
Vacation rentals in Blackiston
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Top-rated vacation rentals in Blackiston
Guests agree: these stays are highly rated for location, cleanliness, and more.

King's Landing, Simple & Unique
Our charming home, built circa 1800's, updated with addition's in the 1930's and brought into the 21st century, totally revamped and modernized, 2020. Located within walking distance of downtown Historical Smyrna, where charming pubs and stores await you. Enter your quarters, through the 'Milk Room', pass your private full bath, by the spiral staircase to your spacious private bedroom suite, nestled below a cathedral ceiling on the second floor. Oh, Dover Downs and Wesley college are close by
LocationValueWalkability
4.79 out of 5 average rating, 147 reviews
The Hidden Gem•Heated pool•Pickleball Court
Beautiful spacious house and property with in ground heated pool, breeo fire pit, lots of patio space for outdoor grilling and an indoor pickleball and basketball court Pool is open April 1st to Oct 20th (approx) This 2 story, 6 bedroom, 4 bathroom house has all the amenities you need to make your weekend getaway or family vacation enjoyable! If you have a large group we can accommodate more guests in the cottage across the driveway. Click on my profile to find the listing (Little Gem Cottage)
LocationValueOutdoor spaces
4.99 out of 5 average rating, 90 reviews
Connection Pointe•River views•Quiet•Peaceful
Connection Pointe is a great getaway for your family vacation or to reconnect with friends, you will be sure to enjoy this beautiful property that sits right along the Sassafras River, it is quiet and peaceful with amazing views from the house and the screened in deck. Come enjoy the sounds of nature as you take time to relax and refocus! There is no boat access to the river from the property. There is a fairly steep bank going down to the river, so please be mindful of this with children.
ValueLocationKitchen
4.96 out of 5 average rating, 79 reviews
Entire house sleeps 8 with parking, Wi-fi, kitchen
Welcome to our home! Located in the heart of DE, in front of Smyrna rest stop on exit 119 on route 1, making it convenient to explore North or South: Dover Airforce 16 miles away, Ballys Dover casino is 11 miles away, DE Turf complex 29 miles away, Harrington Casino 36 miles away, Smyrna downtown 3 miles away full of shops and restaurants, Middletown downtown 11 miles away, Bay health hospital 13 miles away, Neumorus Children Hospital 38 miles away, Wilmington River front 35 miles away.
LocationValueAmenities
4.75 out of 5 average rating, 83 reviews
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
FamilyLocationView
4.77 out of 5 average rating, 62 reviews
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!
FamilyLocationCleanliness
4.93 out of 5 average rating, 45 reviews
Home away from Home in Dover DE
Spacious 4-Bedroom Home with Backyard, Game Room & Great Location! Welcome to your home away from home! This comfortable and spacious house offers everything you need for a relaxing stay. It features 4 cozy bedrooms, 2 full bathrooms, a fully equipped kitchen, a welcoming living room that turns into a sofa bed, and a fun basement with a pool table, perfect for relaxing or spending time with family and friends. Enjoy the backyard with a BBQ grill for outdoor meals and quality time.
FamilyLocationAmenities
4.9 out of 5 average rating, 67 reviews
Cozy 2 bedroom home on wooded private lane
Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.
ValueFamilyLayout
4.97 out of 5 average rating, 145 reviews
River front cottage with private dock & water fun
Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!
FamilyLocationPets
4.96 out of 5 average rating, 105 reviews
Top of the Chesapeake - Private Waterfront Home
Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.
LocationValueQuiet
4.92 out of 5 average rating, 249 reviews
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.
FamilyValueGetting around
4.84 out of 5 average rating, 212 reviews
The Garden Estate: Historic Town Center Home
Step back in time without sacrificing luxury. Nestled in Chestertown’s historic district, this rebuilt 19th-century estate blends grand character with modern comfort, just 4 blocks from Washington College. Sprawling across a rare town-center acre, the sanctuary features magnificent gardens, a fenced yard, a fire pit, and a Weber grill for evenings under the stars. Inside, find a flawless layout designed for privacy, rest, and premium comfort.
LocationFamilyGetting around
5.0 out of 5 average rating, 253 reviewsPopular amenities for Blackiston vacation rentals
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