Vacation rentals with a kayak in Anne Arundel County

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Popular amenities for Anne Arundel County kayak rentals

House rentals with a kayak

Guest favorite
A waterfront home is surrounded by lush greenery, showcasing a screened porch and wooden steps leading up to the entrance. Colorful adirondack chairs are positioned by the private pier, which extends into calm waters reflecting the vibrant landscape.
Home in Annapolis
5 out of 5 average rating, 17 reviews

Annapolis waterfront, private pier with kayaks

MeghanRating, 5 stars4 weeks ago
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.
Top guest favorite
A serene view of the Rhode River is captured, highlighting a row of dark green Adirondack chairs positioned on lush grass, facing the water. A private pier with multiple boats moored is visible in the distance, framed by trees that provide shade and a sense of tranquility.
Home in Edgewater
5 out of 5 average rating, 11 reviews

Stunning waterfront views with dock near Annapolis

CynthiaRating, 5 stars3 weeks ago
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.
Guest favorite
A wooden dock extends over calm waters toward a spacious two-story house nestled among lush greenery. Large trees frame the property, with a serene backdrop of nature enhancing the peaceful atmosphere. The dock provides direct access to the water, inviting leisurely activities.
Home in Shady Side
5 out of 5 average rating, 26 reviews

Peaceful Waterfront Getaway

PamRating, 5 stars4 months ago
This was a fabulous place for a family gathering over Thanksgiving! Kayaks, basketball, and shooting pool kept all generations active and having fun. There are several parks and beaches near by for walking as well. The bedrooms are well appointed with high quality linens and towels. Tanya’s place is highly recommended!
Superhost
Home in Edgewater
4.81 out of 5 average rating, 21 reviews

South River Beach Front House

TammyRating, 5 stars6 months ago
Great location, beautiful home that was very comfortable.
Guest favorite
The exterior of a two-story blue cottage is presented, featuring a prominent porch with railings. An American flag is displayed on the front, while a vehicle is parked nearby on the grassy area. Laundry is seen hanging to dry, and lush greenery surrounds the home.
Home in Shady Side
4.93 out of 5 average rating, 45 reviews

Cozy Bay home w/180 degree view

DeanaRating, 5 stars2 months ago
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.
Guest favorite
A single-level home in a serene setting is viewed from the water. The exterior is clad in light blue with large windows. A shaded area is present for outdoor seating. Kayaks are stored nearby, and a wooden dock extends into the calm water.
Home in Pasadena
5 out of 5 average rating, 51 reviews

Waterfront CHeerful 2 with Private home

DavidRating, 5 stars2 weeks ago
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.
Superhost
A serene view of the waterway features multiple docks leading into the peaceful waters. The surrounding area is framed by charming homes, with greenery and autumn foliage adding color to the scene. Calm water reflects the waterfront landscape.
Home in Shady Side
4.83 out of 5 average rating, 12 reviews

Chesapeake Bay - West River Home

JenniferRating, 5 stars7 months ago
Fabulous house in a terrific location. The house was very clean and Rick was a great host.
Top guest favorite
Four white Adirondack chairs are positioned in a semi-circle around a fire pit overlooking the waterfront. Calm waters reflect the blue sky, while a line of docks and boats can be seen in the distance, enhancing the serene atmosphere of the outdoor space.
Home in Shady Side
4.98 out of 5 average rating, 47 reviews

Sunset Cottage

SharonRating, 5 stars6 days ago
The house was clean, neat and perfectly set up. The view out of the living area and back bedroom is fabulous; a beautiful way to begin and end each day. Our stay was very comfortable and relaxing. We did not want for anything. Nicole was very helpful, responsive and easy to work with.

Cottage rentals with a kayak

Guest favorite
Cottage in Edgewater
4.99 out of 5 average rating, 154 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

IsabelRating, 5 stars4 weeks ago
Heather’s place is a little paradise on the water. Peaceful, quiet, and perfect for some real rest and relaxation. The house was exactly as described—spotless, all new, and super comfortable inside, with beautiful outdoor spaces to enjoy. Annapolis is just a short 25-minute drive away if you’re looking for great food and things to do. Communication with Heather was easy and fast. I’d come back anytime I’m in the area again!
Guest favorite
A charming bayside cottage is visible from the water, surrounded by lush green trees. A private dock extends into the calm water, offering ample space for relaxation and fishing, and leading up to the welcoming entrance of the home.
Cottage in Edgewater
4.92 out of 5 average rating, 48 reviews

Waterfront Cottage with Private Pier

SarahRating, 5 stars1 day ago
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!
Superhost
An aerial view captures the waterfront cottage surrounded by lush greenery, with boats visible along the shore. The community pier can be seen, providing access to the water. The serene backdrop of trees complements the peaceful setting of the property.
Cottage in Annapolis
4.87 out of 5 average rating, 82 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

RachelRating, 5 stars2 weeks ago
Very cute place with a great view
Guest favorite
A sandy beach stretches along the Chesapeake Bay, where two colorful lounge chairs are positioned near the water's edge. Lush greenery and a manicured lawn are visible in the background, complemented by nearby cottages that offer a serene atmosphere.
Cottage in Deale
4.96 out of 5 average rating, 158 reviews

Chesapeake Bay Cottage

AndyRating, 5 stars1 week ago
fantastic stay. clean and very quiet right on the bay. highly recommended. would definitely revisit again.
Top guest favorite
Cottage in Annapolis
4.98 out of 5 average rating, 112 reviews

Weems Creek Cottage, Annapolis Waterfront

BenjaminRating, 5 stars3 weeks ago
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.
Guest favorite
A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.
Cottage in Pasadena
4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars4 months ago
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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