- USA
- Maryland
- Church Hill
- Cassinelli Winery and Vineyards
- Rentals by Owner
Discover Your Ideal Cassinelli Winery and Vineyards Rental by Owner in Church Hill, Maryland for a Memorable Stay
Discover Your Perfect Cassinelli Winery and Vineyards Rentals by Owner
-
Rentals by Owner
-
Luxury Vacation Rentals
-
Pet Friendly Vacation Rentals
-
Unique Vacation Rentals
-
Cabin Rentals
-
Cottage Rentals
-
Ski Chalet Rentals
-
Timeshares
-
Villa Rentals
-
Hotels with Suites
-
Resort Rentals
-
Family Vacation Rentals
-
Vacation Rentals with Pools
-
Oceanfront Vacation Rentals
-
Beach House Rentals
-
Summer Vacation Rentals
-
Winter Vacation Rentals
-
Short Term Rentals
-
Corporate Accommodation
-
Large Group Vacation Rentals
-
Sustainable Travel
Cassinelli Winery and Vineyards Rentals by Owner
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Why Choose Rent By Owner for your Cassinelli Winery and Vineyards vacation rental?
What makes our Rentals by Owner special?
Best Times to Visit Cassinelli Winery and Vineyards
When should you plan your Rentals by Owner stay?
Timing your visit to this charming region can enhance your experience, as each season offers unique opportunities to enjoy the scenic beauty and peaceful atmosphere of Cassinelli Winery and Vineyards, making it an ideal destination for a memorable getaway.
Peak Season Highlights
Spring (March to May)
During springtime, the area around this destination blossoms with vibrant colors and mild temperatures, making it an ideal time for outdoor activities and vineyard tours.
Fall (September to November)
Autumn offers a picturesque setting with fall foliage and harvest events, perfect for exploring the region's scenic beauty and enjoying seasonal wine tastings.
Off-Season Highlights
Summer (June to August)
In summer, the warm weather encourages outdoor exploration, though it can be busier with visitors seeking outdoor leisure activities in the region.
Winter (December to February)
Winter tends to be quieter, offering a peaceful atmosphere for those looking to enjoy the tranquility of the vineyards and surrounding countryside.
Weekly Weather Forecast for Cassinelli Winery and Vineyards
How to Book Your Cassinelli Winery and Vineyards vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Cassinelli Winery and Vineyards
Common Rentals by Owner Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy the scenic outdoors with a private outdoor seating area perfect for relaxing after exploring the region’s vineyards.
- Make the most of the fresh air with access to a spacious patio or deck, ideal for outdoor dining or morning coffee.
- Take advantage of beautiful walking trails or garden spaces that showcase the natural beauty of the area.
- Experience outdoor recreational activities such as picnic areas or designated lounging spots within the property grounds.
- Benefit from well-maintained lawns and open spaces for outdoor games or simply unwinding in the fresh Maryland air.
- Utilize on-site parking facilities that keep your outdoor excursions convenient and hassle-free.
- Enjoy the serenity of outdoor surroundings that complement the region’s vineyard landscape, providing a peaceful retreat during your stay.
Top Attractions Around Cassinelli Winery and Vineyards
What attractions are nearby?
Nearby, you can enjoy a variety of relaxing activities in this charming region, from exploring local vineyards to outdoor pursuits that highlight the area's natural beauty, making it an ideal destination for your stay booked through Rent By Owner.

Family Activities
- Vineyard Tours: Take a guided walk through the lush vineyards, providing an engaging experience for your family to learn about grape growing and wine production in this scenic region.
- Family Picnic Areas: Enjoy a relaxing picnic amid beautiful vineyard views, offering a perfect outdoor activity for families seeking quality time together here.
- Wine & Food Pairing Events: Participate in family-friendly tasting sessions that combine local wines with delicious regional cuisine, making it a delightful culinary adventure suitable for all ages.
- Seasonal Festivals and Events: Join seasonal celebrations hosted by the vineyard, where families can partake in entertainment, music, and activities that showcase the area’s vibrant community spirit.
Adult Activities
- Wine Tasting Experience: Indulge in exclusive wine tastings at Cassinelli Winery and Vineyards, where you can sample and savor regional wines crafted with local expertise.
- Tours of the Vineyard and Winery: Take a guided tour through the vineyards and production facilities to learn about the winemaking process right here in the region.
- Event Participation and Live Music: Attend seasonal festivals or live music events hosted amidst the scenic backdrop of this destination’s lush landscapes.
- Relaxing Picnic Areas: Enjoy a peaceful picnic surrounded by the beauty of the area’s vineyards, perfect for unwinding after exploring here.
Cassinelli Winery and Vineyards Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit During Peak Seasons: Schedule your trip to align with the best weather and local events to enhance your overall experience in this charming area.
- Explore Nearby Attractions: Take advantage of the region's scenic countryside and nearby vineyards to make your stay more memorable and diverse.
- Communicate Your Needs Clearly: When booking directly through Rent By Owner, specify any special requirements to ensure a comfortable and personalized stay here.
- Utilize Local Recommendations: Ask hosts or locals for insider tips on the best spots to enjoy authentic regional flavors and hidden gems within the area.
Transportation Options
- Rental Car Services: You can conveniently access national rental car companies nearby for flexible transportation around the region.
- Local Taxi and Rideshare Options: Reliable taxi services and ridesharing apps are available to help you explore this area comfortably during your stay.
- Public Transit: Local bus routes offer an affordable and straightforward way to navigate the surrounding vicinity of the vineyard and beyond.
- Private Transportation Arrangements: Consider booking private shuttles or chauffeur services for a personalized travel experience here in Maryland's scenic region.
Local Customs Options
- Respect for Winery Traditions: When visiting, you’ll find that locals value preserving the longstanding wine-making customs that define this region.
- Quiet Hours Etiquette: Maintaining a calm and peaceful atmosphere during evening hours is appreciated by those seeking a relaxing experience here.
- Local Harvest Celebrations: Participating in seasonal festivals or events often involves honoring agricultural customs passed down through generations.
- Environmental Respect: Visitors are encouraged to follow sustainable practices, such as proper waste disposal and minimal disturbance, to protect the area's natural beauty.
Frequently Asked Questions About Cassinelli Winery and Vineyards Rentals by Owner
1. What are the top vacation rentals in Cassinelli Winery and Vineyards?
There are a lot of options in Cassinelli Winery and Vineyards. If you plan on staying in the Cassinelli Winery and Vineyards area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cassinelli Winery and Vineyards:
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Carriage House Hideaway in Middle of Chestertown
- Eastern Shore Get Away
- Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
- Country Estate in Historic District
- 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
- Historic Downtown Garden Oasis with Private Patio
2. How many Rentbyowner vacation rentals are available in Cassinelli Winery and Vineyards?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 79 in the Cassinelli Winery and Vineyards area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cassinelli Winery and Vineyards.
3. What is the cancellation policy for rentals by owner near Cassinelli Winery and Vineyards?
4. How do I confirm my booking at a rental property close to Cassinelli Winery and Vineyards?
5. Are there any specific check-in or check-out times I should be aware of when staying near this region?
6. What amenities are typically included in rentals near Cassinelli Winery and Vineyards?
7. Is it possible to modify or extend my stay at a rental by owner in this area?
More Rentals You May Like Near Cassinelli Winery and Vineyards
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool