73+ Vacation Rentals Near Tilmon's Island Winery |
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Old Mansions - Vacation Rentals in Tilmon's Island Winery

Property Image From $527
         

10.0 (83 Reviews)
House
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $182
         

9.7 (3 Reviews)
Apartment
Carriage House Hideaway In Center of Chestertown
  • Air Conditioner
  • Pet Friendly
  • View

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Property Image From $127
         

8.6 (785 Reviews)
Hotel
Comfort Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $331
         

10.0 (76 Reviews)
House
Circa 1900 Home in the Heart of Historic Downtown Chestertown
  • Air Conditioner
  • Parking
  • TV

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Property Image From $1,758
         

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New
House
Thornton
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $90
         

7.2 (406 Reviews)
Hotel
Red Roof Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $344
         

10.0 (70 Reviews)
House
Country Estate in Historic District
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,162
         

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New
House
River Heights Retreat
  • Air Conditioner
  • Pet Friendly
  • View

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Property Image From $70
         

5.2 (174 Reviews)
Hotel
Driftwood Inn
  • Air Conditioner
  • Parking
  • TV

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Property Image From $963
         

10.0 (61 Reviews)
House
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $186
         

10.0 (40 Reviews)
Apartment
Historic Downtown Garden Oasis with Private Patio
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Property Image From $448
         

10.0 (25 Reviews)
House
Harbor View Haven | Waterfront w/Hot Tub + Dock!
  • Air Conditioner
  • Parking
  • TV

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Property Image From $239
         

10.0 (18 Reviews)
House
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
  • Air Conditioner
  • Parking
  • TV

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Property Image From $194
         

10.0 (18 Reviews)
House
Peaceful country home away in the wilderness
  • Air Conditioner
  • Parking
  • TV

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Property Image From $232
         

10.0 (10 Reviews)
Cabin
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $517
         

10.0 (7 Reviews)
House
Waterfront Millington Vacation Rental w/Hot Tub!
  • Air Conditioner
  • Parking
  • Security/Safety

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Property Image From $456
         

10.0 (5 Reviews)
House
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
  • Air Conditioner
  • Parking
  • TV

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Property Image From $227
         

10.0 (4 Reviews)
House
Your perfect Maryland escape awaits!
  • Air Conditioner
  • Parking
  • TV

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Property Image From $1,337
         

10.0 (2 Reviews)
House
Guest Lodge | Private Pool | Outdoor Dining | Game Room
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $324
         

10.0 (2 Reviews)
Apartment
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access
  • Air Conditioner
  • Parking
  • TV

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Property Image From $545
         

10.0 (1 Review)
House
Countryside Cottage in Sassafras
  • Air Conditioner
  • Parking
  • TV

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Property Image From $526
         

10.0 (1 Review)
House
Stunning Historic Downtown Home! Within 2 Blocks of Fountain Park!
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Property Image From $521
         

9.8 (85 Reviews)
House
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $293
         

9.8 (27 Reviews)
Apartment
Newly restored apartment in the heart of Chestertown
  • Air Conditioner
  • Parking
  • Security/Safety

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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 Tilmon's Island Winery.

Weather in Tilmon's Island Winery

View the weather forecast for Tilmon's Island Winery before booking your Tilmon's Island Winery Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Tilmon's Island Winery, MD

Old Mansions offers a large selection of top attractions around Tilmon's Island Winery. Research things to do on your vacation before you visit Tilmon's Island Winery.


Dover International Speedway Dover Downs Casino Ripken Stadium Harrington Raceway and Casino Delaware State University Hollywood Casino Dover Mall Washington College Firefly Music Festival Woodland Beach Delaware State Fairgrounds Queenstown Premium Outlets Union Hospital Killens Pond State Park Queenstown Harbor Golf Club Havre de Grace Promenade Elk Neck State Park Delaware State Visitor Center Delaware Agricultural Museum and Village Harford Memorial Hospital