
Holiday rentals with a kayak in Southern Maryland
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Top-rated rentals with kayak in Southern Maryland
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House rentals with a kayak

2 Bedroom Cozy Beach Cottage
Michelle is a great host. The place is clean and has many conveniences. I highly recommend!

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

Spacious Gorgeous Waterfront Home with Sunset View
My family of 10 had a great stay here! There was plenty of space to spread out and the location is perfect and serene. We were able to fish out on the dock and caught a few spot! One of the friendly neighbors even stopped by to offer some raspberries from their bush and extra firewood. We did run into an issue after check in with one of the bathrooms, but Karina was quick to respond and sent someone out to handle it as quickly as possible. Thank you for the wonderful stay!

Waterfront home, private dock
We had a wonderful vacation here. Although it rained during our stay, we found the treehouse to be a great place just for listening the rain drops and having some inner peace.

Luxury Modern Waterfront Retreat
Kelly and Thomas were amazing host. Very responsive and accommodating The home was very clean and the location was great.. 10/10. Definitely would book again!

River Refresh - Waterfront with Spa on Placid Bay
Nicola’s place is beyond the photos and descriptions! We have good time there and had the luck to experience the beauty of both rainy and sunny days there. The house is beautifully renovated and pristine clean. Every single spot is well equipped with a lot of surprising details. The screened porch is the perfect to enjoy the view no matter what weather , and free of bug/mosquitoes inside! River view Hot tub is very relaxing. We are also able to enjoy Kayaking, crabbing (several biggest blue crabs I’ve ever caught) along the river and never get bored among the peaceful environments surrounding!

Waterfront Cabin! FishCrab~BigPorch~Paddle~Karaoke
5 stars! Well deserved! From the beginning to the end! Jian is the great host. Very helpful, friendly and super responsive! The place is awesome, exactly like the photos. We enjoyed watching movies on the screened in porch, bird watching, fishing, kayaking, relaxing on the dock, playing games inside, karaoke too. The place is very comfortable and has everything even more than you need. I really appreciate how much thought went into lighting, decor and convenience with QR codes and labels. Some days it was raining and we took our 7yo to Compass Entertainment center, which is 30 min away. I recommend checking it out. Last before the departure was a storm and we lost power and WiFi, the reception is bad without the WiFi but the host notified us promptly and kept us informed about what’s going. Customer service was excellent! We enjoyed our time at LaMemoriia

Panoramic Waterfront: Fire pit, Game Room, Kayaks!
stayed with family, very comfortable, loved being on the water. took out a kayak, and much fun with corn hole. Enjoyed watching baby osprey from backyard!
Cottage rentals with a kayak

Chesapeake Bay Cottage
Lovely stay on the water! Mini beach is an added bonus. Great restaurants nearby!

Cottage with a view!
Beautiful place to stay. Quite peaceful area with friendly neighbors. Home was cozy and welcoming. Kitchen had everything you could need. Amenities were amazing. Had a spectacular time would definitely come back to stay again.

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.

Modern 2 Bdrm Cottage in Historic River Community
Loved staying at this quiet retreat! Mornings listening to birds, afternoons in the sunny backyard, stars and stars! Really loved this place and will be back again.

Where Eagles Soar *Stunning Waterfront Views*
My friends and I immediately felt relaxed and cared for in this delightful home. We loved that it was right on the water and that we could enjoy seeing the Potomac River from so many rooms. The beds were very comfortable. Sue is a thoughtful and very pleasant host. We enjoyed our stay very much.

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!

Charming Waterfront Cottage with Sunset Views
We had an amazing holiday weekend at Dave and Jenny’s cottage! They were always so quick to respond with any requests we had! The cottage as perfect and just like the pictures. They literally had thought of everything! The sunsets were absolutely stunning and it was truly the most relaxing time we’d had in a while! It was just what we needed !

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
I think this is my 5th time staying there. Always thinking of my return visit before even leaving!
Cabin rentals with a kayak

*Private Waterfront Retreat w/3 Cabins Close to DC
This place could not be more perfect for our trip to DC. It was the perfect distance to the metro. Our group of 8 had so much space of our own, yet plenty of room to be together in the common spaces and not be on top of each other! We went in the coldest month of the year, so unfortunately we didn’t get to experience the best of what the outdoor areas had to offer but the views were breathtaking regardless. Melanie’s place was extremely clean and everything was provided and then some! Everyone in our group would like to go back in warmer months to spend more time outside. Before we got there, Melanie explained that there was an issue with one of the sinks in the cabins and said she would credit us accordingly. I thought that was great! It did not hinder or create a problem whatsoever! I hope we get to make it back sometime!

True St. Michaels 6 Acre Waterfront w/heated pool
WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.

"Elderberries" Chesapeake Bayfront Cottage
We enjoyed our stay here. Very quiet area, nice comfortable space. The gravel road leading in (maybe a half-mile long) and driveway gave us a good area for morning and evening dog walks. We did not end up doing any fishing but the pond looked like a great place for kayak fishing. Not specific to the house but in the area: Rita's Cafe in Weems was great (food truck on a small road)--Chef Craige usually has a special and some regular menu items. Leadbellys (at Fairport Marina) had good oysters and hush puppies and was convenient for our first night. River Market in White Stone has good food to be ordered at the rear counter and prepared items in the coolers. Out of the Oven Bakery (White Stone) had great bread Miss Mary's seafood, also in White Stone had great fresh fish and prepared items. The three places in White Stone are very close to each other so convenient when running out.

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.

Cozy Historic Cabin on the Water
Staying at Shawna and Keith's cabin was a wonderful experience. Peaceful and serene, it was relaxing just to wake up in this private oasis. Shawna and Keith were very friendly and easy to get in touch with if we had any questions. They even provided items for some of the activities we decided to try while staying there. The cabin was clean, quaint, quiet, well-equipped; and looked exactly as described. We would definitely return for another weekend getaway! Thanks again!

Pizza Friday
Pizza Friday was an amazing find! We spent a family reunion on the porch making pizza's in the oven. We obtained crusts from an Italian restaurant in California on our way and it proved to the perfect choice for us. We also enjoyed the dock and even caught a few crabs to show the kids. In addition we sat around the fire pit in the evenings. The beds were comfortable and everything was clean inside although we spent most of our time outside on the porch.

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!

Luxury cabin - Pond - 16 acres
We had a great stay at Blake's place! the fire pit and grill were easy to use. We loved how peaceful the home and surrounding areas were. Thank you for a great stay!
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- Nationals Park
- The White House
- National Mall
- Georgetown University
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
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- Maryland Renaissance Festival
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- Library of Congress
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