Vacation rentals in Bennett Harbor

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Top-rated vacation rentals in Bennett Harbor

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

Guest favorite

Home in Virginia Beach

4.93 out of 5 average rating, 15 reviews

Incredible Location! Amazing Comfort!

Location, Location, Location!! Approximately 200 yards from your toes in the sand and the incredible blue Atlantic. A home away from home with all the amenities you could possibly need to make your stay, or extended stay a comfortable and memorable experience. The bunk room is ideal for an extended family or a comfortable room only for the little people. Virginia Beach has everything you need whether you're coming for vacation, relaxation, activity, or work. Experience Virginia Beach while stayi

Guest favorite

Home in Cape Charles

4.98 out of 5 average rating, 81 reviews

Cape Charles cottage, family friendly, in town

Welcome to Cape Charles Cottage in the historic district! We are 6 blocks to the beach and 4 blocks to Mason ave (shops, restaurants). The town is very walkable or golf cartable…you can rent ours! We can host up to 10 guests with 4 bedrooms and a bonus room with a daybed w trundle that pulls to side by side twins. One bedroom has an ensuite bathroom and the others share a hall bath with a tub/shower. Kitchen is fully equipped, fenced yard, outdoor shower,fire pit, grill & shed with beach gear.

Superhost

Home in Norfolk

4.81 out of 5 average rating, 16 reviews

Family Vacation Beach House

Experience the ultimate beachfront getaway in this stunning coastal haven! Our charming beach house offers 3 bed/3 bath, inside noise monitor, outside recording security cameras(front&back) for safety, close to beach access. Immerse yourself in seaside serenity and relax with stylish interiors, modern amenities. Whether you’re seeking a romantic retreat or a family beach adventure, this coastal gem is an unforgettable escape. Book now and let the waves be your lullaby! Weekly/Monthly Discounts

Superhost

Cottage in Norfolk

4.79 out of 5 average rating, 117 reviews

Beach Cottage-Bay Views Loft on Beach & Veranda

We are on the Beach. Look at the Chesapeake Bay from the elevated veranda and living room from this second floor loft vacation rental. Our private wood walkways lead you from this rental to our beach. 100 year old duplex Cottage with large deck & Bay Views. Fully restored, modern & newly appointed. The rental isnt on the beach-side of the property so you will need to walk around the building to the beach which is only a few feet away. Read on about all of the amenities that await you here

Guest favorite

Condo in Virginia Beach

4.93 out of 5 average rating, 59 reviews

VA Beach Retreat! Quiet and perfect for families!

Relax with the whole family at this peaceful place to stay. This property is ON the beach (unit itself is not facing the ocean) with access to 3 pools, a gym, local restaurants and much more! As you can see, guests LOVE my place! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! ** I am currently replacing furniture! Pics may not match exactly but it is for the better. Expect brand new: King and queen mattresses. Bedding. Living room furniture.

Guest favorite

Home in Cape Charles

4.96 out of 5 average rating, 100 reviews

Cape Charles Retreat - 2 Blocks from Beach/Town

Welcome to Cape Charles Retreat! Come on up to the porch, grab a lemonade and settle into the porch swing for some much deserved rest and relaxation. Cape Charles Retreat is a beautiful 100+ year old American Foursquare located two blocks from the beach, Central Park, and town! Our home has been restored to preserve much of its original charm while adding modern amenities and outfitted with everything you’ll need for a great beach vacation. So grab your bathing suit and come for a visit!

Guest favorite

Townhouse in Virginia Beach

5 out of 5 average rating, 31 reviews

Wave Break Hideaway

Welcome to your perfect beach getaway in Virginia Beach's vibrant Vibe district! Enjoy this centrally located, stylish townhome, located one block from the future Atlantic Park. You're near eclectic restaurants, breweries, and entertainment! Now under new ownership, we're committed to the same attention to detail that made this a top rental in the past. Enjoy sunsets on your private balcony. Ideal for romantic getaways or family vacations. Book now for an unforgettable experience!

Guest favorite

Home in Virginia Beach

4.96 out of 5 average rating, 188 reviews

Salida del Sol, 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!

Guest favorite

Tiny home in Cape Charles

4.89 out of 5 average rating, 105 reviews

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

Superhost

Townhouse in Williamsburg

5 out of 5 average rating, 8 reviews

Lovely 4BDR- Perfect for BIG Families!

If you are looking to take your family on a vacation that will be not only loads of fun, but filled with plenty of opportunities to teach your kids about U.S. history without having them feel like they are learning anything, you need to visit Williamsburg, Virginia. Now, you are going to want a great place to stay that has everything any vacationer could ever want, and that place is The Historic Powhatan Resort.

Guest favorite

Guesthouse in Hampton

5 out of 5 average rating, 51 reviews

Fantastic Getaway

You need to see this fully furnished, stunning guest house located along the historic section of Chesapeake Ave. Wake-up to breathtaking views of the Chesapeake Bay. Great fishing, crabbing, sailing, bike trails, kayaking and more. Enjoy herons, osprey, dolphins and other wildlife. Centrally located to shopping, casinos, restaurants and public beaches!

Guest favorite

Home in Cape Charles

5 out of 5 average rating, 44 reviews

Captain's Cottage

The Captain's Cottage was originally built in 1886 and has recently undergone extensive renovations to create a home of charm, history, and comfort. Located a block away from Cape Charles's Central Park, four blocks from the beach, and two blocks from Mason Avenue, the Captain's Cottage is in a prime location in Cape Charles.