Holiday rentals in Showell

4.9 out of 5 average rating, 150 reviews

Cottage in Ocean Pines

Cozy Beach Getaway in the Lovely Ocean Pines North

Welcome to our Cozy Beach Getaway!! ☀️🌊👙⛱️🐚🏖️🌞🌅⛅️ This beautiful and peaceful home is located in Ocean Pines North. 3 bedrooms, 2 bathrooms. Peaceful front porch and back deck. 🏡🏝️ Whether you’re looking for a summer family vacation, girls weekend getaway, or just a break from reality, this is the perfect place! Washer/dryer 🧺, two smart TV’s 📺, driveway fits 4 cars comfortably 🚗. Enjoy the hustling city of Ocean City during the day and stay in the tranquility and peaceful Ocean Pines at night! 🏖️💞☀️

Guest suite in Ocean Pines

4.95 out of 5 average rating, 377 reviews

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

5 out of 5 average rating, 233 reviews

Ranch in Selbyville

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.

4.97 out of 5 average rating, 167 reviews

Apartment in Ocean Pines

Getaway in Ocean Pines

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

4.98 out of 5 average rating, 120 reviews

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

4.95 out of 5 average rating, 115 reviews

Home in Selbyville

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

Guest suite in Ocean Pines

4.99 out of 5 average rating, 120 reviews

Newly built bright and airy guest suite!!!!

Welcome to our new 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a breathtaking waterfront Yacht Club with restaurant and live music (seasonal), Robert Trent Jones Sr. golf, farm market, playgrounds, 5 pools/fee (4 seasonal), and racquet club.

4.96 out of 5 average rating, 448 reviews

Townhouse in Ocean City

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 :)

4.96 out of 5 average rating, 274 reviews

Apartment in Ocean City

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.

4.99 out of 5 average rating, 201 reviews

Guest suite in Berlin

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin,Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

4.92 out of 5 average rating, 51 reviews

Home in Berlin

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

Come stay in our 2nd Floor Condo on our private 5-Acre Property! Enjoy the Barn-Like look from the outside, but inside, find a modern & spacious condo with a fully-equipped kitchen. Located in Berlin, Maryland, you are minutes to Historic Berlin and only 15 minutes to all the fun that Ocean City, Maryland has to offer! Have your morning coffee on the deck and soak in the scenic views or pitch a tent, light up the fire pit, let the kids run wild! We'll see you soon!

4.99 out of 5 average rating, 123 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

Newly renovated, sparkling, spacious house with room for seven and waterfront views is waiting for you. Perfect for a single or double family getaway, girls weekend, or quiet retreat. *Please note this is a No Smoking and No Pet Property. **We are located in a quiet, residential neighborhood with lovely neighbors in close proximity. Please consider this when booking. ***We do not supply sheets and towels. Rental License #2162

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Other great holiday rentals in Showell

4.96 out of 5 average rating, 49 reviews

Summer By The Sea

MarlenneRating, 5 starstoday

This was my second time staying at this location and continues to be great spot. Susan is very responsive and hospitable. The place is cozy and clean in a very quiet/peaceful neighborhood. There lots to do within a short driving distance. It will continue to be a must stay spot when we are in the area!

Superhost

Home in Berlin

5 out of 5 average rating, 4 reviews

Mins to Golf & Beach! Private Pool & Luxe Firepit

CaroleRating, 5 stars2 weeks ago

Lindsay and Andrew’s Summer Breeze home in Berlin met all of our expectations. We particularly enjoyed the pool, grill and outdoor amenities - which made it perfect for our family holiday weekend getaway. The house is well kept, comfortable, neatly stocked with all essential amenities as described and, is staged and modeled exactly as pictured in the photos. We appreciated a quiet retreat, off the beaten path, yet we had an easy and quick drive to stores, restaurants and to the Ocean City boardwalk. As hosts, they were very responsive and efficiently communicated what we needed to know in advance, making our stay easy and smooth. From the booking process to assisting us with a couple of adjustments, they did not hesitate to help us. If there is an opportunity for us in the future, we’d love to stay again. Thank you Lindsey and Andrew!

5 out of 5 average rating, 17 reviews

Sunshine at Ocean Pines

DominicRating, 5 stars1 month ago

We had an amazing time at Phillip’s place in Ocean Pines! The home was clean, comfortable, and had everything we needed for a relaxing getaway. It’s located in a peaceful, wooded neighborhood that still offers easy access to Ocean City, beaches, and local restaurants. Phillip was a fantastic host—very responsive and thoughtful, making sure our stay was smooth from check-in to check-out. The back deck and cozy living space made it easy to unwind after a day of exploring. We would definitely stay here again and highly recommend it to anyone visiting the area!

4.98 out of 5 average rating, 61 reviews

Guest house in Berlin

Resilience of Berlin, Charming 2 Bedroom Cottage.

LilyRating, 5 stars2 weeks ago

We loved our stay at Annie’s cottage. It was walkable to the cute and quaint town center where we consumed a year’s worth of ice cream in a few days. It’s was also only a 15-20 mins drive to ocean city beach or assateague island. We were pleasantly surprised when we checked in to the cottage. It was bigger in person and you can feel the love Annie has for the cottage through her decoration. We would highly recommend this place.

5 out of 5 average rating, 34 reviews

Flat in Ocean Pines

Be our guest

ChristinaRating, 5 stars3 weeks ago

This host and our stay were top-notch! This interior was very modern and super comfortable. Honestly, that bed just made the entire stay worth it. I travel for work and have never felt so comfy or slept so soundly in a bed. Directions for everything were easy to understand and use. Host was very responsive. I highly recommend this location for Ocean City travel!

4.94 out of 5 average rating, 16 reviews

Newly Renovated 4BR 3Bath Home with E/V Charger.

RachelRating, 5 stars3 weeks ago

Susans location was great for us working on Ocean Parkway! The neighborhood was quiet and homey feeling. The house itself was very clean and stocked with all the things you would need for a long stay. Susan made sure we were comfortable and had everything we needed for our stay. A great home, great location, and great host!