Holiday rentals with a kayak in Delaware Bay

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Popular amenities for kayak rentals in Delaware Bay

House rentals with a kayak

Guest favourite
Home in Colonial Beach
4.95 out of 5 average rating, 19 reviews

Peaceful and Cozy Waterfront Home (just renovated)

BrianRating, 5 stars1 month ago
Had a great stay ! Would definitely stay again if the time comes for us to go back .
Superhost
Home in Heathsville
4.92 out of 5 average rating, 128 reviews

The Hideaway at Mill Creek

PaulRating, 5 stars2 weeks ago
We had a wonderful long weekend away. The views were amazing. The home is well equipped. We had a lot of fun exploring the area, hiking on trails, banks of the Chesapeake and taking out the kayaks. It was a very relaxing and much needed getaway!
Guest favourite
Home in Deale
4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars1 month ago
This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.
Guest favourite
Home in Lancaster
4.94 out of 5 average rating, 16 reviews

The River House

WhitneyRating, 5 stars7 months ago
We had a relaxing weekend at the river. We had so much privacy and were super happy with the house
Guest favourite
Home in Scotland
4.91 out of 5 average rating, 129 reviews

Spacious Gorgeous Waterfront Home with Sunset View

RonRating, 5 stars1 month ago
This house is perfect for large groups. It is very spacious, with plenty of room to spread out and get comfortable. We enjoyed sitting on the dock taking in the serene natural beauty of the Creek and observing the local birdlife, including Kingfishers, Great Blue Herons, and Bald Eagles. The house is situated very near to the entrance of Lookout Point State Park which we greatly enjoyed exploring on bicycles. Seeing a large wedge of Tundra Swans fly overhead was a special moment. If you want to spend some time relaxing in a beautiful setting in a beautiful and very interesting area with a large group, this house will serve you well.
Top guest favourite
Home in Deale
4.99 out of 5 average rating, 142 reviews

Chesapeake Waterfront HotTub-Kayaks-Crabbing

TimRating, 5 stars3 weeks ago
beautiful location on the water, well-stocked home. very enjoyable for a family weekend!
Guest favourite
Home in Lewes
4.96 out of 5 average rating, 129 reviews

Woodsey Beach House - Beach, Lake, Woods!

ErinRating, 5 stars5 months ago
A great space for 9 adults celebrating Thanksgiving together. Lots of space for everyone to be comfortable. The downstairs pull out couch and TV area was an added bonus.
Guest favourite
Home in Deale
4.98 out of 5 average rating, 106 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

CarolRating, 5 stars2 weeks ago
Our family had a great time - the property was spacious and clean, location was beautiful, and we loved playing outdoors in the open space and getting out on the water. Hosts were very responsive and everything we might need/want was provided!

Cottage rentals with a kayak

Guest favourite
Cottage in Deale
4.96 out of 5 average rating, 159 reviews

Chesapeake Bay Cottage

AndyRating, 5 stars3 weeks ago
fantastic stay. clean and very quiet right on the bay. highly recommended. would definitely revisit again.
Top guest favourite
Cottage in Lower Township
5 out of 5 average rating, 218 reviews

Octopus Cottage: Hot Tub | Kayaks | Fire Pit

KirstenRating, 5 stars6 days ago
The cottage is adorably cute & could not have been more clean. I loved that it is right next to the beach, just a few steps away. I wasn't traveling during beach season, so I don't know if it's a swimming beach - you will want to check that out before you go if that's important to you - but it was nice to walk, & the sunset over the water was glorious. There didn't appear to be much in the way of things to do right in the town, but it's a short drive to lovely Cape May. The hot tub was a delight - albeit not super private, as a picket fence & shrubbery block it from the road. When you're in the hot tub you can't be seen, but when you stand up to get out of it, you can view the road. That being said, it's not a busy road. The house between the cottage & the beach (the owner's house) is gorgeous, but the house across the street on the other side leaves a little bit to be desired. However, as a woman traveling alone, I felt very safe. And Donna brought delicious homemade muffins. LOVED!!
Guest favourite
Cottage in Warsaw
4.94 out of 5 average rating, 115 reviews

Modern 2 Bdrm Cottage in Historic River Community

VyacheslavRating, 5 stars2 weeks ago
As serene as it gets (except Wednesday is the mowing day, but didn’t bother us). Renee is super responsive, which helped a lot. The place is clean and very relaxing, it is remote though, any big city you want to drive to is 1.5-2hr drive. Had fun fishing from the dock, so many catfish there, anyone can catch. Friendly neighbors. Water is on the soft side. Fridge and cupboard had spices and condiments, and a water filter, which was a big plus. Pots and pans need replacing, that’s probably the only negative. Would come back in a heartbeat. Thanks Renee and Ed!
Top guest favourite
Cottage in Smith Island
4.97 out of 5 average rating, 223 reviews

Levering Creek Cottage with Private Dock

LindsayRating, 5 stars1 week ago
We loved our stay at Janet’s place! She was incredibly easy to communicate with, and the house was absolutely perfect—comfortable, clean, and well-appointed. We especially enjoyed being nestled into Ewell, with convenient access to the water, shops, food, and golf cart rentals. It made for a truly relaxing and memorable getaway.
Top guest favourite
Cottage in Annapolis
4.98 out of 5 average rating, 112 reviews

Weems Creek Cottage, Annapolis Waterfront

BenjaminRating, 5 stars1 month 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 favourite
Cottage in Pasadena
4.97 out of 5 average rating, 173 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars5 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 !
Guest favourite
Cottage in Kinsale
4.93 out of 5 average rating, 242 reviews

Great little cottage with a "Rivah" view

KhetagRating, 5 stars2 weeks ago
It’s a house with a stunning view from the hall. It’s a pity that it was a business trip. I didn’t even have time to do a BBQ, but if I will be in this area, I definitely rent this house.
Guest favourite
Cottage in Tall Timbers
4.89 out of 5 average rating, 120 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

JenniferRating, 5 stars2 weeks ago
This was our second stay with Bob and Lolly in Tall Timbers, and it did not disappoint! Immersed in books and history, this quaint cottage was the perfect getaway. We are looking forward to our next visit!

Cabin rentals with a kayak

Guest favourite
Cabin in Saint Michaels
4.99 out of 5 average rating, 109 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KyleRating, 5 stars3 months ago
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!
Guest favourite
Cabin in York Haven
4.95 out of 5 average rating, 115 reviews

Conewago Cabin #1 (No Cleaning Fee!)

VickieRating, 5 stars2 weeks ago
Very comfortable, peaceful gem. Chris was very responsive and even reached out proactively about an additional AC unit given warmer temps to be sure we were comfortable. We used the grill, fire pit and totally enjoyed the trail. Having coffee on the deck each morning was idyllic!!
Superhost
Cabin in Queenstown
4.9 out of 5 average rating, 20 reviews

Warm and Cozy Historic Cabin on the Water

jeffRating, 5 stars2 months ago
Such a cool cabin. Wish we could have stayed longer.
Superhost
Cabin in Elkton
4.73 out of 5 average rating, 48 reviews

Large Cabin w/ RiverView&Hot Tub

KatieRating, 5 stars2 months ago
This cottage was the perfect respite for my family. The big panoramic window that looked out over the water was perfect. The house was so comfortable and the hosts were very responsive. Highly recommend a stay here. There isn’t a lot to do in the immediate area, but the university of Delaware was 20 minutes away and Baltimore an hour south. It was a perfect house for a long weekend getaway.
Guest favourite
Cabin in Sellersville
4.9 out of 5 average rating, 88 reviews

Serene cabin on 6 acre pond in rural Upper Bucks

FaigyRating, 5 stars2 weeks ago
Ricki was super accommodating, she has the most beautiful grounds and you can tell how much effort she put into her cabin to make it welcoming and so rustic that you feel like you’re in another land that you never want to leave!
Guest favourite
Cabin in Lusby
4.9 out of 5 average rating, 259 reviews

Peaceful Waterfront Retreat on The Bay

DonnaRating, 5 stars2 weeks ago
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.
Guest favourite
Cabin in Lusby
4.93 out of 5 average rating, 196 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

PhilipRating, 5 stars2 weeks ago
Fantastic place! Awesome, private spot to enjoy this part of Calvert County. The water was amazing. Would definitely stay again.
Guest favourite
Cabin in Worton
4.95 out of 5 average rating, 86 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

GeorgeRating, 5 stars2 weeks ago
Quiet,peacefull,serene surroundings.Great place to get away and unwind.

Destinations to explore