
Holiday rentals with outdoor seating in Chesapeake
Find and book unique rentals with outdoor seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Chesapeake

Total holiday rentals
Explore 270 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 15,750 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wifi availability
270 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 outdoor seating in Chesapeake
Guests agree: these rentals with outdoor seating 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

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!

Private Guesthouse, Ghent/Downtown near ODU, EVMS
Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Historic Hideaway Private Apartment/Suite
You will be comfortable in this spacious, one bedroom suite. You have your own kitchen, washer/dryer, and living room space with large tvs in the bedroom and the living room. To wind down from your day step into your large beautiful shower that has endless hot water. Try living room sofa pulls out to a sleeper lay down while watching tv, or to use as an extra bed. Enter/exit thru a private entrance. Only you will have access to your space. Clean and inviting. Stay a day, or stay a while!

Modern Luxury Peace & Quiet.
Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Charming cozy apt historic in Old Towne Portsmouth
Newly renovated, newly furnished, cozy and relaxing 1 bd 1 bath apt is available for your stay. Coffee shops, museums, restaurants, bars and the Commodore Theater are all within steps. The ferry to downtown Norfolk is a quick walk and most Saturday mornings the Farmers Market is literally around the corner. If you are in town for a concert, the Amphitheater is a short walk away. This is a 1st floor apartment in a duplex. The only coomon area is the main entrance to the building and foyer.

Sportsman's Paradise ( Hunting & Fishing )
Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

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.

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, where every guest is made to feel like royalty. More than an Airbnb, it’s a one-of-a-kind boutique retreat intentionally designed to create unforgettable memories. From the peaceful atmosphere and thoughtful touches to your private entrance and relaxing escape, every detail has been curated to help you unwind, recharge, and experience something truly special. Come discover The Purple Room experience. 💜

10 min to Ocean View Beach: 20% Off July
Welcome to our charming 3-bedroom retreat nestled near the lake and Ocean View beach, just a short 10-minute drive away. Our property has an outdoor patio with firepit and balcony deck for alfresco dining area. Our Volleyball net in the large backyard is also available for use. This cozy haven is designed for comfort and entertainment, with thoughtful touches to make your stay truly memorable.
Popular amenities for outdoor seating rentals in Chesapeake
House rentals with outdoor seating

*Escape to the Tangerine Dream*

Wooded Wonderland Miniature Golf Hot tub Pool

New Beach Home on the Chesapeake Bay

@Whit’s End? Come in and Relax

Artful Retreat with a Private Pool

Ghent on the Corner: Cozy 3 bed 2.5 bath home

Play by the Bay 1 MIN TO WATER

Perfect Getaway!
Apartment rentals with outdoor seating

Serene Tree House Retreat | Spacious 1br/1bth Home

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

The Cottage at Sojourn: Buckroe - one bedroom

Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach

Private apartment only 3 blocks from the Beach

Best location in Olde Towne Portsmouth

The Coastal Studio

The Sun Room - 2BR/1BA
Apartment rentals with outdoor seating

Comfy 1BR w pond view Kingsmill

Beachfront Getaway, Pet Friendly, Mermaid Suite

Walk to beach lovely 2/2 in "Kingsmill on James"

Oceanfront Condo with Spectacular Beach View

Spacious Captain’s Beach Suite Near Rudee Inlet

Oceanfront Gem VaB Studio Exceptional Views

Ocean & Bay Views - Newly Renovated! Local Family!

Oceanfront Studio: Boardwalk, Beach, & Pool Views
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $155 SGD | $154 SGD | $156 SGD | $155 SGD | $164 SGD | $168 SGD | $177 SGD | $175 SGD | $149 SGD | $149 SGD | $162 SGD | $162 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 |
Destinations to explore
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- Family-friendly rentals Chesapeake
- Rentals with a firepit Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
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- Rentals with outdoor seating Virginia
- Rentals with outdoor seating 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
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Ocean Breeze Waterpark
- Regent University
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- Neptune's Park
- Currituck Beach Lighthouse
- Currituck Club
- The Military Aviation Museum
- Nauticus
- The Mariners' Museum
- Town Point Park





