Holiday rentals with a fireplace near Assateague Island National Seashore

Pony Pines!Your Waterfront Getaway Cottage Awaits!

Imagine a quiet retreat on the water where the sunsets are magnificent, and wildlife such as geese, raccoons, deer, owls, and egrits are to be experience in the backyard. Pony Pines offers a firepit, a master bedroom with a jacuzzi tub, and a clawfoot tub on the main floor. We have 2 Kayaks for your use on the canal, and a storage shed with some of the beach accessories you may need for your days at the Ocean. Linens are provided! Relax with your whole family at this peaceful, Happy Place.

Private pool, waterfront, kayaks, bikes, firepits!

The Golden Quarter Farm is 150-acre waterfront, nature preserve, centrally located 5 miles from Assateague Island and its wild ponies, small town charm of Berlin, and OC Boardwalk. With a pool, kayaks, SUP, hiking trails, bikes, and birding, there's little reason to leave the property! Max of 8 adults. No parties. No Pets. Renters must sign a Rental Agreement & provide $250 refundable damage deposit. Pool open April-Sept 30th, NOT heated. 5% local room tax will be collected after booking.

Jay's Retreat

Welcome to Jay’s Retreat, a charming waterfront oasis nestled in scenic Oyster Bay. This beachy 3-bedroom, 2-bathroom home accommodates up to 6 guests and is pet-friendly, making it an ideal space to vacation with your entire family. The spacious screened porch offers the perfect perch to savor your morning coffee with the sunrise or relax with friends and family while enjoying fresh, locally sourced seafood. End your days by the fire pit, soaking in the peaceful bay views and coastal breeze.

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!

Snug Harbor Hideaway

Escape to Snug Harbor Hideaway, a 4-bedroom, 2-bath bayfront and canalfront retreat located in Berlin, MD. This cozy bungalow offers stunning water views from every angle, a peaceful front porch for your morning coffee, and a spacious backyard perfect for family dinners under the sky. Bring along a small boat and dock right at the bulkhead for effortless adventures. Enjoy a 10 min drive to Assateague Island and Ocean City’s beaches, restaurants, and nightlife!

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

Welcome to our stunning oceanfront retreat! This luxurious property offers the perfect combination of comfort, style, and breathtaking views. With a spacious J-shaped wraparound balcony, you can indulge in panoramic vistas of the sparkling ocean waves from every angle. Ideal for groups of up to 8 guests, this two-bedroom, two-bathroom getaway provides ample space for everyone to unwind. Book today for the vacation you'll never forget!

Whimsical and Wonderful Retreat near the Ocean

This home is located in beautiful Snow Hill Md, which sets in between to popular beaches. You can be in Ocean City Md within 25 short miles ( all highway), or visit wonderful wildlife and ponies at Assateague Island MD, or Assateague Va, which is only 23 miles. Bridle parties for Castle Farms can stay and be at your event within 7 miles from my home.

Once Upon A Tide

A quaint beach cottage located in the heart of Chincoteague Island. A five minute walk to all the main attractions and a 15 minute bike ride to the Beach. This newly renovated cottage is a tranquil getaway that invites you to refresh and relax.

Contemporary & Cozy Guesthouse

Take a peek at this contemporary quick stay! Our cozy guesthouse features private entry beyond the 6 feet privacy fence gate. Guests may also enjoy the outdoor seating in a quiet country setting.