Vacation rentals in Greenwood

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Greenwood

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

1 of 1 pages1 / 1

Top guest favorite

A stately historic home is depicted from the front, showcasing a charming design with white siding and a blue front door. The property features a peaked roof and is surrounded by lush greenery, including several trees and well-maintained shrubs.

Place to stay in Denton

4.95 out of 5 average rating, 101 reviews

Turnbridge Manor - Waterfront Historic House

A waterfront property located in the heart of downtown Denton, on Maryland's Eastern Shore, the stately historic home built in the 1860’s offers modern amenities and luxurious accommodations. Guests can take in the charm of Denton from our sunny front porch or sit in the many outdoor oases to relax and enjoy the beautiful terraced grounds overlooking the tranquil Choptank River. Located less than 60 minutes to the beach, 35 minutes to historic St. Michaels and minutes to the Harriet Tubman Byway

Top guest favorite

A spacious living room is defined by a large flat-screen television mounted on the wall. Comfortable seating includes two dark sofas and an armchair, arranged around a coffee table. Natural light enters through two wide windows, enhancing the warm ambiance of the space.

Home in Federalsburg

5.0 out of 5 average rating, 43 reviews

Welcome to the Cornfield!

Conveniently located right off highway 404 outside of Denton this spacious 3 bedroom modular home is ready to welcome you. Electric car charger, Nectar mattresses, filtered water, a dedicated fiber connection and 2 large televisions are some of the amenities to enjoy. Centrally located in Caroline County, this home is 20 minutes to Seaford or Harrington, 30 minutes to Easton and around an hour to Rehoboth Beach. Pet friendly home on a couple acres with convenient access to Martinak and Tuckahoe.

Top guest favorite

Home in Milford

4.97 out of 5 average rating, 37 reviews

Stunning Home-DE Turf 2 min & Gateway to beaches

Your family will be close to everything when you stay at our well appointed yet comfortable, 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! ✅ 3bed/2 bath- sleeps 9 ✅ Sleep number King, 2 Full, 2 Twin beds, pack-n-play ✅ Open LR, DR, Kitchen w/pellet stove FP 📺 Fast/secure Wifi & TV’s 🐾 Pet friendly ⭐️ HUGE, private fenced in yard(1.5 acres), fire pit, patio,basketball court!

Top guest favorite

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, 689 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 favorite

The spacious living area features two comfortable gray couches and a central coffee table, surrounded by natural light from large windows. A textured accent wall and decorative plants enhance the room's ambiance, while neutral-toned stools provide additional seating.

Home in Milton

4.96 out of 5 average rating, 131 reviews

Gracious & Spacious- Near DE Turf Complx & Beaches

🏡✨ Welcome to our charming home with Modern French decor, tucked just off Coastal Highway (SR1) in Milton. 🌿 A tranquil coastal retreat with easy access to DE Turf 🥍, Lewes Beach 🏖️, and Rehoboth Beach 🌊 — convenience meets calm. Two bedrooms 🛏️, two sofa beds 🛋️, and two bathrooms 🛁 anchor a sunlit, spacious living area that feels warm, refined, and inviting. The kitchen is made for gathering 🍽️🥂, with a washer and dryer for added ease. Coastal living at its absolute finest! 🌅

Top guest favorite

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, 54 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 favorite

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

5.0 out of 5 average rating, 40 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.

Guest favorite

A modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator, microwave, and dishwasher. A granite countertop provides ample workspace, complemented by bar seating with black stools. Natural light enters through a nearby window and the entrance door, enhancing the bright atmosphere.

Home in Milford

4.94 out of 5 average rating, 220 reviews

Downtown Milford | Near DE Turf & Beaches

Experience Riverwalk Retreat, a beautifully renovated home in historic downtown Milford. Walk to restaurants, breweries, coffee shops, boutiques, and the scenic Riverwalk. Perfect for beach trips, sports tournaments, casino weekends, or relaxing getaways. Private parking, fully equipped kitchen, fast Wi-Fi, Roku TV, washer/dryer, and dog-friendly. Minutes from DE Turf, Sports at the Beach, Killens Pond, Dover, and Delaware’s beaches. Please note our home is dog-friendly. 🐶

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 favorite

The master suite features wooden beams and log walls, creating a rustic atmosphere. A plush bed is positioned next to a classic bench. Soft lighting illuminates the space, while a colorful woven rug adds warmth to the wooden floor.

Cabin in Goldsboro

4.86 out of 5 average rating, 179 reviews

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...

Guest favorite

A modern living area features a light-colored sectional sofa alongside a dark blue armchair. A round coffee table displays a decorative item, while a bright kitchen with stainless steel appliances is visible in the background. Natural light enters through large windows, enhancing the openness of the space.

Apartment in Seaford

5.0 out of 5 average rating, 38 reviews

Apartment in Seaford, DE

Enjoy a stylish suite at this centrally-located place in Seaford. We are within 45 min to 1 hour to the beach and minutes to the Nanticoke River. A golf course is located a couple miles away. Everything you need for your stay included in kitchen and bath. 1 parking spot available. Steps lead up to your private apartment.

Guest favorite

Tent in Denton

4.91 out of 5 average rating, 11 reviews

The TuckAway Tent

Escape to your private glamping retreat on 2 serene acres surrounded by open fields and trees. Your spacious luxury wall tent that awaits blends both comfort and solitude.