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

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

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.

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.

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.

Cook's Country Escape - House nestled in woods
Escape your day to day life to enjoy this house in the country. This countryside home will be great for you, your family and/or friends to be away from the city life yet close to a lot of destinations. We are 1/2 way in between VA Beach and OBX, NC so many guests will visit while they are in the area. This home is quaint like a cabin but has all the house amenities. From the moment you walk in, you will feel the warmth and comfort of a country home to enjoy and relax in during your stay.

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.

Sweet Suite!
Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Beachfront Exclusive Bay front Suite
This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay

Gorgeous Olde Towne historic home - modern updates
Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!

Quilted Quarters by the Bay with Private Entrance
Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Country Living Guest House (Upstairs/Downstairs)
This country living guest suite is conveniently positioned on Lone Star Lakes Park. It is located in a quiet, private drive. Prepare quality meals in the down-stairs fully equipped eat-in kitchen with built-in cabinets, spacious countertops, a full-sized fridge, an electric stove, and everything you need to feel at home. Just off the kitchen is a half-bath. NO PETS ALLOWED.

THE POINT! Private waterfront Oasis!
Enjoy breath taking views and a fully equipped home with many amenities. If you are looking for a private and intimate experience of quality time and a relaxing retreat with nature, this is IT!!! Convenient to Virginia Beach Oceanfront, Oceanview Beach in Norfolk, Downtown Norfolk, Rivers Casino, Ocean Breeze water park, Waterside District and a host of popular attractions.
Popular amenities for Chesapeake outdoor seating rentals
House rentals with outdoor seating

Wooded Wonderland Miniature Golf Hot tub Pool

Bungalow at the Bay

New Beach Home on the Chesapeake Bay

The Chesapeake St Retreat - Pet and Kid Friendly

Quiet Stay near Bay. Walk to Oceanview access

One block from the Beach

Country Comfort Close to the Beaches

Spanish Style Casita • 2BR/2BA • Dogs Welcome
Apartment rentals with outdoor seating

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

Sojourn Guest House: Buckroe Beach Suite B

Private apartment only 3 blocks from the Beach

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

Best location in Olde Towne Portsmouth

The Coastal Studio

Elegant Cozy Colonial/Private/Self Check-in

Cozy Ground Floor Apt in Historic Home
Condo rentals with outdoor seating

Beachfront Getaway, Pet Friendly, Mermaid Suite

Cozy & Fun Hampton Condo ~ WIFI & W/D!

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

Spacious Captain’s Beach Suite Near Rudee Inlet

Ocean & Bay Views - Local Family Owned & Operated

Oceanfront Gem VaB Studio Exceptional Views

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Paradise at the Beach
Quick stats about vacation rentals with outdoor seating in Chesapeake
Total vacation rentals
Explore 270 vacation rentals in Chesapeake
Nightly prices starting at
Chesapeake vacation rentals start at R347 ZAR per night before taxes and fees
Verified guest reviews
Over 15,160 verified reviews to help you choose
Family-friendly vacation rentals
150 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 90 rentals that welcome pets
Vacation rentals with a pool
40 properties feature pools
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Wi-Fi availability
260 of Chesapeake vacation rentals include wi-fi 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 Cinemark Chesapeake Square
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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
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Wilkins Beach
- James River Country Club
- Little Creek Beach