Posted on 9/26/2024

10 Cozy Vacation Rentals for a Relaxing Off Season Getaway

When you’re looking for a cozy retreat by the sea this Fall or Winter, Chincoteague Island and Ocean City, MD have a host of vacation rentals that offer comfort, charm, and beautiful surroundings. Whether you’re looking for a quiet, romantic escape or a quick family getaway, these handpicked rentals provide the perfect setting for your next getaway. Here are 5 vacation rentals from each destination complete with all of the comforts of home.


Beach Blessing

Gather around a cozy fire or spend your evenings on the screened in porch after  exploring Chincoteague at this beautiful Boothe Street home. With a great location close to a number of dining options such as The Ropewalk and Bill's Prime Seafood and Steaks, you're always just a short drive or bike ride away from delicious seafood!


Sunny Shack

There's SO much to do at this South Main Street home. Bike around town using the included bikes, or spend those cold or rainy days inside with so much to do including a Billiards table, Table Tennis, Board games, more! 


Assateague Inn

The Assateague Inn is perfect for a weekend getaway for a couple or small family. Head out to the private pier and take in the area’s natural beauty, or take a short walk to one of the nearby restaurants and attractions. If you’re looking to visit Chincoteague without breaking the bank, you’ll want to start your vacation rental search at the Assateague Inn!


Marsh Madness

If you’re looking to bring the entire family to Chincoteague (or multiple families,) Marsh Madness is a perfect vacation rental to start your search! Sleeping up to 11 guests, the home has plenty of space for everyone, including your family dog! The home’s new fenced in area is perfect for letting your four legged family members burn off some energy, and the theater room is the perfect space to gather for a family movie night! Oh, and have you seen the views?!


Marsh Madness

You'll feel like you're pulling onto your own private island when you finally turn onto Marsh Island and  make it to this luxury townhome! A lovely end unit, Captain's Rest sits right on the water's edge, and allows you to fish and crab right from the backyard! Oh, and don't forget your boat! Captain's Rest has access to the pier with boat slips!




Golden Sands 614

Golden Sands 614 has it all for the couple looking for a quick getaway in Ocean City, MD. A Penthouse Level Indoor Pool, Fitness Center, and Game Room await guests on the 22nd floor, and the condo’s open layout will make you feel right at home. Wake each morning to amazing views and the sound of crashing ocean waves, and know that you’re in a great location close to some OCMD’s best dining and entertainment options!


57 Wood Duck Drive

Located in the tranquil Ocean Pines community, 57 Wood Duck Drive offers access to wonderful amenities including an Indoor Pool, Playground, Library, Restaurants, and Golf! The home’s garage has plenty of entertainment for your family including Air Hockey, kayaks, and fishing poles!


Marigot Beach 1105

Like Golden Sands 614, Marigot Beach 1105 is perfect for a couple’s getaway. The condo also features a spacious Indoor Pool! Grab your favorite book or morning coffee, and relax while enjoying the ocean view from the private Oceanfront Balcony, or head out for a day full of exploring your favorite beach town!


Belmont Towers 606

It’s hard to beat Belmont Towers’ location. Right on the famous OCMD Boardwalk, this 2 bedroom condo puts your right in the heart of the OC action. Begin and end your days on the wonderfully furnished balcony, and spend your days strolling the boardwalk and exploring all that OC has to offer at this peaceful time of year!


Summer Beach 501

Newly renovated throughout, this 5th floor condo has everything you need to create priceless family memories year after year. Take in the sprawling views of the ocean from the extra large living room, or from the kitchen while you’re bringing together your family’s favorite meals. With room for up to 6 guests, there entire family is welcome at this 35th Street staple.




We're so excited to share these beautiful properties with you and your family, and will be adding MORE properties throughout the off season! Be sure to check back for updates, or give our team a call at (757) 336-7070 if you need any help finding the perfect place to call home during your next getaway!

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