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Compare 68 Cottages in Churchton with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (179)
"I have stayed in almost every hotel and Vrbo is St Michael’s and this is my favorite house. The screen porch is a dream and there is plenty of space for my family. Just dreamy."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

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

10.0 out of 10, Exceptional, (207)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

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

9.6 out of 10, Exceptional, (118)
"Shower was disappointing. Hard to get in and out."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (138)
"Wow! Property was great. Like steping back in time with all the amenities. Only 1 block from shops and restaurants. Just a few blocks to beautiful boats and park. Highly recommend "
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (25)
"Perfect place for a family, centrally located to everything you need for a fun vacation."
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

10.0 out of 10, Exceptional, (80)
"We had a wonderful stay! Very cozy with beautiful views. Our host was very helpful and made sure our stay was great! Will definitely be back! "
Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (31)
"Our family was in town to attend the promotion in the air force of a nephew at Ft. McNair. Close to everything. Beautiful house prefect for us. Enjoyed walking the boardwalk. Would highly recommend this property. Excellent communication with the host. "
North Beach Cottage - Walk to Chesapeake Bay

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

10.0 out of 10, Exceptional, (86)
"Fantastic property and hosts. Highly recommend!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (3)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9.6 out of 10, Exceptional, (91)
"Great location for a wedding stay. Beautiful home, professionally managed!"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (40)
"We loved our stay. The house was spotless; Mark and Karen have provided everything one could possibly need, and they were super responsive. We enjoyed the porch, sauna, and fire pit; and our dog enjoyed the fully fenced backyard, nearby hikes, and dog-friendly local restaurants. Highly recommend!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

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

9.6 out of 10, Exceptional, (114)
"The house is quaint and very clean. It could use a refresh. Can't beat the location. You can walk to everything. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (43)
"Quiet and tranquil. Nicely decorated and will definitely stay here again when we return to the area. "
The price is AED 588
AED 1,137 total
includes taxes & fees
24 Apr - 25 Apr
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (9)
"We had a very lovely stay . This is an excellent location . "
The price is AED 1,469
AED 2,470 total
includes taxes & fees
5 May - 6 May
Secluded Cozy Cottage in Historic Downtown
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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Other property types in Churchton

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (76)
"We stayed at the host property for a long weekend in town for a family baby shower nearby. We were totally impressed with the cleanliness of the location, spacious accommodations and responsiveness of the host. There is a weekend farmers market and we wound up getting fresh produce to cook and some great food and desserts to eat. Parking was a breeze and the nearby park was wonderful for our daily walks. Highly recommended! 10 out of 10!!"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (25)
"Rainy weather limited activities but would return to property"
Chesapeake Houseboat Getaway on Kent Island, Maryland
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.