House holiday rentals in Chesapeake

4.81 out of 5 average rating, 339 reviews

A bright kitchen is highlighted by light-colored cabinetry and natural wood flooring. The countertop displays a cutting board, and the sink is complemented by a stylish faucet. Large windows allow natural light to fill the space, enhancing the tile backsplash's subtle patterns.

Home in East Ocean View

Charming Home by the Sea, a block from the beach!

Single family home steps from the beach. Parking for vehicles including garage. Outdoor/indoor dining areas. Gas grill & fully equipped kitchen with cooking essentials for stay at home meals. 3 bedrooms sleeps 8. Can accommodate additional guests for an up charge with air mattress and sheets provided. Pets welcome! Hardwood flooring and central AC/heat throughout. Walking distance to restaurants in the local area. 15 minutes to Norfolk Naval Station, 10 mins to Airport, 20 mins to VB boardwalk.

4.97 out of 5 average rating, 118 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 space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

4.85 out of 5 average rating, 136 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, 120 reviews

The three-story farmhouse-style home features a charming brick facade and a front porch with blue double doors. Lush greenery surrounds the entrance, while a path leads toward the driveway. Sunlight highlights the roof and front yard, creating a welcoming exterior.

Home in Colonial Place

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

5 bed / 2.5 bath - Sleeps 10! Our cozy, farmhouse-style Norfolk home is 5 min from Historic Ghent / ODU. Free Wi-Fi, parking for 4 cars. Coffee, grill, & fire pit provided. Pet-friendly! NO cleaning fee or checkout instructions! Driving Distances: ODU - 5 min Sentara Norfolk General - 5 min CHKD / EVMS - 8 min Norfolk Naval Station - 14 min Virginia Beach Oceanfront - 25 min Monthly: $4,200. Fully furnished rental with all utilities, Wi-Fi, weekly housekeeping, pest & lawn care included.

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, 151 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

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.

4.96 out of 5 average rating, 125 reviews

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.

4.86 out of 5 average rating, 177 reviews

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.

Home in East Ocean View

☼ 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

4.98 out of 5 average rating, 184 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 beach scene at sunset features individuals playing volleyball in the sand. The calm water reflects shades of pink and orange from the setting sun. Silhouettes of a pier and distant structures are visible along the horizon, framed by beach grass in the foreground.

4.93 out of 5 average rating, 287 reviews

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.

A charming, two-story home with a light blue exterior is surrounded by tall trees and a well-maintained lawn. The roof features dark shingles, while steps lead to a welcoming front door, framed by greenery. Sunlight filters through leaves, creating a serene atmosphere.

4.8 out of 5 average rating, 263 reviews

Waterfront Maryview/Naval Hosp Casino close to all

This lovely, quaint home has been completely updated for your comfort. The great room is bright and open. The home is located on the Elizabeth River in an upscale neighborhood with a large yard. This is perfect for a family vacation, or a long weekend. There is an attached mother-in-law suite in the rear of the house. This is rented out separately. It has a private entrance at the rear of the house.

4.99 out of 5 average rating, 134 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

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.

4.97 out of 5 average rating, 125 reviews

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 house rentals in Chesapeake

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 205 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.

4.95 out of 5 average rating, 100 reviews

Artful Retreat with a Private Pool

4.93 out of 5 average rating, 123 reviews

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.

Home in Norfolk

Gorgeous Vacation House

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

4.83 out of 5 average rating, 138 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, 227 reviews

Sunrise, North End Beach

4.87 out of 5 average rating, 101 reviews

A beach house with a light blue exterior showcases two levels and multiple balconies. The inviting covered entry is flanked by a parking area beneath the structure. Outdoor seating is visible on the upper deck, providing a space for relaxation.

Home in Corolla

MillerLight

4.96 out of 5 average rating, 283 reviews

The open kitchen and dining area is highlighted by bright blue walls and natural light. A spacious granite counter with bar stools invites casual dining. Nearby, a staircase leads to the upper level, while large windows provide views of the surrounding greenery.

Home in Corolla

Spotless Treehouse | Pool | HotTub | Pickle | Pets

Weekly house rentals

4.75 out of 5 average rating, 214 reviews

A spacious living area features a large sectional sofa in neutral tones, complemented by vibrant yellow and blue pillows. A wooden coffee table sits in front, with a patterned area rug enhancing the warmth of the space. Large windows allow natural light to fill the room.

Home in Willoughby

Beach House~Hot Tub~3 Min to Sand~HUGE Kitchen

4.93 out of 5 average rating, 231 reviews

A cozy living area features a striped sofa and two light armchairs, arranged around a soft, plush area rug. Natural light enters through two windows, and a mounted television is placed on the wall. A dining area is visible in the background, adorned with a simple floral centerpiece.

Home in East Ocean View

Cozy beach cottage! One block to the beach!

5 out of 5 average rating, 45 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

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.

4.88 out of 5 average rating, 32 reviews

Cornick Corner near "Rivers Casino"

4.92 out of 5 average rating, 208 reviews

Home in Suburban

Sunset Sanctuary on the Water- Fast Wifi/Netflix

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.

4.95 out of 5 average rating, 37 reviews

Quiet 3/2 beautiful Chesapeake

5 out of 5 average rating, 25 reviews

Home in Ocean View

Casa del Sol – Game Room, Firepit & Walk to Beach!

Private house rentals

4.66 out of 5 average rating, 71 reviews

Chesapeake. Comfy & Cozy. 4 Beds 2 Bath

The exterior of a single-story home features a brick facade complemented by white paneling. A covered entryway protects the front door, and well-maintained landscaping with small plants and a pathway leads up to the entrance. Windows allow natural light to enter the interior.

4.78 out of 5 average rating, 78 reviews

Southern Charm Warm and Welcome

A modern gray sectional couch is positioned against a light gray wall. It features several decorative pillows in varying shades. Two table lamps with simple shades stand on either side on dark side tables, and a patterned area rug covers the hardwood floor.

5 out of 5 average rating, 13 reviews

The Mayfield

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, 83 reviews

R & R River House

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.

4.94 out of 5 average rating, 68 reviews

Chesapeake Haven - Relaxing Space + Lux Kitchen

4.82 out of 5 average rating, 61 reviews

A well-lit living area features a comfortable gray sofa paired with a wooden coffee table. Natural light filters through two windows, illuminating a small workspace with a desk and chair. A decorative plant adds a touch of greenery, while a mounted television offers entertainment options.

Home in Phoebus

The Marilyn: Beautiful 2-Bdrm Home Near the Beach

A cozy living area is presented with a comfortable gray sofa adorned with decorative pillows. A flat-screen television is mounted on the wall, and a marble coffee table sits on a patterned rug. Natural light filters through a large window covered with vertical blinds.

4.71 out of 5 average rating, 217 reviews

Modern, Homely 3-bdrm|wParking|Centrally located.

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.