House holiday rentals in Chesapeake

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.

5.0 out of 5 average rating, 106 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

FamilyValueIndoor spaces

4.97 out of 5 average rating, 324 reviews

A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.

Home in Smithfield

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

LocationFamilyGetting around

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.

4.82 out of 5 average rating, 168 reviews

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.

LocationFamilyCondition

A spacious living area features a soft sectional sofa adorned with decorative pillows. A glass-top coffee table is centered on a patterned rug, flanked by side tables with lamps. Natural light streams through two large windows, complemented by light curtains.

4.96 out of 5 average rating, 104 reviews

2 Master Suites, Sleeps 6-8, King bed, 2.5 baths

Bring the whole family to this spacious home with plenty of room to relax. This is one side of a duplex featuring two master suites, each with its own en-suite bathroom, plus a convenient half bath downstairs. The home includes a king bed in one suite and two queen beds in the second, along with walk-in closets, washer and dryer, central heat and air, and a wonderful deck. Centrally located. Traveling with a larger group? Both sides of the duplex can be booked to accommodate up to 16 guests.

ValueFamilyBathroom

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.

4.92 out of 5 average rating, 172 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!

LocationValuePool

4.94 out of 5 average rating, 399 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 )

Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

FamilyValueAir conditioning

4.94 out of 5 average rating, 148 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!

FamilyLocationTV

4.85 out of 5 average rating, 115 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!

LocationValueHospitality

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, 136 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 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. Bring your fishing poles!

FamilyValueBathroom

A spacious living room features a comfortable sectional sofa, a wooden entertainment center with a large TV, and a decorative console table. Light-colored walls complement the area rug, and framed artwork adds interest. A staircase is visible, leading to the upper level.

4.89 out of 5 average rating, 216 reviews

3 bedroom private home a block from the beach!

Relax with the whole family at this peaceful home. A block to the beach! 3 bedrooms and 2 bathrooms, with an outdoor shower and finished basement with extra living space. Outdoor patio with gas grill and patio furniture. All amenities included sheets, towels, cooking utensils, etc. Fast Wi-Fi throughout the home. Can sleep up to 8! Pets always welcome. All bedrooms are on main level no stairs required. Weekly and monthly discounted rates upon inquiry.

FamilyLocationWi-Fi

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.

4.96 out of 5 average rating, 140 reviews

Cook's Country Escape - Cozy Retreat

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. It’s been a great rental with great ratings.

LocationFamilyAir conditioning

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.

4.99 out of 5 average rating, 212 reviews

Historic Gem - Walk to Dining, Ferry & Waterfront

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!

LocationFamilyParks

Popular amenities for Chesapeake house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 125 reviews

Artful Retreat with a Private Pool

LocationFamilyComfort

4.87 out of 5 average rating, 102 reviews

An outdoor pool is positioned on a deck overlooking a tranquil canal. Surrounding the pool, several lounge chairs are arranged for relaxation. The landscape features houses lining the opposite bank, with greenery in view. A small boat dock is also visible in the distance.

Home in Sandbridge

Ocean Pearl- Canal View and Minutes to the beach

ValueLocationHot tub

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.

4.91 out of 5 average rating, 140 reviews

Gorgeous Vacation House

ValueLocationCleanliness

4.91 out of 5 average rating, 137 reviews

Home in Hampton

4BD home w/ game room & pool near Langley & PTC!

ValueFamilyCondition

4.95 out of 5 average rating, 130 reviews

A welcoming living area features a large orange sofa adorned with white cushions, paired with two light-colored armchairs. A round wooden table sits at the center, complemented by a beige area rug. The open kitchen behind includes modern bar stools and stylish pendant lighting.

Home in Sandbridge

Designer Beach House | Pool, Hot Tub, Walk to Sand

LocationFamilyParks

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.

4.96 out of 5 average rating, 136 reviews

Country Comfort Close to the Beaches

LocationFamilyAccuracy

4.9 out of 5 average rating, 110 reviews

A backyard patio offers seating at a rectangular table with four chairs, shaded by a large umbrella. A cozy seating arrangement is visible nearby, featuring bright cushions. The in-ground pool reflects the sky, while the tranquil river and greenery create a serene backdrop.

Home in Hampton

The Great River Escape *Hot Tub!

LocationFamilyKitchen

4.89 out of 5 average rating, 150 reviews

Half house w/pool & new patio all to yourself

LocationValueAccess

Weekly house rentals

The living room features a cozy seating arrangement, including an orange couch and a blue armchair. A round coffee table sits in the center, adorned with books. A mounted TV can be seen on a light-colored wall, contributing to a welcoming atmosphere.

4.89 out of 5 average rating, 137 reviews

10 min to Ocean View Beach: 20% Off Aug

LocationFamilyOutdoor spaces

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.

4.96 out of 5 average rating, 142 reviews

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

FamilyValueLayout

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.

4.82 out of 5 average rating, 118 reviews

Cozy Retreat

FamilyValueDecor

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.

4.9 out of 5 average rating, 104 reviews

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

ValueLocationNearby

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.

4.92 out of 5 average rating, 193 reviews

5 Min to Downtown & Ghent, Fenced Yard, Firepit

FamilyValueParking

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.

4.99 out of 5 average rating, 232 reviews

Play by the Bay 1 MIN TO WATER

LocationValueParking

4.84 out of 5 average rating, 132 reviews

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

ValueFamilyParking

4.86 out of 5 average rating, 413 reviews

A spacious home is depicted with a welcoming front porch featuring a gentle ramp for accessibility. Lush greenery surrounds the exterior, and the peaceful atmosphere is enhanced by the colorful sunset sky. The house showcases a combination of brick and siding with large windows.

Home in Hampton

Family Holiday House. Events and Beaches Nearby

FamilyLocationCheckout

Private house rentals

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.

4.94 out of 5 average rating, 64 reviews

Quiet 3/2 beautiful Chesapeake

LocationFamilyParking

4.82 out of 5 average rating, 68 reviews

Riverfront 3BR Retreat • Near Rivers Casino

FamilyLocationComfort

A bright living area features a light-colored sofa adorned with patterned cushions. A round wooden coffee table sits on a colorful area rug, and a wall-mounted television displays a scenic landscape. Sunlight enters through partially open window treatments, complementing the room's neutral tones.

4.89 out of 5 average rating, 36 reviews

Cowbell Cottage

FamilyLocationQuiet

A cozy bedroom is showcased, featuring a spacious bed with decorative bedding and pillows. A small white chair is placed at the foot of the bed. Wall-mounted shelves display various items, while a lamp provides soft lighting next to the bed. The grey walls create a calming backdrop.

4.9 out of 5 average rating, 63 reviews

The Bird’s Nest

FamilyValuePets

4.94 out of 5 average rating, 35 reviews

Blessed and peaceful home

FamilyValueAmenities

A dining area features a sleek wooden table surrounded by six chairs. Above, a chandelier provides soft lighting. The space connects to a well-lit living area visible in the background, with a modern recliner and additional furnishings enhancing the room's functionality.

4.98 out of 5 average rating, 40 reviews

Simply Amazing in Chesapeake

FamilyLocationSleep quality

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.

4.96 out of 5 average rating, 98 reviews

R & R River House

LocationFamilyCheck-in