Waterfront holiday rentals in Eastern Shore of Virginia

We went to Southern Maryland to celebrate our 44th Wedding Anniversary as it was where we met back in high school. We were greeted at Tom & Michele’s place with a sweet chalkboard message, flowers and a nice little cake to help us feel special and celebrated. That was very kind. Their apartment is extremely clean and very comfortable. The backyard is absolutely beautiful and very relaxing. We didn’t need help with navigating the area as we grew up there so we spent most of our time visiting places from our youth. Tom & Michele reached out to us during our visit to make sure we were doing okay. We are quiet people and don’t require a lot of assistance so it was nice to be asked but we were good. For us it was nice to have a chance to spend quiet time alone together and Tom & Michele gave us that. Should we find ourselves back in Southern MD we would definitely stay there again. Thank you for a wonderful visit ♥️

Super safe and beautiful gated neighborhood. Gorgeous setting. Quick drive to all things Williamsburg. Thanks so much, Lisa!

Anne's place was just spectacular! Perfect for 2 couples as our home-base to explore Williamsburg, Yorktown and Jamestown. The high end furnishings are beautiful. The patio, yard and lake view were wonderful. We enjoyed the theater room each night. Thank you for a great vacation.

We had a wonderful stay at Carla & Shannon’s place. Everything was neat and in order. The check in was super easy & flexible. We enjoyed the beautiful sunsets and walked around the town. They’re both very quick to reply back & we had a chance to talk with Shannon in person & she was super sweet.

What a calm and peaceful private retreat! My fiancée and I spent a couple of days enjoying the brisk bay breezes and beautiful sunsets at Vickie’s. Everything was exactly as advertised and Vickie (and Scott) are true treasures—extremely responsive and thoughtful hosts who want you to have everything you need. Plus, their knowledge of the area gave us a great introduction to Leonardtown. So much more to the area than we thought! Whether birdwatching from “the best view on the block” or reflecting on the glider by the bay, we loved every moment of quiet and can’t wait to visit again. Thank you!

We loved this space! We stayed the night for a concert in the area and were able to walk to and from the venue which was awesome! We got to the space and everything was very nice and felt like home! Would definitely recommend and stay here again!

Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

Bernadette's place is a fantastic getaway - very peaceful. The place is exactly as described. I thoroughly enjoyed the use of Bernadett 's kayak and paddle board (as well as walking ans running in her neighborhood and visiting Bethel Beach). I'd love to come back another time!

Connie’s place was great! Looked just like the photos. The house was clean and in a great area. Nice and friendly neighbors. We enjoyed the community beaches that are super close, clean and dog friendly. It was a prefect weekend trip. We would book here again!

We visited Southern Maryland for a family wedding. The property is beautiful and peaceful. Beds are comfy, house comfy, and they thought of the little things like : a full sized ironing board & Iron, beach towels, good soaps, and all you need for s’mores!Their welcome handbook was very detailed. Our only regret was that we could not spend more time on the property itself (because of family events). Would have loved to use the kayaks and the fire pit. My brother did use hot tub. Great stay! Highly recommend

My mom, sisters, friends and I enjoyed a relaxing fun filled time at the Coastal Oasis at the Chesapeake for our Mother's Day Retreat. The view is amazing and truly can be seen from every room in the house! Being able to see the beauty and calmness of the water helped each of us kick back and let the stress melt away. The big dinning room table allowed all of us all to enjoy breakfasts, dinners and touching conversations together. My guests loved the décor and raved about every detail. The beds and furniture were comfortable and house clean. I would definitely come back!

Thanks again! We feel at home here. I am noting that holiday weekends are less peaceful in the Northern Neck! We'll remember that. Fondly, Lois and Ken

Wonderful accommodations for a relaxing visit to a beautiful island!

this was our second time visiting after 2 years it looked fresh and clean and beautiful as our first stay the house is beautifully appointed with furnishings and all the comforts of home right down to drink shaker and hand mixer needed for me to make goodies to take to my families home nearby they also filled fridge with all sorts of goodies like eggs butter bagels juice pancake mix and strawberries just all sorts of things it really made us feel just like home can’t wait to go back again next year

We truly enjoyed our stay at the Colonial Beach Airbnb. The house is very cozy, well stocked, clean, updated and Carmen is a thoughtful host. The deck is a great area to relax overlooking the water and a few tried their luck fishing off the dock. Very nice!

Had a great week fishing and crabbing from the doc, kayaking, game playing, eating and visiting local attractions! Can’t say enough about how friendly Melissa was. Would definitely return!

Bao was prompt at responding to questions. The home was immaculately clean and much more spacious than appeared in the photos. The price was worth what we paid. My family and I were quite comfortable and we appreciated the starter items included with the rental. There were ample cooking utensils and the appliances were clean and in excellent condition. We travelled from out of state and brought a suitcase with our own linen. Not ideal, but this was a much more financially prudent option than paying the linen providers $190.00 for sheets and towels. Overall, we thoroughly enjoyed our stay at Bao’s rental. We were close to restaurants and the beach and had a view of the water. We highly recommend this property.

I traveled here from Pittsburgh with my three kiddos, and as a single mom this was a perfect location and a great spot. Very clean, lots of board games to play provided for you. I personally loved the extra towels!!! Will definitely be coming back to this location

This was our second time staying at one of Rebecca and Sean’s VA Beach condos — and the experience did not disappoint! This is just a perfect location, at the very end of the Boardwalk, with a private grassy lawn and outdoor seating just for the condo residents. Lots of restaurants in the surrounding blocks. Our favorite thing is the view — you look right out onto the ocean from the patio, and you can see the beach and the sunrise from the comfortable bed each morning. We spent unhurried hours sitting on the patio in the evenings enjoying the sound of lapping waves and the night sky. This cozy studio was just right for the two of us. Highly recommend. I’ve no doubt we’ll stay there again in the future!

We loved staying at Heathers place. Very comfortable and felt like home. We really appreciated the Welcome book she provided which gave us all kinds of recommendations for food, drink and activity. We will be coming back!

Amazing views! We watched the sunrise over the ocean from bed. The bathrooms are small with not much room to store your toiletries, but otherwise the space was great for my partner & I. We had a wonderful stay!

My husband and I decided to go on a getaway last minute. We found Seth’s place and were able to book the unit for the days we had available. It was great and met all of our expectations. We have been to OC and Fenwick many times and knew this is where we wanted to stay. It did not disappoint and we hope to rent again in the near future.

Really enjoyed our stay at Stephanie's. Awesome condo that was clean, comfortable and roomy. Wonderful views from Living Room, Balcony and Master Bedroom. Close enough to the water to hear the waves breaking. Plenty of restaurants and shops close by. Definitely hope to be back!

We had a wonderful stay at Liz’s studio. Perfect location on the boardwalk and beautiful view of the beach! The condo was just right for us. It was, clean, comfortable and had everything we needed. And Liz was very responsive with our questions. We hope to come back soon!