Holiday houses in Greenwood

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Top-rated holiday rentals in Greenwood

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.
Apartment in Greenwood
4.97 out of 5 average rating, 678 reviews

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)

Top Guest favourite
Home in Milford
4.97 out of 5 average rating, 31 reviews

Stunning Home-DE Turf 2 min & Gateway to beaches

**Only a few dates in July left** Your family will be close to everything when you stay at our well appointed, centrally-located home! Just 2 min to the Turf Field Complex, 5 min to restaurants, movie theater, bowling, and shopping. 12 min to DAFB, only 20 min to the beaches!!! -3 bed and 2 bath -Sleep number King, 2 Full, 2 Twin beds- sleeps 9 -Open LR, DR, Kitchen w/pellet stove FP -Fast Wifi & tv’s -Pet friendly -HUGE, private fenced in yard(1.5 acres), fire pit, patio,basketball court!

Top Guest favourite
Guest suite in Lincoln
4.93 out of 5 average rating, 215 reviews

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.

Top Guest favourite
A cabin nestled among tall trees presents a rustic appearance. A flowering garden features pink blooms and lush greenery, complementing a wooden fence. The cabin's dark exterior contrasts with the vibrant natural surroundings, creating a serene atmosphere.
Cabin in Greenwood
4.98 out of 5 average rating, 49 reviews

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.

Top Guest favourite
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 524 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Top Guest favourite
A comfortable seating area is presented with a dark sofa featuring cushions. A small coffee table sits on a patterned area rug, while large windows allow natural light to illuminate the space. The kitchen area is visible in the background, with modern appliances.
Guesthouse in Greenwood
5 out of 5 average rating, 34 reviews

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.

Top Guest favourite
A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.
Home in Greensboro
4.97 out of 5 average rating, 137 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.

Top Guest favourite
A living area is featured, highlighted by a red sectional sofa and two brown armchairs. A small round table sits between the chairs, complemented by large windows adorned with orange curtains. A cozy black rug covers the floor, adding warmth to the space.
Home in Denton
5 out of 5 average rating, 11 reviews

Welcome to Harmony House!

Welcome to our cute, tiny but mighty home that offers a convenient location with just the perfect amount of space to relax and recharge. Each of the three bedrooms comes with a Nectar mattress and plenty of comfortable options for sleeping, along with storage for your items and luggage. The walk-in shower and complete kitchen will allow you to bring comforts from home and the lightning fast wi-fi signal keeps you connected during your stay. Convenient access to Highway 404.

Guest favourite
Home in Bridgeville
5 out of 5 average rating, 14 reviews

Helen's Homestead

Welcome to Helen’s Homestead, a beautifully rebuilt farmhouse in Bridgeville, Delaware. With 5 bedrooms, 3 bathrooms, and space for up to 12 guests, it’s the perfect setting for family getaways, group retreats, or intimate celebrations. Enjoy relaxing on the patio, or spend time outdoors on our new putting green, perfect for a little friendly competition. Whether you’re planning a quiet escape or hosting a small gathering, Helen’s Homestead offers warmth, space, and charm.

Superhost
Home in Harrington
4.92 out of 5 average rating, 12 reviews

Frederica-Milford-Harrington, DE Cozy Retreat!

Stay close to it all in this centrally located Rancher home! 🏡 Pet-friendly 🐾 with a fully fenced backyard 🔒🌿, it’s perfect for families and furry friends. Just minutes from: • Frederica Sports Complex ⚽ (10-mins) • Delaware beaches 🌊 (35–45 mins) • Outlet shopping 🛍️ (25–30 mins) • Harrington Casino 🎰 (5–10 mins) • Killens Pond State Park (5-mins) • Local Milford & Harrington businesses 🏪✨ (5–15 mins) Convenience, comfort, and fun all within easy reach!

Superhost
A single-story cabin is framed by trees, featuring a covered front porch with a light green door. The building is surrounded by manicured shrubs and a gravel driveway, leading to a spacious outdoor area for recreational activities.
Cabin in Houston
4.84 out of 5 average rating, 25 reviews

Rustic Cabin sleeps 4 on farm setting private

Adventures Await Retreat presents this spacious Cabin on a working farm with plenty to do. Hiking on our 2.5m nature trail or catching and releasing in one of our stocked ponds to a 9hole mini golf or just hanging out with our personable farm animals there is something for everyone. Local food all around and if trying your luck at the slots there is a casino only 6 miles away. Their is an adventure for everyone.

Guest favourite
The exterior of a single-story home is showcased, featuring a light-colored facade with a front porch and white railings. A manicured lawn and several trees are visible, creating a serene atmosphere. A paved driveway leads up to the house, while dark rain clouds suggest a potential rainstorm.
Home in Seaford
4.92 out of 5 average rating, 111 reviews

Cozy home in Seaford

Relax with your family in this quiet & peaceful home located in the heart of Seaford Located near state parks to hike, hunt, fish A short 50-minute drive to the Delaware beaches Conveniently located 5 minutes from Heritage Shores golf course and wedding venue Less than 5 miles from Vanderwende Acres and Willowbrook Weddings 5-10 minutes from Walmart, Dunkin Donuts, Starbucks, and many fast food option

Popular amenities for Greenwood holiday rentals

  1. Airbnb
  2. United States
  3. Delaware
  4. Sussex County
  5. Greenwood