Vacation rentals in Blackiston

Ruby's Sea Glass Cottage near Betterton Beach

This cute 1900 cottage in the center of Betterton has a full kitchen & three beautiful outdoor porches to unwind. There's one bathroom ON THE FIRST FLOOR (shower only). An outdoor shower is available seasonally! There are three bedrooms-ALL ON THE SECOND FLOOR. Enjoy the beach down the street to find sea glass or watch the sunset! SEE LISTING PHOTOS FOR INFO ABOUT THE AREA. BETTERTON DOES NOT HAVE A GROCERY STORE. Kids items upon request. Furniture/decor may be change from listing pictures.

Creekside Cabin: Sauna | Hot Tub | Fire Pit |Cozy

🏡 Creekside Cabin: A Rustic-Luxury Retreat Along Fishing Creek Tucked into a wooded stretch along Fishing Creek, Creekside Cabin is the kind of place that slows your heartbeat the moment you arrive. Just 45 minutes from Lancaster and York, this beautifully renovated cabin was built for couples and solo travelers who want the charm of the outdoors without giving up the comforts inside. A private sauna, hot tub, a fire pit, spa-style finishes — it's all here. Save it to your wishlist! ❤️

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!

Sweet Bay Overlook

Take it easy at this unique home overlooking the Chesapeake Bay. You will enjoy watching the amazing sunsets on the bluff as the eagles, ospreys and boats drift by. Our little house was built in the 1960’s by a brick mason who was very good at his trade. In recent years, the home had fallen into disrepair, but a talented Amish craftsman purchased the house and renovated it from top to bottom. The Sweet Bay that you see today reflects his incredible attention to detail and quality.

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!

Spacious Rural Home

Our home is nestled on a serene country road in the Dover/Lepsic area. It offers a peaceful backdrop with fields both behind and across the street, ensuring a true escape from the hustle and bustle. This single-story residence features four cozy bedrooms, two full bathrooms, a spacious kitchen, two inviting living areas, and a relaxing backyard deck. Conveniently located, you're just a 10-minute drive from the heart of Dover, Delaware, and 20 minutes from DE Turf Complex.

Long Beach Cottage, Hot Tub, Beachfront

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.

257 Spacious Suite Studio w/private bathroom

Enjoy a charming Victorian suite on the entire private third floor—no shared spaces on this level. Features 1 king bed in the main open area with TV, living space, and coffee station, plus 1 queen bed in a private room with 65” TV and direct bathroom access. Includes a large private bathroom and a breakfast setup with coffee, tea, fridge, air fryer, kettle, and utensils. Shared first floor offers a full kitchen, guest bathroom, and patio.

Mom’s Basement: A Slice of Paradise

PLEASE READ DESCRIPTION BEFORE INQUIRING. No long term stays. Internet and cell service is VERY limited in our area. No wifi, limited TV. NO bully/aggressive breed pets. Damage or extra cleaning from pets is independently assessed by our cleaning staff. The ceilings are very low in some areas. Safety padding has been installed but proceed at your own discretion. If you have any questions about the space, just ask!

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

Private entrance King Suite

Forget your worries in this spacious and serene space. Brand new private room on historic waterfront Chesapeake City Farm. You will have a private entrance to your roomy king suite, complete with luxurious bathroom, kitchenette efficiency, and coffee bar. You will have access to the Bohemia River, and a 200 acre horse farm, where wildlife abounds and the views are spectacular.