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Compare 74 Cottages in Grasonville 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)
"Host was amazing. Property is perfect. Will be staying here again. "
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)
"Really enjoyed our stay, pool was nice and had plenty of amenities. We will definitely be coming back for another stay."
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)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
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)
"Really like this place "
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)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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

10.0 out of 10, Exceptional, (25)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (110)
"Bay Haven was in a great lication and property mananger was very responsive to al my questions. "
Peaceful getaway convenient to local amenities including beach, boating & food

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

10.0 out of 10, Exceptional, (80)
"Great spot, loved the place and the area. James was super helpful and seemed to want to do everything possible to make sure we had a great stay."
Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown

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

10.0 out of 10, Exceptional, (26)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (288)
"Great location, wonderful interactions with owners, beautiful scenery, and easy check-in"
The Heron's Nest at Atlantic Marina

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away

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

10.0 out of 10, Exceptional, (86)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
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

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (8)
"Easy and flexible check in, clean and comfortable in a great location. Darling home. "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

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!

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)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
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 Grasonville

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (26)
"We really enjoyed our stay. Looking forward to staying again!"
Cass-N-Reel Luxury Houseboat

Kent Island Waterfront | Pool | Outdoor Dining | Stunning View | Private Dock

8.0 out of 10, Very Good, (6)
"This property was awesome! From the large, spacious home to the pool, to the sunsets...this home delivered! Everything you need to entertain! The hosts made it easy to book and were able to answer our questions along the way! They even checked on us after bad storm rolled through! We hope to return!"
Kent Island Waterfront | Pool | Outdoor Dining | Stunning View | Private Dock

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

10.0 out of 10, Exceptional, (214)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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.