Pelican Beach Costa Rica - Vacation Rentals in Tilmon's Island Winery

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From US $501

         

10.0 (84 Reviews)

House

Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $1,758

         

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New

House

Thornton

• Parking
• Pet Friendly
• Pool

• Maryland
• Chestertown

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From US $113

         

8.6 (857 Reviews)

Hotel

Comfort Inn & Suites Chestertown

• Air Conditioner
• Parking
• Pool

• Maryland
• Chestertown

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From US $331

         

10.0 (77 Reviews)

House

Circa 1900 Home in the Heart of Historic Downtown Chestertown

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $1,162

         

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New

House

River Heights Retreat

• Air Conditioner
• Pet Friendly
• View

• Maryland
• Golts

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From US $80

         

7.2 (419 Reviews)

Hotel

Red Roof Inn & Suites Chestertown

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $384

         

10.0 (70 Reviews)

House

Country Estate in Historic District

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $537

         

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New

House

Waterfront Millington Vacation Rental with Hot Tub!

• Parking
• Accessibility
• Security/Safety

• Maryland
• Golts

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From US $70

         

5.2 (175 Reviews)

Hotel

Driftwood Inn

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $963

         

10.0 (61 Reviews)

House

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $169

         

10.0 (43 Reviews)

Apartment

Historic Downtown Garden Oasis with Private Patio

• Air Conditioner
• Parking
• Balcony/Terrace

• Maryland
• Chestertown

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From US $461

         

10.0 (27 Reviews)

House

Harbor View Haven | Waterfront w/Hot Tub + Dock!

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $206

         

10.0 (19 Reviews)

House

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $194

         

10.0 (18 Reviews)

House

Peaceful country home away in the wilderness

• Air Conditioner
• Parking
• TV

• Maryland
• Golts

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From US $221

         

10.0 (12 Reviews)

Cabin

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $528

         

10.0 (7 Reviews)

House

Waterfront Millington Vacation Rental w/Hot Tub!

• Air Conditioner
• Parking
• Security/Safety

• Maryland
• Golts

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From US $409

         

10.0 (5 Reviews)

House

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $227

         

10.0 (4 Reviews)

House

Your perfect Maryland escape awaits!

• Air Conditioner
• Parking
• TV

• Maryland
• Galena

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From US $480

         

10.0 (3 Reviews)

House

Stunning Historic Downtown Home! Within 2 Blocks of Fountain Park!

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Maryland
• Chestertown

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From US $323

         

10.0 (3 Reviews)

Apartment

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $1,333

         

10.0 (2 Reviews)

House

Guest Lodge | Private Pool | Outdoor Dining | Game Room

• Air Conditioner
• Parking
• Pool

• Maryland
• Sudlersville

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From US $545

         

10.0 (1 Review)

House

Countryside Cottage in Sassafras

• Air Conditioner
• Parking
• TV

• Maryland
• Golts

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From US $546

         

9.8 (85 Reviews)

House

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $293

         

9.8 (27 Reviews)

Apartment

Newly restored apartment in the heart of Chestertown

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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