
Holiday rentals with a patio in Chesapeake
Find and book unique rentals with patio on Airbnb
Top-rated rentals with patio in Chesapeake
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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.

Charming coastal home w/ outdoor area and river views
Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the Williamsburg historic triangle (Busch Gardens), or just take it easy around the house and enjoy the outdoor area, the choice is yours.

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.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guest, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

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!

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.🛳🌊🚢🏠😊!

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.

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.

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

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

5 Min to Downtown & Ghent, Fenced Yard, Firepit
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

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 rentals with patio in Chesapeake
Flat rentals with a patio

Virginia Beach, Getaway

Paradise in Williamsburg next to Busch Gardens

Cozy Mermaid Hideaway

The Liberty Flat

The Cottage at Sojourn: Buckroe - one bedroom

Sandbridge Beach Bay Getaway

Works 4 Me: New listing

Cozy apartment close to a beach
House rentals with a patio

The "Bison" contemporary retreat (King Bed)+

Cozy Single Family Home

Beautiful home in Chesapeake

The Bartlett Inn

Portsmouth's Finest

Quiet Stay near Bay. Walk to Oceanview access

Pointe Haven near Historic Yorktown

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!
Apartment rentals with a patio

Bay Breeze At Ocean View Beach Home

Cher's Place @ The Beach

The Port - Large condo on Mason Avenue!

New Oceanfront 2bd, 2bth / Beach / Pool / Boat

2BD2BA Condo w/Pool2Blocks2Beach

2BD/2BA Villa across Currituck Beach Lighthouse

Paradise at the Beach

*Mid/Long Term Rental* Cozy Home at Mary Roberts
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 87 | € 91 | € 95 | € 95 | € 97 | € 106 | € 112 | € 108 | € 95 | € 87 | € 89 | € 89 |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about holiday rentals with a patio in Chesapeake

Total holiday rentals
Explore 480 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at € 9 per night before taxes and fees

Verified guest reviews
Over 20,350 verified reviews to help you choose

Family-friendly holiday rentals
240 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 160 rentals that welcome pets

Holiday rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wifi availability
470 of Chesapeake holiday rentals include wifi 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 Cinema Cafe-Greenbrier Mall
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Jersey Shore Holiday rentals
- Myrtle Beach Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Jersey City Holiday rentals
- Cape Fear River Holiday rentals
- Ocean City Holiday rentals
- Rappahannock River Holiday rentals
- Flat rentals Chesapeake
- Guest house rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with pools Chesapeake
- Rentals with beach access Chesapeake
- Rentals with outdoor seating Chesapeake
- Cottage rentals Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Waterfront rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Fitness-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- House rentals Chesapeake
- Rentals with breakfast Chesapeake
- Beachfront rentals Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with a firepit Chesapeake
- Apartment rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a patio Virginia
- Rentals with a patio United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach
- Red Wing Lake Golf Course




