Wilmer Park All-Inclusive Resorts, Hotels & Rentals

Plan Your Next Vacation to Wilmer Park to Relax, Recharge & Re-imagine

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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 $199

         

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9.6 (19 Reviews)

Bed & Breakfast

Brampton 1860

• Air Conditioner
• Parking
• Pet Friendly

• 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 $342

         

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New

House

Pet-Friendly Home on Chester River with Dock!

• Parking
• Pet Friendly
• Pool

• Maryland
• Chestertown

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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 $252

         

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New

House

Walk to Historic Chestertown Dog-Friendly Retreat

• Parking
• Pet Friendly
• Accessibility

• 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 $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 $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 $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 $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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From US $1,160

         

9.8 (23 Reviews)

House

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $131

         

9.6 (108 Reviews)

Apartment

First Floor Studio Apartment in Historic Chestertown

• Air Conditioner
• Parking
• Pool

• Maryland
• Chestertown

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From US $683

         

9.6 (18 Reviews)

House

Pet-Friendly Home on Chester River w/Dock!

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $253

         

New

Apartment

Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $207

         

New

House

Walk to Historic Chestertown: Dog-Friendly Retreat

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $560

         

10.0 (107 Reviews)

House

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $713

         

9.8 (24 Reviews)

House

Victorian Hideaway: Beautiful Exterior, Modern interior

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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