Eastern Shore vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Eastern Shore

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

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Top guest favorite

A comfortable living area features two light gray sofas and an armchair, all adorned with patterned throw pillows. A ceiling fan is positioned in the center, while natural light enters through two windows. A doorway leads to the dining area in the background.

Home in Fruitland

4.97 out of 5 average rating, 354 reviews

Johnna's House

Two story dwelling in a prime location on the Eastern Shore of Maryland. It is conveniently located 32 miles from Ocean City. It is equipped with central air and heat, a two car garage, WiFi and cable. It is centrally located and is within walking distance of eateries and Super Wal-Mart. Pharmacies are in close proximity. It is also in walking distance from the local college, Salisbury University. And is less than a 1/2 mile from Salisbury City Limits. The local mall is only a 10 minute drive.

Top guest favorite

A houseboat is positioned along the water, featuring a light-colored exterior and dark roof. A spiral staircase leads to a rooftop deck, where bright orange umbrellas provide shade. Wooden docks extend towards the boat, with views of greenery and boats in the background.

Houseboat in Grasonville

4.99 out of 5 average rating, 179 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Top guest favorite

Ranch in Selbyville

5 out of 5 average rating, 237 reviews

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

Top guest favorite

A silhouette of a pygmy goat is positioned atop a wooden beam, framed by bare trees and a softly illuminated sky at dusk. The fading light casts a calming atmosphere over the hobby farm.

Apartment in Greenwood

4.97 out of 5 average rating, 591 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

Cottage in Frankford

4.99 out of 5 average rating, 166 reviews

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. 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!

Guest favorite

Guesthouse in Cambridge

4.99 out of 5 average rating, 123 reviews

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Guest favorite

Two charming cottages are positioned on a well-kept lawn, showcasing shingled exteriors and welcoming front porches. A paved pathway leads to both cottages, surrounded by trees and open space, with American flags displayed on each porch, reflecting a friendly atmosphere.

Tiny home in Ocean View

4.91 out of 5 average rating, 193 reviews

Tiny Cottage at Good Earth, near Bethany Beach

Welcome to the "Tiny Thyme Cottage" at Good Earth. The cottage is super cozy, perfect for a couple, with 1 queen bed, a kitchen & bathroom, and a small living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include 2 on-site restaurants, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, and 2 cottages on the property. Staying at Good Earth is more than just a beach trip!

Guest favorite

Two friendly goats are positioned within a fenced area, displaying their distinct black coats and prominent horns. Sunlight casts shadows on the ground, creating a pattern that contrasts with the earthy tones of the surrounding environment.

Bus in Frankford

4.95 out of 5 average rating, 121 reviews

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

Superhost

A charming outdoor area is showcased along a wooden walkway beside the water. Colorful banners and umbrellas adorn the pavilion, while wooden chairs invite relaxation. The grassy space features tiki torches, and boats can be seen docked in the distance under a bright blue sky.

Houseboat in Snow Hill

4.87 out of 5 average rating, 134 reviews

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

Top guest favorite

Guesthouse in Milton

4.97 out of 5 average rating, 185 reviews

The Book Nook - A Private Downtown Retreat

In the heart of downtown Milton, you will find a newly renovated guest cottage less than 10 miles to the beach! If you plan on staying local, simply park your car at the designated off-street parking space and travel by foot to the many shops, restaurants, and attractions offered in historic Milton. Whether you're walking the few short blocks to Dogfish Head Brewery or spending an evening at the theater, The Book Nook will serve as the perfect location!

Top guest favorite

A rustic barn loft is nestled among tall trees, with warm light spilling from upstairs windows. The exterior features wooden siding and a welcoming staircase leading to the upper deck. A gravel path guides visitors to the entrance, enhancing the secluded atmosphere.

Loft in Hebron

5 out of 5 average rating, 104 reviews

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

Top guest favorite

A wooden boardwalk extends toward a sandy beach, flanked by tall grasses and wetlands. The peaceful water is visible in the distance under a clear blue sky, with a few clouds adding texture to the scene.

Cottage in Westover

4.99 out of 5 average rating, 228 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.