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Bay Creek Blessed at The Fairways

Summary... Enjoy an upscale stay with a downhome feel. Unwind to an island vibe of comfort with our vintage Tommy Bahama furnishings. All the basics for coffee, laundry, bathing, cooking & grilling provided. Plus beach chairs, towels, coolers & toys. Check out the pool (steps away), Nature Trails (short bike ride), Bay Creek private beach (3 min drive), Cape Charles public beach (5 min drive). You'll love exploring back waters & towns between the ocean & the bay! *No pets, smoking, parties*

BayBliss: Beach-Paddle Boards-Games-Private Yard

BayBliss is a sanctuary of modern coastal elegance, thoughtfully redesigned to inspire relaxation and connection. Bathed in natural light, an open-concept design creates the perfect gathering space, flowing seamlessly to a serene outdoor oasis. Nestled on the 1st hole, this Bay Creek getaway offers a private beach, historic tavern, miles of scenic trails, a community pool and courts. Every detail evokes a sense of ease and fun, inviting you to slow down and embrace the rhythm of coastal living.

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Whether you are looking for some rest and relaxation, a home-base for the beach or water activities, or a place that comfortably allows you to bring your pets, you are sure to find your desired experience at Paws at the Beach. Open concept space with large glass doors and window to bring in natural light. Sunset room with multiple entertainment options, a massage chair in the living room and a Hot Tub. Four bedrooms that comfortably sleep 10. Rental includes access to a four-seater golf cart!

Rendezvous at the Bay

A luxurious 1550 sq foot 2nd floor resort condo that offers comfort and tranquility in a private beach and country club setting. Imagine your most prefect beach vacation: sun, sand, morning walks, pool, time with the family, relaxing, exploring nature, great restaurants, golf cart rides around town, romantic sunset walks, and evening ice cream. Experience these things and so much more when you stay at Rendezvous in Cape Charles on the Virginia Eastern Shore. Come experience it for yourself!

Sunshine Baydream Cape Charles

Sunshine Baydream is bay living at its finest! Vacation comfortably with 3 master suites, including one on the main floor. The kitchen has all you need for a comfortable stay. Have some fun playing head-to-head Ms Pac Man! The open floor plan is great for entertaining! Enjoy the grill on the rear deck or the large second floor deck. The home is in a quiet community with a pool on Stone Road just outside Historic Cape Charles. Owners' 6-person golf cart may also be rented in advance!

East of the Sun Victorian - Private Pool

Back after a 2-year hiatus! East of the Sun is a fully-restored ca. 1890 Victorian (3 en-suites) with a large screen porch and private, 12' round plunge pool. Our place is ideally suited for 3 couples or families with older children. We welcome younger children as long as parents confirm they're okay with 3 floors/2 sets of stairs, antiques, and a pool. We have a strict limit of 6 guests (however, children under 2-years do not count). We offer a 3-night minimum both low and high season.

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Family Retreat, In-Ground Pool, plus Private Beach

5 bedrooms and 3 full baths plus an outdoor shower. Sleeps 10 adults. 1/2 mile walk, bike, or drive to our private community beach. Kiptopeke Park, Cape Charles, VA Beach, and Williamsburg. Ideal family get-a-way. Modern and private. Please note: Parties, loud music, or lots of screaming in the yard, are not allowed or tolerated. This is a peaceful and quiet community and we need you to honor that. Otherwise, please book another home for your vacation. Thank you.

Oyster Point Cabin

Go glamping in one of our Deluxe Cabins. There is enough space for the whole gang featuring a queen bedroom, a room with a twin over full bunk bed, and a sleeper sofa in the living room. The full kitchen comes with a cooktop and the essentials for dining. Relax on the screened porch and enjoy time together. A fire ring and a picnic table are included with most Deluxe Cabins. You will enjoy our private beach, onsite restaurant, and one (1) private resort pool!