Apartment holiday rentals in Chesapeake

4.98 out of 5 average rating, 231 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.

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.

4.95 out of 5 average rating, 142 reviews

"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, 126 reviews

A cozy living space features a sectional sofa with plush cushions, complemented by decorative throw pillows. Large windows dressed with sheer blue curtains allow natural light to brighten the room. A coffee table sits at the center, surrounded by a tasteful area rug and a plant.

Flat in Phoebus

Near Beach Eclectic Retreat

Unwind in our urban oasis: a 2-bed, 1-bath apartment moments from dining, shops, and entertainment. Your comfort is paramount, with a fully equipped kitchen, cozy living space, and a pull-out sofa. With proximity to Virginia Beach, Portsmouth Casino, Buckroe Beach, Busch Gardens, Boo Williams Sportsplex, Virginia Beach Sportsplex and Hampton WaterPlex, your dream vacation is at your doorstep. Count on us for personalized suggestions to elevate your stay. Welcome to the ultimate city retreat!

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, 174 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, 299 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.

4.84 out of 5 average rating, 482 reviews

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.

Flat in Williamsburg

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.

A cozy common area features a green sofa adorned with patterned cushions, and a neon sign on a palm-patterned wall. Natural light enters through large windows beside a rattan chair and a decorative mirror, enhancing the cheerful ambiance.

4.96 out of 5 average rating, 115 reviews

Fully Renovated Beach Loft Block Off OceanFront

Come enjoy everything Virginia Beach has to offer. Our newly renovated beach condo has all of the comforts of home and accommodates 2-3 adults perfectly. Bedroom has a queen size bed and common area has a futon that pulls out into a bed. Smart TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. You can walk to the beach in 3 minutes or less! Come have a relaxing and fun vacation at the beach.

4.97 out of 5 average rating, 102 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, 125 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.

A cozy bedroom is featured, showcasing a spacious bed with crisp white linens and a golden throw blanket. Natural light enters through a glass door, illuminating the room. A mirror and bedside lamps provide additional warmth, complemented by a decorative wall art piece of boats.

4.95 out of 5 average rating, 356 reviews

3 Blocks 2 Beach! A ViBe District Beach Retreat!

1 BLOCK 2 THE DOME AND SURF PARK. Private efficiency in the heart of the ViBe District! Perfect for 2! Only 3 blocks to beach, convention center & sport center. Walk to brewery, restaurants, shopping, arts district. Cozy space with comfortable queen bed. Kitchenette with coffee maker, refrigerator, microwave and water cooler. Coffee, linens & toiletries provided. Free off street parking. We also provide beach cruisers, beach towels, chairs, & cooler.

An open-concept living area features a blue sofa with colorful throw pillows and a light-colored rug. A pair of small woven tables is situated in front, while a well-equipped kitchen is visible in the background, featuring white cabinetry and modern appliances.

4.77 out of 5 average rating, 143 reviews

THE OLD SALT B | Beach Living

Relax in the historic home of The OLD SALT. Built in 1910 and renovated in 2021 this home is the perfect beach getaway. Nestled in heart of the highly sought after Virginia Beach Boardwalk area, close to the area’s best attractions, top restaurants and bars, you will find yourself right at home in this cozy haven. Just steps to the boardwalk and a beautiful view of the Atlantic Ocean. This cozy getaway sleeps 4 and has a private back deck patio!

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

4.93 out of 5 average rating, 15 reviews

Relax & Enjoy 2 blocks to beach w/ pool

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.

4.95 out of 5 average rating, 81 reviews

Private studio

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

4.91 out of 5 average rating, 22 reviews

Flat in Wards Corner

In the Heart of Norfolk

A comfortable living area features two reclining armchairs and a spacious leather sofa, all arranged around a circular coffee table. A large television displays a scenic view, while sliding glass doors provide ample natural light and reveal the ocean beyond.

4.94 out of 5 average rating, 64 reviews

A Wave From It All

4.93 out of 5 average rating, 15 reviews

A vibrant bedroom features a full-size bed with a colorful patterned quilt and decorative pillows. Two bedside lamps illuminate the room, and a tapestry hangs on the wall, depicting a historical scene. Wooden flooring and a small table add warm accents to the space.

Flat in Suffolk

Private Guest Suite in Historic house

Private apartment rentals

Flat in Chesapeake

5 out of 5 average rating, 3 reviews

Sleek 1-BR in Greenbrier!

A bright living area features a light-colored sofa, a woven coffee table, and a dining set with transparent chairs. Natural light filters in through the large windows with white curtains, while a ceiling fan provides air circulation. The kitchen is subtly visible in the background.

4.73 out of 5 average rating, 78 reviews

Shipside Suite~Modern~ Fast WI-FI~Cozy

4.97 out of 5 average rating, 106 reviews

A welcoming living area features a comfortable gray sofa and a dining table set with colorful placemats. A television is positioned in front of a window, allowing natural light to brighten the neutral walls. Decorative light fixtures complement the cozy atmosphere.

Flat in Newport News

Cindy’s Haven - quiet private 1 bedroom studio apt

A charming garden pathway made of red and gray bricks leads to an ornate black gate. Lush greenery, including flower bushes and tall plants, surround the area, creating a tranquil and inviting atmosphere. Natural light filters through the trees, enhancing the serene outdoor space.

4.99 out of 5 average rating, 196 reviews

Elegant Cozy Colonial/Private/Self Check-in

A modern bathroom is featured, showcasing a white vanity with a mirror above. A patterned shower curtain complements the clean design. Stylish tile flooring is visible, and a gray bath mat is placed in front of the toilet. Natural light illuminates the space through a nearby window.

Flat in Bayview

4.76 out of 5 average rating, 427 reviews

The SEA-clusion lV

Flat in Ghent

4.68 out of 5 average rating, 38 reviews

Spiral Ceiling

5 out of 5 average rating, 44 reviews

A wide sandy beach stretches alongside gentle ocean waves under a clear blue sky. Colorful resort buildings line the beach, creating a welcoming coastal atmosphere. Footprints in the sand suggest leisurely strolls along the shore, inviting relaxation in this serene setting.

Flat in Sandbridge

Bayside condo on the beach in Sandbridge

4.89 out of 5 average rating, 66 reviews

Oceanfront 2BR Luxury • Private Balcony

Apartment rentals with a hot tub

Virginia Beach 3 Bedroom Suite!

A nighttime view along the Virginia Beach boardwalk showcases tall buildings illuminated by warm lights. The sandy beach stretches along the shoreline, while palm trees and benches line the path, providing a welcoming atmosphere. Stars and a dark sky frame the scene.

Virginia Beach 1 Bedroom Villa

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

4.9 out of 5 average rating, 20 reviews

A two-story beach house is shown, featuring a wide front porch with outdoor seating and umbrellas. The driveway provides ample space for parking, and flags adorn the house, adding a coastal touch. Surrounding landscaping includes greenery, enhancing the inviting exterior.

Flat in Sandbridge

Works 4 Me: New listing

Flat in Willoughby

4.76 out of 5 average rating, 149 reviews

902 B Historical Beachfront Duplex Sauna & Hot Tub

2 Bedroom Ocean front, Ocean Beach Club Resort

An aerial view captures the proximity of Ocean Key Resort to the marina and surrounding landscape. The vibrant blue water contrasts with the sandy beach and city buildings, while the resort's pool area and nearby dining options offer accessible leisure opportunities.