
Bay Creek Retreat | Chesapeake Properties
Two-story home with a central gable and peaked roof, featuring a circular window and diamond-patterned garage doors.

Bay Creek Retreat | Chesapeake Properties

9.6 out of 10, Exceptional, (8)
"We enjoyed the bikes, the pool and the beach. The large screen TV and Netflix were highly appreciated. We will come again. Thank you!!"
Bay Creek Retreat | Chesapeake Properties
Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities!
Experience the charm of this traditional hotel, featuring a brick facade and peaked roof, with a conservatory offering an enclosed outdoor space and comfortable seating areas.

Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities!

9.6 out of 10, Exceptional, (5)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Perfect"
Modern Coastal Retreat in Bay Creek Featuring Access to Club Amenities!
Park Place - Comfy Condo Close to Beach
Relax and dine al fresco with a grill at your fingertips.

Park Place - Comfy Condo Close to Beach

9.8 out of 10, Exceptional, (50)
"We are all retired, and made the trip as a spring vacation. Perfect location, condo, and neighborhood. We had a great time and enjoyed Cape Charles , Vergina."
Park Place - Comfy Condo Close to Beach
Pocahontas - Brand new condo in downtown Cape Charles!
Enjoy breathtaking harbor views from this rooftop terrace with a seating area and scenic views of the surrounding ships and cranes.

Pocahontas - Brand new condo in downtown Cape Charles!

6.0 out of 10, (1)
"Nice unit, great location, zero amenities on site. Had to go buy paper towels , napkins, dishwasher rabs, laundry on site but no detergent. Towels were meant for a small human!"
Pocahontas - Brand new condo in downtown Cape Charles!
Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach
Guests can enjoy a charming outdoor seating area with Adirondack chairs and a balcony overlooking the surroundings.

Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach

9.6 out of 10, Exceptional, (29)
"It was a wonderful apt with a great location to walk to everything. Shop owners were all super friendly! Our only disappointment was that the beach was actually closed the first 2 days for “reconstruction “ and the main reason we chose there was to walk to the beach. "
Beach, beach, beach in historic Cape Charles. Lovely 2BR Apt1Block from beach
Cape Haven - Condo 1.5 Blocks from Beach
Relax in a shaded outdoor space with a wicker sofa and table, surrounded by large windows offering views of the surrounding buildings and trees.

Cape Haven - Condo 1.5 Blocks from Beach

9.8 out of 10, Exceptional, (45)
"Our first time staying in town. With a teenager it worked out great. Nice to be near beach and right next to shops. "
Cape Haven - Condo 1.5 Blocks from Beach
Coastal Comfort & Endless Adventure in Cape Charles – Bay Creek Condo Retreat
Experience the vibrant atmosphere of this bustling marina, where boats and people come together.

Coastal Comfort & Endless Adventure in Cape Charles – Bay Creek Condo Retreat

9.4 out of 10, Exceptional, (3)
"We had a great stay at Bay Creek!! The condo was great and had everything you could possibly need while on vacation! We loved using the bikes, playing pickleball and exploring the beach! Cape Charles and Bay Creek have become one of our new favorites and we cannot wait to come back!"
Coastal Comfort & Endless Adventure in Cape Charles – Bay Creek Condo Retreat
Bayside Getaways Crab Crib | Chesapeake Properties
Relax in this stylish living space with a sofa, coffee table, and colorful rug.

Bayside Getaways Crab Crib | Chesapeake Properties

8.0 out of 10, Very good, (1)
Bayside Getaways Crab Crib | Chesapeake Properties
Virginia Lee - Brand new condo in downtown Cape Charles!
Enjoy breathtaking views of the waterfront from this rooftop retreat.

Virginia Lee - Brand new condo in downtown Cape Charles!

10.0 out of 10, Exceptional, (1)
Virginia Lee - Brand new condo in downtown Cape Charles!
Fireplace, Bikes, Community Pool | Bay Bliss
Relax on the beach with comfortable sun loungers and umbrellas, surrounded by a rocky breakwater and lush greenery.

Fireplace, Bikes, Community Pool | Bay Bliss

10.0 out of 10, Exceptional, (3)
"Bay Bliss is a special place for creating lifetime family memories. It’s your home away from home in one of the most scenic and welcoming small coastal villages. We wil surely come back for more memory making next year!"
Fireplace, Bikes, Community Pool | Bay Bliss
Beach Access Near State Park
Relax on the deck with a view, surrounded by a picket fence and comfortable seating.

Beach Access Near State Park

9.4 out of 10, Exceptional, (22)
"Thank you for a beautiful, clean place to stay. Location is the key for us, so close to the park. We will be back "
Beach Access Near State Park
Crabba-Dabba-Doo | Chesapeake Properties
Enjoy cooking in this well-equipped kitchen with a large island, sink, and dining area.

Crabba-Dabba-Doo | Chesapeake Properties

10.0 out of 10, Exceptional, (3)
Crabba-Dabba-Doo | Chesapeake Properties
"Seahorse Retreat" Condo 1 block from Beach in historic Cape Charles!
Step into The Coffee House, where a warm welcome awaits amidst lush greenery and large windows.

"Seahorse Retreat" Condo 1 block from Beach in historic Cape Charles!

9.6 out of 10, Exceptional, (74)
"Long weekend for a mother/daughter trip. This is the 2nd time we have stayed here as the location and accommodations are great. We love the balcony views of Mason street and people watching."
"Seahorse Retreat" Condo 1 block from Beach in historic Cape Charles!
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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Top Oyster Hotel Reviews

Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex

10/10 Excellent
"Such a fantastic location and home! We came with my two young children and my parents and we had a wonderful time! You can’t beat the location, it is across the street from the park, and you can walk to all the main stores and restaurants and it’s a short walk to the beach! "
Becca W. 3-night trip
Posted 19 hours ago
Next to the park and 2 blocks to the Beach and restaurants! RIGHT side of Duplex