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:10 Oct - 17 Oct
Image gallery for Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Chestertown, MD
8% off
Price is NZ$14,712
NZ$14,712
NZ$2,102 per night
includes taxes & fees
Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
1010 out of 10 rating
Exceptional
(5 reviews)
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD
17% off
Price is NZ$4,810
NZ$4,810
NZ$687 per night
includes taxes & fees
Image gallery for HGTV quality, private guest suite, country getaway with hot tub & fire pit
1010 out of 10 rating
Exceptional
(5 reviews)
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville, MD
8% off
Price is NZ$3,720
NZ$3,720
NZ$531 per night
includes taxes & fees
Image gallery for Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
1010 out of 10 rating
Exceptional
(6 reviews)
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Centreville, MD
8% off
Price is NZ$14,237
NZ$14,237
NZ$2,034 per night
includes taxes & fees
Image gallery for Kent Island Luxury Waterfront
1010 out of 10 rating
Exceptional
(6 reviews)
Kent Island Luxury Waterfront
Stevensville, MD
17% off
Price is NZ$9,040
NZ$9,040
NZ$1,291 per night
includes taxes & fees
Image gallery for Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
1010 out of 10 rating
Exceptional
(45 reviews)
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall, MD
12% off
Price is NZ$2,961
NZ$2,961
NZ$423 per night
includes taxes & fees
Image gallery for Peaceful getaway convenient to local amenities including beach, boating & food
9.89.8 out of 10 rating
Exceptional
(113 reviews)
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall, MD
8% off
Price is NZ$2,855
NZ$2,855
NZ$408 per night
includes taxes & fees
Image gallery for Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
Rock Hall, MD
8% off
Price is NZ$16,045
NZ$16,045
NZ$2,292 per night
includes taxes & fees
Image gallery for Blissful Retreat In Rock Hall
1010 out of 10 rating
Exceptional
(111 reviews)
Blissful Retreat In Rock Hall
Rock Hall, MD
6% off
Price is NZ$3,189
NZ$3,189
NZ$456 per night
includes taxes & fees
Image gallery for Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Galena, MD
8% off
Price is NZ$7,657
NZ$7,657
NZ$1,094 per night
includes taxes & fees
Image gallery for Circa 1900 Home in the Heart of Historic Downtown Chestertown
1010 out of 10 rating
Exceptional
(71 reviews)
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Chestertown, MD
17% off
Price is NZ$3,912
NZ$3,912
NZ$559 per night
includes taxes & fees
Image gallery for BEACH WITHOUT THE BUSTLE
1010 out of 10 rating
Exceptional
(30 reviews)
BEACH WITHOUT THE BUSTLE
Betterton, MD
8% off
Price is NZ$2,692
NZ$2,692
NZ$385 per night
includes taxes & fees
Image gallery for Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
1010 out of 10 rating
Exceptional
(98 reviews)
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown, MD
8% off
Price is NZ$6,841
NZ$6,841
NZ$977 per night
includes taxes & fees
Image gallery for Harbor View Haven | Waterfront w/ Hot Tub + Dock!
1010 out of 10 rating
Exceptional
(22 reviews)
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
Chestertown, MD
7% off
Price is NZ$7,219
NZ$7,219
NZ$1,031 per night
includes taxes & fees
Image gallery for Beautiful Retreat Located in Rock Hall - walk to everything!
1010 out of 10 rating
Exceptional
(60 reviews)
Beautiful Retreat Located in Rock Hall - walk to everything!
Rock Hall, MD
16% off
Price is NZ$4,227
NZ$4,227
NZ$604 per night
includes taxes & fees
Image gallery for Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
9.89.8 out of 10 rating
Exceptional
(61 reviews)
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Rock Hall, MD
8% off
Price is NZ$3,777
NZ$3,777
NZ$540 per night
includes taxes & fees
Image gallery for Newly restored apartment in the heart of Chestertown
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Newly restored apartment in the heart of Chestertown
Chestertown, MD
8% off
Price is NZ$3,557
NZ$3,557
NZ$508 per night
includes taxes & fees
Image gallery for Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
1010 out of 10 rating
Exceptional
(8 reviews)
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall, MD
8% off
Price is NZ$3,312
NZ$3,312
NZ$473 per night
includes taxes & fees
Image gallery for Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
1010 out of 10 rating
Exceptional
(8 reviews)
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall, MD
8% off
Price is NZ$2,253
NZ$2,253
NZ$322 per night
includes taxes & fees
Image gallery for Cottage within walking distance to the Bay!
1010 out of 10 rating
Exceptional
(5 reviews)
Cottage within walking distance to the Bay!
Chestertown, MD
31% off
Price is NZ$2,424
NZ$2,424
NZ$346 per night
includes taxes & fees
Image gallery for River Front, Private Single Family Home
1010 out of 10 rating
Exceptional
(15 reviews)
River Front, Private Single Family Home
Grasonville, MD
8% off
Price is NZ$6,432
NZ$6,432
NZ$919 per night
includes taxes & fees
Image gallery for The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
9.89.8 out of 10 rating
Exceptional
(7 reviews)
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Clayton, DE
17% off
Price is NZ$1,916
NZ$1,916
NZ$274 per night
includes taxes & fees
Image gallery for Relaxation Haven on the Shore near Choptank River
1010 out of 10 rating
Exceptional
(5 reviews)
Relaxation Haven on the Shore near Choptank River
Greensboro, MD
7% off
Price is NZ$2,800
NZ$2,800
NZ$400 per night
includes taxes & fees
Image gallery for Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Betterton, MD
12% off
Price is NZ$4,244
NZ$4,244
NZ$606 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Cassinelli Winery and Vineyards
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Sleeps 10 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
Sleeps 13 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
286 reviews(286 reviews)
Waterfront Retreat with Private Dock and Beach
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
BAYSIDE BUNGALOW
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
89 reviews(89 reviews)
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