Holiday rentals in Blackiston

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

Quaint 1st floor 1 BR apt in Historic Firehouse

1 bedroom apt. in historic building in town (1800's Firehouse). Newly remodeled for those looking for quaint getaway. Within sight of small park with gazebo, coffee shop (old Town hall), 1 block to local pizza shop. Just a short drive to Smyrna where you will find anything else you are needing. Central to the beach, the bay, Baltimore, Philadelphia, Lancaster, and so many small towns along the way. Anything you dont find in Smyrna we have Dover to the south or Middletown to the north.

Tiny Home on a Farm

Escape to nature in our cozy 12x12 A-Frame tiny home cabin at Huck and Buck Farm, perfect for two guests. Enjoy a queen bed, mini fridge, microwave, and Keurig for your convenience. Relax in your private hot tub, lounge in the hammocks, or gather by the fire pit under the stars. A short walk leads to a luxury bathhouse with a hot shower and flushing toilets. Pet-friendly with free parking, surrounded by farm animals, gardens, and fresh seasonal food for a peaceful getaway.

Cozy Camper Escape Near Dover

Escape to a cozy camper in Hartly, DE! This stylish retreat sleeps 3 with a queen sized bed with memory foam mattress, and pull-out sofa. Enjoy amenities like AC, a fridge, freezer, 3-burner gas stove, oven, and instant hot water. A space heater is provided for chilly nights. Just 20 minutes from Dover attractions like Dover Motor Speedway and Delaware State University, it’s perfect for a peaceful getaway or event-filled stay. Book today for comfort and convenience!

Heart of Smyrna 3 bd near all

3 bedroom sleeps 7, next to acme shopping center. walk to downtown Smyrna and many restaurants. Easy access to route 13 and route 1. Close to Dover and Middletown. This is a unique commercial property that contains a 3 bedroom 1 full bath living area and attached office with 1/2 bath. We also run a yoga studio in the detached pole barn behind the house and offer discounts to classes. Only you will have access to the home and attached office space.

Private Guest Suite Close To Dover Downs/DSU

Cozy guest suite in Smyrna, DE, perfect for solo travelers or couples seeking a relaxing getaway. Unwind in the comfortable living room with a TV, challenge friends to games in the dedicated game room lounge, and enjoy a restful sleep in the well-appointed bedroom. The suite also includes a private bathroom for your convenience. Located in a peaceful neighborhood, you'll be close to local attractions while enjoying the tranquility of the area.

Lark's Nest on the Chester River

Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the views and dine alfresco on the oversized deck. Centrally located just 20 minutes from all of the events, eateries, shops and galleries in Historic Chestertown. Perfect, family and pet-friendly home for Washington College students, parents and alumni. Book today for your family reunion, wedding parties, or romantic get-away!

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.