Holiday rentals in Chesapeake Beach

Upstairs Room in Ocean View

Welcome to Ocean View! Sleep and relax comfortably in the small bedroom furnished with a Queen size bed and dresser. Watch streaming services on a 50” TV. Included are Disney+, Netflix, Max, and Prime. Snacks and waters are on us! Non shared bathroom with dual sinks, towels, and bathroom toiletries. Shared spaces include Kitchen, Dining, Living Room, and Outdoor Front and Back yards. Laundry Room available with detergent and iron if needed. Please note there is NO view of the ocean from the home

The Seaglass Cottage by the Chesapeake Bay

The Seaglass Cottage by the Bay is located in the charming & beautiful neighborhood of Ocean Park just a quick 5-10 minutes stroll to the Chesapeake Bay beach. Our vintage beach house from the 1940’s has been fully remodeled and decorated in local art and beach décor. There are beautiful live oaks on the property and 3 private parking spaces for you and some first-come-first-serve street parking in front of the house. Easy load in with a ramp into the house and a mudroom for all your beach toys.

Welcome to the Sea Suite!

Take it easy at this unique and tranquil getaway. This perfect little guest suite has a private entrance with spectacular views of the Chesapeake Bay. You can see the Bay Bridge Tunnel, watch Navy ships arrive and depart, and spot dolphins daily—all from your sofa! Just steps away, you have private beach access! Our beach is beautiful and yet not overcrowded. The suite has a QUEEN bed & TWIN bed in an open floorplan, a fully stocked kitchenette, nice size closet & a full bath with a shower

Military - Active/Retired/Family at Cape Defoe B&B

Showing my military family some much needed love! This special discounted rate is extended to active duty/retired service members, and their immediate family. As everyone knows, if you have a spouse or loved one in the military, the whole family is in the military! I have a private room with a queen sized bed and private bathroom in my home complete with flat screen TV, cable, Wifi and coffee in the morning for my military guys and gals! Need to get off base for a night or two? Come relax!

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Private Bedroom & Bath Suite for Females Only

Our story? We listed on Airbnb after a friend's son used Airbnb as a dorm. So, we decided to use our space to serve long-term female guests such as military wives, students & traveling nurses as well as short-term travelers. We consider it a true blessing getting to host so many great guests. Because we value our guests, we offer 10% student, military, 1st responder, clergy plus long-term discounts. Breakfast items, snax, coffee/tea provided.

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Luxury By the Bay!

This is an apartment in my home, I live upstairs. The home is in East Beach one block from the Chesapeake Bay. You will enjoy easy access to everything from this centrally located place. You have access to the Chesapeake Bay one block away, on 15th Street. Towels, beach chairs and Beach umbrella are available. If you want to go to the Virginia Beach oceanfront it is a 25 minute drive!

Home sharing with privacy

Spacious, sunny(5 windows),7 miles from oceanfront, minutes away from Town Center shopping and restaurants, located on quiet court, self check-in, parking on premises. Guest suite that includes bedroom and bath and offers privacy. There is an outside entrance leading to space. It is a shared home that offers privacy.