81+ Vacation Rentals Near Tilmon's Island Winery |
  1. USA
  2. Maryland
  3. Sudlersville
  4. Tilmon's Island Winery

Sonoma Villas - Vacation Rentals in Tilmon's Island Winery

Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! From US $537
         

10.0 (90 Reviews)
House
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Porterhouse Farm From US $1,539
         

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New
House
Porterhouse Farm
  • Air Conditioner
  • Parking
  • Pool

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Comfort Inn & Suites Chestertown From US $119
         

8.6 (929 Reviews)
Hotel
Comfort Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pool

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Wren Retweet- Country Estate in Center of C’Town From US $552
         

10.0 (75 Reviews)
House
Wren Retweet- Country Estate in Center of C’Town
  • Air Conditioner
  • Parking
  • Pet Friendly

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River Heights Retreat From US $1,162
         

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

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Red Roof Inn & Suites Chestertown From US $75
         

7.2 (464 Reviews)
Hotel
Red Roof Inn & Suites Chestertown
  • Air Conditioner
  • Parking
  • Pet Friendly

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Historic Downtown Garden Oasis with Private Patio From US $227
         

10.0 (54 Reviews)
Apartment
Historic Downtown Garden Oasis with Private Patio
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Pet-Friendly Home on Chester River w/Dock! From US $799
         

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New
House
Pet-Friendly Home on Chester River w/Dock!
  • Parking
  • Pet Friendly
  • Pool

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Harbor View Haven | Waterfront w/Hot Tub + Dock! From US $618
         

10.0 (31 Reviews)
House
Harbor View Haven | Waterfront w/Hot Tub + Dock!
  • Air Conditioner
  • Parking
  • TV

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Lovely Home in Chestertown - Free EV Charging for guests From US $291
         

10.0 (27 Reviews)
House
Lovely Home in Chestertown - Free EV Charging for guests
  • Air Conditioner
  • Parking
  • TV

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Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm! From US $300
         

10.0 (23 Reviews)
Cabin
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Peaceful country home away in the wilderness From US $257
         

10.0 (19 Reviews)
House
Peaceful country home away in the wilderness
  • Child Friendly

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The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown From US $545
         

10.0 (6 Reviews)
House
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
  • Air Conditioner
  • Parking
  • TV

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Guest Lodge | Private Pool | Outdoor Dining | Game Room From US $1,557
         

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

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Countryside Cottage in Sassafras From US $666
         

10.0 (2 Reviews)
House
Countryside Cottage in Sassafras
  • Air Conditioner
  • Parking
  • TV

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Blue Heron Farm Waterfront Chalet From US $415
         

10.0 (2 Reviews)
House
Blue Heron Farm Waterfront Chalet
  • Air Conditioner
  • Parking
  • TV

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Pool + Hot Tub + Pickleball | Waterfront From US $809
         

10.0 (1 Review)
House
Pool + Hot Tub + Pickleball | Waterfront
  • Air Conditioner
  • Pool
  • TV

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Newly restored apartment in the heart of Chestertown From US $385
         

9.8 (29 Reviews)
Apartment
Newly restored apartment in the heart of Chestertown
  • Air Conditioner
  • Parking
  • TV

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Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful. From US $826
         

9.8 (25 Reviews)
House
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
  • Air Conditioner
  • Parking
  • TV

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Beautiful, spacious waterfront home, an easy walk to historic Chestertown From US $1,658
         

9.8 (23 Reviews)
House
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
  • Air Conditioner
  • Parking
  • TV

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Guest Suite for up to 2 in a Victorian on the Chester River From US $125
         

9.8 (23 Reviews)
Apartment
Guest Suite for up to 2 in a Victorian on the Chester River
  • Air Conditioner
  • Parking
  • TV

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The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE From US $182
         

9.8 (10 Reviews)
Apartment
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
  • Air Conditioner
  • Parking
  • TV

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First Floor Studio Apartment in Historic Chestertown From US $159
         

9.6 (116 Reviews)
Apartment
First Floor Studio Apartment in Historic Chestertown
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Home on Chester River w/Dock! From US $1,030
         

9.6 (23 Reviews)
House
Pet-Friendly Home on Chester River w/Dock!
  • Air Conditioner
  • Parking
  • Pet Friendly

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

Sonomavillas 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

Tilmon's Island Winery Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Tilmon's Island Winery?

Currently, the total number of properties listed in 2026 is over 81 in the Tilmon's Island Winery area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Tilmon's Island Winery.