
Cabin vacation rentals in Chesapeake Beach
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Top-rated cabin rentals in Chesapeake Beach
Guests agree: these cabins are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chesapeake Beach cabin rentals
Cabin rentals with a hot tub

Waterfront Cabin: beach, kayaks, hot tub & firepit
This is a wonderful place on a large creek off the Chesapeake Bay. This place oozes with charm and ambiance and feels so peaceful. We spent the first day just relaxing and doing nothing but looking at the water and chilling on the front porch. The house is updated on the inside and has a large lot with kayaks and a fishing pier. Great hiking at the natural preserves in the area too. We're grateful to the hosts for opening their home to us and we'll definitely come back.

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
This is a gem! The other 5* reviews and the description and photos are all accurate. My family had one of the best times we’ve had in a vacation rental…and we have done several all over the world. Wonderful place to relax, but also have things to do. Great for kids and adults alike.

The Black Log Cabin - Hot Tub & Game Room
This is a fantastic stay. I had a group of 8 and it was the perfect amount of space for us. The secluded and private back yard and hot tub are a treat. There are no neighbors so it really has a remote feeling even though you are 2 minutes from downtown.

Your own private beach? Horizon views of the bay?
This was our second time staying at this cute place. We knew what to expect; took all linens, pillows, towels, kitchen towels, etc. as she lists. Also took two door mats and non-skid mats for the showers (the master shower was quite slippery so I knew to bring a non-skid mat). The place was pristine, from the kitchen to the bathrooms. The floors were spotless. Landscaping is mature and nice. The little beach was perfect for us -- while it is not private, and anyone can use it, during the two times we have visited, spring and fall, during the off season, there were only a couple of folks who walked; nobody set up chairs; we had it to ourselves. I imagine during the summer that is not the case. Liezel is delightful to deal with, friendly, responsive, concerned. We love her little funky log house, and will definitely return! Thank you Leizel!
Pet-friendly cabin rentals

COZY BLACK LoG HoUSe
We absolutely loved our stay at Cinthia’s cabin. Everything about the home was so beautiful. Very quiet and peaceful surrounding. Didn’t have any trouble getting around. The rest of the ladies enjoyed the cabin as well. I would absolutely book and recommend this space to anyone!

Charles Creek Cabin
Our favorite spot to visit and recommend it enough. Always feel right home and relaxed as soon as you walk in the door

*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!

Rustic Quaint Cabin In the woods--Pets welcomed
location is private and quiet. perfect getaway for a peaceful retreat. not a whole lot to do in Warsaw, which was perfect for me, but there is a really nice restaurant, Relish, that is definitely worth checking out. thank you Kevin for a wonderful few days!

Relaxing Cabin Get Away Near Annapolis & DC
This is such a nice spot if someone wants to get away from a suburban/city enviroment. Super cozy vibes and the hosts were kind and checked in on us while we were there during a snow storm. Overall highly recommend. Very private and comfortable cabin experience.

RRR remote rustic retreat
Nice quiet place for a retreat. David was friendly and very responsive. Everything was great.

1943 Beach House Walk to Town & Beach & Boardwalk.
I was in town for work, and this place was perfect. It was walkable to several restaurants and to the calming water. Christopher was a wonderful host and very responsive. I'd definitely stay again if in town.
Private cabin rentals

Lovely Detached Guest House
We really enjoyed our stay. Thank you!

River Island
Wonderful and cozy stay in stunning setting - great if you want to go camping with a bit more comfort. The train was quite loud so good to be aware of that, but we had anticipated it so it didn’t take away from the overall experience. Hope to come back next year!

Pizza Friday
The weather blessed us with warmth upon arrival to Pizza Friday. Although making pizza was a new skill we gained in the moment, the fun we had while doing it was everything we wanted. We had a chance to use the fire pit, kayaks and games in the house. The kids enjoyed sleeping in tents on the ground and the Easter egg hunt scattered along the lovely property. The host was super responsive and allowed us to check in early at no additional cost. I think I may have messaged him a few times about AC and fire wood and there was no hesitation on getting back to me. The family loved this Airbnb and we have already planned an additional trip in the future.

Crisfield Cabin by Homelystay
Quiet and cozy place for a weekend getaway. Check-in nd check-out were very easy and the host was very flexible and friendly!

Cottage #4 Chesapeake Blue down the drive way.
I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.

Camp Heron : Waterfront Cabin on the Potomac
Just a stunning location! The bird watching was marvelous, every morning a pair of swans landed and swam around until dusk. Lots of blue herons, too. Good fishing right out of the back yard. The kitchen was very well appointed, good cookware, plates, cups, etc. bed were comfortable with really nice pillows. We spent most of our time around the fire pit or on the screened porch. A great place for relaxing!

Cabin on the Creek ~ Kayaks and Fire Pit
Pros: absolutely beautiful setting, great fire pit area, nice wood burning stove, plenty of wood, blankets provided for outdoor fire pit, the area is great! Went to Crow vineyard and winery it was absolutely amazing, The Kitchen for Sunday Brunch and The Granary for oysters. We actually did a Scavenger hunt on Lets Roam App that was lots of fun. The weather rained for 2 days but we we got 1 day by the fire pit which was awesome!!!! The only thing I would keep in mind is the steps to the water are very very steep. Might be hard for kids or out of shape 50 year old like me.
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