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 out of 5 average rating, 107 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

ValueFamilyAmenities

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, 169 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.

ValueLocationSolo travel

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, 173 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!

ValueLocationAmenities

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.

FamilyLocationCondition

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

This is is the perfect home away from home! Enjoy cozy furnishings and modern amenities in this 3bed/2.5 bath house located in the vibrant city of Norfolk oceanview. The house is renovated with top notch material and artistic touch. The kitchen, living room, and private backyard with deck/patio swimming pool make it the ideal place to relax. Shopping, restaurants, and entertainment are all within minutes; plus onsite parking and self-check-in make this an ideal destination for travelers.

FamilyValueLong stay

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.

ValueFamilyRiver

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!

ValueLocationKitchen

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.

4.94 out of 5 average rating, 137 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!

FamilyValueIndoor spaces

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.

LocationFamilyTV

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, 213 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!

LocationValueWi-Fi

The living area is designed with a mix of modern furnishings and artwork. A comfortable sectional sofa and an accent chair surround a coffee table. Light streams in through a window, highlighting a TV and a decorative cabinet. Artwork adds a pop of color to the neutral walls.

4.93 out of 5 average rating, 148 reviews

3BR Mid-Century Modern Home • Near Airport

Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!

LocationValueCheckout

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.

4.99 out of 5 average rating, 160 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

FamilyLocationCleanliness

Popular amenities for Chesapeake house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming coastal cottage exterior is depicted, featuring a white clapboard façade and a shingled roof. The blue front door is framed by decorative shutters, with a welcoming wreath displayed. An American flag hangs proudly, completing the inviting entrance.

4.8 out of 5 average rating, 164 reviews

Retreat with Pool, Walk to Beach

LocationValueComfort

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, 126 reviews

Artful Retreat with a Private Pool

ValueFamilyCondition

5 out of 5 average rating, 24 reviews

Home in Currituck County

The White Lotus: Oceanview Retreat + Wild Horses

LocationFamilyDecor

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

ValueLocationLayout

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, 132 reviews

Private Pool at the Oceanfront in a Spacious Home

LocationValueParking

4.94 out of 5 average rating, 18 reviews

Home in Sandbridge

Luxe Sandbridge Beach, Waterfront, Pool, Arcade

ValueLocationCheckout

4.84 out of 5 average rating, 147 reviews

Home in Sandbridge

Bayfront Pool Retreat, Walk to Beach

LocationValueQuiet

Home in North Virginia 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, 245 reviews

Sunrise, North End Beach / Oceanfront Area

FamilyLocationShared spaces

Weekly house rentals

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.

4.93 out of 5 average rating, 273 reviews

Cozy beach cottage! One block to the beach!

LocationFamilyHospitality

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, 219 reviews

3 bedroom private home a block from the beach!

LocationFamilyNearby

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

ValueLocationDecor

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, 105 reviews

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

LocationFamilyParking

4.83 out of 5 average rating, 135 reviews

Walk to Beach! Fully Updated + Hot tub!

ValueLocationWalkability

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, 233 reviews

Play by the Bay 1 MIN TO WATER

FamilyValueComfort

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

FamilyValueDecor

A charming single-family home is framed by well-maintained landscaping, featuring a red brick exterior and a welcoming front porch. Brightly colored flowers line the pathway, leading to a white front door. A garage door is visible on the left side, completed by a clear blue sky overhead.

4.93 out of 5 average rating, 122 reviews

Murphy's Manor

FamilyValueGetting around

Private house rentals

4.95 out of 5 average rating, 38 reviews

Blessed and peaceful home

FamilyLocationAir conditioning

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, 99 reviews

R & R River House

ValueFamilyIndoor spaces

A light-filled living area features a comfortable sectional sofa and a coffee table centered on a textured rug. Adjacent, a dining table accommodates several chairs, while a wall-mounted television is positioned above a decorative fireplace. Windows provide views of the outdoor space.

4.93 out of 5 average rating, 69 reviews

Spacious 3 Bedroom Home | Near many Shops & Dining

FamilyValueAccuracy

4.84 out of 5 average rating, 38 reviews

Riverfront Portsmouth Home Near Casino & Patio

FamilyValueHospitality

A classic Cape Cod home is surrounded by well-maintained greenery. The brick exterior is complemented by a gravel pathway leading to the front steps. A concrete driveway provides access to an attached garage, while flags are displayed on the front porch, enhancing the home's welcoming appearance.

4.94 out of 5 average rating, 54 reviews

The Bartlett Inn

LocationFamilyDecor

4.81 out of 5 average rating, 27 reviews

Modern Comfort Minutes from Waterside & Downtown

FamilyLocationParking

4.95 out of 5 average rating, 76 reviews

Beach Bungalow • Navy Base • Quiet St • Dogs OK

LocationFamilyComfort

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.