Vacation rentals in Greensboro

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Greensboro

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

%{current} / %{total}1 / 1
Top guest favorite
A cozy bedroom features a full-sized bed covered with a nautical-themed quilt. A nightstand and a dresser with multiple drawers are situated against the walls. Decorative wall art adorns the yellow walls, while soft lighting creates a welcoming ambiance. A plush area rug adds warmth to the space.
Guest suite in Lincoln
4.93 out of 5 average rating, 254 reviews

Nicencozy, near DE Turf, Bayhealth, beaches, AFB

Stay in peace at this smoke-free, quiet abode. Within 10 mins of Milford (Bayhealth Sussex, Walmart, shopping, pharmacies, restaurants, etc.). 15 mins: DE Turf, Milton, breweries. 20-30 mins: Bowers Bch, Pickering Bch, Sports at the Bch, Dover & Georgetown, theaters & casinos. 30-45 mins: other beaches and outlets. Please review Guide Book and House Manual after booking, and call us after a last minute booking, so we can tell you how to get in. Snacks, water, etc. provided while supplies last.

Top guest favorite
A modern houseboat is anchored at the dock, featuring a covered deck with two lounge chairs. Large windows offer views of the waterfront and allow natural light into the interior. The structure sits on wooden stilts above calm waters, showcasing a serene boating environment.
Houseboat in Kent Narrows
4.97 out of 5 average rating, 176 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Top guest favorite
A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.
Home in Chestertown
4.97 out of 5 average rating, 155 reviews

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

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, 637 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
A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.
Cottage in Frankford
4.99 out of 5 average rating, 198 reviews

19th Century Cottage with Modern Amenities

Book your Hallmark Christmas stay today, fully decorated by Thanksgiving until the end of January!! Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Top guest favorite
A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.
Apartment in Chestertown
4.97 out of 5 average rating, 258 reviews

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Top guest favorite
The exterior of a large, historic house is viewed from the river, surrounded by leafless trees and greenery. A deck is visible, along with a patio area featuring white chairs. The structure showcases multiple levels and a traditional architectural style.
Apartment in Chestertown
5 out of 5 average rating, 130 reviews

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!

Top guest favorite
The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.
Guesthouse in Easton
4.99 out of 5 average rating, 632 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Top guest favorite
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
4.96 out of 5 average rating, 114 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 favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville
4.99 out of 5 average rating, 317 reviews

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Superhost
A comfortable living area features a cozy gray sofa facing a stone fireplace. A wooden coffee table sits on a decorative rug, while a flat-screen TV is mounted on the wall. Light enters through a nearby window, illuminating the space.
Guesthouse in Dover
4.83 out of 5 average rating, 161 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.

Top guest favorite
The chalet is depicted at night, showcasing its A-frame structure with large illuminated windows. The wrap-around deck features outdoor seating, while the surrounding trees provide a sense of seclusion. Soft lighting from inside highlights the inviting interior layout.
Farm stay in Chestertown
4.94 out of 5 average rating, 176 reviews

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.

Popular amenities for Greensboro vacation rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Caroline County
  5. Greensboro