
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.

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!

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.

3 bedroom private home a block from the beach!
Relax with the whole family at this peaceful home. A block to the beach! 3 bedrooms and 2 bathrooms, with an outdoor shower and finished basement with extra living space. Outdoor patio with gas grill and patio furniture. All amenities included sheets, towels, cooking utensils, etc. Fast Wi-Fi throughout the home. Can sleep up to 8! Pets always welcome. All bedrooms are on main level no stairs required. Weekly and monthly discounted rates upon inquiry.

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.

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

Spacious 3 Bedroom Home | Near many Shops & Dining
Nestled in a prime location, this bright and inviting 3-bedroom home puts you minutes from shopping, top restaurants, beaches, golf, hospitals, and military bases. Enjoy the perfect blend of comfort and convenience, plus a huge fenced backyard ideal for relaxing, pets, or outdoor fun. Whether for a family getaway, business trip, or long-term stay, your unforgettable Chesapeake stay starts here.

Waterfront Oasis: Fishing Pier, Pool, Beach Access
Escape to our waterfront retreat in Chesapeake's premier Bryan's Cove community! This modern 3-bedroom townhome comfortably sleeps 8. Enjoy resort-style living with a community pool, pier on Deep Creek, and a dog park. Perfect for families and groups seeking a peaceful coastal getaway with modern comforts and convenient access to local attractions. Your serene Virginia vacation starts here.

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.

Comfy House! The Perfect Getaway
Bring the whole family to this great place with lots of room for fun! This spacious 4 bedrooms , 2-bathroom home is the perfect blend of comfort and style, offering a relaxing escape for families, groups, or anyone looking for a peaceful retreat. Whether you're here for a short getaway or an extended stay, you'll find everything you need to make your time unforgettable.
Popular amenities for rentals with patio in Chesapeake
Flat rentals with a patio

Virginia Beach, Getaway

The Liberty Flat

The Cottage at Sojourn: Buckroe - one bedroom

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

The Lighthouse-2 blocks to beach
House rentals with a patio

The Artist House

The Bird’s Nest

Beach Stay

Modern Comfort Minutes from Waterside & Downtown

Beach Bungalow • Navy Base • Quiet St • Dogs OK

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

The Couple’s $pot @ The Dock Near Casino

Penny’s Palace 1 Bed/1 Bath Home
Apartment rentals with a patio

Bay Breeze At Ocean View Beach Home

August Suite | Beach | Balcony | Fire Pit

Paradise at the Beach

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

Oceanfront Condo/ Pool/ Surfing/ Fishing / EW 1002

Paradise by Busch Gardens & beach, lovely 3bd/3ba

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

Sun & Fun! Ocean/Bay views /3 pools, gym, arcade
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €99 | €95 | €96 | €96 | €97 | €106 | €113 | €109 | €96 | €96 | €100 | €99 |
| 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 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
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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
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Old Dominion University
- Regent University
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- Neptune's Park
- First Landing Beach
- Currituck Club
- Currituck Beach Lighthouse
- The Military Aviation Museum
- The Mariners' Museum
- Nauticus
- Back Bay National Wildlife Refuge-N





