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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 87 Cottages in Sherwood with updated reviews, rates, and availability.

Cozy Cottage with access to and partially obstructed views of the bay.
Miscellaneous

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (19)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (245)
"This is a beautiful site and the hosts were incredibly welcoming and hospitable. We highly recommend it to anyone looking for a place to stay in the area."
Family and Pet-Friendly, Waterfront with Pier
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

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
Outdoor dining

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
Exterior

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
Marina

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
On the beach, sun loungers, beach towels

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
Property grounds

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

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.
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

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,
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (32)
"The place was wonderful, clean and well stocked. It was a great place to stay - kudos to the hosts for an inviting atmosphere."
North Beach Cottage - Walk to Chesapeake Bay
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

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
Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Beach towels

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (91)
"Great property right outside of north beach"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

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
View from property

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

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

9.6 out of 10, Exceptional, (115)
"Perfect stay in a historic home in the heart of town."
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.
Outdoor pool

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

10.0 out of 10, Exceptional, (43)
"Fantastic property! Welcoming, good amenities, accommodating host, and comfortable with amazing views. Will definitely stay here again!"
The price is AED 588
AED 1,141 total
includes taxes & fees
6 May - 7 May
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (9)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is AED 1,653
AED 2,726 total
includes taxes & fees
2 Jun - 3 Jun
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 Sherwood

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sun loungers, beach towels

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (33)
"Perfect large space on a quiet and pretty area. Really great space. "
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

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!
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
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.