
Cottage vacation rentals in Calvert County
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Top-rated cottage rentals in Calvert County
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Popular amenities for Calvert County cottage rentals
Cottage rentals with a hot tub

Waterfront cottage w/hot tub/ gated/ pier/ firepit
Nice house, very secluded, lots of entertaining space, hot tub was great, back patio, fire pit, everything was great. Isaac was very communicative with all aspects of our stay. An excellent getaway.

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks
A fantastic weekend getaway! Natalie’s home is beautifully located, offers spectacular views, and is incredibly well appointed with thoughtful touches like extra plush towels and spices and coffee. We enjoyed everything and even though the weather did not cooperate we had days of exploring the natural beauty, history, and local towns.

Hays Beach House - Hot Tub - Private Beach
Hays Beach House was the perfect home base for my group of 10 sailors. We were able to comfortably sleep, relax in the hot tub, and cook enough to feed a small army. The beds are comfy, the kitchen is well stocked, and the sunrises here are stunning. Tim is a friendly and helpful host and overall the experience was nothing but pleasant.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit
From start to finish, Cheryl and Tom’s property made for the perfect weekend in the St. Michaels area! Clear instructions, absolutely gorgeous property/amenities/activities - it is an absolutely jaw dropping property. Our only regret was not staying longer!!! Thank you!!

Nautical Vibe Walk 2 Harbor Pubs USNA
Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.

Waterfront Home w/ Guest House in Colonial Beach
This was our second stay at the property and we enjoyed it as much as the first time. Jon was very responsive and we throughly enjoyed the use of the paddle boards and kayaks.

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
I book this place for my bday I just wanted to have fun & have a break from routine but at the same time feel comfortable like home, and that’s how it was and better we all had a great time. Really nice property, fabulous decoration, great surroundings to visit, and nice backyard to relax and enjoy. The jacuzzi and fire pit unforgettable part of the trip, really nice atmosphere. If there was an issue super easy and efficient way to respond to the situation. Made my bday really special for me and my family <3

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Genuinely one of the most pristine and peaceful places I’ve ever been at a great time, weather with family or friends
Pet-friendly cottage rentals

The Little Anchor Cottage, St. Michaels, MD
This was now our second time staying here and if possible, it was even better than the first. The hosts are so welcoming and the house is fully set up with everything we needed. The location is just a dream as well with easy walking access to all the restaurants and shops of this charming town. A great stay for the whole family.

Perfect St. Michaels Getaway
This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.

Relaxing Water Views - Mill Creek Cottage
The listing first reported that the home is typically booked -- I now believe it probably would have been had it not been for sheer good fortune. The location on the water in the private-like inlet called Mill Creek adjacent to the Severn river near Annapolis Harbor and the Naval Academy was perfect. Though close to so many things -- including hearing bugles played in the evening and morning from the Academy -- it was also peaceful and calming. Michael was responsive within minutes of my texts and even accommodated an extra day's stay. Every possible amenity was available from add'l drinking water to makeup remover. All was clean and even the bedding in a humid environment was pristine. Remote controls were labeled and extra batteries in the pantry. Lots of Keurig pods. With easy evening bird watching on the side porch after working during the day on fast wireless internet, we were spoiled in this idyllic house. We will soon return with our spouses for more retreats!

Bayside Cottage- In the Town with views
We thoroughly enjoyed our stay at this AIRBNB. It was walking distance to a nice Mexican Restaurant as well as to a brewery. We spent hours on the front porch in the nice rocking chairs. The back of the property overlooked the water which was beautiful! It was close to everything in town! The house was clean and had all of the necessities. We also enjoyed the front sitting area during the morning. The owner was responsive and helpful! We would definitely recommend this property.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Shawn's place is great! It is well-cared for and has everything you need to enjoy the indoors and the outdoors. The views of the water are beautiful and you can spend a lot of time watching the different birds. Getting there is easy and not far from restaurants and grocery stores. Shawn makes you feel special and wants to ensure you have a wonderful stay. Hope to go back soon.

Secluded Cottage_ A+ Amenities in Historic Dwntwn
Perfectly located, walked everywhere. Clean and comfortable.

Cozy Cottage on the Bay
My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!

Rockhold Creek Cottage
We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.
Private cottage rentals

Chesapeake Bay Cottage
The cottage was great. It was exactly we needed. We enjoyed going go Flag Ponds and searching for sharks teeth on the beach

The Blue Crab Beach House - Free beach passes
Very thankful for Danielle’s hospitality and flexibility! We were a last minute booking and had to extend more than once while waiting on movers for our home, and Danielle was ultra helpful in the process. The house was clean, cute, and in a great location for beach visitors. We will absolutely be checking to make sure either the Lazy Crab or Blue Crab are available when we plan to visit the area again! After a cross country trip that consisted of several underwhelming hotels and stays along the way, Danielle’s property was a much needed refresher for my family!

The Lazy Crab Beach House - Free Beach Passes
We had such a wonderful time staying at the Lazy Crab. The house fit our needs perfectly. For a family with a 2 & 4 year old, that isn’t easy to do. The house was clean and we appreciated the extra blankets for the cool nights. The kitchen was also well stocked for cooking at home. If you’re looking for a safe and quiet neighborhood the Lazy Crab is the place for you and your family. Danielle was also a very responsive and friendly host. She even let us leave our bags at the house after check in as our flight was later in the day. Overall, this was a great experience for our first Airbnb as a family and we hope to make this a getaway for us in the future. Thank you Danielle!

The Bayside Cottage STRN 23-3
Most peaceful, relaxing and beautiful place, most responsive host and a comfortable house. We had a great time swimming, exploring the surroundings and watching sunsets from the porch.

Amazing, Secluded Luxury waterfront cottage!
Beautiful place! My family loved it there. Perfect staycation. Lots to do just at the house! KJ was a great host.

The Little Blue Cottage
The Little Blue Cottage was comfortable and clean! Krista was extremely flexible with the check in and check out procedures.

Saint Cozy Cottage | waterfront family getaway
Kyli is an excellent host and beautiful home on the water . Great communication and responsive. Awesome place to stay if you are visiting.

Full house rental in Twin Beach. 1 bk from the Bay
Huge parking pad and proximity to the beach made this a great home base for the vacation.
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- Nationals Park
- The White House
- National Mall
- Georgetown University
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- District Wharf
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Meridian Hill Park
- Lincoln Park
- Maryland Renaissance Festival
- American African Museum
- Quiet Waters Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- Leesylvania State Park
- Ragged Point Beach
- International Spy Museum
- Library of Congress