Holiday rentals with outdoor seating in Chesapeake

Guest suite in Virginia Beach

The spacious bedroom features a queen-size bed with a tropical-patterned comforter. A leather sofa is positioned beside a small dining table with two chairs. A surfboard decoratively hangs on the wall, complementing the room's casual beach theme.

4.98 out of 5 average rating, 405 reviews

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!

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, 345 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, 119 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.

4.97 out of 5 average rating, 668 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.

Guest house 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, 101 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, 173 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.

Flat 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, 112 reviews

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

Home in Norfolk

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 spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

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, 605 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, 131 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!

Guest suite in East Ocean View

Two comfortable white Adirondack chairs are positioned on a wooden deck, facing the peaceful expanse of the Chesapeake Bay. The scene includes soft grass in the foreground and a clear sky above, creating a serene viewing spot for enjoying the beach.

4.93 out of 5 average rating, 616 reviews

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

4.98 out of 5 average rating, 173 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!

4.98 out of 5 average rating, 126 reviews

A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.

Home in Norfolk

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

Popular amenities for outdoor seating rentals in Chesapeake

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.99 out of 5 average rating, 320 reviews

The front view of a charming blue house is displayed, featuring a welcoming porch with white railings and decorative elements. A small garden with manicured bushes flanks either side of the pathway leading to the front door. An American flag is proudly displayed on the left side.

Home in Williamsburg

Cozy Single Family Home

4.93 out of 5 average rating, 141 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

4.84 out of 5 average rating, 135 reviews

A coffee table is adorned with a lit candle, a notebook, and two books. Comfortable blue chairs are positioned in the background, while a patterned rug adds warmth to the space. Soft natural light illuminates the room, enhancing the decor.

Home in Willoughby

Bungalow at the Bay

4.92 out of 5 average rating, 383 reviews

The image captures a serene beach scene at sunset, with soft pink and orange hues reflecting off calm waters. The sandy shoreline features gentle dunes and sparse vegetation, creating an inviting atmosphere for relaxation and contemplation.

Home in East Ocean View

New Beach Home on the Chesapeake Bay

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, 212 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

4.94 out of 5 average rating, 374 reviews

A house with a blue and white exterior is situated on the edge of the water, reflecting in the calm surface. Lily pads float nearby, while flags adorn the porch railing, indicating a welcoming environment. Greenery surrounds the area, enhancing the serene landscape.

Home in Moyock

Sportsman's Paradise ( Hunting & Fishing )

4.92 out of 5 average rating, 165 reviews

A three-story house features a light gray exterior with a welcoming yellow front door. Flanking the entrance are neatly trimmed shrubs and small trees, complementing the spacious front porch. The surrounding area includes well-maintained neighboring houses and a glimpse of a fenced backyard.

Home in Norfolk

5 Min to Downtown & Ghent, Fenced Yard, Firepit

Apartment rentals with outdoor seating

4.83 out of 5 average rating, 151 reviews

Flat in Willoughby

902C Coastal King Retreat Steps from Beach + Sauna

4.89 out of 5 average rating, 134 reviews

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.

Flat in Buckroe Beach

The Cottage at Sojourn: Buckroe - one bedroom

4.91 out of 5 average rating, 572 reviews

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.

Flat in Virginia Beach

Private apartment only 3 blocks from the Beach

4.9 out of 5 average rating, 176 reviews

The living area features a cozy seating arrangement with a yellow sofa, a woven coffee table, and a decorative rug. Large glass doors allow natural light to enter, illuminating the space. A television is mounted on the wall opposite a wooden workspace, enhancing functional design.

Flat in Corolla

Corolla Oceanside Hideaway, 5 min walk to beach

4.85 out of 5 average rating, 169 reviews

A studio condo features a spacious bed with a teal and navy blanket. A gray couch with orange pillows is positioned beside a white coffee table stacked with books. The kitchen area, visible in the background, is equipped with modern appliances, all enhancing a comfortable living space.

Flat in Virginia Beach

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

4.96 out of 5 average rating, 124 reviews

The exterior of a historic home features classic architectural details, including a covered porch with white columns. An American flag is prominently displayed, and mixed flower pots are arranged on the brick pathway. Large windows allow for natural light, showcasing the home’s inviting presence.

Flat in Olde Towne

Best location in Olde Towne Portsmouth

4.97 out of 5 average rating, 150 reviews

A bright bedroom is bathed in natural light from multiple windows, featuring a spacious bed with crisp linens. Two wicker chairs flank a small side table, and wall art depicting serene landscapes adds to the calming decor. Soft lighting from bedside lamps complements the warm ambiance.

Flat in Corolla

The Coastal Studio

4.95 out of 5 average rating, 249 reviews

The cozy living area features a comfortable seating arrangement with a brown leather loveseat and armchair, complemented by decorative cushions. A wooden coffee table holds magazines and a glass, while a TV is positioned nearby. Natural light filters through the window adorned with white blinds.

Flat in Virginia Beach

TreeTopBeach Bungalow 4 blocks 6 min walk to beach

Apartment rentals with outdoor seating

4.81 out of 5 average rating, 109 reviews

A guest room features two spacious beds adorned with patterned linens. An artistic display of vintage vinyl records decorates the wall above, enhancing the room's character. Warm wooden flooring complements the overall design, while a small nightstand stands between the beds.

Apartment in Hampton

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

Apartment in Williamsburg

A tranquil lakeside scene captures two individuals on paddleboards gliding across calm water. Sandy shores are lined with chairs, offering a peaceful spot to relax. In the background, a spacious building features a wraparound deck, providing views of the serene landscape.

4.96 out of 5 average rating, 114 reviews

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

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, 143 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.

Apartment 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.

4.87 out of 5 average rating, 246 reviews

Oceanfront Gem VaB Studio Exceptional Views

A clear blue saltwater pool is framed by a smooth beige deck. Sun loungers are positioned around the pool, offering space for relaxation. Nearby buildings create a simple backdrop, with bright blue skies overhead enhancing the inviting atmosphere.

4.97 out of 5 average rating, 118 reviews

Oceanfront Studio: Boardwalk, Beach, & Pool 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.