Chesapeake vacation rentals

A sandy path leads to the beach, bordered by wooden fences on either side. Grasses sway gently in the breeze, and the calm waters can be seen in the distance under a clear blue sky.

4.87 out of 5 average rating, 101 reviews

The Happy Place-Quiet, North End 1 block to ocean!

Nicest area in VA Beach & 5 minute walk to the beach! Enjoy a private, peaceful, vintage beach house and fully fenced yard in exclusive North End's quiet family neighborhood! Away from the crowds w/ easy access to everything. Great for surfing, swimming, walking, biking (1st State Landing park nearby), kayaking, fishing, dreaming, or reading. Cul-de-sac location. Detached house with dog-friendly yard! Comes w/ sheets & towels, 3 bikes, surfboard, beach chairs, buggy & umbrella. Equipped kitchen.

A large statue of Neptune is depicted, holding a trident with sun rays radiating behind it. The scene captures the early morning light, creating a warm glow that highlights the statue’s intricate details and the surrounding paved area.

4.91 out of 5 average rating, 159 reviews

Beach Cottage #2 19th - 3 Blocks from Beach

Welcome to ResortCottages19. Cozy authentic beach cottage with many original features centrally located on 19th street, the heart of the VIBE district; boardwalk, beach, convention and sports center within 3 blocks. Walk or bike to local coffee shops, breweries, and restaurants. Take in the live music from various venues along the boardwalk. Shop at the Old Beach Farmer's Market on Saturdays. Enjoy the privacy of your own deck and backyard with plenty of parking. Easy access to the interstate.

4.87 out of 5 average rating, 233 reviews

The image features a walkway leading from a concrete path to an expansive beach, with smooth sand extending towards the ocean. A large trash receptacle is visible beside the pathway, and the calm sea can be seen in the distance, under a clear blue sky.

Condo in Sandbridge

Ocean Escape

Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

4.86 out of 5 average rating, 137 reviews

A bright living area features expansive floor-to-ceiling windows with ocean views. A spacious sectional sofa is arranged around a central coffee table. Two upholstered chairs and a small dining table offer additional seating options. The walls are painted in a calming blue, complementing the decor.

Condo in Virginia Beach

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

4.94 out of 5 average rating, 126 reviews

A scenic golf course is set against a backdrop of a sunset sky, casting warm tones over the lush green fairways. Sand traps and tall trees are positioned along the edge, with a peaceful waterfront visible in the distance.

Condo in Williamsburg

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

Guest suite in Virginia Beach

Soft illumination from ground-level lights highlights the lush landscaping surrounding the property. Various plants and flowers are visible, and a calm ambiance is created by the gentle glow. In the background, trees silhouette against the evening sky, enhancing the serene setting.

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

A welcoming living room features a light-colored sofa with decorative pillows, a wooden coffee table, and a plush area rug. Large windows allow natural light to fill the space, which opens to an inviting entryway with stairs leading up.

4.93 out of 5 average rating, 190 reviews

Spacious home for up to 10! GREAT for families!

Experience the heart of Virginia Beach's Vibe District! *Spacious 4BR, 3.5BA home; accommodates up to 10 guests *Two separate living rooms for relaxation and entertainment *Just 2.5 blocks from the beach; beach cart and gear provided *1 mile to the Convention Center; perfect for event attendees *Fully equipped kitchen for home-cooked meals *High-speed WiFi; stay connected during your getaway *Washer & dryer available for your convenience Book your dream family vacation today with us!

A bright and airy living area features two teal sofas adorned with colorful cushions, inviting relaxation. A large flat-screen TV is mounted on a white wall, complemented by a cozy coffee table. The open kitchen is visible, showcasing modern appliances and vibrant pendant lights.

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.

4.97 out of 5 average rating, 242 reviews

An aerial view showcases a private beach beside a rectangular saltwater pool, surrounded by open grassy areas, perfect for outdoor activities. The landscape features a clear path leading from the property to the beach, with residential buildings on one side.

Cottage in Norfolk

Positano Villa

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

A serene sunset is captured over calm ocean waters, where hues of orange and pink blend softly into the sky. The horizon is defined by the setting sun, reflecting light across the water's surface, creating a peaceful atmosphere.

4.96 out of 5 average rating, 195 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!

A spacious bathroom is seen featuring a dual-sink vanity with a marble countertop and neatly stacked towels. Glass doors lead to a bright sitting area that overlooks the outdoors, while large mirrors reflect ample natural light.

4.96 out of 5 average rating, 320 reviews

Lakeside Oasis - Walk 2 everything! 3Blocks2Beach

Beautiful lakefront townhome located 3 blocks from the beach - walking distance to ocean, boardwalk, best restaurants in Virginia Beach, shopping & entertainment! Perfect for groups of 6 or less. 2 large bedroom suites - great for friends/families that want to get away together yet still have their own space. We provide complimentary beach chairs, umbrella, cooler & boogie boards. Just bring the sunscreen!

4.95 out of 5 average rating, 161 reviews

A wooden deck features two light blue chairs positioned towards an open sliding door. The interior reveals a glimpse of a spacious room beyond the door, framed by soft curtains. The deck provides a view of the neighborhood and outdoor surroundings.

Home in Chic's Beach

Steps to Beach at Chics Beach! Sleeps 12 + Garage!

Experience the perfect blend of convenience and excitement at this beautiful 3 bedroom, 3 1/2 bath home in Virginia Beach. Featuring 3 king size beds and 2 fulls, it’s ideal for a family getaway. Enjoy a fully stocked kitchen, Wi-Fi, Smart TV, and laundry. We are only a 20 second walk from the beach! Whether for a weekend or an extended stay, this home has it all!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Chesapeake vacation rentals

Stay near Chesapeake's top sights

Waterside46 locals recommend

Chrysler Museum of Art56 locals recommend

Nauticus78 locals recommend

MacArthur Center20 locals recommend

Waterside District54 locals recommend

Topgolf41 locals recommend

Vacation rentals with jacuzzis in Chesapeake

4.88 out of 5 average rating, 147 reviews

A charming blue beach house features a multi-level design with large windows that invite natural light. A spacious deck offers unobstructed views of the surrounding sandy landscape. Steps lead up to the entrance, enhancing accessibility to the home. Wild grasses frame the property.

Cottage in Corolla

Horses-Views-Dog Friendly-4WD Area

Vacation home in Sandbridge

A covered hot tub offers a soothing retreat, with jets creating gentle bubbles. Nearby, lounge chairs are positioned by the pool, allowing for relaxation. Natural light filters through the slatted walls, enhancing the serene atmosphere of the outdoor area.

4.89 out of 5 average rating, 38 reviews

VB Paradise / Private Pool, Hot Tub

4.98 out of 5 average rating, 119 reviews

An aerial view depicts the guest suite, nestled among lush greenery, with a spacious swimming pool nearby. The main house, along with various outdoor amenities, is visible, showcasing well-maintained landscaping and open fields surrounding the property.

Guesthouse in Suffolk

Country Living Guest House (Upstairs/Downstairs)

4.67 out of 5 average rating, 9 reviews

The exterior of Beach Quarters Resort is showcased, featuring a modern design with cream and beige striped walls. A round, glass entrance highlights the main lobby area, surrounded by lush green landscaping. A multi-level parking garage is visible in the background, under a clear blue sky.

Condo in Virginia Beach

Beach Quarters- studio Oceanfront

4.97 out of 5 average rating, 198 reviews

A private Jacuzzi is positioned on a covered porch, surrounded by greenery. LED lights illuminate the water, creating a relaxing atmosphere, while a ceiling fan provides airflow. Adjacent to the hot tub, a clock is mounted on the wall, enhancing the outdoor space.

Guesthouse in Portsmouth

Spring Hill Guest Cottage - Portsmouth

Apartment in Williamsburg

A spacious bedroom features a light blue accent wall and a large white bed with a decorative throw blanket. On either side of the bed, stylish lamps provide soft lighting, and a colorful pillow adds a subtle pop of color.

5 out of 5 average rating, 3 reviews

Williamsburg King's Creek Plantation 1BR, 1BA Unit

Apartment in Virginia Beach

The Ocean Key Resort building stands prominently against a sunset backdrop, highlighting its multiple stories and modern architectural design. The beach is visible across the street, with surroundings including nearby roads and structures, emphasizing the resort's convenient location.

4.8 out of 5 average rating, 5 reviews

Ocean Key Resort-Unit with balcony-1 bedroom

4.89 out of 5 average rating, 141 reviews

A charming log cabin features a front porch with a wooden railing and seating area. Surrounding the cabin are landscaped flower beds, tall trees, and a well-kept lawn. The cabin's rustic design is complemented by its natural setting, offering a peaceful view of the waterfront.

Cabin in Smithfield

Wickline Cabin on Moon Creek

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House rentals in Chesapeake

4.92 out of 5 average rating, 131 reviews

A spacious living room features a comfortable sectional sofa, a wooden entertainment center with a large TV, and a decorative console table. Light-colored walls complement the area rug, and framed artwork adds interest. A staircase is visible, leading to the upper level.

Home in Norfolk

3 bedroom private home a block from the beach!

4.91 out of 5 average rating, 110 reviews

Home in Buckroe Beach

3 bedroom home minutes from Buckroe Beach

An open and inviting living area features two sofas in blue and gray, complemented by a light wooden coffee table. Natural light filters through large windows, highlighting the subtle wall art and a mix of seating options including stylish chairs and a lamp.

4.94 out of 5 average rating, 114 reviews

Lakefront House @ Oceanfront

4.86 out of 5 average rating, 113 reviews

The covered porch features a seating area with two white chairs and a small table, surrounded by hanging flower baskets. The front door is framed by large windows, allowing natural light into the space. Lush trees are visible in the background.

Home in Moyock

Cozy Country Cottage

4.87 out of 5 average rating, 254 reviews

A dining area is set with a round table surrounded by eight upholstered chairs. The walls are painted in a calming blue, and large windows allow natural light to fill the space. In the background, a kitchen can be seen, featuring a modern layout.

Home in Williamsburg

Bamboo Bungalo Duplex Near Busch Gardens

The open living area features warm wooden floors, with a cozy seating area and a television on one side. A dining table with colorful chairs occupies the center, while a staircase leads to the upper level. Decorative elements add a personal touch throughout the space.

4.95 out of 5 average rating, 139 reviews

Family hideaway

4.95 out of 5 average rating, 104 reviews

A cozy living room is featured, showcasing a light-colored sofa paired with two yellow accent chairs. A wooden coffee table sits at the center, and two windows are dressed with sheer curtains, allowing gentle light to brighten the space. A ceiling fan is present above.

Home in Chesapeake

The Cozy Cottage Two Bedroom, King bed House

A balcony area features two brightly colored chairs, one blue and one red, positioned on a wooden deck. The view includes tree-lined surroundings and a quiet street, emphasizing a tranquil outdoor space.

4.8 out of 5 average rating, 145 reviews

Chesapeake Bay Beach house (Chic’s Beach) 1 block!

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House rentals with jacuzzis in Chesapeake

An outdoor gathering space is illuminated by string lights, featuring a fire pit surrounded by several black adirondack chairs. The two-story blue house looms in the background, showcasing multiple balconies and steps leading to the lower level.

5 out of 5 average rating, 17 reviews

*May specials LUX, Firepit pool/hot tub,ocean view

4.94 out of 5 average rating, 108 reviews

Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.

Home in Portsmouth

Wooded Wonderland Miniature Golf Hot tub Pool

4.92 out of 5 average rating, 76 reviews

A four-person hot tub is illuminated with blue light, set within a cozy space featuring string lights overhead. Large windows with decorative shutters provide natural light, while a comfortable swing chair is positioned nearby, enhancing the relaxation area.

Home in Newport News

1-Bedroom Home Near Christopher Newport University

A shaded deck area features two wooden rocking chairs with blue cushions and a small side table. Large windows are visible in the background, allowing natural light to brighten the space. The expansive wooden flooring complements the tranquil atmosphere.

5 out of 5 average rating, 16 reviews

Lazy Palm Carova 4x4 Beach

4.87 out of 5 average rating, 39 reviews

A hot tub is enclosed within a shaded gazebo, illuminated by soft lights. The surrounding fence adds privacy, while the serene blue water invites relaxation. The evening setting creates a calming atmosphere, perfect for unwinding after a day of activities.

Home in Buckroe Beach

Baybreeze @ Buckroe -hot tub, sauna, game rm. 5bd

4.96 out of 5 average rating, 77 reviews

A spacious hot tub is situated on the deck, overlooking the vast expanse of the water. The tranquil surface ripples under the cloudy sky, creating a serene ambiance. A black lounge chair is positioned nearby, inviting relaxation while enjoying the captivating views.

Home in Buckroe Beach

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

A hot tub is displayed, featuring a clean water surface with gentle ripples. The surrounding area is enclosed by wooden fencing and green foliage is visible in the background, providing a sense of privacy and tranquility.

5 out of 5 average rating, 16 reviews

Splash of Lime Carova 4x4 Beach Cottage

A hot tub is positioned on a concrete pad in a grassy backyard. The hot tub features multiple seats and jets, with jets activated, creating a relaxing water motion. A charcoal grill is covered nearby, and a doorway leads to the side of the house.