Old Mansions - Vacation Rentals in Rolphs Wharf Marina

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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 $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 $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 $384

         

10.0 (70 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 $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 $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 $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 $880

         

8.4 (6 Reviews)

House

Private Peaceful Waterfront House with Pool & Hot Tub

• Air Conditioner
• Parking
• Pool

• Maryland
• Church Hill

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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 $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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From US $764

         

10.0 (37 Reviews)

House

Breathtaking waterfront home on the Chester River

• Air Conditioner
• Parking
• Pool

• Maryland
• Chestertown

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From US $461

         

10.0 (31 Reviews)

House

Hidden gem with water and golf course views! Bike ride to downtown!

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $459

         

10.0 (60 Reviews)

House

Charming Chestertown Waterfront Cottage

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $200

         

10.0 (11 Reviews)

Cottage

Owl Cottage

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $1,166

         

9.8 (22 Reviews)

House

Private pier and pool at this waterfront Chestertown home

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Chestertown

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From US $722

         

New

House

Down by the River - Charming house on river & walkable to historic Chestertown

• Air Conditioner
• Parking
• TV

• Maryland
• Chestertown

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From US $401

         

New

House

Historic luxury townhouse in the heart of downtown Chestertown

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Maryland
• Chestertown

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★ Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions 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 Rolphs Wharf Marina.