Apartment vacation rentals in Chesapeake

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Popular amenities for Chesapeake apartment rentals

Weekly apartment rentals

Guest favorite
The renovated duplex features a modern exterior with a well-maintained yard. A spacious living area showcases a comfortable seating arrangement and a dining table under soft lighting. Nearby, a scenic view offers sandy pathways leading to the bay, emphasized by clear blue skies.
Apartment in East Ocean View
4.93 out of 5 average rating, 97 reviews

Home away from home

AbigailRating, 5 stars2 weeks ago
We had an overall great stay at Sam’s place! My group and I were only in town for one night for a concert and this place accommodated us very well. It was exactly as described and everything was clean. It may seem small but it holds 6 people very comfortably! It was easy to find and easy to check-in. Thank you for hosting us and accommodating and early check-in!
Top guest favorite
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.
Apartment in Virginia Beach
4.96 out of 5 average rating, 80 reviews

North End Beach Cottage Apt - One Block from Beach

EricRating, 5 starstoday
Our stay here was fantastic! Very close to the beach which you can walk to, and only a short drive away from the waterfront that has great restaurants and lots to do! The place itself was clean, quiet and the perfect size for 2 people. If you’re looking for something with great amenities for the size, and in a great location this is it!
Guest favorite
The living area showcases a light-colored couch and armchair, complemented by a coffee table adorned with decorative books. Two framed palm tree prints hang on the wall, and a small dining table with chairs is visible under a window that allows natural light to fill the space.
Apartment in Virginia Beach
4.98 out of 5 average rating, 42 reviews

2 Bdrm Condo 1 block from VB Oceanfront

DarciRating, 5 stars6 days ago
This was our first time in Virginia Beach, and this stay was the perfect choice! The space was spotless and exactly as pictured. We really appreciated the thoughtful extras—games, snacks, and awesome beach chairs—that added such a special touch. The location was ideal, just a short walk to the boardwalk, beach, and Atlantic Ave., with plenty of activities nearby. We barely needed our car, though having a designated parking spot was definitely a plus, even if space was a bit tight. The kids were captivated by the military jets flying overhead—it really added to the unique vibe of the area. The free trolley and bus passes were a wonderful bonus, too! This place was a great fit for our family, especially with the easy access to the sports complex and convention center. We hope to return—thank you!
Guest favorite
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.
Apartment in Norfolk
5 out of 5 average rating, 7 reviews

LiveEOV: Beachcomber Two

PamRating, 5 stars2 weeks ago
The place was great it had everything that we needed it was walking distance to the beach
Superhost
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.
Apartment in Portsmouth
4.78 out of 5 average rating, 45 reviews

Shipside Suite~Modern~ Fast WI-FI~Cozy

HaileyRating, 5 stars1 week ago
Nice clean place , easy to find and worked well for me and my two children while we were in town.
Guest favorite
A private porch area is shown with two cushioned chairs and a small table between them. A potted plant adds a touch of greenery. Sliding glass doors lead into the guest suite, while wooden decking provides a natural feel.
Apartment in Sandbridge
4.96 out of 5 average rating, 27 reviews

Sandbridge Beach Bay Getaway

DavidRating, 5 stars8 months ago
We loved our stay at Jule’s place. She was incredibly helpful with local recommendations and perfect communication. Her spot was well located for our visit to False Cape State Park. Would absolutely stay here again!
Guest favorite
A balcony offers a view of the sandy beach and ocean waves. Two black chairs are positioned beside a round table, inviting relaxation. The sky is partly cloudy, and the beachfront promenade is visible below.
Apartment in Virginia Beach
4.86 out of 5 average rating, 36 reviews

Oceanfront Views! 2 BR, 2 BATH!

KevinRating, 5 stars2 days ago
Our stay was amazing!. Sierra's place was impeccable. The place was spotless, just as advertise in the pictures. I'll be booking again soon.
Guest favorite
A bright living room is presented with large windows allowing natural light to fill the space. Two red sofas with cushions are arranged around a wooden coffee table. A small television stands on a console, surrounded by potted plants, enhancing the room's inviting atmosphere.
Apartment in West Ghent
4.9 out of 5 average rating, 156 reviews

Spacious Recently Renovated Apartment

BrittanyRating, 5 stars2 weeks ago
Sammy and JB were fantastic hosts. The apartment was WAAAAAY bigger than the photos portrayed and the area was quiet and seemed safe to walk around in. everything was clean. I personally fell in love with the comforters on the bed.

Private apartment rentals

A broad pier extends over water, featuring wooden benches along both sides where individuals are seen fishing and enjoying the scenery. The background includes buildings, with clear blue skies and light clouds overhead, suggesting a pleasant day at the beach.
Apartment in Willoughby Spit
4.81 out of 5 average rating, 135 reviews

Poseidon - 120 Year Old Beach Cottage with Sauna

PeggyRating, 5 stars1 month ago
We were sad when it was time to come home, we didn’t want to leave! Our home away from home was immaculate. Instructions for parking and entrances were detailed and very easy to figure out. John responded to all texts promptly. Everything we needed was there. The landscaping, the gardens, the seating areas outside were absolutely gorgeous! There was even a mama bird nesting with her baby in the flowers outside. And the backyard is the beach! It was a perfect place for relaxation and enjoying the outdoors. John even provided seven days of perfect weather! ☀️ Thank you for a wonderful stay!
A panoramic view showcases the marina and boats anchored at Rudee Inlet, with the winding road inviting access to the water. The backdrop features a serene landscape of trees and residential buildings under a partly cloudy sky.
Apartment in Virginia Beach
4.5 out of 5 average rating, 8 reviews

Marina View - One Bedroom Condo

JeremyRating, 5 stars2 weeks ago
Good location, good amenities, and helpful staff
Guest favorite
A sandy beach is viewed, leading towards a grassy dune. Residential homes are visible in the background against a clear blue sky. White barrels rest on the sand, indicating beach access and outdoor activities in this coastal neighborhood.
Apartment in Chic's Beach
5 out of 5 average rating, 5 reviews

Sojourn's Sea Views with Balcony Sleeps 4

MichaRating, 5 stars4 weeks ago
We had a great stay at Sojourn's place! We were impressed with the neighborhood and location. The beach is right around the corner and there is plenty of areas to walk around the neighborhood. We didn't try any of the restaurants, but there were some within walking distance which is nice. Sojourn's place itself was lovely and clean. Not only were the essential necessities provided, but there were additional amenities and gestures that really made us feel welcomed. Sojourn was very responsive when we had questions and also reached out and anticipated our questions which made the whole visit very easy and seamless. We visit Virginia Beach often and look forward to staying at Sojourn's place again!
An open living space is presented, featuring a cozy sofa and a small dining area. The kitchen island, topped with wood, includes a sink and a dish rack. Light gray walls enhance the room, complemented by soft lighting, and the layout offers a clear view of the inviting sleeping area.
Apartment in Portsmouth
4.75 out of 5 average rating, 8 reviews

The Lounge

TilwakaRating, 5 stars2 weeks ago
I enjoyed the space. It was cute and quaint for my short stay in the area. Ameenah was friendly prior to and after my checkout. The space was a hit for my grandkids too!!! The loft had everything needed for a comfortable stay.
A cozy living area is presented, featuring a comfortable gray sofa adjacent to a coffee table. A wall-mounted projector displays a screen with a vibrant image. A decorative arrangement of skis adds a unique touch, while a soft glow emanates from a nearby lamp.
Apartment in Ghent
4.54 out of 5 average rating, 13 reviews

Spiral Loft

LiamRating, 5 stars1 month ago
Good host, active communication, nice neighbourhood, great place to stay
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.
Apartment in Sandbridge
5 out of 5 average rating, 3 reviews

Works 4 Me: New listing

BaileyRating, 5 stars1 week ago
Wendy was an exceptional host. She was always very timely in her responses if we had any questions/concerns. The property was so beautiful and Wendy made my husband and I feel right at home. We wouldn’t hesitate to book with Wendy again! :)
Guest favorite
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.
Apartment in Virginia Beach
4.98 out of 5 average rating, 52 reviews

Beach Luxury Oceanfront

JackRating, 5 stars2 weeks ago
We have visited Virginia Beach numerous times in the last 20 years. This was, by far, the most pleasant visit we ever had. Magued was an exceptional host, responding quickly to any questions. The unit was immaculately clean and well furnished. Sitting on the balcony, listening to the ocean's roar, and watching the dolphins' daily migration was the best part! We would definately stay again.
Guest favorite
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.
Apartment in Virginia Beach
4.96 out of 5 average rating, 24 reviews

Newly Built Apt Near Oceanfront

BrendanRating, 5 stars3 weeks ago
Larry’s place was exactly as advertised and exactly what me and my group needed for our work trip for the weekend! The place is clean and spacious and Larry was very easy to get in contact with if you needed anything. Would absolutely recommend.

Apartment rentals with a hot tub

Guest favorite
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.
Apartment in Williamsburg
4.92 out of 5 average rating, 25 reviews

*No Resort Fees Powhatan 4 bdrm

KeithRating, 5 stars2 months ago
We had a wonderful stay. The accommodations were outstanding, the staff was also outstanding.
Superhost
An aerial view showcases a recreational area featuring a large swimming pool surrounded by lounge chairs. Adjacent, a miniature golf course is outlined by vibrant greenery, complemented by tennis courts and playground structures. The overall setting is designed for leisure and enjoyment.
Apartment in Williamsburg
4.89 out of 5 average rating, 27 reviews

Kingsgate 1 BedrooM

DianeRating, 5 stars1 month ago
Enjoyed my stay and will definitely stay again!! Beautiful and comfortable interior with so many option for things to do on site. Great area of town.
Guest favorite
A serene scene features a tranquil pond with a central fountain, surrounded by well-kept greenery. Apartment buildings in a colonial style are visible in the background, showcasing multiple balconies and light-colored façades against a clear blue sky.
Apartment in Williamsburg
5 out of 5 average rating, 8 reviews

KingsGATE Resort 1 Bedroom

PaulRating, 5 stars2 days ago
Had a great time in Williamsburg, VA. Staying at Michael’s place made it an easy place to rest and recharge in between activities. Having multiple pool options was delightful, we swam and soaked almost every night we were there. Sitting on the private back porch in the mornings with my coffee under the crepe Myrtle was idyllic. The entire place was super clean, inside and outside. And most importantly, the beds were high quality and comfortable!
Superhost
A spacious bedroom features a light blue accent wall and a large white bed with a decorative throw blanket. On either side of the bed, stylish lamps provide soft lighting, and a colorful pillow adds a subtle pop of color.
Apartment in Williamsburg
5 out of 5 average rating, 3 reviews

Williamsburg King's Creek Plantation 1BR, 1BA Unit

MelissaRating, 5 stars15 months ago
We used this space while our home was being worked on, do it was more of a “staycation” and did not use all of the amenities. The space was clean and newly renovated, so we were pleased with how nice things were. I highly recommend it for people visiting the Williamsburg area. Great location to Busch Gardens, W&M, etc. The only negative is that it is a time share, and they don’t take no for an answer.
Top guest favorite
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.
Apartment in Sandbridge
5 out of 5 average rating, 36 reviews

Bayside condo on the beach in Sandbridge

ClaressaRating, 5 stars2 weeks ago
We absolutely loved our stay . The Condo was beautiful and Eddi was kind she allowed me and my sister to check in early. The beach at Sandbridge is lovely we had a nice time .
Guest favorite
A view from the interior showcases large glass doors leading to a private balcony. Two wicker chairs are positioned on the balcony, providing a serene spot to enjoy open sky and scenic vistas. Soft drapes frame the view, complementing the cozy bedding.
Apartment in Sandbridge
4.96 out of 5 average rating, 25 reviews

Sunset Retreat

JamesRating, 5 starstoday
It's exactly what you are looking for. Quiet, private, and surprisingly spacious. Aimee is a great host she is very up front about everything gives great details on check-in and locating everything. once we walked into the condo it was the little things setup that made the stay very easy to get settled, she is a very thoughtful and you can tell that she cares about her condo and your stay. I highly recommend staying here.
Superhost
A well-lit kitchen features a large island with seating for three, complemented by warm wooden beams overhead. White cabinetry and stainless steel appliances offer a modern touch, while natural light floods in through the windows, enhancing the spacious atmosphere.
Apartment in Virginia Beach
4.77 out of 5 average rating, 30 reviews

Cape Henry Full Suite Inn at Old Beach

KristenRating, 5 stars3 days ago
Great spot and amazing location. Super responsive host but still very private location for the set up. The porch sitting paid for itself ! Would definitely not hesitate to stay here again.
Superhost
A beachfront hotel with multiple floors features a variety of private balconies. The ground level is lined with umbrellas over beach chairs, while guests can be seen enjoying the sand and surf. Lush greenery is visible in the background, complementing the coastal environment.
Apartment in Virginia Beach
4.8 out of 5 average rating, 10 reviews

Barclay Towers Ocean Front 2, Virginia Beach

KeniRating, 5 stars10 months ago
It is a beautiful place, close to everything, the only dislike is we saw roaches on our last 2 days of our stay. Than we notice the roach traps.

Quick stats about apartment rentals in Chesapeake

  • Total rentals

    150 properties

  • Nightly prices starting at

    G$2,098 GYD before taxes and fees

  • Total number of reviews

    5.4K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    30 properties have a pool

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