Cassinelli Winery and Vineyards All-Inclusive Resorts, Hotels & Rentals

Plan Your Next Vacation to Cassinelli Winery and Vineyards to Relax, Recharge & Re-imagine

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From US $238

         

10.0 (105 Reviews)

Cottage

Secluded Waterfront Cottage on 200 acre farm near Queenstown

• Air Conditioner
• Parking
• TV

• Maryland
• Centreville

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From US $1,200

         

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10.0 (2 Reviews)

Villa

Blake House Historic Estate with Private Inn

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Centreville

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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 $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 $829

         

|

10.0 (1 Review)

House

Lansdowne Manor

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Centreville

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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 $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 $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 $70

         

5.2 (175 Reviews)

Hotel

Driftwood Inn

• 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 $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 $526

         

10.0 (59 Reviews)

House

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Rock Hall

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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 $938

         

10.0 (21 Reviews)

Villa

Blake House Historic Estate with Private Inn

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Centreville

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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 $1,611

         

10.0 (13 Reviews)

House

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Centreville

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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 $719

         

10.0 (8 Reviews)

House

Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Centreville

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From US $311

         

10.0 (8 Reviews)

House

HGTV quality, private guest suite, country getaway with hot tub & fire pit

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Centreville

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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 $175

         

10.0 (6 Reviews)

Cottage

Cozy, unique, historic registered cottage on the Corsica River!

• Air Conditioner
• Parking
• TV

• Maryland
• Centreville

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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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