
Holiday rentals with a patio in Chesapeake
Find and book unique rentals with patio on Airbnb
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 $13 SGD per night before taxes and fees

Verified guest reviews
Over 21,590 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wifi availability
480 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
Top-rated rentals with patio in Chesapeake
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

Hidden Gem.4/bedroom cozy home fenced in yard
Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

The Western Branch Professionals Townhome
Centrally located in quiet neighborhood w/parking & fast Wi-Fi. < 5 min to groceries, coffee, restaurants, & shopping. Perfect place to explore all Hampton Roads beaches, entertainment, nightlife, shopping & more! About 45 min to Virginia Beach Oceanfront, Atlantic Park Surf, Ocean Breeze Waterpark/Motor World, Adventure Park, VA Marine & Science Museum . < 20 mins to Downtown Norfolk/ Waterside, Norfolk Outlets, Rivers Casino Portsmouth. < 1hr to Busch Gardens/Water Country USA, Williamsburg.

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!

Lovely 2-bedroom 1100 sq ft Apt with free parking
You will enjoy easy access to everything in downtown Portsmouth from this centrally located place. You are in a residential area two blocks from the heart of downtown Portsmouth, a half a mile to the Portsmouth Naval Hospital in the Historic Olde Towne district and a Starbucks one block away. The Virginia Beach ocean front is a half hour away by car. This is a historic building on the National Register of Historic Places. It consists of four apartments; one on the second floor is your Airbnb.

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 space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, 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!

Quiet 3/2 beautiful Chesapeake
Enjoy a peaceful stay at this lovely 3-bedroom house nestled in the Great Bridge area of Chesapeake. The bedrooms feature a King size bed, queen bed, and two twin beds, perfect for a variety of guests. With amenities like WiFi, AC, full kitchen, covered/screened-in back patio, large fenced in yard and a washer/dryer machine, your comfort is guaranteed. The two bathrooms offer convenient shower facilities. Feel at home in this fantastic property and make the most of your stay in Chesapeake.

Serene Tree House Retreat | Spacious 1br/1bth Home
Step inside a tucked-away hidden oasis surrounded by trees and waterfront views. The apt is on the 2nd floor amongst the trees. One of the trees is a 200-year-old Magnolia Tree, which is why the space is called Magnolia Tree House. The tall windows make the space bright and airy and give you a 180-degree scenic view of the treetops. To bring the outside in, we decorated the apt to feel like the trees are also inside. The cozy furnishings will make it hard to leave.

Cook's Country Escape - Cozy Retreat
Escape the everyday and enjoy this cozy countryside retreat! Nestled halfway between Virginia Beach and the Outer Banks, this home offers the charm of a cabin with the comforts of a full house. Perfect for families or friends, it’s a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, you’ll feel the warmth and relaxation of a true country home. It’s been a great rental with great ratings.

The Harlequin Cottage
This unique place has a style all its own. Cottages on the Point was launched in 2018 and offers timeless interior styling and stunning resort style outdoor views. The property features a seasonal (Mid-April to the end of October) 14,000 SF outdoor tiki bar with a shared saltwater pool with swim up bar, outdoor kitchen, and live music. The residences are adjacent to the tiki bar deck and include open layouts, terraces, and custom décor.

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

Best Temporary Rental in Chesapeake
Owner is a Real Estate Agent in the State of Virginia. Comfortably and Elegantly Furnished townhome conveniently located in the Greenbrier area of Chesapeake where you'll find tons of shopping, restaurants and close proximity to the interstate. Two reserved parking spaces right at your front door. Quiet location, comfortable beds, super clean! Welcome to your home away from home.
Popular amenities for rentals with patio in Chesapeake
Flat rentals with a patio

Virginia Beach, Getaway

The Cottage at Sojourn: Buckroe - one bedroom

Private Boutique Apt •W/D• Near Casino & Downtown

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

The Sun Room - 2BR/1BA

Works 4 Me: New listing

Cozy apartment close to a beach

Vibe District, Atlantic Surf Park, VB Sports Ctr
House rentals with a patio

Grandview Island Beach Cottage Private Fenced Yard

Cozy beach cottage! One block to the beach!

R & R River House

Spacious 3 Bedroom Home | Near many Shops & Dining

Modern Comfort Minutes from Waterside & Downtown

Beach Bungalow • Navy Base • Quiet St • Dogs OK

Contemporary 5 BR, 4BA, Over 3500 SF Water Front

Bay and Sea
Apartment rentals with a patio

Bay Breeze At Ocean View Beach Home

Clean, Calm, Contemporary home mins from Beach

Oceanaire Resort with Ocean View, Pool, 1br/4

2BD2BA Condo w/Pool2Blocks2Beach

Paradise at the Beach

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

Coastal Living Luxury Oceanfront Condo, Pool Beach

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $147 SGD | $141 SGD | $142 SGD | $142 SGD | $145 SGD | $158 SGD | $168 SGD | $162 SGD | $142 SGD | $142 SGD | $149 SGD | $147 SGD |
| 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 |
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- Rentals with a patio Virginia
- Rentals with a patio United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Chrysler Museum of Art
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- The Mariners' Museum
- Nauticus
- Town Point Park





