Vacation rentals in Eastern Shore

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Top-rated vacation rentals in Eastern Shore

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Top guest favorite

Guest suite in Delmar

5 out of 5 average rating, 106 reviews

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1 bedroom studio centered on a quiet street in historic Delmar, MD. Kylan Barn - 6 min. Venue 54 - 7 min. Downtown Salisbury - 15 min. SU - 20 min. OCMD - 45 min. Sleeps (4). Queen bed and full size pull-out couch. Workspace, fast WIFI, kitchenette, private laundry. Safe neighborhood, off-street parking, well lit walkways. Inviting backyard patio with 6' tall privacy fence all just for you. Stylish, super clean and comfortable. Sorry no pets or smoking.

Top guest favorite

Cottage in Frankford

4.99 out of 5 average rating, 165 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!

Top guest favorite

The historic building features prominent columns at its entrance, adorned with vibrant banners displaying the words 'Make Tomorrow Yours.' A neatly landscaped garden with bright green shrubs enhances the building's inviting appearance under a clear blue sky.

Home in Salisbury

4.99 out of 5 average rating, 206 reviews

Salisbury Cottage

Relax in a quiet part of Salisbury in this cozy, 3 bedroom, 2 full bath home. A farmhouse feel welcomes you home after a long day at work, a sports trip, or vacation. Enjoy all new furniture including luxury bedding and smart TVs. Centrally located and close to downtown for shopping and dining at one of the many local restaurants. Only 30 minutes from the beaches of Ocean City & Assateague Island. One mile from Tidal Health PRMC and a half block away from Salisbury University.

Guest favorite

A wide-angle view captures the beach and ocean, with soft waves lapping at the shore. The surrounding buildings are visible, including the condominium structure featuring floor-to-ceiling windows. A beachfront pool and tennis courts occupy the area below, while sunbathers and umbrellas dot the sandy beach.

Condo in Ocean City

4.96 out of 5 average rating, 277 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

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, 191 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, 119 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, 131 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, 184 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 wooden table features a plate of oysters and a bottle of red wine, accompanied by a glass filled with wine. A fire pit emits a warm glow nearby, with the scenic view of a creek and trees in the background.

Loft in Hebron

5 out of 5 average rating, 103 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 private outdoor space features stone flooring complemented by lush greenery and colorful flowers. Two blue chairs are positioned for relaxation beneath a spacious deck. A white staircase leads to the upper level, surrounded by vibrant planters and a white picket fence.

Guest suite in Ocean City

4.98 out of 5 average rating, 371 reviews

The Elbridge Bayfront Studio

The Elbridge is a luxury studio apartment in downtown Ocean City. Beautiful bay view from studio windows. This bayside studio includes parking, a private garden entrance, and luxurious king bed. Located 4 blocks from the beach, the space is in a downtown residential neighborhood. Additionally included are bikes, bodyboards, beach chairs and a beach umbrella. Walking distance to delicious local restaurants, the boardwalk, and the beach!

Guest favorite

A fire pit is surrounded by four red Adirondack chairs, situated on a gravel surface. Lush green trees form a natural backdrop, enhancing the outdoor space's connection to nature. Two torches are positioned nearby, providing ambient lighting for gatherings.

Tiny home in Salisbury

4.85 out of 5 average rating, 136 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

Top guest favorite

A wooden gate opens to a gravel path, leading toward a charming tiny house surrounded by greenery. A colorful sunset casts warm hues over the landscape, while a decorative pergola adorned with climbing plants frames the scene.

Tiny home in Selbyville

4.98 out of 5 average rating, 281 reviews

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.

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Popular amenities for Eastern Shore vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Eastern Shore

An elevated beach house stands gracefully by the canal, with a spacious upper deck visible under a colorful twilight sky. Lush trees frame the property, while a wooden dock provides direct access to the water, creating a serene and inviting coastal atmosphere.

Home in Ocean View

5 out of 5 average rating, 6 reviews

Cozy Stylish Waterfront 3BR Kayaks Fireplace Porch

ArnavRating, 5 stars3 days ago

This place was amazing. Sage and Shannon were wonderful hosts and they were super helpful. Anytime I texted they always responded immediately and gave us assistance when we needed it. They also organized the house very nicely and gave us everything we needed. The coffee maker was also great to have in the mornings. The neighborhood is very serene and the neighbors were very friendly as well. I also enjoyed the nice stream at the back of the house. There was also a nice shopping center 5 minutes away for any groceries we needed to cook at home. In addition, the deck was very nice and the lights lit up very nicely at night. Overall, they really made this place feel like home throughout our stay and the beds were very comfortable as well. Great experience staying here and we look forward to staying here again at this place in our future trips to Bethany.

Guest favorite

Home in Ocean City

4.95 out of 5 average rating, 255 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

ErikaRating, 5 stars1 month ago

Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!

A compact laundry area is visible, featuring a stacked washing machine and dryer in white. Shelving units with cleaning supplies and storage bins are positioned on either side, providing additional space for organization. A stainless steel refrigerator is located to the right.

Condo in Ocean City

4.67 out of 5 average rating, 208 reviews

Hidden Gem (North OC) - 2 mins to Beach

AltonRating, 5 stars6 days ago

Ryan’s spot was an absolute gem! Super clean, stylish, and had everything we needed for a smooth and comfortable stay. The location was perfect—close to everything, but still quiet enough to relax. Ryan was super responsive and made check-in a breeze. You can tell he really cares about the guest experience. Would 100% stay here again and recommend it to anyone looking for a hassle-free getaway!

A cozy outdoor seating area features a sectional sofa with soft cushions and a central firepit emitting a warm glow. In the background, a swimming pool is visible, surrounded by a black safety fence and shaded by tall trees.

Tiny home in Millsboro

4.81 out of 5 average rating, 129 reviews

Farm Cottage - POOL - 30 Min to BEACH

PolRating, 5 stars3 days ago

Second time at Renee's place and once again it was perfect. We stay on a Saturday night and really enjoy the place, it's quiet and very comfortable. It's perfect if you want to relax and disconnect from the city. It's not far from Bethany beach. Renee is very reactive and charming. We really recommend Renee's place!

Guest favorite

The outdoor space features a private pool with a uniquely shaped design, surrounded by a spacious deck. The vibrant green lawn adds a refreshing touch, while a covered seating area is visible nearby. The two-story house provides a picturesque backdrop with plenty of windows and outdoor seating.

Home in Salisbury

4.9 out of 5 average rating, 62 reviews

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

ChristineRating, 5 stars3 days ago

We cannot say enough good things about this home. It had everything we could have wished for! Our family of 11 enjoyed every moment and wished we didn’t have to leave. The house was immaculate. The host (Caleb) was so quick to respond to our messages and even popped by to help us figure out the surround sound one evening. We cooked and ate every meal at the house and had all kinds of things to do just minutes from the house (disc golf, golf, pickle ball, a zoo, shopping). We even decided to forego our plans to go to the beach because why would we go when they have their amazing private pool. We were entertained from morning to night with all the games and surround sound movie room. There was NOTHING we didn’t love about this home. Thank you, Glen and Caleb! I would give you 10 stars if I could!

Top guest favorite

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

5 out of 5 average rating, 11 reviews

Waterfront Cottage in Mt. Vernon

KylieRating, 5 stars3 days ago

Can’t beat the views. It’s a quick drive into town. There is a great take out seafood restaurant!

Top guest favorite

Tiny home in Lower Township

5 out of 5 average rating, 31 reviews

Coastal Quad: Hot tub | Mini Golf | Arcade | Gym

NicoleRating, 5 stars1 day ago

We had an absolutely wonderful stay during our mini-moon! The accommodations were incredibly spacious for a tiny home, and the bed was super comfortable. Everything was spotless with high end finishes and we really enjoyed the private hot tub and the well-equipped gym. It was the perfect getaway! We will be back to stay in another one of the tiny homes in the coastal quad collection. As an interior designer, it was up to my standards on style and comfortability! Thank you Donna!

Guest favorite