Holiday houses 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.

Secluded Getaway in the Historic District

Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer. We also host ‘Wren Retweet”, a 5 bedroom house by the carriage house.

Quiet Country Relaxing Farm

Forget your worries in this spacious and serene space. This 3 bedroom 2 bath home is set way out in the country surrounded by state hunting lands .With some farm animals on the property now and then .So much wild life. Lots of deer and turkeys to name a few . Would be a perfect place to stay during hunting season with a short walk out the front door you will be deep in the state hunting lands .Also just up the road is Double Tap Tavern cold drinks and amazing food. High speed internet

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Hunter's Lodge

Escape to our charming countryside cottage nestled on a picturesque farm on the Eastern Shore and just a stone’s throw from Delaware. Surrounded by rolling fields, this cozy retreat offers the perfect blend of rustic charm and modern comfort. Enjoy morning coffee on the porch, explore nearby towns and outdoor experiences. With easy access to local attractions, you can experience farm life while being close to charming towns and beautiful landscapes. Your serene getaway awaits!

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & 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...

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

Private Suite Close To Casino/DSU/Racetrack

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.

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.

Beautiful newly updated apartment in Fairton.

Forget your worries in this spacious and serene space. This recently renovated second floor apartment boasts natural light and nature at your footsteps. It has every comfort needed to feel like you're right at home. It is conveniently located close to New Jersey Motor Sports Park and the Delaware Bay. It has plenty of space to park large trailers and boats. NO SMOKING PET FRIENDLY (pets must be clean)