Chesapeake Bay Vacation Homes
Walk to dining and entertainment from these charming locations
Reviews
Trent
March 2026 · Airbnb
⭐⭐⭐⭐⭐
We had an amazing stay! The home was absolutely beautiful, spotless, and very well stocked with everything we needed, which made the trip so easy and comfortable. The pool and hot tub were incredible and definitely one of our favorite parts of the stay, we spent so much time relaxing out there. It truly felt like a home away from home. We would absolutely stay here again and highly recommend this property to anyone visiting St. Augustine!
Clint
March 2026 · Airbnb
Our family of 4 stayed here for a few nights in early March and the home was perfect for us! Clean, easy to find, walkable to the beach and restaurants and shops. Loved having the washer and dryer and dishwasher. Well-stocked kitchen for cooking. Comfy beds. Very responsive host. We hope to return in the summer!
Mihaela
March 2026 · Airbnb
Loved the Casa Fresa! The design is sooo beautiful!!! We really loved that there were toys for our little kids available on the second floor. Also, the welcome gifts were sooo nice :)! Most importantly, the place is just a few minute walk from the beach and shops! We will certainly be back!!!
Kirstain
March 2026 · Airbnb
We had a brief, but exceptional stay! The place was in an excellent location, very clean, and the hosts were very hospitable. They even left a sweet treat for us and our pup. We would come back our next time in town!
Miranda
March 2026 · Airbnb
Loved this home! There was everything we needed in the bathroom, kitchen and bedrooms. We were having some issues with the pool and hot tub heating. However chip and courtney were VERY responsive and wanted to solve the problem ASAP. Super close to the lighthouse and not too far from downtown. We spent many nights outside by the propane fire talking with music and had no problems with the neighbors.
Karen
February 2026 · Airbnb
We enjoyed our time on Chincoteague Island. It was pleasant to return to the condo, watch movies, read and relax. The unit is equipped with many amenities which are greatly appreciated when traveling. Good location, close to the trails, lighthouse and beach. Many restaurants to choose from. Chip was always responsive, quick to respond and gave wonderful recommendations. Thanks for a lovely stay.
Heather
February 2026 · Airbnb
Great location! You can see downtown from the lovely front porch. This home feels so cozy like a home away from home. Very clean and cute coastal with an excellent Chef’s kitchen. Visiting during the off season was made easier with the well equipped kitchen and dining room. Would stay again!
Michelle
February 2026 · Airbnb
We had a great stay! The house was spotless and very cozy. The location was perfect, quiet and just a short drive from so many things to do, and places to eat. Chip was very helpful and responsive. Highly recommend!
Amanda
February 2026 · Airbnb
We came in during a snowstorm and Chip was very responsive and helpful as we navigated coming into town and everything being shut down. The house was great! I hope to come again in better weather!
Sarah
February 2026 · Airbnb
We had a wonderful stay. It was off season and very quiet. The trees are tall pines and more beautiful than I expected. It was easy to get into town by car. The house is new and very comfortable.
Our Properties
Heated Pool & Hot Tub ~ Walk Downtown & 2 The Amp!
St. Augustine, FL, United States
Guests 10
Bedrooms 4
Bathrooms 2
Walk to Dining, Beach & Park~Family Friendly Home!
Cape Charles, VA, United States
Guests 6
Bedrooms 2
Bathrooms 1.5
King Bed~ Walk 2 Beach & Restaurants~Central Park!
Cape Charles, VA, United States
Guests 6
Bedrooms 2
Bathrooms 1.5
Bay Creek Home~ King Suite & Family Friendly Loft!
Cape Charles, VA, United States
Guests 8
Bedrooms 3
Bathrooms 2.5
Central Location~Walk to Dining! Beach Pass & Gear
Chincoteague, VA, United States
Guests 6
Bedrooms 2
Bathrooms 2.5
Golf Cart~ Chef Kitchen~ Fire Pit~ Outdoor Shower!
Cape Charles, VA, United States
Guests 8
Bedrooms 4
Bathrooms 2
Ultimate Kid-Friendly Escape! Fenced Yard-Firepit!
Cape Charles, VA, United States
Guests 8
Bedrooms 4
Bathrooms 2
Walk 2 Town~1st Floor King Bed~Fire Pit~Large Yard
Mathews, VA, United States
Guests 9
Bedrooms 4
Bathrooms 2
Duplexes by Central Park-2 Blocks 2 Beach-King Bed
Cape Charles, VA, United States
Guests 12
Bedrooms 4
Bathrooms 3
Peaceful Waterfront Retreat-Private Dock-Fire Pit!
Onancock, VA, United States
Guests 8
Bedrooms 4
Bathrooms 2.5
Remodeled by the Park-Family Friendly-Fenced Yard!
Cape Charles, VA, United States
Guests 4
Bedrooms 2
Bathrooms 2
NEW-Family-Friendly Duplex-Outdoor Shower-Fire Pit
Cape Charles, VA, United States
Guests 5
Bedrooms 2
Bathrooms 2
1st Floor King Suite~Fire Pit~3 Patios~Bunk Room!
Cape Charles, VA, United States
Guests 11
Bedrooms 4
Bathrooms 3.5