Pacific Islands - Vacation Rentals in Tilmon's Island Winery

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From US $1,162

         

|

New

House

River Heights Retreat

• Air Conditioner
• Pet Friendly
• View

• Maryland
• Golts

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From US $115

         

8.6 (870 Reviews)

Hotel

Comfort Inn & Suites Chestertown

• Air Conditioner
• Parking
• Pool

• Maryland
• Chestertown

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From US $527

         

10.0 (87 Reviews)

House

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

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $537

         

|

New

House

Waterfront Millington Vacation Rental with Hot Tub!

• Parking
• Accessibility
• Security/Safety

• Maryland
• Golts

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From US $80

         

7.2 (426 Reviews)

Hotel

Red Roof Inn & Suites Chestertown

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $336

         

10.0 (78 Reviews)

House

Circa 1900 Home in the Heart of Historic Downtown Chestertown

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $342

         

|

New

House

Pet-Friendly Home on Chester River with Dock!

• Parking
• Pet Friendly
• Pool

• Maryland
• Chestertown

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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 $375

         

10.0 (73 Reviews)

House

Country Estate in Historic District

• 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 $524

         

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 $217

         

10.0 (14 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 $456

         

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 $507

         

10.0 (4 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 $324

         

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 $1,277

         

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
• Galena

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From US $502

         

10.0 (1 Review)

House

Welcome to the secluded waterfront oasis

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Golts

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From US $293

         

10.0 (1 Review)

House

Walk to Historic Chestertown: Dog-Friendly Retreat

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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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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★ Pro Tip: Pacificislands makes it easy to compare the best listings on Pacificislands homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Pacificislands homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Tilmon's Island Winery.