
Holiday rentals with a kayak in Kent Island
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Top-rated rentals with kayak in Kent Island
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House rentals with a kayak

Waterfront Getaway with Dock
Went to location as a family get-away. The views were breathtaking, who knew we would find such peace so close to home. Literally sat on the couch and stared outside for hours. The home was small enough to enjoy each other's company but large enough to allow everyone the time and space to do their own thing. The price was more than reasonable and we can't wait to return.

River House on the Choptank
Great place! very charming, relaxing, peaceful! No problem feeling right at home. We would stay here again in a heartbeat. Here are a few pointers for those who are planning to stay here: - Its pretty far from grocery / convenience stores - about 30 minutes one way. Do your homework before you get to the place, and try to get all the supplies you will need ahead of time. - The bathrooms are Jack and Jill's so if you're going to a big event - in our case a wedding, make sure that you have a bathroom plan in place as you will have to make sure both sides of the door are ready for who is going to take their time first. No biggie if you're used to j&j bathroom arrangements. I totally recommend this place for a group of 4 - 6 who want together time to relax!

Stunning waterfront views with dock near Annapolis
Absolutely beautiful lakefront home. Bob’s place boasted a fantastic chefs kitchen including everything needed to catch your own crabs! The master suite featured a spa like bathroom and stunning sunset views from the private balcony. The location was quiet and very private and located within driving distance of DC and Baltimore. Bob and his wife were lovely hosts and had several recommendations for beautiful day trips and restaurants. We truly felt on vacation in luxury.

Stylish waterfront retreat, 1 hr to DC
Great house. Clean, clutter-free, and nicely furnished. Amazing hosts. Lovely location. Clear instructions. It was just a lovely time overall. Thanks so much for hosting us.

River Front, Private Single Family Home
We were delightfully pleased with our stay here. The house was clean and comfortably fit our 3 adults and 2 kids. We were happy with the “extras” like having our linens and towels cleaned and wrapped in plastic, shampoo/conditioner, kitchen stocked with cookware, and the decor. The best part was the view and proximity to the water. The pictures do not do the sunset justice. We will definitely come back.

Bayside Blue Waterfront w Pier
Had a great stay at Tiffany and Jack's, with my adult children. The layout provides easy opportunities for both privacy and group activity. We enjoyed setting the crab traps and paddling their very maneuverable kayaks. The house was fully stocked and very comfortable. The location is super close to several convenient stores and gas stations, and Baltimore is easy to access. I would highly recommend staying at Tiffany and Jack's air bnb.

Waterfront CHeerful 2 with Private home
The cottage /house was peaceful on the edge of an inlet from the Bay. The patio was lovely. It was chilly so we couldn’t use the kayaks. The kitchen was very well equipped. The dishes, utensils, cookware were quality. The extra cozy blankets were nice. He responded to a request very timely. We enjoyed the stay very much.

Stunning Chesapeake waterfront home
Where should we begin? Lucas and Heather were wonderful hosts. Excellent and quick communication. Their home has been thoughtfully curated with top notch, kitchen appliances, bed and bath linens, entertainment amenities, and more. Even on a cool and rainy day, you can sit around the fireplace, listen to music, play games and look out the window to a stunning view of the water. No stone was left unturned. This is indeed a special place in the lovely little town of Oxford. We hope to stay again. Thank you, Lucas and Heather for the exceptional hospitality.
Cottage rentals with a kayak

Waterfront cottage w/hot tub/ gated/ pier/ firepit
Very cute place with a great view

Sailor's Cottage - Private Waterfront
Jessica and Richard were very welcoming and friendly. Place was great right on water. Very private. Grandson and I fished off dock with good success. J&R lent us a crab pot and we had a blast.

Cozy Cottage on the Bay
My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!

Weems Creek Cottage, Annapolis Waterfront
What a beautiful off the beaten path place to stay. You are within walking distance of restaurants, coffee, and grocery. But feel like you’re miles away. That’s the effect the cabin has on you. There is a beautiful waterfront that you can enjoy from just about every area of the home. Jim was more than helpful. He really went above and beyond over most host. We would definitely Stay again. It’s the perfect spot if you need to relax.

Cottage on Cabin Creek
We would highly recommend this peaceful and relaxing cottage. We especially loved the views, the dock for fishing, & the views from the bedroom. Janelle was very helpful with places to visit as well as working out an issue that came up at the property. She was quick to respond & made every effort to make sure we were comfortable. Would definitely stay here again! 😊

Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet F
We stayed at this property in December for a wedding with a group of friends, and overall, it was a wonderful experience. The house is beautiful, clean, and the perfect size for what we needed. It was well-equipped with all the amenities, which made our stay comfortable. There were a few minor issues worth mentioning. We encountered a bit of a ladybug situation upstairs, likely due to the sudden cold snap. While unexpected, we took it as a sign of luck for the wedding weekend! The main concern was the temperature when we arrived—it was absolutely freezing, and it took most of the night to warm up the entire house. While we understand the reasoning, starting at 60-65°F would have been much more comfortable upon arrival and would have made our first night of sleep more comfortable. Despite these small hiccups, we had a great stay and would recommend this property for its charm and convenience!

Waterfront Cottage with Private Pier
This is a gem of a cottage. The host was lovely , the decor was wonderfully curated, and the house was fully stocked with anything we needed! Coffee, travel soaps, full kitchen, even a dog dish! We had such a relaxing time enjoying the perfect views. Felt like we were in another time!

Duck Cove Waterfront Cottage
The cottage was a perfect place for a relaxing anniversary getaway. Beautiful views, peaceful setting. House is very well maintained, clean and comfortable. Easy to launch canoe /kayaks from the dock, campfire by the water watching the moonrise over the water. Perfect, would love to return. Highly recommend.
Cabin rentals with a kayak

Peaceful Waterfront Retreat on The Bay
A fair and open spaced home. Free of clutter. Many updated electronics I didn't expect. Only drawback was the microwave. It had a lagging door switch that locked when it was ready. If your impatience, it would test your nerves. A shower that was plenty hot and spacious. Loved the size of the home and location, I want to rent this again.

True St. Michaels 6 Acre Waterfront w/heated pool
Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!

Hideaway on the Bay: Waterfront Vintage A Frame
Fantastic place! Awesome, private spot to enjoy this part of Calvert County. The water was amazing. Would definitely stay again.

Warm and Cozy Historic Cabin on the Water
Such a cool cabin. Wish we could have stayed longer.

Cabin on the Creek ~ Kayaks and Fire Pit
Quiet,peacefull,serene surroundings.Great place to get away and unwind.

Cottage #4 Chesapeake Blue down the drive way.
I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.
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- Nationals Park
- Betterton Beach
- The White House
- National Mall
- Hampden
- National Museum of African American History and Culture
- Georgetown University
- Sandy Point State Park
- Washington Monument
- Smithsonian National Museum of Natural History
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