Vacation rentals with outdoor seating in Chesapeake

Guest suite in Chesapeake

The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.

4.96 out of 5 average rating, 351 reviews

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!

4.97 out of 5 average rating, 129 reviews

A cheerful cottage is framed by tall trees and surrounded by a spacious lawn. The front porch features white railings and a welcoming green door. A mailbox stands at the edge of a quiet road, highlighting the tranquil neighborhood setting.

Cottage in Sunbury

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.

4.85 out of 5 average rating, 135 reviews

The bedroom features soft blue walls and a spacious bed with a light blue quilt. A decorative painting of flowers hangs above the bed. Natural light enters through the window, highlighting the room's warm-toned carpet and modern furnishings, including a nightstand and a mirror.

Home in West Park View

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.

4.97 out of 5 average rating, 675 reviews

A bright sleeping area features a spacious bed with light blankets, accented by a decorative throw. A large circular window allows natural light to fill the space, complemented by dark curtains. A cozy armchair sits nearby, enhancing the room's inviting ambiance.

Guesthouse in Ghent

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.

Guest suite in Portsmouth

A comfortable living room area is featured, showcasing a light-colored sectional sofa with dark blue accent pillows. A dark coffee table is set in front of the sofa. A vibrant world map painting adorns the wall, and natural light streams through a nearby window.

4.95 out of 5 average rating, 104 reviews

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!

4.99 out of 5 average rating, 174 reviews

A dining area features a wooden table set for six, accompanied by cross-back chairs. A standing lamp casts soft light. Large windows above allow natural light to illuminate the space, while a few pieces of artwork add a splash of color to the walls.

Apartment in Chesapeake

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.

4.96 out of 5 average rating, 299 reviews

A fully stocked kitchen is presented, featuring a gas stove, a refrigerator, and a microwave. A dark wooden hutch displays dishes and glassware, while a Keurig coffee maker is located on the countertop. Natural light filters in through a nearby window, illuminating the tiled floor.

Apartment in Olde Towne

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.

Guest suite in Virginia Beach

A spacious studio area is highlighted by a king-size bed with a white bedspread and decorative pillows. A cozy seating arrangement and dining table are seen, alongside a fireplace and wall-mounted TV. Soft lighting enters through the windows adorned with wooden blinds.

4.97 out of 5 average rating, 177 reviews

Quiet Suite with Private Entrance

Looking for a place to relax away from the chaos of the oceanfront? Quiet, private and secluded but conveniently located. Less than a 10 minute drive to the beach. Walking distance to breweries, local restaurants, grocery stores and other amenities Beautiful 2 acre property with plenty of outdoor space to find a place to relax, play games or take a nap Leesa king size mattress Luxurious bathroom with soaker tub Microwave and fridge, Kurig, k-cups snacks and popcorn Smart TV, WiFi

Guest suite in Chesapeake

The exterior of a private attached suite is shown, featuring a welcoming entrance with white steps and a small porch. Lush greenery and colorful flowers frame the walkway, leading to a paved driveway. A wooden fence provides privacy, while a well-maintained lawn enhances the setting.

4.95 out of 5 average rating, 616 reviews

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.

4.94 out of 5 average rating, 133 reviews

A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.

Home in Knotts Island

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

4.98 out of 5 average rating, 183 reviews

The living room features comfortable navy sofas with decorative cushions and an ottoman in a warm tone. A lamp stands beside a built-in bookshelf adorned with books and decor. Light streams through the windows, and a decorative fireplace adds to the room's character.

Home in Olde Towne

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!

4.97 out of 5 average rating, 125 reviews

A cozy bedroom features a four-poster bed adorned with soft linens and decorative pillows. A vintage armchair is positioned nearby, while a window dressed with light blue curtains allows natural light to brighten the space. Subtle wall stripes in calming colors add character.

Home in Chesapeake

Cook's Country Escape - Cozy Retreat w/ Big Deck

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.

Popular amenities for Chesapeake outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.93 out of 5 average rating, 150 reviews

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

Wooded Wonderland Miniature Golf Hot tub Pool

5 out of 5 average rating, 44 reviews

Home in Ocean View

Cozy Home Near Hospitals & Beach

4.98 out of 5 average rating, 128 reviews

The exterior of a two-story home is showcased, featuring natural wooden siding and two private balconies. Each balcony is equipped with a railing and simple seating, providing a comfortable space to enjoy the outdoors. A surrounding green area offers a touch of nature.

Home in Willoughby

One block from the Beach

4.94 out of 5 average rating, 114 reviews

A single-story ranch house is showcased, featuring a white exterior and a welcoming front door. A large tree and manicured shrubs are visible in the yard, enhancing the home’s curb appeal. Windows are seen along the front, allowing natural light into the living spaces.

Home in East Ocean View

Quiet Stay near Bay. Walk to Oceanview access

4.95 out of 5 average rating, 121 reviews

A spacious brick home is surrounded by well-maintained landscaping featuring lush green grass and mature trees. The front porch, adorned with potted plants, provides a welcoming entrance. Natural light filters through the windows, enhancing the overall charm of the property.

Home in Virginia Beach

Country Comfort Close to the Beaches

4.99 out of 5 average rating, 213 reviews

A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.

Home in Virginia Beach

Play by the Bay 1 MIN TO WATER

4.85 out of 5 average rating, 107 reviews

A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.

Home in Suffolk

Perfect Getaway!

4.95 out of 5 average rating, 37 reviews

A brick house is presented, featuring a traditional single-story design. A large front lawn is visible, complemented by trees in the background. The home is accented by a welcoming front door and large windows, with a driveway leading to an attached garage.

Home in Chesapeake

Quiet 3/2 beautiful Chesapeake

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 30 reviews

A light-filled living space features a comfortable leather sofa and a modern dining table. A TV is mounted on the wall, and a large window allows natural light to illuminate the room. A small indoor plant adds a touch of greenery, enhancing the airy ambiance.

Apartment in Chesapeake

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

Apartment in Chimney Hill

4.89 out of 5 average rating, 37 reviews

Virginia Beach, Getaway

Apartment in Williamsburg

The dining area features a modern table set with black dishware, complemented by a decorative runner. A clear vase filled with bright lemons serves as a centerpiece. The adjoining living space is accented by blue seating, floral wall art, and a mounted flat-screen TV.

4.88 out of 5 average rating, 145 reviews

Paradise in Williamsburg next to Busch Gardens

4.69 out of 5 average rating, 109 reviews

A furnished living space features a modern sofa adorned with patterned cushions and a round dining table with two chairs. The kitchen area includes stainless steel appliances, including a refrigerator and microwave, complemented by light wood cabinetry.

Apartment in Ghent

The Rosalie Suite 2, Steps from Norfolks Hospitals

Apartment in Buckroe Beach

A spacious bedroom is depicted, featuring a large bed with a light-colored blanket. A ceiling fan is installed above, and large windows are dressed with dark curtains. A couch and a small table with a chair are positioned to the side, contributing to the room's layout.

4.89 out of 5 average rating, 135 reviews

The Cottage at Sojourn: Buckroe - one bedroom

Apartment in Virginia Beach

An open-concept living area features a blue sofa with colorful throw pillows and a light-colored rug. A pair of small woven tables is situated in front, while a well-equipped kitchen is visible in the background, featuring white cabinetry and modern appliances.

4.77 out of 5 average rating, 143 reviews

THE OLD SALT B | Beach Living

Apartment in Virginia Beach

A wooden deck is showcased, surrounded by lush greenery. The railing is made of wood with black metal accents. The space offers an inviting outdoor area, nestled in a tranquil environment with a view of trees and a fenced yard.

4.91 out of 5 average rating, 573 reviews

Private apartment only 3 blocks from the Beach

Apartment in Newport News

A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.

4.98 out of 5 average rating, 231 reviews

Centrally Located Sleek Studio Apartment

Condo rentals with outdoor seating

4.82 out of 5 average rating, 33 reviews

A serene seascape captures the tranquil waterfront at sunset, with soft hues of orange, blue, and pink blending in the sky. A calm shoreline reflects the colors, while silhouettes of birds are seen at a distance, enhancing the peaceful atmosphere of the beach.

Condo in Bayview

Bay Breeze At Ocean View Beach Home

4.99 out of 5 average rating, 97 reviews

A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.

Condo in Willoughby

Beachfront Getaway, Pet Friendly, Mermaid Suite

Two light blue Adirondack chairs are positioned facing the ocean, accompanied by a small table. The sandy beach stretches into the distance, meeting gentle waves under a pastel sky at dusk. A lounge chair rests nearby on the green grass.

4.9 out of 5 average rating, 234 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

The living room showcases two spacious leather sofas facing a flat-screen television. Natural light floods the room through two large windows, adorned with light-colored blinds. A coffee table centers the space, complemented by decorative plants and artwork on the wall.

4.95 out of 5 average rating, 132 reviews

Spacious Captain’s Beach Suite Near Rudee Inlet

4.93 out of 5 average rating, 144 reviews

A spacious living area features a large sectional sofa and two light blue chairs, with a farmhouse-style dining table visible nearby. A shiplap fireplace wall complements the large electric screen displaying a movie. Natural light streams through multiple windows, enhancing the welcoming atmosphere.

Condo in Sandbridge

Ocean & Bay Views - Local Family Owned & Operated

A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.

4.88 out of 5 average rating, 249 reviews

Oceanfront Gem VaB Studio Exceptional Views

A sunset view over the ocean is captured from a balcony, where warm colors blend in the sky. Gentle waves lap at the shore, and silhouettes of distant boats are visible on the horizon. The sandy beach offers a serene atmosphere.

4.87 out of 5 average rating, 154 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.