104+ Vacation Rentals Near Cassinelli Winery and Vineyards |
  1. USA
  2. Maryland
  3. Church Hill
  4. Cassinelli Winery and Vineyards

Sell Off Cruises - Vacation Rentals in Cassinelli Winery and Vineyards

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

10.0 (91 Reviews)
House
Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Blake House Historic Estate with Private Inn From US $1,200
         

|
10.0 (2 Reviews)
Villa
Blake House Historic Estate with Private Inn
  • Air Conditioner
  • Parking
  • Pet Friendly

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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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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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Lansdowne Manor From US $564
         

|
10.0 (1 Review)
House
Lansdowne Manor
  • Air Conditioner
  • Parking
  • Pet Friendly

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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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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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Brampton 1860 From US $397
         

|
9.6 (19 Reviews)
Bed & Breakfast
Brampton 1860
  • Air Conditioner
  • Parking
  • Pet Friendly

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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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Blake House Historic Estate with Private Inn From US $1,032
         

10.0 (24 Reviews)
Villa
Blake House Historic Estate with Private Inn
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully From US $1,548
         

10.0 (17 Reviews)
House
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
  • Air Conditioner
  • Parking
  • Pet Friendly

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Family Retreat at Lansdowne Manor From US $424
         

10.0 (12 Reviews)
House
Family Retreat at Lansdowne Manor
  • Air Conditioner
  • Parking
  • TV

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The Colonial Farmhouse with Private Boat Rental From US $1,108
         

10.0 (8 Reviews)
House
The Colonial Farmhouse with Private Boat Rental
  • Air Conditioner
  • Parking
  • Pool

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Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach | From US $1,013
         

10.0 (8 Reviews)
House
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
  • Air Conditioner
  • Parking
  • Pet Friendly

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Grays Inn Creek Waterfront Pvt Dock Kayaks & View From US $691
         

10.0 (8 Reviews)
House
Grays Inn Creek Waterfront Pvt Dock Kayaks & View
  • Air Conditioner
  • Parking
  • Pet 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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Walk to Historic Chestertown: Dog-Friendly Retreat From US $261
         

10.0 (5 Reviews)
House
Walk to Historic Chestertown: Dog-Friendly Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Welcome to the secluded waterfront oasis From US $634
         

10.0 (4 Reviews)
House
Welcome to the secluded waterfront oasis
  • Air Conditioner
  • Parking
  • Pet Friendly

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A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. From US $1,337
         

10.0 (3 Reviews)
House
A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.
  • Air Conditioner
  • Parking
  • Pool

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Waterfront! Private Dock, Boat Tie-Up & Near Town From US $413
         

10.0 (3 Reviews)
House
Waterfront! Private Dock, Boat Tie-Up & Near Town
  • Air Conditioner
  • Parking
  • Pet Friendly

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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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Private Waterfront Cottage On Langford Creek With Hot Tub & Pier From US $694
         

10.0 (2 Reviews)
House
Private Waterfront Cottage On Langford Creek With Hot Tub & Pier
  • 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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Secluded Cottage in Middle of Chestertown From US $279
         

10.0 (2 Reviews)
Apartment
Secluded Cottage in Middle of Chestertown
  • Air Conditioner
  • Parking
  • TV

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

Weather in Cassinelli Winery and Vineyards

View the weather forecast for Cassinelli Winery and Vineyards before booking your Cassinelli Winery and Vineyards 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 Cassinelli Winery and Vineyards, MD

Selloffcruises offers a large selection of top attractions around Cassinelli Winery and Vineyards. Research things to do on your vacation before you visit Cassinelli Winery and Vineyards.


Dover International Speedway Dover Downs Casino U.S. Naval Academy Ripken Stadium Harrington Raceway and Casino Delaware State University White Marsh Mall Westfield Annapolis Mall Annapolis City Dock Chesapeake Bay Bridge Dover Mall Sandy Point State Park Washington College Anne Arundel Medical Center Maryland State House Firefly Music Festival Navy-Marine Corps Memorial Stadium Delaware State Fairgrounds Kunta Kinte–Alex Haley Memorial St. Michaels Winery

Cassinelli Winery and Vineyards Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Cassinelli Winery and Vineyards?

Currently, the total number of properties listed in 2026 is over 104 in the Cassinelli Winery and Vineyards area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Cassinelli Winery and Vineyards.