Beach house holiday rentals in Chesapeake

New place to stay

Gorgeous Remodel Vibe Dstr Fenced Yrd Walk 2 Beach

Bring the whole family to this great place with lots of room for fun.BRAND NEW FULL REMODEL This entire house is perfect for a large family or multi-families to enjoy everything Virginia Beach has to offer. In quiet neighborhood, this 2 story 3BR , 2.5 bath home sleeps up to 10. Fenced in backyard, driveway parking for 2 cars. First floor has plenty of open space. 12 min walk to beach and fishing pier, and few blocks from Sports Complex and Convention Center. Dining, coffee shops, and much more.

4.86 out of 5 average rating, 151 reviews

Home in Cape Charles

Family Rental Close to Beach

Large Victorian home one block from the center of town in Cape Charles. One of only a handful of rentals with FIVE bedrooms. Features renovated bathrooms w/ oversized showers and endless hot water. Walking distance to beach, park, restaurants, shops and more. Large three-story layout with living room, dining room, kitchen, three porches and nine beds. Kitchen is equipped and linens are included. The house is completely outfitted - with high speed internet, Apple TV, YouTube TV and Sonos Stereo.

4.94 out of 5 average rating, 96 reviews

Home in Norfolk

Bayview Beach/Airport/3 Bedrm/6 Beds/2 Bath/ 4TV

Entire house/3 Bedrm+3 sofa bed/2 Bathtub/shower. 1 mile from Ocean View BEACH (Bay). Spacious 1500 sq ft. Quite, safe side street, approx. 25 min to VA Beach front! 4.5 miles from Airport. Naval base, dining, shopping, near. New furniture & appliances! 2 queen w/pillowtop and 1 full bed w/ Serta mattresses, 3 sofa beds, 4 smart TVs to include 2 large size (70+"), Gig WiFi, Roku/retro/Atari games! Leather recliner! Beach chairs&umbrellas, towels, soaps, bbq grill, cooking/utensils, etc. avail.

4.58 out of 5 average rating, 26 reviews

Home in Corolla

WhaleSound -Pool/Pet Friendly/0.2 mile to Beach

Relax with the whole family at this Corolla getaway! Just north of the Town of Duck and just south of where the Wild Horses roam! There are so many possibilities for gathering and entertaining, in and outside, of this home! WhaleSound is an older home that was recently updated so that we may offer this space to you and yours to make many memories! Situated on a large lot, just a short flat walk to the beach, convenient to all the attractions, shopping, and restaurants of the northern beaches!

4.76 out of 5 average rating, 136 reviews

Home in Willoughby Spit

Poseidon - Beach-Front with Fireplace & Sauna

Unique & gorgeous beachfront rental. This area was a gathering spot for rowdy commercial sailing captains that moved goods between Norfolk & Baltimore & an alleged meeting spot for Rum Runners in the 1920's. Includes wood floors, sailing inspired sconces, fireplace & shared laundry room & sauna. Beautiful wood trim & wainscoting created by craftsmen that trimmed ship interiors over a century ago, beach-front windows, large open kitchen, dishwasher, microwave oven, shared sauna, & washer/dryer

4.81 out of 5 average rating, 53 reviews

Home in Corolla

Welcome to Song of the Sea, perfectly located in a low traffic area ideal for biking, jogging and dog walking. While you might be tucked away in this private HOA, you are right around the corner from fine dining, lots of shopping and wonderful attractions perfect for a vacation filled with family fun. Song of the Sea is pet friendly (pet fee) and ready for you and your family to have an unbelievable family vacation with lots of fun! Community pool, tennis courts or 2 minute walk to the beach!

4.96 out of 5 average rating, 49 reviews

Steps to the Beach | Quiet | Multi-Family | Groups

Welcome to the Blue Dog Beach House!! A Coastal Escape Just Steps from the Beach! This 2,500 sq. ft. retreat in the sought after, semi-private neighborhood of Croatan, offers 4 bedrooms (2 primary suites), 3.5 baths, and expansive decks for the perfect beach getaway. Just a 2-minute walk to the sand, enjoy open, high-ceiling indoor spaces and plenty of outdoor living. Updated yearly, this home blends modern comfort with coastal charm. Relax, unwind, and experience the best of Croatan Beach!

5 out of 5 average rating, 4 reviews

Home in Carova Beach

The White Lotus, Luxury Vacation in Carova Beach

Welcome to The White Lotus - a bespoke coastal retreat. Perched high above the Atlantic in the 4x4 area of Carova, this new home has sweeping ocean views. The top level stuns with an open living, dining, and kitchen with white quartz countertops and high end appliances. Wraparound decks offer 360-degree outdoor living. On the mid-level, three primary suites invite you to drift away with spa-inspired bathrooms. The ground level offers a second living space that opens to a sparkling pool.

Top Guest favourite

Home in Ocean View

5 out of 5 average rating, 94 reviews

Charming & Cozy Getaway Steps to Beach/Shops

Escape to The Peche Beche and find everything you need for a relaxing & fun-filled stay! Situated just blocks from the Ocean View beach on the Chesapeake Bay and steps from local favorites, shops, & grocery. You'll find everything you need for the beach, kiddos, pups, remote work, relaxing, feasting, and restful sleep to recharge & enjoy all that Norfolk has to offer! Life’s a peach at the beach! You won't want to leave the coziness and charm as you create unforgettable memories here!

4.9 out of 5 average rating, 10 reviews

Home in East Ocean View

Casa del Mar - Bold, Bright & Steps to the Sand!

"So cute....." Welcome to Casa Del Mar, a vibrant beach cottage 2 minutes ' walk to the sand! Step into an artful oasis where the exterior mural pops with ocean-inspired colors! Start your mornings with coffee on the sunny front deck or gather around the outdoor dining table for a breezy lunch. Enjoy the fire pit under the shade of mature trees. This 2-bed, 1-bath coastal charm welcomes you whether you are in town for a coastal getaway or a weekend surf session.

Top Guest favourite

4.99 out of 5 average rating, 200 reviews

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic large beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, for guests exclusive use( 2 floors).Guest has entire 2nd and 3rd floor. TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill. Washer-dryer. Owner occupies first floor with their own living area and additional bdrm in this multi-level structure. Any questions contact the host.