House holiday rentals in Chesapeake

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Top-rated house rentals in Chesapeake

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite

Home in Smithfield

4.97 out of 5 average rating, 207 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Guest favourite

Home in Hampton

4.97 out of 5 average rating, 178 reviews

The Water's Edge

The "Water's Edge": a fantastic 100-year old waterfront home.Owner/host lives next door.(Please also check out their additional property, "Sun, Sea and Sand".) At The Water's Edge, the base rate includes 2 bedrooms and 2 full bathrooms.Additional bedrooms to accommodate additional guests may be available upon request for additional nightly fees. Great view of a Chesapeake Bay inlet.Private deck & dock. Modern appliances.Washer/dryer.Smart TVs.Free wifi.Keurig coffee maker.Fully equipped kitchen.

Superhost

Home in Williamsburg

4.83 out of 5 average rating, 180 reviews

Colonial Retreat

Enjoy a getaway in our 1940 Cape Cod home minutes from Colonial Williamsburg & Jamestown. Within biking distance to many attractions such as Williamsburg Winery, Jamestown Island & Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The house was refinished in 2021; you'll find an updated kitchen, smart TVs, large back patio & front porch. Please read the house rules before booking. No smoking. Need more space? Inquire about our other units

Guest favourite

Home in Virginia Beach

4.88 out of 5 average rating, 116 reviews

Half house w/pool & new patio all to yourself

PLEASE READ TO THE END!!!!!! Our home is close to restaurants, parks, the resort oceanfront and art and culture. You’ll love our place because of the location and the ambiance. Our space is good for couples, solo adventurers, business travelers or small families. Please know that my wife and I live in the other half of the house. There is NO shared space!!! You have a private entrance with full & private access to all amenities. Our home is LGBTQ+ friendly because LOVE IS LOVE!

Superhost

Home in Norfolk

4.84 out of 5 average rating, 122 reviews

Cozy Coastal Home

Cozy Coastal Home is located on the second floor of a duplex. It is a quiet 2 Bedroom 1 bath less than a block away from the beach. Close to shops and restaurants in the Ocean View area of Norfolk. Fully furnished with refrigerator, stove, microwave & wine fridge. Come back from the beach, relax and take a chilled bottle of wine and enjoy. Enjoy the 55" smart TV or just take a short stroll to the local COVA Brewery or local restaurants. Food Lion is 1.1 miles and H-Teeter 3 miles

Guest favourite

Home in Moyock

4.93 out of 5 average rating, 286 reviews

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.

Guest favourite

Home in Virginia Beach

4.92 out of 5 average rating, 260 reviews

Master bedroom suite 3 blocks from the beach

Entire top floor of 3 story townhouse with balcony overlooking Holly Lake. Private bath. Newly renovated, three blocks from the beach (7-10 min walk). Short walks to the ocean, boardwalk, Rudee Inlet. Hardwood floors, queen size bed, mini fridge, microwave, Keurig coffee. No stove Wifi internet, 500 mbps wifi, internet TV. You must be 21 to rent. Exceptions considered based on information provided in your profile, past reviews, description of your trip plans. No pets.

Guest favourite

Home in Norfolk

4.91 out of 5 average rating, 104 reviews

Near Ghent | Open Concept | Fenced Yard | Grill

Welcome to Norfolk! This is a large 3 story, 4 BR/3.5 BA house located just outside of the popular Ghent district in and walking distance to many breweries, restaurants & coffee shops! This is a fast growing area of town and for good reason, we’re so exited to host you! 15 min drive to Norfolk International Airport 12 min drive to Naval Base 8 min drive to Downtown/waterside district/freemason historic district 6 min drive to ODU campus 4 min drive to Virginia Zoo

Guest favourite

Home in Williamsburg

4.97 out of 5 average rating, 179 reviews

Casita on the Corner

Our cozy little 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens/Water Country. This area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. Take a tour on The Colonial Parkway or If you are a cyclist bring your bike and ride the Capitol trail or hit the trails at Freedom Park or New Quarter Park.

Guest favourite

Home in Virginia Beach

4.9 out of 5 average rating, 211 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Guest favourite

Home in Norfolk

4.92 out of 5 average rating, 124 reviews

The Cozy Beach House

We keep it simple here in this small, cute, and charming, home. Room is great for 1 or 2 people. A 10 minute walk, to a public access, that takes you straight to the beach. There are a few public parking spaces. 10 minutes to Norfolk International Airport. The Oceanview Pier is a great place to fish and have dinner and is only 3 miles away. Come and enjoy! There is also a NEW CASINO only 20 minutes away.

Guest favourite

Home in Williamsburg

5.0 out of 5 average rating, 206 reviews

Cozy Single Family Home

Enjoy a little bit of home away from home in our 120 year old fully refurbished house. Property is centrally located with just an 8 minute drive to Historic Colonial Williamsburg, 2 minute drive to Route 199 access, 2 minute drive to the Williamsburg Winery, and 15 minute drive to Busch Gardens. Have morning coffee on the front porch or a BBQ on the back.