Holiday rentals in Chesapeake

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Top-rated holiday rentals in Chesapeake

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

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Guest favourite

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

Top guest favourite

Guest house in Gloucester County

4.98 out of 5 average rating, 155 reviews

Moody Cabin: Hot Tub/ Creek Fire Pit Park Setting

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Guest favourite

Home in Cape Charles

4.94 out of 5 average rating, 116 reviews

Bakery Next Door | Renovated | Golf Cart Avail.

Nectarine 13 is a centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

Guest favourite

Home in Cape Charles

4.96 out of 5 average rating, 103 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!

Top guest favourite

Guest suite in Virginia Beach

4.98 out of 5 average rating, 148 reviews

Quiet Suite with Private Entrance

Looking for a place to relax away from the chaos of the oceanfront? Quiet, private and secluded but conveniently located. Less than a 10 minute drive to the beach. Walking distance to breweries, local restaurants, grocery stores and other amenities Beautiful 2 acre property with plenty of outdoor space to find a place to relax, play games or take a nap Leesa king size mattress Luxurious bathroom with soaker tub Microwave and fridge, Kurig, k-cups snacks and popcorn Smart TV, WiFi

Top guest favourite

Townhouse in Virginia Beach

5 out of 5 average rating, 47 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 favourite

Apartment in Corolla

4.98 out of 5 average rating, 44 reviews

Luxury Oceanside Corolla Condo, Pool, No Stairs

Welcome to Corolla Luxury Rentals - TERRAPIN POINT an Oceanside vacation rental with no stairs to climb, located in the newly built Beacon Quarters community in the popular area of Corolla Light with access to Whalehead Beach. ~Terrapin Point is fully furnished with high end beach decor ~ Open concept living room / kitchen ~ Vaulted ceilings throughout to provide a spacious feel and room for all. ~ Community Pool steps away; Open May 2025 TBD ~ Gas Grill - 7 min walk to beach

Guest favourite

Apartment in Sandbridge

4.94 out of 5 average rating, 63 reviews

Cher's Place @ The Beach

Relax with the whole family at this peaceful place to stay in Sandbridge! 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 and bedding so pics may not match perfectly. Need more room?? See my other property!

Guest favourite

Home in Corolla

4.94 out of 5 average rating, 106 reviews

Summer fun at Summer Salt!

Awesome off road getaway! You will need 4 Wheel Drive (not awd) vehicle to access the property as there are no roads. Newer construction on the beach in Carova right next to the wild horse preserve. You will likely see horses on a daily basis! Home has 3 bedrooms and 3 baths with 3 deck areas to enjoy the ocean views, sunsets and breezes! Easy walk to the beach, parking passes included. New party deck with hot tub, grill, table, seating and string lights.

Top guest favourite

Home in Virginia Beach

4.96 out of 5 average rating, 196 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!

Guest favourite

Tiny home in Cape Charles

4.88 out of 5 average rating, 121 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!

Guest favourite

Home in Cape Charles

5 out of 5 average rating, 49 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.