
Holiday rentals with outdoor seating in Eastern Shore of Virginia
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Top-rated rentals with outdoor seating in Eastern Shore of Virginia
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Popular amenities for outdoor seating rentals in Eastern Shore of Virginia
House rentals with outdoor seating

Waterfront Retreat| Kayak+Beaches+Pool | Gameroom
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!

Peace Point - Waterfront, Secluded, Home w/hot tub
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

The Glebe
We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!

Hidden Treasure
This is my third visit to Hidden Treasure, but will not be my last! Each time we come we stay a bit longer. 😊 I adore this house with the shark and mermaid theme and its peaceful location. It’s so nice being able to park in the garage! The beds are super comfortable and while not big, the house has everything my 3 dogs and I could need or want. There are trails cut into the wooded back yard that are perfect for pottying dogs after a day exploring or a quick morning walk. Sandi could not be nicer or more responsive to any and all messages. She is always ready to recommend local activities and restaurants and even shared some local history when I asked. We had zero issues so I sent photos of my dogs enjoying her place and the beach at Kiptopeke state park. Love this place!

Steps to the Sea at Salt Box
We stayed here a week ago and are still talking bout the awesome time we had. Beautiful home, easy walk to the beach and shops. Hosts were extremely nice, friendly, helpful and communicative. Would love to stay there again and are referring anyone who asks for a wonderful quiet getaway to this place. Stay here, you won’t be disappointed!

3 bedroom/2.5 bath Smith Island bungalow with dock
Wonderful accommodations for a relaxing visit to a beautiful island!

Hutch's Bluff - Waterfront near Williamsburg
Hutch’s Bluff was a great house in a fabulous location. There was all that you needed for your stay as well as beautiful view of the river. We felt right at home and it was so peaceful and relaxing. Will definitely return.

The Rosé Retreat: Pool-Screened Porch-RELAX
We had a really nice stay at the Rose Retreat! The home is wonderfully appointed with nice furnishings. We especially appreciated the well stocked kitchen with upscale drink and dinnerware. The hand written welcome note, bottle of wine and snacks were so thoughtful - thank you! A perfect location from which to enjoy Irvington and the surrounding towns. We hope to come back in warmer weather to enjoy the pool!
Apartment rentals with outdoor seating

“Little City by The Sea”
Glenn and Susan have a great place in a very cute town. Perfect for a quick get away to the Eastern Shore or if you need a place to stop for the night. Very clean and the bed was very comfy.

The Fish House
The Fish House is a beautiful and comfortable place to stay! My husband & I found it to be quite spacious for 2 people. The location was perfect; we were there from Sunday-Wednesday, and it was quiet and peaceful the whole time. It was conveniently located to Irvington, White Stone and Kilmarnock and all those towns have to offer! The A/C is brand new, and very effective against the Virginia heat and humidity. The kitchen had all the essentials for preparing food, and we appreciated the coffee & tea supplies that were provided! The bed is comfortable and we slept well. We spent a lot of time on the deck overlooking the water. As a bird watcher, it was so relaxing to view the local wildlife with the binoculars provided. Michelle is a wonderful host! Her instructions are clear, and checking in and out was easy. She also answered all our questions promptly, and thoroughly. If you are looking for a quiet, peaceful getaway on the Northern Neck, stay at The Fish House!

Private suite .5 mile from beach/no shared spaces
This was a lovely place to stay! Brianna was very communicative and the place was very clean and pleasant to stay in when we arrived.

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
Very cute place with lots of nice touches. Two patios to enjoy, one with ocean view. Very comfortable bed. Full cable TV. Great location at end of boardwalk - we sat and watched while enjoying our morning coffee or evening wine. Owners were very responsive!

Newly Constructed 2nd-Story Studio Apartment
Good place, nice and clean, well maintained as Airbnb type, freshly colored, several things to make place beautiful. Everything was there as described no surprises. I didn’t have to ask for anything during my stay, that made stay so much smooth.

Sunset Haven Downtown
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.

Private apartment only 3 blocks from the Beach
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!

Historic St. Mary's City, MD
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.
Apartment rentals with outdoor seating

Kingsmill 1bed/1ba on Golf Course 9th Fairway
Crystal's condo was spotless and an easy place to stay. Crystal was very proactive and made us feel welcome. her dinner suggestions were superb too! perfect for a weekend getaway in a resort atmosphere. Thank you so much, we highly recommend!

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!

Family Condo Oceanside in Midtown OC
Brian was super responsive and responded immediately to all questions, willing to work through any issues. The place was great and in a fantastic location. I 100% recommend a stay here!

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool
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!

Luxury Riverfront Condo w/ sunrise & sunset views
The condo was very clean with all necessary essentials. We loved sitting on the porch watching the wildlife, especially the numerous ospreys. It is centrally located, only a short drive to historic Williamsburg, Jamestown and Yorktown. Plan for about a day at each to fully enjoy everything. The grounds of the resort are lovely and a great place to walk or ride bikes. Rodica was very easy to communicate with and was most helpful with all checking instructions, especially with our late arrival. We would definitely like to return.

Direct Oceanfront close to Northside Park!
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!

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.

Luxury Oceanfront Escape!
This place is absolutely beautiful. Loved being able to sit on the balcony and watch the waves. Place is as described and looks just like photos. Definitely recommend this place!
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- Chesapeake Bay
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