
Vacation rentals with a kayak in Southern Maryland
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House rentals with a kayak

Waterfront Escape!
We had such a nice visit! Ryan was very responsive to questions and requests. The house is very cute and perfect for a family with kids. Lots of toys and games and outdoor equipment - and a fun tree swing! The little sandy area was just right for our three kids (ages 1, 4 and 7). We ate all our meals outside on the deck overlooking the water. The neighbors were very friendly. Everything was great!

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

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!

Cozy & Content River Retreat Beach Hot Tub & Games
We had a great time at Nicholas and Dana's place! It was both fun and relaxing. We really enjoyed the little beach, the dock and the kayaks. We caught some catfish and one tiny crab in the crab trap (and threw everything back in). It was nice to have the firepit and hot tub to use too. And, the kids really liked being downstairs in their own space. The only issues were that the key pad wasn't working to get in to the front door which was frustrating after a long drive and the grill was very slow to heat up and probably needs to be replaced. Overall, this home was a really good choice for us and we would stay again when visiting family in the area.

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!

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
Cottage rentals 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! ☺️

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

Cottage with a view!
We came to relax and it was successful. A cute little cottage by the river.

Private point on the Bay🌤hammock, hot tub, kayaks❤️
If you are looking for a beautiful and peaceful location to unwind, this is a great place! The home is very comfortable and has everything you could need. But the highlight was the amazing views of the bay from practically every window in the house. We would definitely recommend staying here!

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.

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!

Waterfront Chesapeake Bay Sunrises w/Private PIER!
I had an amazing stay for my wedding weekend. The view of the water was unbeatable and the brand new outdoor furniture was great! Heather was very responsive and it was overall a great place to stay!

Pretty Byrd Cottage, a Victorian Bayfront Getaway!
Pretty Bird Cottage was a magical place to spend a quiet few days unplugged with family. Would recommend to anyone looking for a peaceful getaway. It’s pretty secluded, so we planned groceries on the way there rather than venturing out for most meals. Also, cell service is spotty so be sure to keep the door code instructions somewhere you can access them offline. It was a wonderful vacation!
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.

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.

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.

Wilderness Resort- Hot tub Rancher
Amazing peaceful place

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
This property was gorgeous! The house was clean, spacious, and comfortable, and we loved relaxing on the porch and the dock. Blake was very responsive and communicated check-in/check out instructions well. The location feels serene and remote, but it is just a short drive away from a grocery store, multiple places to eat, Kings Dominion, and a local theater. The kitchen is a bit bare-bones, so be sure to bring everything you need if you plan to cook. We would love to come back in the future!

Dinna Fash-3 BR Waterfront Log Cabin
So relaxing! So cozy! Such a cool spot and neighborhood! All the little details didn’t go unnoticed!
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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
- Georgetown Waterfront Park
- National Air and Space Museum
- Great Falls Park
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Congressional Country Club
- Quiet Waters Park
- Lee's Hill Golfers' Club
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Library of Congress
- Gerry Boyle Park