Apartment holiday rentals in Chesapeake

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.

4.91 out of 5 average rating, 573 reviews

Private apartment only 3 blocks from the Beach

Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 1 gig mbps Wifi, internet tv. Futon-like couch.

4.98 out of 5 average rating, 232 reviews

A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.

Flat in Newport News

Centrally Located Sleek Studio Apartment

Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.

4.95 out of 5 average rating, 143 reviews

A cozy living area is furnished with a beige sofa and a blue armchair. A coffee table with a decorative runner sits in front, surrounded by wooden paneling. Natural light enters from a nearby window, complemented by patterned curtains. Wall art adds subtle character to the space.

Flat in Portsmouth

"The Ponderosa B" - Close to the Casino & Concerts

Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood about 1/2 mile Rivers Casino! -, Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth 5.9 miles to Norfolk, 22 mi to VB Oceanfront.

4.88 out of 5 average rating, 141 reviews

A cozy living area features a light-colored sectional sofa with decorative pillows, positioned adjacent to a round coffee table on a soft area rug. Large windows adorned with sheer turquoise curtains allow natural light to fill the space, complemented by a ceiling fan and wall-mounted television.

Flat in Phoebus

Getaway Minutes from the Beach

Discover our 2-bedroom, 1-bathroom apartment at the heart of the city, steps from top dining, shops, and entertainment. Enjoy a well-equipped kitchen, comfy living space with a pull-out sofa, and a bathroom with amenities. Conveniently near Buckroe Beach, Boo Williams Sportsplex, Hampton Virginia Aquaplex, Williamsburg, and Busch Gardens, it's your ideal vacation spot. We're dedicated to ensuring your fantastic experience and offer assistance with recommendations. Welcome to your city escape!

A well-lit bedroom features a spacious bed with decorative pillows and a cozy throw blanket. Natural light enters through a window, while a standing lamp and a woven basket add functional elements. A ceiling fan and light fixture enhance the room's comfort.

4.84 out of 5 average rating, 130 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Enjoy easy access to everything from this perfectly located, fully furnished home. Walk to fine dining, museums, a historic theater. Visit the waterfront where you can view the Navy ships or ride the Ferry to Norfolk to experience Waterside & MacArthur Mall. This is a great place for traveling professionals or those in town for sightseeing or local events. Virginia Beach Oceanfront is 30 minutes away. Home is located in a beautiful, historic area and only 8 minutes from the new casino!

4.99 out of 5 average rating, 176 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.

A fully stocked kitchen is presented, featuring a gas stove, a refrigerator, and a microwave. A dark wooden hutch displays dishes and glassware, while a Keurig coffee maker is located on the countertop. Natural light filters in through a nearby window, illuminating the tiled floor.

4.96 out of 5 average rating, 300 reviews

Cozy Ground Floor Apt in Historic Home

Charming 1st floor apartment with private entrance in circa 1795 home in the Olde Towne historic neighborhood. Guests enjoy an easy walk to downtown shops, restaurants, breweries, museums, and a movie theater. The waterfront is close with marinas, restaurants, and the Elizabeth River ferry to transport you to Norfolk to enjoy events on the waterfront. Business or military travelers are two blocks from the Renaissance Hotel and a 15-minute walk from the Portsmouth Naval Hospital.

The exterior of a cozy apartment is depicted, featuring a white facade with green shutters. A small porch is visible, accompanied by a sign indicating the apartment's name. Lush greenery and floral plants frame the entrance, while a gravel pathway leads to the door.

4.84 out of 5 average rating, 486 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

4.94 out of 5 average rating, 126 reviews

A cozy living space features a light-colored sofa with blue cushions and an armchair. A wooden coffee table sits on a patterned rug, accompanied by two lamps providing soft light. Artwork adorns the walls, and a small plant adds a touch of greenery.

Flat in Portsmouth

Lovely Two Bedroom, 1 1/2 bath, King bed Townhouse

Your family will be close to everything when you stay at this centrally-located place. Beautiful re-done townhouse. New carpet and luxury vinyl, new vanities and toilets, Maytag washer and dryer, central heat and air, brand new hot water tank, small patio in back. Close to shopping, Kroger, T J Maxx, Walmart, CVS, and other shops. Plenty of take out food, like chick-fil-A, Panda Express, Wendys, Rallys, Dunkin Donuts, and more. Brand new Rivers Casino less than a mile away!

4.97 out of 5 average rating, 103 reviews

A modern kitchen features light cabinetry and granite countertops, complemented by stainless steel appliances. An island with two stools offers additional seating, and a window allows natural light to brighten the space. Essential kitchen items are neatly arranged on the countertop.

Flat in Great Bridge

Blissful Nook @ Washington

This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor above the car garage. While relaxing or vacationing just know that this apartment is centrally located to Virginia Beach Oceanfront, Outer banks N.C. museums, Colonial Williamsburg, Busch garden, Water Country USA and many restaurant. This apartment is attached to the main home with a dedicated private entrance. This location is safe and private for our guest.

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.

4.94 out of 5 average rating, 126 reviews

Best location in Olde Towne Portsmouth

This apartment is available for up to 6 months upon request. Perfect location for traveling medical professionals. Very convenient to the Naval Medical Center. Enjoy Historic Old Towne and stay in a home built in 1850. Stroll the neighborhood where you will see houses from the late 1700's. Take a short walk to numerous restaurants or take in a movie at the historic Commodore Theater. Two blocks away is the ferry terminal to Waterside in downtown Norfolk.

Two blue Adirondack chairs are positioned on a grassy area overlooking the beach. A small round table sits between them, providing a place for drinks or snacks. The ocean stretches out in the background, with gentle waves and a pastel sky at sunset.

4.88 out of 5 average rating, 213 reviews

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Popular amenities for Chesapeake apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A welcoming living space is revealed through an open door, featuring a stylish kitchenette with modern appliances and a white shelf displaying various items. Comfortable seating is provided by a patterned armchair and wooden dining chairs, while a small table offers a pop of color.

4.97 out of 5 average rating, 88 reviews

North End Beach Cottage Apt - One Block from Beach

4.86 out of 5 average rating, 21 reviews

A modern living area features a stylish teal sofa paired with decorative pillows. A round coffee table sits atop a patterned rug. Two large windows allow natural light to fill the space, complemented by soft brown curtains. A potted plant adds a touch of greenery.

Flat in Bayview

LiveEOV: Beachcomber Two

5 out of 5 average rating, 5 reviews

Flat in Downtown Norfolk

Beautiful historic apartment

4.94 out of 5 average rating, 16 reviews

Relax & Enjoy 2 blocks to beach w/ pool

A historic brick building is surrounded by vibrant flower beds featuring yellow, purple, and white pansies. Lush green grass leads up to the entrance, which is framed by neatly trimmed shrubs and trees, adding to the charm of the property.

5 out of 5 average rating, 8 reviews

Historic Powhatan - 2 Bedroom

4.76 out of 5 average rating, 21 reviews

The sleeping area features two spacious beds dressed in dark bedding with white accents. Decorative lamps on nightstands provide a soft glow. Artwork adorns the walls, adding visual interest, while a plush rug lies beneath the beds, enhancing the comfort of the space.

Flat in East Ocean View

Luxury By the Bay!

4.95 out of 5 average rating, 81 reviews

A modern kitchenette showcases sleek cabinetry and stainless steel appliances, including a refrigerator and dishwasher. Open shelving displays decorative items. A round dining table with white chairs is positioned nearby, complementing the inviting wood flooring and soft lighting from overhead fixtures.

Flat in Portsmouth

Private studio

A modern kitchen and dining area features a round marble table surrounded by black chairs. White cabinetry and stainless steel appliances are visible, with natural light illuminating the space. A framed art piece is displayed on the wall, and a potted plant adds a touch of greenery.

4.93 out of 5 average rating, 43 reviews

Newly Built Apt Near Oceanfront

Private apartment rentals

5 out of 5 average rating, 7 reviews

Flat in Cape Charles

Golf Cart Included! Pet Friendly

A spacious living area is highlighted by large windows overlooking the ocean, allowing natural light to fill the room. A light-colored area rug rests on the floor, with two sofas and a coffee table arranged for comfort. The decor features soft tones, complemented by lamps and wall art.

4.9 out of 5 average rating, 68 reviews

Oceanfront 2BR Luxury • Private Balcony

An expansive view of the beach is captured from the balcony, featuring golden sands and gently rolling waves. The ocean reflects the sunlight, creating a serene ambiance, while the boardwalk is lined with lights and greenery, offering a clear pathway along the shoreline.

4.98 out of 5 average rating, 59 reviews

Beach Luxury Oceanfront

A beachfront scene features the Four Sails resort towering in the background next to a brightly colored volleyball net. Soft sand stretches across the foreground, where beachgoers enjoy activities under clear skies.

5 out of 5 average rating, 3 reviews

Four Sails - 1B/1BA - X-Large Oceanfront Balcony!

A historic queen bed with a decorative wooden headboard and matching bedding is positioned in the room. An elegant pink bench with intricate detailing is placed at the foot of the bed. A painting with a tranquil outdoor scene adorns the wall, complementing the soft green walls.

4.92 out of 5 average rating, 85 reviews

Old world charm

4.81 out of 5 average rating, 89 reviews

A cozy living area features gray sofas and a coffee table atop a striped rug. A colorful mural of tropical plants creates a vibrant backdrop. A ceiling fan is visible above, with a view into the kitchen and dining area showcasing modern bar seating.

Flat in Willoughby

Ocean Getaway

5 out of 5 average rating, 62 reviews

Flat in Yorktown

Granny-Chic Suite | King Bed Retreat with W/D

4.84 out of 5 average rating, 81 reviews

A light-filled living area features soft blue walls and a plush gray sofa complemented by a cozy armchair. A small coffee table sits at the center, and a flat-screen television is positioned on a white media console. Natural light filters through large windows with blinds.

Flat in Buckroe Beach

Cozy Beachside Condo | 5-Min Stroll to Buckroe Bch

Apartment rentals with a hot tub

A historic brick building is framed by lush greenery, featuring symmetrical architecture with tall windows and a central entrance. Brick pathways lead to the entrance, bordered by well-maintained gardens, enhancing the picturesque setting under a clear blue sky.

4.9 out of 5 average rating, 41 reviews

*No Resort Fees Powhatan 4 bdrm

A row of charming cottages is framed by lush greenery and colorful flowering bushes. Paved walkways lead to the entrances of the homes, where distinctive architectural details, including gabled roofs and decorative railings, are visible. A white goose is seen walking along the well-maintained grass.

5 out of 5 average rating, 6 reviews

Historic Powhatan Resort 2 Bdrm! Sleeps 6

4.85 out of 5 average rating, 176 reviews

A resort pool area is depicted, featuring a vibrant blue swimming pool surrounded by lounge chairs. The brick building in the background is characterized by rows of windows and a variety of green umbrellas, set against a clear blue sky.

Flat

Westgate Historic Williamsburg One Bedroom

An aerial view of Ocean Key Resort, displaying its modern architecture set against the backdrop of the Atlantic Ocean. The coastline stretches into the distance, with nearby roads and buildings suggesting accessibility to local amenities.

4.75 out of 5 average rating, 4 reviews

Ocean Key 2BD/2BA Ocean Across the Street

A comfortable sleeping area features a spacious bed with crisp white linens and several pillows. Natural light enters through a sliding glass door that leads to a private oceanfront balcony. A dresser and nightstand complement the room, while a piece of artwork adds a coastal touch.

4.83 out of 5 average rating, 6 reviews

FourSailsResort Double Balcony OceanfrontJettedTub

A historic manor house is set amidst well-kept greenery, framed by mature trees and a white picket fence. The elegant brick façade and classic roofline reflect colonial architecture, providing a charming and welcoming entry to the expansive grounds.

5 out of 5 average rating, 17 reviews

Williamsburg 3 Bedroom Suite!

4.78 out of 5 average rating, 18 reviews

Our Home Away from Home

A comfortable sleeping area is presented with a spacious bed, adorned with a light-colored blanket. Soft lighting is provided by bedside lamps on wooden nightstands. A large window invites natural light, framed by patterned curtains, alongside a dresser and a television.