Vacation rentals in Greenwood

Gracious & Spacious- Near DE Turf Complx & Beaches

Welcome to our charming home with Modern French decor, conveniently located off Coastal Highway (SR1) in Milton. This tranquil retreat offers easy access to DETurf, Lewes Beach, and Rehoboth Beach, blending convenience and relaxation. With two bedrooms, two sofa beds, and two bathrooms, our spacious living area is warm and inviting. The kitchen is perfect for gatherings, and a utility room with a washer and dryer adds convenience. Experience the best of coastal living in this delightful getaway!

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Guest Suite with Private Entrance

My wife Justine and I are pleased to host this guest suite with private secure entrance and private bathroom. We do live in the main part of the house full time so you may hear us rattling around from time to time and coming and going or working in the yard but most of our time is spent at the opposite end of the house. The room is completely private and inaccessible from the main house. The screened in porch is shared with the main house. We do not currently have WiFi access in the Airbnb.

Mast Cabin

Enjoy a peaceful stay in our cabin set in the edge of the woods. The cabin is 100 feet from our house, and has its own gravel driveway along the woods. We are located in a rural area on 8 acres, 30 miles from DE beaches. Absolutely no marijuana use anywhere on the property, and no smoking in the cabin. When requesting to book, please include a message telling us who is coming (max 2 guests) and the purpose for your travel plans. Requests without this basic info won’t be approved.

Tiny Bay House on Delaware Bay/2 Min Walk to Beach

Bay Views – Nestled among tall pines, this serene retreat offers stunning sunrises & sunsets. Perfect for guests seeking peace & fresh coastal air. Surrounded by nature and birdlife, it’s an ideal place to slow down and unwind. A short walk leads to the beach. The bay water NOT suitable for swimming, as it’s a shallow, tide-influenced habitat for marine life like horseshoe crabs. Bring bug spray & sunscreen. Sleeps up to 5. De Turf 17 min away. Must be 25 or older to book a stay.

Stylish 2BR • Near DE Turf, Beaches & Dining

This brand new 2 bedroom apartment is right in the heart of downtown Milford, walking distance from local boutiques, night life & restaurants. Our apartment is dog & family friendly! We are located 20 minutes from beaches and shopping & about 10 minutes from the DE turf complex! We own a local restaurant & distillery (EasySpeak) and restaurant called Fondue. where you'll receive 20% off at during your stay! WE ARE PET FRIENDLY READ RULES IN "THE SPACE SECTION" BEFORE BOOKING

Guest Suite, Private Entrance

One bedroom guest suite w/ private coded entrance. The space is complete with full kitchen stocked with the essentials, including microwave and Keurig coffee maker. Queen size bed in bedroom w/ extra pillows and blankets. Sofa queen size pull out bed complete w/linens. 12 miles to DE Turf, 7 miles to First State BMX, 26 miles to Lewes, 29 miles to Rehoboth, 27 miles to Dover Downs, 16 miles to Dogfish Brewery. Our home is attached and we are happy to answer any questions.

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.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

Woodsong Suite & Getaway!

Contemporary pieces blended with rustic decor creates a relaxed and eclectic feel in the great room. The 2 bedrooms are a spa-romantic style in one bedroom (new queen!) and an elegant travel feel in the other (queen). This is a one-floor, private suite with a separate entrance. Full bathroom and simple galley-style kitchen. I am nestled a half a mile off of a secondary road on a ten-acre wooded lot. Lots of wildlife and extremely peaceful, a perfect getaway!

Beachin' Inn Milton

Welcome to Beachin' Inn Milton! This cozy apartment located in the quaint, historical town of Milton, DE is the perfect getaway. Our apartment is light and airy with a beach theme. Enjoy the entire apartment to yourself with a keyless private entrance, full bath, washer/dryer, free Wifi and stocked assorted coffee pods. There is no stove/oven, however, we offer a microwave, toaster oven, Air Fryer and induction burner.There is private parking right out front