Chesapeake Bay Vacation Homes

Walk to dining and entertainment from these charming locations

Reviews

Ashley

August 2025 · Airbnb

This was our first time staying in an air bnb, and Chip and his family have set the bar high! Minutes after we booked our stay Chip reached out to introduce himself and offer any assistance we made need. Any questions that I had were answered promptly and politely. On the day of arrival Chip informed us that the house was ready for check in a few hours before our scheduled time, which was helpful because we arrived earlier than expected. Right away we felt at home, and our boys and pup found the toys that were thoughtfully provided. Every room was sparkly clean, and tastefully decorated without being cluttered. The location was excellent and walking distance (even for small children) to dining and activities. They thought of every emergency toiletries, and kitchen supplies you may have forgotten- which was great when I realized I forgot something to put our sandwiches in. Our expectations were exceeded for our first airbnb stay. Would we stay there again- absolutely!

Gabriela

August 2025 · Airbnb

We had such a great time at this beach house! The place was very clean, well-kept, and had everything we needed for our stay. It felt welcoming and peaceful from the moment we walked in. Highly recommend this spot for anyone looking for a comfortable and clean beach retreat — especially if you're bringing your furry friend along! Thanks for everything.

Jessica

August 2025 · Airbnb

We had a wonderful short stay at the Chesapeake Bay Vacay home! The house was very clean and had plenty of space for all 8 of us. The kids especially loved the bunk beds, which made their stay extra fun. One of our favorite parts was sitting outside in the backyard at night—it was so peaceful and quiet. Host Chip was very helpful and proactive. He let us know ahead of time that the keypad might have issues and made sure we had a backup plan with a key, which made check-in smooth and stress-free. A perfect spot for a relaxing family getaway. Highly recommend!

Macy

August 2025 · Airbnb

We were searching for a small beach getaway before the end of summer, and Chip's place was exactly what we needed! I reached out to Chip with a few questions before finalizing my reservation, and he was very helpful and accommodating. Our pets loved his home so much that I think they believed it was their new forever home. I definitely recommend this place!

Tracy

August 2025 · Airbnb

We came for the pony swim- this was the perfect abode for the 6 of us. Great kitchen- able to grill steaks, make pizza and chill with happy hours! This was just a lovely location with wonderful hosts. I highly recommend checking it out. Thanks from all of us.

Hayley

July 2025 · Airbnb

My family of 5 had a wonderful time in Mathews! The house was exactly as described and actually exceeded our expectations. We were able to walk to town and enjoy dinners and ice cream :) Chip was so helpful with any concerns I had and replied immediately to all my questions. We will definitely be back! Highly recommend to any family with kids or no kids!

Laura

July 2025 · Airbnb

We had a fantastic week. Being close to everything was very helpful as parking at certain popular places can be limited. We loved walking to dinner, ice cream, and the Blueberry Festival.

Kaley

July 2025 · Airbnb

The home is beautifully decorated and provided a sense of calm. It is furnished perfectly- not cluttered, but homey and containing everything one needs for a comfortable stay. The location is walkable and bikeable to all sorts of shopping, restaurants, and activities.

Nicholas

July 2025 · Airbnb

Chip and Courtney were great from day 1!! Super responsive and proactive. The house was just as advertised, very clean and easy to find and to get inside. Very close to all the restaurants and attractions the island has to offer. I would 100% stay here again and would recommend anyone looking for a trip to Chincoteague to stay with Chip and Courtney.

Sierra

July 2025 · Airbnb

We spent the weekend with our kids. Its so close to everything. The home was more beautiful. The bedrooms were set up so cozy. Everything was clean. We forgot a few items for the beach but it was ok because they had it for us! Outdoor shower was amazing after the beach. We cant wait to stay again. Also the neighbors were very friendly.