
Holiday rentals with a kayak in Anne Arundel County
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Top-rated Accommodation with a Kayak in Anne Arundel County
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Holiday House Rentals with a Kayak

Annapolis waterfront, private pier with kayaks
The place was great! Amazing spot located right on the water. Beautiful open space that was perfect for a large group wanting to spend time together. Calling ubers into town was a little tricky and came with some long wait times, but we were always able to connect with a ride and get where we needed to go.

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.

South River Beach Front House
Great location, beautiful home that was very comfortable.

Cozy Bay home w/180 degree view
Madeline place was great to watch cruise ships and other boats come and go into Baltimore. Beautiful sunrises and sunsets right off the balcony. Quiet and peaceful. Madeline was very helpful and responded quickly. We would highly recommend staying here.

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.

Chesapeake Bay - West River Home
Fabulous house in a terrific location. The house was very clean and Rick was a great host.

Luxury Modern Home on Water+Hotub- Annapolis 25min
An Unforgettable Couples Getaway Thank you so much for allowing us to host our couples gathering at your beautiful property. The home was not only stunning and well-appointed, but it also created the perfect atmosphere for a weekend filled with connection, laughter, and unforgettable memories. The care and attention to detail in preparing the space did not go unnoticed. From the beach towels by the hot tub to the extra bedding that came in handy (especially since I forgot to mention my feather allergy!), everything was thoughtfully stocked and readily accessible. Our group felt immediately at home. Finding a property that can comfortably and effortlessly accommodate a group like ours is rare—but yours exceeded every expectation. We’re incredibly grateful for your warm hospitality and would gladly recommend your home to anyone looking for a cozy, welcoming place to stay. We hope to return again in the future!

Sunset Cottage
The house was so beautiful and was even bigger than the pictures make it look. The beds were comfy, the host had great communication, and the outdoor area was as so gorgeous. Highly recommend!
Cottages with a kayak

Waterfront Chesapeake Bay Sunrises w/Private PIER!
Great place. Spotless with tons of amenities. Beautiful sunrise over the water in the morning. Nice sized newer dock to walk out on to feel closer to water and nature. Stylish and comfortable furnishings. Can’t wait to come back!

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!

Waterfront cottage w/hot tub/ gated/ pier/ firepit
The host was very kind, accommodating, and had a quick response time to all messages. The house is adorable and was a great fit for 5 friends wanting to get away for a night! I would highly recommend this house and encourage you to use the outdoor space!

Chesapeake Bay Cottage
fantastic stay. clean and very quiet right on the bay. highly recommended. would definitely revisit again.

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.

Beachfront & dog-friendly home just mins to DTA
My family really enjoyed our stay! The most amazing part of the home is the private beach right outside your back door! Absolutely beautiful to wake up to the sunrise each morning. The location was great, quick drive into town (under 10 minutes) where you have access to incredible restaurants, pubs, shopping and the Naval Academy rich with history. Also easy access to supermarkets, pharmacies…etc. this was our first trip to Annapolis and the house and location did not disappoint. The hosts were very kind and responsive and the house felt very cozy with lots of natural light and amenities.

Ft. Smallwood Overlook. Waterfront with Kayaks!
The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !
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- Nationals Park
- Betterton Beach
- The White House
- Lincoln Park
- National Mall
- Hampden
- National Museum of African American History and Culture
- Georgetown University
- Sandy Point State Park
- Oriole Park at Camden Yards
- District Wharf
- Six Flags America
- Smithsonian National Museum of Natural History
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Smithsonian American Art Museum
- Patterson Park
- National Air and Space Museum
- National Harbor
- Meridian Hill Park
- Great Falls Park
- M&T Bank Stadium
- Congressional Country Club