House holiday rentals in Chesapeake

A spacious living area is presented, featuring a large flat-screen television mounted on a wooden console. A comfortable seated area includes plush armchairs and a sofa, while natural light enters through a window, complementing the neutral carpet and walls.

4.88 out of 5 average rating, 115 reviews

3 bedroom home, King's Forest Va. Beach, Virginia

Quiet neighborhood in the heart of Va. Beach w/ private driveway, 100 yds from a huge park w/ tennis courts, playground, long paved walking trail, grills & fishing pond. Blocks to the interstate, 6 miles to the Ocean Front and 2 miles to Town Center! I live in my own space behind the main house. The home is 100% private, soundproof and completely in your hands. My guests are thrilled to have a private home and an easily reached fix everything guy when needed! IMPORTANT! NO SMOKING INSIDE HOUSE.

4.87 out of 5 average rating, 128 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.

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.

4.96 out of 5 average rating, 114 reviews

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.🛳🌊🚢🏠😊!

A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.

5 out of 5 average rating, 135 reviews

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.

4.96 out of 5 average rating, 122 reviews

A cozy living room is featured, showcasing a light-colored sofa paired with two yellow accent chairs. A wooden coffee table sits at the center, and two windows are dressed with sheer curtains, allowing gentle light to brighten the space. A ceiling fan is present above.

Home in Chesapeake

The Cozy Cottage Two Bedroom, King bed House

This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has brand new central heat and air conditioning, new stainless steel refrigerator and smooth top stove, microwave, and new carpeting. It’s centrally located and there is plenty of space for parking. This is truly a home away from home.

4.84 out of 5 average rating, 138 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

This wonderfully decorated home is the perfect spot for a beach getaway with the whole family. Inside you will find a spacious living room, kitchen, bathroom, and two guest rooms with one queen, and a full. Outside there is a backyard porch, perfect for socializing, and a sizable backyard protected by a fence that stretches the property! Free parking is available inside and outside the property. Beach access and free parking is located on 11th view street about a two-minute walk away!

A cozy living area features two armchairs and a leather sofa, arranged around a circular coffee table on a patterned rug. A fireplace is situated against the wall, complemented by a television mounted above. Natural light is allowed in through the window with white blinds.

4.84 out of 5 average rating, 145 reviews

Beach Hideaway 2 bdr/2bth- Pet friendly!

Great home for days at the beach and a fire pit at night! Beach access 1 1/2 blocks from the home. Heat/AC, dishwasher, w/d, and deck. Linens, bath towels, beach chairs, and beach towels are provided. Quiet family beach, bay water is calm- perfect for children. Large back yard for kids to run around, deck, and enclosed front porch. Close to Virginia Beach, Norfolk military bases and ODU, EVMS, NSU, Virginia Wesleyan, Hampton Univ. Approx 25 min from downtown Virginia Beach and W-burg.

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!

The living room displays two spacious couches adorned with blue decorative pillows. A white coffee table is centered on a light carpet. Natural light enters through two large windows, highlighting a wall-mounted artwork and a small workspace equipped with a desk and lamp.

4.86 out of 5 average rating, 168 reviews

☼ Coastal Cottage- 5 min walk to beach | parking ☼

Enjoy close proximity to all the best attractions the area has to offer, or simply bum it on the beach while snagging a local cup of coffee or craft beer - all within a few steps! A wonderful location for a beach getaway with friends or family. -5 min walk to the beach -8 min walk to a local coffee shop/brewery -25 min drive to Virginia Beach/boardwalk area -10 min drive to Norfolk Botanical Garden -20 min drive to the Zoo -10 min drive to Ikea / Norfolk Premium Outlets

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!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

4.98 out of 5 average rating, 176 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!

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.

4.98 out of 5 average rating, 128 reviews

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 Chesapeake house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.93 out of 5 average rating, 144 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

4.99 out of 5 average rating, 204 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

A private pool area features comfortable lounge chairs with floral cushions, surrounded by a clean concrete patio. A screened-in porch is visible in the background, with two inviting chairs for relaxing. The fenced yard offers additional privacy and space for outdoor enjoyment.

4.96 out of 5 average rating, 94 reviews

Artful Retreat with a Private Pool

A cozy living area features a brown sofa adorned with decorative pillows against a warm yellow wall. A small desk holds books and a decorative item, while natural light fills the space through sheer curtains. A doorway leads to a bathroom area.

4.96 out of 5 average rating, 70 reviews

The Seaglass Cottage

A private pool is surrounded by a spacious patio, featuring lounge chairs and a shaded gazebo. Lush greenery encircles the pool area, providing a sense of privacy. The clear blue water reflects the sky, inviting relaxation and enjoyment.

4.86 out of 5 average rating, 118 reviews

Private Pool at the Oceanfront in a Spacious Home

A two-story house features a light-colored exterior with a peaked roof. A spacious driveway leads to a garage door, framed by manicured grass and trees. A balcony extends from the top floor, providing outdoor space above the ground level.

4.92 out of 5 average rating, 119 reviews

Gorgeous Vacation House

4.82 out of 5 average rating, 136 reviews

The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.

Home in Sandbridge

Stunning Views of Back Bay & Seconds to the Beach

A modern kitchen area is visible, featuring stainless steel appliances and a granite countertop with bar seating. Two stylish light fixtures hang above, while the space is illuminated by natural light from large windows covered with light curtains. A seating arrangement includes sleek black bar stools.

4.97 out of 5 average rating, 223 reviews

Sunrise, North End Beach

Weekly house rentals

A bright living area features a large flat-screen television mounted on the wall and a comfortable seating arrangement. Large sliding doors open to a view of the water outside, while a soft area rug adds warmth to the space.

4.95 out of 5 average rating, 81 reviews

R & R River House

A modern dining area features a round table with a sleek black surface, surrounded by stylish chairs. A small potted plant sits at the center. The open-concept kitchen is visible in the background, showcasing light cabinetry and stainless steel appliances.

4.76 out of 5 average rating, 17 reviews

Portsmouth's Finest

4.92 out of 5 average rating, 72 reviews

The living room features a welcoming layout with plush blue couches and two light-colored round ottomans. A ceiling fan hangs above, and natural light streams in through multiple windows. The front door is painted in a vibrant teal, adding a cheerful touch.

Home in Bayview

Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ

A spacious living area is highlighted by a grey sectional sofa adorned with colorful throw pillows. A rectangular coffee table is centered on a striped area rug. Natural light enters through windows, illuminating the room, while a ceiling fan enhances airflow.

4.86 out of 5 average rating, 99 reviews

Cozy Retreat

A single-story bungalow features a welcoming brick exterior, surrounded by well-maintained landscaping. A spacious driveway leads to the house, which is framed by tall trees. The front porch, adorned with white railings, provides an inviting entryway. A detached garage is visible in the background.

4.9 out of 5 average rating, 30 reviews

Cornick Corner near "Rivers Casino"

A modern kitchen features light cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are visible. Soft lighting highlights the spacious layout, which is complemented by tiled flooring and a seamless flow into the adjacent dining area.

5 out of 5 average rating, 84 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

The front porch features a light blue door framed by white trim, complemented by wooden decking. A hanging lantern provides soft lighting. A fenced yard is visible in the background, with greenery and a gravel area, creating a welcoming first impression.

4.97 out of 5 average rating, 89 reviews

Historic 3BR • Fenced Yard • Long Stays OK

4.94 out of 5 average rating, 32 reviews

Artful Cottage, 2-Min Walk to Beach

Private house rentals

4.82 out of 5 average rating, 124 reviews

A spacious living room is featured, containing a large sectional sofa and a coffee table. A flat-screen TV is positioned against the wall, with natural light coming in through two windows. Decorative touches on the wall and a rug add comfort to the space.

Home in Downtown Hampton

The "Bison" contemporary retreat (King Bed)+

4.75 out of 5 average rating, 8 reviews

Cozy 3Bed/3Bath Home near Portsmouth Naval-Casino

4.61 out of 5 average rating, 46 reviews

A two-story coastal house is featured, showcasing a light blue exterior with large, arched windows. A garage is visible on the left, and a driveway leads to the front entrance, flanked by a small porch. The surrounding area includes a gravel driveway and grass.

Home in Willoughby

*Escape to Beach Dream*

4.94 out of 5 average rating, 67 reviews

A modern kitchen is highlighted by a spacious island featuring four wooden bar stools. Natural light filters through sheer curtains, illuminating the sleek cabinetry and white countertops. A stylish centerpiece is positioned on the island, complementing the contemporary design.

Home in Chesapeake

Chesapeake Haven - Relaxing Space + Lux Kitchen

4.94 out of 5 average rating, 97 reviews

A single-story house is framed by vibrant flowering bushes and trees. A red flag is prominently displayed near the entrance. The front yard is spacious with grassy areas, and a paved driveway leads to a single-car garage.

Home in Newport News

1-Bedroom Home Near Christopher Newport University

A modern living room is presented, featuring a spacious sectional sofa with light fabric. A wall-mounted smart TV dominates the area, and a glass coffee table is placed in front. Two black bar stools are positioned near a kitchen counter in the background, enhancing the open layout.

4.93 out of 5 average rating, 15 reviews

Home Away From Home

A three-level home is showcased, featuring a wide staircase leading to a spacious front porch. The exterior is complemented by large balconies on the upper levels, while two garages are situated beneath the structure. Lush trees provide shade in the front yard.

4.97 out of 5 average rating, 79 reviews

Oceanview Oasis- Close Beach, Game Rm & Volleyball