Vacation rentals with a patio in Chesapeake

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Top-rated patio rentals in Chesapeake

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

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Top guest favorite
A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.
Home in Smithfield
4.97 out of 5 average rating, 293 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 favorite
A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.
Boat in Willoughby
4.93 out of 5 average rating, 114 reviews

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

Guest favorite
The bedroom features soft blue walls and a spacious bed with a light blue quilt. A decorative painting of flowers hangs above the bed. Natural light enters through the window, highlighting the room's warm-toned carpet and modern furnishings, including a nightstand and a mirror.
Home in West Park View
4.87 out of 5 average rating, 128 reviews

Penny’s Palace 1 Bed/1 Bath Home

Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

Guest favorite
Condo in Chesapeake
5 out of 5 average rating, 10 reviews

Luxe Cozy Condo in - Western Branch

Come relax and enjoy this cozy stylish newly renovated smart home. This home includes two bedrooms and one bathroom with a fully equipped kitchen and laundry room. The main bedroom has a private balcony. The living room includes a sleeper couch for extra guests. This unit is located on the second floor of a family-friendly condominium community. This home caters to long-term traveling professionals. This home is located near a YMCA, Bowling Alley, Mall, Restaurants, Shops, and Hospitals.

Top guest favorite
A spacious guest suite features a large bed with layered bedding, accompanied by a cozy green throw. A vibrant area rug enhances the room's warmth, while a small table and chair provide a work or relaxation space. A kitchenette area is visible in the background.
Place to stay in Virginia Beach
4.99 out of 5 average rating, 206 reviews

Salty Willow-a “suite retreat” in the heart of VB!

We love welcoming people to our home in the heart of Virginia Beach! Come and go as you please in our guest suite with a separate entrance and privacy latches-no one will enter your space. You will also have the added convenience of having the host family on site. We do our best to provide the comforts of home. -fridge/freezer -beach essentials -toaster -coffee bar -extra essentials We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

Top guest favorite
A cozy living area is furnished with two light blue sofas and a light-colored area rug. A ceiling fan hangs above, providing air circulation. In the background, a dining area with a wooden table and blue chairs is visible through an arched entryway, framed by bright natural light from window blinds.
Cottage in Norfolk
4.93 out of 5 average rating, 135 reviews

Cozy Cottage - NEW hot tub, dogs OK, fenced yard

Welcome to Wayland Beach Cottage, your home away from home! Here are some of the things you can look forward to: - queen beds - smart TVs in each room - fully equipped kitchen & laundry room - fully fenced backyard - 6-person hot tub *new!* - outdoor seating under a pergola - 4-burner gas grill - long, private driveway - speedy Wi-Fi We're nearby to so many fun things to do, shop, and eat! Bring the family, see the sights, and come relax at Wayland Beach Cottage. We'd love to have you!

Guest favorite
Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.
Home in Norfolk
4.97 out of 5 average rating, 115 reviews

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 spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

Top guest favorite
A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.
Cottage in East Ocean View
4.99 out of 5 average rating, 280 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Top guest favorite
A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.
Home in East Ocean View
5 out of 5 average rating, 135 reviews

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

Guest favorite
A spacious studio area is highlighted by a king-size bed with a white bedspread and decorative pillows. A cozy seating arrangement and dining table are seen, alongside a fireplace and wall-mounted TV. Soft lighting enters through the windows adorned with wooden blinds.
Guest suite in Virginia Beach
4.97 out of 5 average rating, 174 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 favorite
A charming single-level home is viewed from the exterior, featuring light blue siding and a well-maintained front yard with green grass. Concrete pathways lead to the front porch and drive, with trees providing a pleasant backdrop and blue skies overhead.
Home in Norfolk
4.94 out of 5 average rating, 110 reviews

Bayview Beach/Airport/3 Bedrm/6 Beds/2 Bath/ 4TV

Entire house/3 Bedrm+3 sofa bed/2 Bathtub/shower. 1 mile from Ocean View BEACH (Bay). Spacious 1500 sq ft. Quite, safe side street, approx. 25 min to VA Beach front! 4.5 miles from Airport. Naval base, dining, shopping, near. New furniture & appliances! 2 queen w/pillowtop and 1 full bed w/ Serta mattresses, 3 sofa beds, 4 Large smart TVs , Gig WiFi, Roku/retro/Atari games! Beach chairs&umbrellas, towels, soaps, bbq grill, cooking/utensils, etc. avail. NO PETS, INSIDE SMOKE

Top guest favorite
A view of the beach stretches towards the horizon, framed by green grass and a flower pot. White lounge chairs are arranged for relaxation, while colorful umbrellas dot the sandy shore, providing shade to beachgoers enjoying the ocean.
Condo in Virginia Beach
4.96 out of 5 average rating, 157 reviews

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family

Popular amenities for Chesapeake patio rentals

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$20,901 GYDG$21,946 GYDG$22,991 GYDG$22,991 GYDG$23,409 GYDG$25,499 GYDG$27,171 GYDG$26,126 GYDG$22,991 GYDG$21,110 GYDG$21,528 GYDG$21,528 GYD
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Quick stats about vacation rentals with a patio in Chesapeake

  • Total vacation rentals

    Explore 480 vacation rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake vacation rentals start at G$2,090 GYD per night before taxes and fees

  • Verified guest reviews

    Over 20,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    240 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 160 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wi-Fi availability

    470 of Chesapeake vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

  • 4.8 Average rating

    Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square

Destinations to explore