Holiday rentals near Cassinelli Winery and Vineyards
We found 173 holiday rentals — enter your dates for availability
If you are looking to stay near Cassinelli Winery and Vineyards, scroll through and discover private holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a pool. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Cassinelli Winery and Vineyards
Showing deals for:3 Oct - 10 Oct
Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

10 out of 10 rating
Exceptional
(5 reviews)
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD
17% off
Price is AU$4,497
AU$642 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Cassinelli Winery and Vineyards
Showing deals for: 3 Oct - 6 Oct
BAYSIDE BUNGALOW
Sleeps 2 · 1 bedroom · 1 bathroom
10 out of 10
exceptional
(40 reviews)
The current price is AU$1,162
for 3 nights, 1 home
AU$387 per night
includes taxes & fees
Top rated rentals - Cassinelli Winery and Vineyards

Great place for a family reunion
10 out of 10
exceptional
(187 reviews)
Our family was gathered in the area for a wedding. Although we only had nine people sleeping here, we accommodated other relatives for meals and a crab feast. The house has several seating areas, including the beach area, where people could sit down and catch up. Had it been warmer weather, we would have also enjoyed the kayaks and paddle boards. Overall, it suited our needs perfectly.
Kathryn A.
Stayed Oct 2023
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value