More Summer Fun Discount

Book a Summer Vacation in Chincoteague and get ready to enjoy more, starting with a 15% discount on any Week Rental that is booked for any stay thru June 9th. Save on your rental so you can enjoy more during your next Summer Vacation!


You MUST use the Promo code, summer2023, in order to receive this discount.

Call us at (844) 662.2583 if you need any assistance.


Properties Available 45 properties available
Happy Pines has some great updates including New Floors throughout and updated Bathrooms!As you turn onto Pine Creek Drive, you will feel the hustle and bustle of the busy world melt away. Happy Pines is located near the end of this quiet street, nestled in a Pine Grove, and surrounded by beautiful trees and Beach Grasses. This lovely 3 Bedroom, 2
Hot HOT 21
Happy Pines
House
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Casa Playa - Peace, Love, and Sandy Feet……Life is busy - too busy at times, it seems. When was the last time you grabbed those who matter most and just broke away from the daily grind? We’ve had quite a bit of “togetherness” this year, but isn’t it time for “experiences” together once again?! This is what Casa Playa is all about - kicking back, tak
Hot HOT 20
Casa Playa
House
$100 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
We travel not to escape Life, but for Life not to escape us…..When was the last time you slowed down - took time to watch the birds dance over the water, or just listen to the breeze rustle the trees? Life is crazy - we know! We’re rushing to work, the kids are rushing to school - and the family pup just wants to tag along for all of it. What you n
Hot HOT 18
The Mane Escape
House Pet Friendly
$125 - $450 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Whispering Pines, salty breezes, and chirping Tree Frogs - ahhhh. Can't you just picture yourself here right now? Beach Pines is a delightful Vacation Home located on Piney Island, which the is the closest community to Assateague National Seashore on Chincoteague Island. Wild Ponies, Beach Combing, and one of the most gorgeous beaches in our countr
Hot HOT 30
Beach Pines
House
$90 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Welcome to Island Sage on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with those who matter most. This cozy Vacation Home is just that - a HOME, not just a place to lay your head at night. Located in popular Piney Island, which happens to be the closest community to Assateague National Seashore, you will lo
Hot HOT 8
Island Sage
House
$90 - $350 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Serenity Now -  It's exactly what you need!Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept secrets on the Eastern Shore of Virginia! This spectacular Vacation Home will make all your dreams come true with something for everyone in the family. Located directly on the Chincoteague Bay, this home is only 25 short minutes by c
Hot HOT 30
Serenity Now
House
$250 - $395 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Just give me the Sea, and a little Cottage just to be…..Work, meetings, school, traffic, homework, repeat - right?! It’s time for a break - a Beach Break, that is! Get ready to relax, unwind, and simply….be. Be with those who matter most - giggle, frolic on the Beach, and make memories that will forever be treasured. Take in that salty, sweet sea b
Hot HOT 25
Serendipity
Town House
$110 - $225 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Sugar Shores - Your next Vacation can be both Salty and Sweet!When was the last time you had a Vacation that took your breath away? It’s the perfect combination of the right Destination, the right Vacation Home, and the perfect Location. Sugar Shores on beautiful Chincoteague Island is all of that and more, and only a few minutes from Assateague Na
Hot HOT 18
Sugar Shores
House Pet Friendly
$125 - $325 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Beach Blessing - a beautiful Chincoteague Island Vacation Home ready to make your Vacation Dreams come true! This breathtaking New Home is located on Boothe Street - a quiet and serene location nestled between Main Street and Willow, yet close to everywhere you want to be. You can easily walk or ride your bike to the Carnival Grounds, Re
Hot HOT 21
Beach Blessing
House
$125 - $400 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Relax, Rejuvenate, and Reconnect…..Welcome to ‘Shellfish Time’ on the beautiful Eastern Shore of Virginia! If you have been looking for a “different” kind of Vacation - a totally new Experience, yet not too far from Home, boy, do we have the place for you! Get ready for an awesome Adventure at this fabulous Brand New Home - the Beach, Wild Ponies,
Hot HOT 24
Shellfish Time
House Pet Friendly
$125 - $300 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 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
Hot HOT 31
Saltwater Cottage
House Pet Friendly
$85 - $275 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Traveling - it leaves you speechless, then turns you into a Storyteller. Welcome to the Chincoteague Island Retreat you've been longing for - tucked away on a quiet lane in the heart of our tiny Island. George's Retreat is in the perfect location, just off of Maddox Boulevard, aka the Beach Road - you can walk or ride your bike to many, Restaurants
Hot HOT 10
Georges Retreat
House
$75 - $240 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

Tell us what you're looking for and someone will contact you with available options.

I agree