
Holiday rentals with a kayak in Eastern Shore of Virginia
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Top-rated Accommodation with a Kayak in Eastern Shore of Virginia
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Holiday House Rentals with a Kayak

Sunnybank Getaway - Waterfront w/Pier & Kayaks
We love our stay here! The house had everything we needed and more. It was easy to find, and the views were amazing. We spent the whole time outside in the nature, and we loved how quiet it was. Kevin was easy to reach for any questions we had, and we appreciated his help. We would definitely come back here 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!

Waterfront Home - Dock, Kayaks, Fire Pit, Grill
Talk about being sad 😢to leave! Sometimes a location for an air BnB just hits it out of the park, and this is a great example. We LOVED our stay and took advantage of the yard and beautiful view daily! We fished off the dock and shore. Tip, since it is tidal water as long as you are on the shore or dock you don’t need a fishing license. Our pups loved the yard and going for a swim. There are a lot of great places to eat within a 30min drive. We were on a work trip, but would love to come back when we could take advantage of everything this place has to offer. It’s a gem! The surrounding area is fun to explore if you like antiques and boutiques. We loved the local vibe! You will have a great time.

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.

Blue Heron WaterSide
Of my many Airbnb stays, Laura’s comes up with the very best. Her home is lovely, inside and out, with a lot of fun activities to choose from. Located on a beautiful creek opening to wide water gave us a chance to explore in her kayaks and paddle board. Rainy weather meant indoor board games, reading etc on the beautiful protected porch. The kitchen had all sorts of amenities for cooking. Plenty of bedrooms for sleeping in the peaceful atmosphere. I can’t wait to return there!

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!

Living on Island Time
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!

Peaceful Waterfront Escape on Church Creek
We enjoyed our stay at this peaceful waterfront house on Church Creek. Communication with the hosts was great. The house was clean and very well equipped and organized. We appreciated having access to kayaks and life jackets. If you're looking for a quiet retreat with easy access to points of interest on the Eastern Shore of Virginia we would highly recommend this rental.
Cottages with a kayak

The Crab Shack
This was our 1st visit to The Crab Shack. All I can say is Wow, just Wow! This was the cleanest, nicest and cutest Airbnb that we have ever stayed at over the years! It was amazing! My husband and I traveled from Sarver, PA with our 2 Golden Retrievers to celebrate our 10 year Wedding Anniversary! We all had the best time ever! We spent most of the time here at the Shack just cooking on the grill and listening to music and the girls did a lot of swimming fetching for balls! Thank you Carlisle and Mary for making our 10 year Anniversary simply perfect! ❤️☀️😎🥂🍾🦀 We can’t wait to come back! ☺️

Private Beach Access at The OV Beach House
Beautiful private beach access, with multiple things to do in the area, fabulous restaurants and shops. Easy drive to Virginia Beach boardwalk. Location is safe, friendly and with all the amenities you need to enjoy a perfect beach vacation.

Private point on the Bay🌤hammock, hot tub, kayaks❤️
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.

Levering Creek Cottage with Private Dock
Janet has a unique property considering the destination is on an island... it has it's own dock which affords guests the ultimate in flexibility. It was the main reason we elected to overnight there. My son and I only had one night for the fishing trip in our own boat over father's day weekend so it was not a deal-breaker we had to book 2 nights. The simplicity of motoring up after a day on the water with all of our gear and the convenience for being up early to catch the right tide was a perfect fit. Wish we had 2 nights to stay and have better luck with the weather... and the fish, but we will be back. Thanks Janet!

A "True" Chesapeake Bay Waterfront Experience!
Awesome house and location. Very nicely furnished and stocked with more items that I am accustomed to for an air bnb.

TooFine Lakehouse, pet friendly waterfront cottage
Beautiful surroundings, with the lake just steps from the door. The cabin had everything we needed for a 4 night stay. Great mix of indoor and outdoor spaces to enjoy. We absolutely loved it!

Newly Renovated 2BR Waterfront Cottage with Dock
What an absolutely beautiful space! Once we arrived, we didn’t want to leave. The house was super clean and well laid out. This is a perfect spot to unwind or recharge. Bring all your food and drink and just enjoy the beautiful views. We saw lots of wildlife, including herons, bald eagles, osprey, little lizards, deer, turtle, and some jumping fishies. We checked out Fossil Beach at Westmoreland State Park. Lots of walking trails and a lot of eagles. We enjoyed some bbq from Fishers at the Barn. The rest of the time we lounged on one of the decks or the dock and just took in the sights and sounds. Thanks for sharing the beautiful space!! We hope to visit again this fall! 10/10.

Little Cottage on the Creek
My wife and I stayed at the cottage while in town for a wedding. The location is very central and walking distance to many of the towns attractions. The neighborhood is quiet and beautiful. Lots of cool nature and kind people. Karen was very friendly and helpful. Would recommend!
Cabin rentals with a kayak

Riverside R&R: Cabin, Dock, Kayak & Game Arcade
We are two families that met up for a relaxing getaway after celebrating a high school graduation. This was the perfect place. The downstairs had lots of games and a big screen for them to hook their switch up to. We watched movies upstairs. And use the well-equipped kitchen each night to make a big dinner. The kids took the kayaks and canoe out one afternoon as well. Although I would say they definitely wouldn’t swim there. Compass entertainment complex is very close and they enjoyed their time there. We also went to a movie there one night. It is a beautiful home in a peaceful setting. Especially down on the dock at night. It was very quiet. We would definitely recommend this home.

Awesome private off grid cabin with creek view.
This place was as described. Very peaceful get away for my family and totally worth the price we paid. Teresa was quick to respond and recommended some place to eat. We will be back to experience the fall weather.

Peaceful Waterfront Retreat on The Bay
Incredible space! Devin’s place on the water has everything you need. It would be tight with more than two adults but it worked great for us and our small dog.

Hideaway on the Bay: Waterfront Vintage A Frame
My stay was exactly what i needed it to be. It was a quick 90 minute drive from the city, but once I got there I found exactly what I needed. 2 days of peace, quiet, and seclusion. I had to make a quick run, to the grocery store, but it was convenient and people were really nice. Next time I come, I’ll probably explore the Solomon Islands.

Wickline Cabin on Moon Creek
We loved this cabin, and Caleb was such a gracious host! Arriving to a dozen farm fresh eggs was such a treat. We grabbed some bacon (Smithfield brand, of course) at the local Kroger and had eggs and bacon every day of our trip. The cabin is so quite and peaceful. It literally feels like you are in the middle of nowhere, but it's a 5 minute drive to all kinds of shops and activities. The povided kayaks were a major selling point for us. It was a very relaxing and beginner friendly paddle up the creek to the river. We saw all kinds of wildlife including otters playing in the creek! It is true that the hot tub is a little glitchy, but it was plenty warm and didn't impact our enjoyment of it at all. Caleb was kind enough to stack wood in the fire pit for us, making our evening campfire easy and streamline. The cabin is really close to great hiking, boutique and antique shops, the brewery, winery and restaurants. I wish we would have taken him up on the offer to bring our dogs. Next time!

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
We stayed at Julie’s home with a group of friends and our families and had a wonderful time. The lakefront setting was incredibly relaxing—we found ourselves rarely leaving the property because it had everything we needed. From soaking in the hot tub to enjoying the game room, there was something for everyone. The kids loved having space to run around in the basement, while the adults enjoyed peaceful mornings and evenings on the screened-in porch. Julie was very responsive and answered all of our questions quickly, which made the entire experience seamless. We would absolutely stay here again!

Dinna Fash-3 BR Waterfront Log Cabin
Said it last time and I’ll say it again; 11/10 stars. This place is undisputed best bang for your buck.l! It’s beautiful, comfortable, and private. This is my favorite place in the area and I try to snag it anytime it’s open! Close enough to do all the exploring; far enough out to do some good relaxing!

Waterfront Cabin: beach, kayaks, hot tub & firepit
Great place! We really enjoyed all of the outdoor amenities. The kayaks, paddle boards, fishing, hot tub, hammocks were all great. Have two teens who very much enjoyed. Was relaxing but a lot to do there also. Lots of jellyfish so we did not swim at all. Definitely a lot of fish and crabs that can be caught right at the dock. If more serious and knowledgeable about fishing then us, may want to bring extra hooks and tackle box. Definitely some size-able fish. Bait shop in town has a lot of supplies but very limited hours. The house had tons of towels, washcloths, etc. which was nice. Kitchen had oil, spices, plenty of cooking utensils, pots / pans, dinnerware etc. Blackstone was nice. Made it very easy to cook. Very few restaurants open M-F. Of those that were, most closed by about 3. Newsome’s was a great local place for lunch. Crab cakes were outstanding. Definitely would stay again. Had a great time!
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