
Beachfront holiday rentals in Eastern Shore of Virginia
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Top-rated beachfront rentals in Eastern Shore of Virginia
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Popular amenities for beachfront rentals in Eastern Shore of Virginia
Pet-friendly beachfront home rentals

Cozy beach cottage! One block to the beach!
Place was perfect for our one night stay. Amazing food nearby along with beach…walkable distance!!

Peaceful beach @Courtyard Cottage+No Cleaning Fee!
Our family of 7 had a wonderful stay. Everything was clean and tidy when we arrived and we felt at home right away. The location was fantastic- private and peaceful but also very convenient to walk out the door and be on the beach in a couple of minutes. My favorite feature was all the amenities provided by the hosts- beach towels, laundry detergent, games and books for the kids, etc. Even just having access to a broom and dustpan to sweep up the sand we tracked in was very helpful (and something we have missed in past Airbnb experiences). We would definitely recommend Richard’s place and would love to stay here again in the future.

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!

The Bird's Nest at Holly Bluff-Riverfront. Beach.
T’s place was absolute perfection! It was beautiful, tastefully decorated and the homemade muffins and cookies were amazing! She and John were so lovely and accommodating. Relaxing on the dock on the river was a sublime experience as well! I really can’t say enough about my time spent there and if I’m ever in the area again I will definitely be staying at T’s! Why would you stay anywhere else!?

Chicks Beachfront
Jeremy’s place could not have been in a better location. Beach is beautiful and not crowded. Nice area to walk to restaurants and all of Jeremy’s recommendations were spot on. The views could not be beat. The unit accommodated us well. Maria

Historic St. Mary's City, MD
Had a lovely stay at Pat and Nell’s. Was able to work in the mornings and take advantage of beautiful outdoors and access to the water from the dock. Highly recommend! Is a quiet, peaceful, clean, comfortable place to stay while adventuring in St Mary’s county.

Harbor View- (Sun - Sun rental June- Aug.)
We absolutely loved the stay at Janie’s place! It was great and such a short walk to the beach. The beach wagon, chairs, and umbrellas were a nice touch and saved us from having to bring our own! There is also a propane and charcoal grill available for use, which is amazing. We look forward to booking our next trip to Cape Charles here, hopefully sooner rather than later! We have heard Christmas time is beautiful!

Charming Waterfront Home with Expansive Views
We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.
Beachfront home rentals with a pool

THE OLD BEACON 1 | Beach Living
Beautiful home within walking distance to everything you need, especially the beach and restaurants. Clean home with cozy feel. My son never wanted to leave the beautiful pool at the property. Would recommended to families!!

Ocean & Bay Views - Local Family Owned & Operated
Had an amazing time with my family which was made very easy with the hosts! Lots of recs for things to do and places to eat. Had kid friendly items in the house which was great. Very clean and in a beautiful location. Would definitely like to return in the future!

Oceanfront Gem VaB Studio Exceptional Views
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!

Amazing oceanfront view 3 blocks from boardwalk
Condo was exactly as described! Amazing oceanfront view! I was also impressed with how much room there was. It was cruiser week so it was a tad bit noisy at night, but other than that and the fact we couldn’t stay longer, we had a wonderful time and enjoyed our stay!

Stunning Views of Back Bay & Seconds to the Beach
Jade & Nathan were great host. Their home was beautiful and exactly what we needed for our trip. My only recommendation is to come with your own cookware if you’re into cooking. They had plenty of kitchen items that I just had to make work. Other than that the neighborhood was peaceful. The kids enjoyed the pool area it was actually warm temperature and the view behind the house was one of the most amazing parts. I will definitely be back.

Direct Ocean Front/Gorgeous Views/Indoor Pool
We had a great time at Seth’s place. The location was perfect, quiet but still plenty to do. Easy beach access and clear directions for everything. Watched dolphins from the balcony and loved hearing the waves.

Direct Oceanfront with a View and Amenities Galore
Bryan is super responsive and easy to communicate with. He notified us of detailed check in and check out instructions. He then checked in on us towards the end of the trip to make sure all of our expectations were met; to which they were. This condo is exactly as described in the listing and pictures. It’s clean and cozy. The view from the bedroom is unmatched. The location is perfect in a sense that it’s not too close to the boardwalk, making the area a little more quiet, but also within 10 mins to the best restaurants and bars. The staff at the condo and even other guests were friendly and courteous. If you’re afraid of heights, this might not be the best place to stay for you, but as I previously mentioned, the view from the master bedroom can’t be beat. That view alone, would have us stay again. I would definitely recommend this stay to others.

Caramar Couples Retreat
There aren't enough words proper enough to describe how spot on this amazing place is. It looks EXACTLY as the photos show. As soon as I walked in the door, I was met with a beautiful & relaxing relief. I literally let out an "Oh my gosh". I just knew, it was going to be enjoyable. It was quiet & so serene. The bed truly is so comfortable. I was also so impressed with the amount of kitchen supplies as well as the products that were offered in the bathroom & kitchen. They were not your typical "hotel brand" products. Plenty of nearby places within walking distance from food to shopping. I hope I was a good a guest for them because I want to return again. I am in love with it. Such an amazing getaway. Thank you ×100!
Private beachfront home rentals

The Waverly Treehouse
We had a delightful stay in the Waverly treehouse. We definitely recommend checking it out. The amenities and host were absolutely wonderful and the trip exceeded all of our expectations. Thank you!!! ⭐️ ⭐️⭐️⭐️⭐️

2-bedroom lake-house with a magnificent view
Beautiful house and beautiful view. Outdoor jacuzzi with the view is not to be missed! Gorgeous and clean home. The private site made it an amazing getaway from busy life. Thank you, we will be back soon!!!

Leave your paw prints by the bay
First of all, this house and the views are STUNNING. This was the first vacation that I have taken with my fiancé and our 2 pups, and we had the best time--it was such a sad day when we had to leave lol. We basically ordered Doordash and Walmart Pickups the entire time we were there and never left the property during our stay. The kitchen was very well stocked with all the cookware you could need, there are kayaks and paddle boards for entertainment, and plenty of floats for relaxing in the bay. There is a little private beach within 1 min walking distance from the house and there is access to the water from the backyard. It had everything we wanted for a relaxing vacation with our pups. I am already working on convincing my fiancé that we need to go back in the near future. 10/10 would recommend.

The Haven On The Chesapeake Bay
The Haven on the Bay is an incredible property - we stayed here last year and loved it so much we had to stay here again. And this won’t be our last time - we plan to make it an annual trip at a minimum! Ashley is an amazing host and ensures her guests have a fantastic experience! Stay at this property - you won’t regret it.

Smokehouse on the Chesapeake Bay
Kenneth was an exceptional host for the following reasons -provided great recommendations for food, adventure on & off the property, & everything in between -approachable when we had questions and/or curiosity -clear & prompt communication -such a cozy, welcoming restored smokehouse (smelled like cedar, oak, & pine in there..LOVED it) -very well kept & clean, his & her robes were perfect for the shower & towels, washcloths, & linens were ready & waiting - fully stocked with treats, coffees & teas -gorgeous property w/ amazing dock for casting a few & enjoying unreal sunsets - super peaceful & serene My husband & I had our mini moon here & it was a continuation of our dreamy marriage to each other. We look forward to our return <3 Love, The Sassers

Little Gray Beach House
We loved our short stay at the Little Gray House. The view alone was worth the stay. The beaches are both easy walks and the area is lovely. Everything was clean and cozy and Bronwyn and Kat gave lots of information ahead of time, including some great recommendations. Would definitely recommend checking out The Hatchery and the Gwynn’s Island Museum on the island and spending some time exploring Mathews. We will be staying here again and hopefully soon!

Family Retreat Private Beach Eastern Shore w dock
Eastview is beautiful, the home and the surroundings. There’s plenty of room if you are traveling with a large group.

Summer Breeze waterfront new home-Private Beach
This is a perfect spot for a girls weekend to just be. The surroundings are gorgeous and the home is fantastic. It is a quiet neighborhood for those who enjoy early morning walks. Every room of the home feels airy and comfortable. I would return for sure.
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Resort Beach
- Assateague Island National Seashore
- Busch Gardens Williamsburg
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