
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.

Just Steps Away to the Beach
Enjoy Nov. thru Feb. at Va. Bch--average day temp. in 60s and 50s. Just steps or bike through a nice area to the beach, restaurants, culture, The Dome, Convention Ctr & other activities. Take a 10-min. walk or bike to the beach (7 short blocks). No traffic or parking hassles! We are close to I264, several military bases & Hilltop Shopping area. This is a quiet neighborhood & convenient location. Perfect for couples & solo travelers. NO animals or pets allowed! NO children under 13 yrs. of age!

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!

The Little House on Park Avenue
Our cottage is a quiet get-away. Sit on the front porch and enjoy the birds and a cup of coffee. Small kitchen provides everything you may need for your stay, including a local yummy treat. A desk in the bedroom gives you a place to work while others in your group utilize the spaces in the living room or dining room. You can leisurely stroll by the Ruritan Park to Studio 32 Gallery and Gift shop on weekends. In 10 minutes drive to Merchants Millpond State Park. Historic Edenton only30 minutes.

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.

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.

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.

Cozy Ground Floor Apt in Historic Home
Charming 1st floor apartment with private entrance in circa 1795 home in the Olde Towne historic neighborhood. Guests enjoy an easy walk to downtown shops, restaurants, breweries, museums, and a movie theater. The waterfront is close with marinas, restaurants, and the Elizabeth River ferry to transport you to Norfolk to enjoy events on the waterfront. Business or military travelers are two blocks from the Renaissance Hotel and a 15-minute walk from the Portsmouth Naval Hospital.

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.

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!
Popular amenities for Chesapeake outdoor seating rentals
House rentals with outdoor seating

Water Oaks at Chic's Beach

Cozy beach cottage! One block to the beach!

Ghent on the Corner: Cozy 3 bed 2.5 bath home

One block from the Beach

Sportsman's Paradise ( Hunting & Fishing )

3 bedroom 3 bathroom beach house pets welcome

5 Min to Downtown & Ghent, Fenced Yard, Firepit

Condo in Buckroe Beach
Apartment rentals with outdoor seating

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

Paradise in Williamsburg next to Busch Gardens

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

902C Coastal King Retreat Steps from Beach + Sauna

The Cottage at Sojourn: Buckroe - one bedroom

THE OLD SALT B | Beach Living

Private apartment only 3 blocks from the Beach

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool
Condo rentals with outdoor seating

Cozy & Fun Hampton Condo, WIFI & W/D! Dogs welcome

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

Oceanfront, beach, boardwalk, fun, dolphin, sunris
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ404 | ﺩ.ﺇ404 | ﺩ.ﺇ415 | ﺩ.ﺇ441 | ﺩ.ﺇ466 | ﺩ.ﺇ477 | ﺩ.ﺇ503 | ﺩ.ﺇ496 | ﺩ.ﺇ422 | ﺩ.ﺇ404 | ﺩ.ﺇ422 | ﺩ.ﺇ422 |
| 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 outdoor seating in Chesapeake

Total vacation rentals
Explore 270 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at ﺩ.ﺇ73 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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