A beach with seagulls, a rocky shoreline, and houses in the background.

Cottages in Calvert County

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Calvert County cottages

Exterior

1. Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Annapolis
9.8 out of 10, Exceptional, (44 reviews)
"Very nice property, everything was as expected and the entire process was easy. Great, quiet spot to enjoy the Bay close to everything fun in Annapolis. I’d go back."
United States
Brian R.
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Exterior

2. Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (137 reviews)
"Fantastic location, the host was quick to respond to questions. Would book again."
United States
Jim K.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

3. "Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman Island
10.0 out of 10, Exceptional, (26 reviews)
"The views are an amazing. The cottage is well appointed. The hosts were responsive. It was an excellent trip"
United States
Paul H.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Exterior

4. Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Fishing Creek
10.0 out of 10, Exceptional, (52 reviews)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Exterior

5. Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Downtown St. Michaels
9.8 out of 10, Exceptional, (208 reviews)
"Really nice cottage in the middle of everything. Loved the screened in porch and large den."
United States
greg b.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

6. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (56 reviews)
"Cute A-frame with all the necessities!"
United States
Anonymous traveler
The price is SAR 593
SAR 1,222 total
includes taxes & fees
9 Sep - 10 Sep
Soul Oasis - home on the Chesapeake Bay
Exterior

7. Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.
Point Lookout
9.8 out of 10, Exceptional, (84 reviews)
"Amazing getaway! Quiet, peaceful, beautiful views. "
United States
Sarah H.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Outdoor dining

8. Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Edgewater
10.0 out of 10, Exceptional, (231 reviews)
"Awesome location and very nice, we had a great stay! "
United States
Megan B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Property grounds

9. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.4 out of 10, Exceptional, (14 reviews)
"The owner was very nice "
United States
karen
The price is SAR 598
SAR 1,033 total
includes taxes & fees
12 Sep - 13 Sep
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

10. The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek
Hillsmere
10.0 out of 10, Exceptional, (179 reviews)
"We had a great time and really enjoyed the cottage."
United States
Craig M.
The Yellow Cottage on Harness Creek
Terrace/patio

11. Sunrise Waterfront Cottage in Beautiful Hoopers Island

Sunrise Waterfront Cottage in Beautiful Hoopers Island
Fishing Creek
10.0 out of 10, Exceptional, (87 reviews)
"It is a beautiful place to visit!"
United States
Yoon G.
Sunrise Waterfront Cottage in Beautiful Hoopers Island
Exterior

12. Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (274 reviews)
"Rob was such a wonderful and inviting host"
United States
Stacy S.
Family and Pet-Friendly, Waterfront with Pier
Terrace/patio

13. Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Point Lookout
10.0 out of 10, Exceptional, (21 reviews)
"We loved our stay and are looking forward to going back! I have already recommended it to friends that are looking for a quiet retreat in a great location."
United States
Melissa K.
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Exterior

14. Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful, private setting, but not far from the town of St. Michaels. House was very clean and beds were comfy. The kitchen was very well equipped for preparing meals. We really enjoyed relaxing in the screened in porch and on the Adirondack chairs overlooking the water. There was so much wildlife to view: bald eagles, herons, tree frogs, crabs…We had a great time! Thank you!"
United States
Melissa B.
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Outdoor dining

15. Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cambridge
10.0 out of 10, Exceptional, (18 reviews)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Outdoor dining

16. Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Saint Leonard
10.0 out of 10, Exceptional, (22 reviews)
"All was great....loved the access to the little private beach with our little ones. Kitchen was clean and orderly and the living room was quaint."
United States
Kristin D.
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Exterior

17. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Downtown St. Michaels
9.6 out of 10, Exceptional, (132 reviews)
"We had a great time. The house was so charming and the location was perfect. Can't wait to go back!"
United States
Anonymous traveler
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior

18. Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (254 reviews)
"The place was very clean and comfortable. Loved the view. Would definitely stay again."
United States
Susan E.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Smart TV

19. Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC

Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time! The cottage was perfect for our needs and clean. We loved spending time in the water on the paddle boat. "
United States
Samantha D.
Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC
Exterior

20. Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Calvert County Hotel Reviews

Gaylord National Resort & Convention Center

Gaylord National Resort & Convention Center

8/10 Good
"This a great place for vacation if you are in the Washington, DC area. There’s a shuttle to the MGM if you are looking for casino. However it is more geared for corporate events."
Rafael 1-night trip
Posted 4 hours ago
Gaylord National Resort & Convention Center