House holiday rentals in Chesapeake

Charming Home by the Sea, a block from the beach!

Single family home steps from the beach. Parking for vehicles including garage. Outdoor/indoor dining areas. Gas grill & fully equipped kitchen with cooking essentials for stay at home meals. 3 bedrooms sleeps 8. Can accommodate additional guests for an up charge with air mattress and sheets provided. Pets welcome! Hardwood flooring and central AC/heat throughout. Walking distance to restaurants in the local area. 15 minutes to Norfolk Naval Station, 10 mins to Airport, 20 mins to VB boardwalk.

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Dog-Friendly Cozy Cottage | Private Fenced Yard

Experience the perfect blend of serenity and centrality at this charming 3-bedroom, 2-bath home in Norfolk. Featuring cozy accommodations and a fully fenced backyard, it’s ideal for couples, solo travelers, or small families - with pre-approved dogs welcome! Enjoy a fully stocked kitchen, Wi-Fi, washer and dryer, and ample parking. Located just 5 minutes from the beach and close to Naval Station Norfolk, Little Creek, ODU, and Waterside District, this home has it all for your Norfolk stay!

Sportsman's Paradise ( Hunting & Fishing )

Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

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.

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

The Cozy Cottage Two Bedroom, King bed House

This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has central heat and air conditioning, updated appliances, and carpeting. It’s centrally located and there is plenty of space for parking. This is a perfect place to recharge whether you’re visiting for work or a getaway!

Walk to Beach! Fully Updated + Hot tub!

Welcome to a fully renovated 3-bedroom, 2-bath rancher in Hampton Roads. Perfect for families or groups, it offers cozy beds plus a pullout couch in the versatile recreation room. Unwind with top-tier amenities like a fire pit and a climate-controlled game room/office. Located just one block from the beach (and complete with beach gear!), you’ll enjoy effortless access to the shore and local attractions. Whether for a weekend or an extended stay, this home has it all!

Cook's Country Escape - Cozy Retreat

Escape the everyday and enjoy this cozy countryside retreat! Nestled halfway between Virginia Beach and the Outer Banks, this home offers the charm of a cabin with the comforts of a full house. Perfect for families or friends, it’s a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, you’ll feel the warmth and relaxation of a true country home. It’s been a great rental with great ratings.

Gorgeous Olde Towne historic home - modern updates

Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!

3BR Mid-Century Modern Home • Near Airport

Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!