Beach house holiday rentals in Chesapeake Bay

4.87 out of 5 average rating, 101 reviews

The Happy Place-Quiet, North End 1 block to ocean!

Nicest area in VA Beach & 5 minute walk to the beach! Enjoy a private, peaceful, vintage beach house and fully fenced yard in exclusive North End's quiet family neighborhood! Away from the crowds w/ easy access to everything. Great for surfing, swimming, walking, biking (1st State Landing park nearby), kayaking, fishing, dreaming, or reading. Cul-de-sac location. Detached house with dog-friendly yard! Comes w/ sheets & towels, 3 bikes, surfboard, beach chairs, buggy & umbrella. Equipped kitchen.

4.92 out of 5 average rating, 48 reviews

Perfect Escape with Ocean Breeze!

A new home constructed in 2021 that is a 5 minute walk to the beach from 25th Street. Located in the heart of Old Beach with numerous restaurants, bars, high end supermarket and the boardwalk all within walking distance from the home. The home consists of 3 bedrooms, a bonus room with a king size bed, and a media room/office with a queen size pullout sofa. The home is professionally designed with detailed amenities for our guests throughout the home. Transcendent Stays is a locally driven group

4.87 out of 5 average rating, 121 reviews

Home

Cozy Beach Cottage — Dog friendly

Bethany Beach Cottage located in Bahamas Beach Cottages - a lovely getaway with family & friends. Approximately 1 mile to the beach. 10 minute bike ride - bring your own or borrow one of our old beloveds. Beach chairs for use in downstairs shed- just BYO beach towels! Quiet cottage with accomodation for 8 - 3 bedrooms, 2 bath, outdoor shower, grill, patio, and screened in porch. Hardwood floors throughout. Parking for 3 cars, overflow parking at front of neighborhood. Dog friendly.

Top guest favourite

Home in Rehoboth Beach

5 out of 5 average rating, 192 reviews

Beautiful Beach House in Rehoboth

Now Available during Summer Season for the first time! Few spots still open: June 2-11; July 6-16; July 26-30; Aug 25-31 Gorgeous modern spacious house in Rehoboth Beach with large open floor plan on quiet street. Five bedrooms/3.5 baths. Walk to town/beach - four blocks from beach right off Rehoboth Ave. Private pool with two levels of decks, grill and table/umbrella on top deck. Big open kitchen/dining/living area, over 3000 square feet of space overall.

5 out of 5 average rating, 9 reviews

Home in Rehoboth Beach

Beach Getaway on Sussex

Welcome to your dream beach getaway! This stunning 4 bedroom, 3.5 bath home is the epitome of casual beach living. Located in the desired community of the Pines, just 3 blocks from the beach and steps from shops and restaurants. Enjoy the first floor outdoor patio for morning coffee or cocktail hour. Rooftop deck has panoramic views of the beach sunsets and includes lounge chairs for sunbathing! Book your stay and enjoy all that downtown Rehoboth has to offer!

4.89 out of 5 average rating, 95 reviews

Home in Milton

"Sandy Feet" Broadkill Beachfront Home

Beachfront home w/ unobstructed bay views. Your group will enjoy front-row seats to breathtaking sunrises & water views from the elevated LR and wrap-around deck. The expansive deck with grill & fire table is a great place to sip your morning coffee or gather for dinner & enjoy the unobstructed sights & sounds of the bay. Stay and discover what makes Broadkill Beach so special! Linens are not provided but can be rented from local linen companies.

Top guest favourite

4.96 out of 5 average rating, 198 reviews

Sunrise, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2025 Pool Season... May 23–September 7. NO HAIR DYE!

4.92 out of 5 average rating, 119 reviews

Cozy North End Cottage 1 block from the sand!

Welcome to our one-of-a-kind 3-bedroom beach bungalow in the heart of Virginia Beach’s historic North End. Located one block from wide, white-sand beaches and one block from the serene trails of First Landing State Park, we offer stylish and pragmatic accommodations all tucked gracefully under two beautiful Live Oaks. If you’re looking for the most relaxing house in Virginia Beach’s most relaxing neighborhood you have found it.

4.81 out of 5 average rating, 107 reviews

Home in Milton

Delaware Beach Bliss, steps from the sand & surf!

Our large, comfortable, pet friendly beach house well suited to families and mellow friend groups is 2 lots from a crescent beach that you can walk for miles in either direction, offers some water views from the top of the steps and one bedroom. We have a sandy area under the house with beach chairs, SUP & 4 adult bikes in beach closet that opens with the house key for your stay. Gather together in the great room at days end.

4.95 out of 5 average rating, 161 reviews

Steps to Beach at Chics Beach! Sleeps 12 + Garage!

Experience the perfect blend of convenience and excitement at this beautiful 3 bedroom, 3 1/2 bath home in Virginia Beach. Featuring 3 king size beds and 2 fulls, it’s ideal for a family getaway. Enjoy a fully stocked kitchen, Wi-Fi, Smart TV, and laundry. We are only a 20 second walk from the beach! Whether for a weekend or an extended stay, this home has it all!

4.88 out of 5 average rating, 114 reviews

Home in Exmore

House Sanctuary on the Chesapeake

We follow the CDC recommendations for cleaning and disinfecting the house. Spacious house on a quiet, private beach offers spectacular sunsets & relaxation with friends & family. Enjoy fishing, swimming, evening bon-fires and more. Main house accomadates 6+; apartment above garage sleeps add'l 4+ (separate listing)