Holiday rentals with breakfast in Eastern Shore of Virginia

Modern Bayfront Escape with Sweeping Water Views

Modern bayfront retreat blending bold design and serene comfort. Floor-to-ceiling windows frame sweeping Chesapeake views, while elegant furnishings and open-concept living invite relaxation. Pet and child friendly with elevated essentials for every guest. Lounge by the fire pit, dine with a view, and wake to the sound of the water. A sophisticated escape for families, couples, or friends seeking style, space, and calm on the coast. Art is for sale + supports charity. Redfish Gallery Irvington.

Family · Location · Comfort

Designer owned Coastal getaway retreat

Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a 5 minute drive away. Please let us know if you plan to use it!

Family · Value · Solo travel

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

5 bed / 2.5 bath - Sleeps 10! Our cozy, farmhouse-style Norfolk home is 5 min from Historic Ghent / ODU. Free Wi-Fi, parking for 4 cars. Coffee, grill, & fire pit provided. Pet-friendly! NO cleaning fee or checkout instructions! Driving Distances: ODU - 5 min Sentara Norfolk General - 5 min CHKD / EVMS - 8 min Norfolk Naval Station - 14 min Virginia Beach Oceanfront - 25 min Monthly: $4,200. Fully furnished rental with all utilities, Wi-Fi, weekly housekeeping, pest & lawn care included.

Family · Location · Laundry

Secluded Waterfront:Kayaks, Sunrises & Unwind

This is a place you come when you need space: real space, quiet, and room to breathe. Set on 18 private acres along the Chesapeake Bay, our Ridge retreat offers a rare kind of calm: uninterrupted nature, open water views, and the feeling of being completely removed from noise, crowds, and schedules-- just land, water, sky, and time. Days unfold slowly with kayaking, crabbing, exploring the land. Evenings end by the fire under dark skies. This is not a tourist destination—it’s a true reset.

Location · Family · Indoor spaces

Walk to Beach, Fire Pit, Game Room, King Beds

“Peace of Blue” - Relax in this bright modern beach home with a game room, fire pit, two King Suites, and lightning-fast fiber Wi-Fi in the heart of Ocean View! Just steps from sand between your toes and surf on your feet, welcome to your coastal getaway just one block from the beach! Watch a movie while the kids enjoy Mario on the Nintendo Switch or sit around a cozy lit fire outback until it's time to unwind in one of our king beds. It's totally up to you... Get your “Peace of Blue!”

Location · Family · Kitchen

Home away from home~Private,quiet, mins to bay

Home away from home is a spacious, comfortable, and private apartment with 1 Queen bedroom, full bath w/ tub, living area, work space, and fully equipped kitchen. Conveniently and centrally located in historic neighborhood: 3 mins to bay, 15 mins to oceanfront. We are within 4 miles of Norfolk Premium Outlets and IKEA, and are within 5 miles to Virginia Wesleyan and 15 miles to ODU. Walk to local favorite restaurants (New River Tap House, The Rustic Spoon, 1608 Crafthouse, Comfy Belly).

Location · Family · Beach

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Location · Family · Accuracy

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.

Location · Family · Walkability

The Shores Shack HOT TUB w/ fully stocked kitchen

Quiet home near the river with about 1200 square feet to spread out. 1 bedroom with a queen bed and a full bathroom across the hall. There are also 2 living room areas that we have extra air beds if needed on request and a pack n play in the hall closet. We have free coffee, tea, hot chocolate, etc. available for guests to make. There is a TV with a firestick, & Alexa along with puzzles, kid toys, & games. Backyard is fenced in with a hot tub, a grill, & attached deck.

Family · Value · Decor

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Location · Family · Comfort

Elm Grove Farm Guest Cottage

Our guest cottage is the perfect retreat for a quiet getaway or a quick commute to local historical sites. We are located on a family farm property dating back to the 1880's. Although the old farmhouse is gone our home with attached cottage is filled with decor built by the owner with reclaimed wood from the original home. We are adjacent to Beaverdam Park and located 2 miles from Main Street which boasts the historic Gloucester Courthouse dating back to 1651.

Family · Location · Breakfast

The Bee Goode House on Main Street

Welcome to the Bee Goode House! We want our future and returning guests to know of our diligence in sanitizing and cleaning every surface after each guest. Linens are fresh and clean, and there is plenty of private space with a large yard surrounding the house. Relax and enjoy Gloucester Main Street from a 1950's renovated home. From Mid Century Modern furniture and renovated retro appliances, you will be comfortable and hip in our home.

Value · Family · TV