
Vacation rentals with a patio in Chesapeake
Find and book unique accommodations with an outdoor patio on Airbnb
Top-rated accommodations with an outdoor patio in Chesapeake
Guests agree: these accommodations with an outdoor 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

Ghent on the Corner: Cozy 3 bed 2.5 bath home
My cozy, 3 bed / 2.5 bath Norfolk home has a spacious 1st floor primary suite with a full bathroom, 2 bedrooms upstairs along with a 2nd full bathroom. No cleaning fee or checkout instructions. Pet-friendly! Free Wi-Fi, parking for 4 cars, grill & gazebo. Distances: CHKD - 5 min EVMS - 5 min Sentara Norfolk General - 5 min Waterside / Downtown - 10 min Ocean View - 20 min VB Oceanfront - 25 min
Popular amenities for Chesapeake accommodations with an outdoor patio
Apartment rentals with a patio

Virginia Beach, Getaway

Paradise in Williamsburg next to Busch Gardens

The Liberty Flat

The Cottage at Sojourn: Buckroe - one bedroom

Stylish Two Bdrm, 1 1/2 bth, King Bed Townhouse

Sandbridge Beach Bay Getaway

Works 4 Me: New listing

Cozy apartment close to a beach
House rentals with an outdoor patio

The "Bison" contemporary retreat (King Bed)+

Cozy Single Family Home

The Bartlett Inn

Portsmouth's Finest

8br, Pool, Lzy Rvr, Pier, Pool, Hot Tub (Sandbridge)

Chesapeake Haven - w/ Lux Kitchen

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

Casa del Mar - Bold, Bright & Steps to the Sand!
Condo rentals with a patio

Bay Breeze At Ocean View Beach Home

The Port - Large condo on Mason Avenue!

2BD2BA Condo w/Pool2Blocks2Beach

Paradise at the Beach

*Mid/Long Term Rental* Cozy Home at Mary Roberts

2BR Condo in Chesapeake - Western Branch

Colonial Williamsburg Spacious 4 Bedroom Suite!

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $140 CAD | $148 CAD | $155 CAD | $155 CAD | $157 CAD | $171 CAD | $183 CAD | $176 CAD | $155 CAD | $142 CAD | $145 CAD | $145 CAD |
| 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 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 $14 CAD 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 and 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

Wifi availability
470 of Chesapeake vacation 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
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- 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
- Wilkins Beach
- James River Country Club
- Little Creek Beach
- Red Wing Lake Golf Course




