Beachfront holiday rentals in Chesapeake Beach

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

If you enjoy majestic ocean views from almost every room & your own exclusive beach just steps below, Bay Bliss is for you! The panoramic views from this luxury home are unmatched & sure to relax you! Sip coffee from the grand deck or take a soak in the hot tub w/ breathtaking views. Cook/eat in the high-end chef's kitchen or watch a movie on a 75" TV all with stunning views! Wake up in the plush, king-sized bed and enjoy views of the water without having to get up. Your bliss at the bay awaits!

New Beach Home on the Chesapeake Bay

New Beach House on the Chesapeake Bay. Entire 2500 SF Home, 1st, 2nd and 3rd floors. Three King size bedrooms, third floor with 2 Sofa Beds. One Full kitchen and one Kitchenette. House on the dune 40 steps to the sandy beach. Balcony view of bay for sunrise coffee & sunset wine. New & old homes surround this newly built home in "East Ocean View." Restaurants short walk, more only a two min. drive. Summer Sailing regattas on Weds. and Sun. evenings, live music at the Pavilion.

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

902 B Historical Beachfront Duplex Sauna & Hot Tub

902.B Historical Beachfront Duplex Sauna, Fireplace Hot Tub, Beachfront Grilling & with rental beach chairs, kayaks and Standup paddle boards on-site. Step back in time at the Historic Carriage House, a beautifully restored 120-year-old gem just 20 feet from the Chesapeake Bay. Once home to horses and rowboats in the early 1900s, this 2-bedroom, 1-bath carriage house now blends timeless charm with modern comfort — offering guests a truly unique and peaceful bayfront getaway.

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with a kitchenette offers breathtaking 180-degree views of the Chesapeake Bay. Enjoy magnificent sunrises and stunning sunsets from your private deck, with the water’s edge just steps away. If you’ve ever wanted to experience life on the beach, this is as close as it gets. This suite reflects our love for the Chesapeake Bay and the relaxed coastal lifestyle, and we’re conveniently located just 10 minutes from ORF Airport

Stylish Beach House, Hot Tub, Pet Friendly

Welcome to your coastal oasis of relaxation & fun. Enjoy beach fun, hot tub & games in a modern open concept living space. This stylish, pet friendly home away from home is perfect for families. It's 1.5 blocks from the beach. This charming SFH offers 2 bedrooms, loft, chef's kitchen, game room, spacious backyard with deck, hot tub, fire pit, BBQ grill, & volleyball/badminton court. It's centrally located near VA Beach, Williamsburg, & Downtown Norfolk.

Life on a Sandbar right on Chesapeake Bay

Two bedroom, two bath cottage located on Willoughby Beach right on the shore of the Chesapeake Bay. Centrally located between Williamsburg, Jamestown, Hampton, and Norfolk, Virginia Beach, and the Outer Banks. Close to Norfolk Naval Bases and Old Dominion University. Great for surf fishing or pier fishing on nearby Ocean View Fishing Pier and Restaurant. THIS PROPERTY CANNOT BE RENTED THOUGH CRAIGSLIST!!! DON'T BE SCAMMED!!!

Beachfront stay with kayaks & paddleboards

Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.

Beachfront Getaway, Pet Friendly, Mermaid Suite

Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.

Chic’s Beach Oceanfront 3BR Home With Deck Views

🌊 Direct beachfront location at Chic’s Beach 🌅 Ocean views from all 3 levels 🏡 Spacious 3BR home sleeps up to 8 🛏️ King, 2 Queen beds + twin-over-full bunk 🌴 Multiple private decks for relaxing outdoors 🍳 Fully stocked kitchen for easy meals 🛋️ Open living area perfect for gathering 📶 Fast Wi-Fi + Smart TVs throughout 🧺 In-home washer and dryer 🚶 Walk to local dining and beach favorites

*Escape to the Tangerine Dream*

**ESCAPE TO THE TANGERINE DREAM** in this stunning beachfront oasis, located just steps away from the sandy shores of Captain's Quarters Park, this 3 bedroom/2 bath home offers the perfect blend of luxury and relaxation. Step inside to the open concept living area which boasts breathtaking views from two balconies, perfect for enjoying your morning coffee or watching the sunset over the ocean.