Rentals
543 properties available
Memories made together last a lifetime…..Welcome to Oyster Bay Oasis in ever-popular Oyster Bay I on Chincoteague Island - the perfect home base for your family’s next adventure! Only 5 minutes from Assateague National Seashore, where our Wild Ponies roam free, this adorable home has all the quintessential Chincoteague Charm you love, plus the mod
Oyster Bay Oasis
House
$103 - $425 / per night
3
bedrooms
1
bath
6
guests
Welcome to Sea Gate 801, a delightful 1 Bedroom/1 Bath Condo thoughtfully designed with relaxation and enjoyment in mind! Nestled in the heart of family-friendly OCMD, this charming getaway offers stunning Views, a Seasonal Outdoor Pool, a prime location near some of the best family attractions, and all the comforts of home!Start your day with brea
Sea Gate 801
Condominium
$125 - $610 / per night
1
bedroom
1
bath
4
guests
Welcome to beautiful Saltwater Cottage, in the heart of Chincoteague Island, Virginia. You've heard stories about our little piece of Paradise - the Wild Ponies running free, Saltwater Cowboys leading the way, the Saltiest, Sweetest Oysters to be found, and hands down THE best Sunsets over the water. Guess what? It's ALL true - isn't it time you di
Saltwater Cottage
House
$85 - $275 / per night
3
bedrooms
2
baths
6
guests
Capri 1805 is a phenomenal 2 Bedroom Condo in fabulous Ocean City, Maryland directly on the Beach and steps from dining, shopping and more!.Were you dazzled by your last Vacation Experience? If not, you clearly were not staying at fabulous Capri 1805. When you enter this breathtaking 18th Floor Condo, you’ll feel on top of the world with stunning V
Capri 1805
Condominium
$125 - $695 / per night
2
bedrooms
2
baths
6
guests
Sea Gate 301 is everything a magical Beach Getaway should be! This breathtaking 1 Bedroom/1 Bath Oceanfront Condo has it all, including stunning, sweeping Views of the Ocean. This completely remodeled home is sure to wow your family from the moment you walk in. The Views alone will stay with you forever! Comfortably sleeping a family of 4, you wil
Sea Gate 301
Condominium
$125 - $683 / per night
1
bedroom
1
bath
4
guests
Channel View Charmer - Every moment has the potential to be amazing….**Now Dog Friendly!** Channel View Charmer is totally Renovated for 2023 - you're going to love it!Looking for the perfect beach getaway for your family? Channel View Charmer will charm it’s way into your heart forever! This adorable Water View Home has to be in one of the best lo
Channel View Charmer
House
$90 - $320 / per night
3
bedrooms
1
bath
8
guests
Welcome to Bradford House - proof that great things can indeed come in small packages! Y’all, a stay at Bradford House feels like a stay with old friends. There’s a warmth and coziness about it that hits you as soon as you walk in - it just feels like home. Tucked in a great location on School Street, you’ll feel a million miles away from the real
Bradford House
House
$99 - $275 / per night
3
bedrooms
1
bath
6
guests
Welcome to Casa Del Sol - “Live in the Sunshine, swim the Sea, drink the Wild Air….”When was the last time your Vacation took your breath away? If that is what you’ve been yearning for, clear your schedule - Paradise awaits you in beautiful Captain’s Cove Golf and Yacht Club!Casa Del Sol is Brand New Construction in 2024, and beyond stunning. Tucke
Casa Del Sol
House
$200 - $538 / per night
5
bedrooms
3
baths
10
guests
Welcome to Marigot Beach 905 - A little slice of heaven right in Ocean City! Have you been yearning for a little sun, a little sand, and some breathtaking Ocean Views? Perhaps a Beach Break that won’t break the bank? If you can make the time, we certainly have the place! Marigot Beach 905 is a delightful Condo in the very heart of OCMD. With a grea
Marigot Beach 905
Condominium
$125 - $383 / per night
1
bedroom
1
bath
4
guests
As they say, time flies - it’s so important to slow down, take in the views, and make memories with those who matter most. Beach Loft 2C offers everything you need to make fantastic memories year after year. Beautifully updated with new floors and furnishings, it is clear that no detail has been overlooked to create this beautiful retreat. Beach Lo
Beach Loft 2C
Condominium
$110 - $514 / per night
1
bedroom
1
bath
4
guests
Are you all about ponies in paradise? If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincoteague Island! Formerly ever-popular ‘Sunshine and Daydreams’, this Seaside Vacations’ fan-favorite is under New Ownership, and y’all are going to LOVE what they’ve done with the place! This adorable 3 Bedroom/2 Full Bath Cottage is
Pony Paradise
House
$125 - $428 / per night
3
bedrooms
2
baths
7
guests
Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When was the last time you broke away from the day-to-day with those who matter most? Well, the time is now, and the Vacation Destination is Gray Pearl in the heart of Chincoteague Island. This beautiful Canal Front Home is located in prestigi
Gray Pearl
House
$350 - $670 / per night
4
bedrooms
2
baths
10
guests
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