Cottage vacation rentals in Calvert County

Find and book unique cottages on Airbnb

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Popular amenities for Calvert County cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Annapolis
4.87 out of 5 average rating, 85 reviews

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

MichaelRating, 5 stars2 weeks ago
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.
Top guest favorite
Cottage in Woolford
5 out of 5 average rating, 63 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

MalgorzataRating, 5 stars3 months ago
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.
Superhost
Cottage in Scotland
4.85 out of 5 average rating, 20 reviews

Hays Beach House - Hot Tub - Private Beach

DelaneyRating, 5 stars3 months ago
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.
Top guest favorite
Cottage in Easton
5 out of 5 average rating, 105 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

LindsayRating, 5 stars3 weeks ago
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!!
Guest favorite
Cottage in Annapolis
4.86 out of 5 average rating, 107 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

JohnRating, 5 stars3 weeks ago
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.
Cottage in Colonial Beach
4.75 out of 5 average rating, 32 reviews

Waterfront Home w/ Guest House in Colonial Beach

TammyRating, 5 stars3 weeks ago
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.
Cottage in Chesapeake Beach
4.52 out of 5 average rating, 21 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

EstherRating, 5 stars1 month ago
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
Guest favorite
Cottage in Montross
4.93 out of 5 average rating, 92 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

MilotRating, 5 stars2 weeks ago
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

Top guest favorite
Cottage in Saint Michaels
4.98 out of 5 average rating, 234 reviews

The Little Anchor Cottage, St. Michaels, MD

GillianRating, 5 stars3 weeks ago
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.
Superhost
Cottage in Wittman
4.87 out of 5 average rating, 151 reviews

Perfect St. Michaels Getaway

SamRating, 5 stars1 month ago
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.
Top guest favorite
Cottage in Annapolis
4.96 out of 5 average rating, 408 reviews

Relaxing Water Views - Mill Creek Cottage

EdwardRating, 5 stars5 days ago
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!
Superhost
Cottage in Colonial Beach
4.93 out of 5 average rating, 169 reviews

Bayside Cottage- In the Town with views

KimberlyRating, 5 stars1 month ago
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.
Guest favorite
Cottage in Deale
4.82 out of 5 average rating, 181 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

BobRating, 5 stars3 weeks ago
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.
Guest favorite
Cottage in Annapolis
4.93 out of 5 average rating, 202 reviews

Secluded Cottage_ A+ Amenities in Historic Dwntwn

RogerRating, 5 stars1 month ago
Perfectly located, walked everywhere. Clean and comfortable.
Guest favorite
Cottage in Cambridge
4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars6 months ago
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!
Guest favorite
Cottage in Deale
4.9 out of 5 average rating, 166 reviews

Rockhold Creek Cottage

ShamsRating, 5 stars1 month ago
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

Cottage in Lusby
4.72 out of 5 average rating, 292 reviews

Chesapeake Bay Cottage

DanielaRating, 5 stars2 weeks ago
The cottage was great. It was exactly we needed. We enjoyed going go Flag Ponds and searching for sharks teeth on the beach
Top guest favorite
Cottage in North Beach
4.95 out of 5 average rating, 64 reviews

The Blue Crab Beach House - Free beach passes

ColinRating, 5 stars5 months ago
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!
Top guest favorite
Cottage in North Beach
5 out of 5 average rating, 41 reviews

The Lazy Crab Beach House - Free Beach Passes

AngelaRating, 5 stars2 months ago
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!
Cottage in 5, Bay Hundred
5 out of 5 average rating, 4 reviews

The Bayside Cottage STRN 23-3

AnnaRating, 5 stars4 days ago
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.
Top guest favorite
Cottage in Lusby
4.98 out of 5 average rating, 63 reviews

Amazing, Secluded Luxury waterfront cottage!

AmyRating, 5 stars1 month ago
Beautiful place! My family loved it there. Perfect staycation. Lots to do just at the house! KJ was a great host.
Top guest favorite
Cottage in Hollywood
5 out of 5 average rating, 38 reviews

The Little Blue Cottage

MaryRating, 5 stars3 months ago
The Little Blue Cottage was comfortable and clean! Krista was extremely flexible with the check in and check out procedures.
Guest favorite
Cottage in California
4.89 out of 5 average rating, 44 reviews

Saint Cozy Cottage | waterfront family getaway

KristenRating, 5 stars3 weeks ago
Kyli is an excellent host and beautiful home on the water . Great communication and responsive. Awesome place to stay if you are visiting.
Cottage in North Beach
4.87 out of 5 average rating, 178 reviews

Full house rental in Twin Beach. 1 bk from the Bay

ManuelRating, 5 stars2 weeks ago
Huge parking pad and proximity to the beach made this a great home base for the vacation.

Destinations to explore