
Apartment holiday rentals in Chesapeake
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Quick stats about apartment rentals in Chesapeake

Total holiday rentals
Explore 40 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 1,070 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Chesapeake holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake rentals

4.8 Average rating
Chesapeake stays are highly rated by guests – averaging 4.8 out of 5!

Nearby attractions
Chesapeake’s top spots include Chrysler Museum of Art, Nauticus and Cinema Cafe-Greenbrier Mall
Top-rated apartment rentals in Chesapeake
Guests agree: these apartments are highly rated for location, cleanliness and more.

Tropical 2BR Condo Getaway 1 Block from the Beach!
Unwind at this gorgeous fully renovated getaway for your family and friends! This two bedroom, one bath beach home is one block from the ocean. This unit accommodates up to 4 adults. Each room is equipped with a smart TV and internet is provided. Our kitchen provides refrigerator, microwave, oven, dishwasher, toaster, Keurig, dishes, cutlery, bowls, pots and pans, and much more! Steps away from shopping and restaurants! This highly sought after vacation spot really is a home away from home.

Good Vibes at the Beach
Boutique style building with a pool, designated parking, and coded door access. 2 bedrooms and 2 baths with a full kitchen and all amenities. Enjoy the pool during the summer months (May28th-Sept. 30th) or walk another block to enjoy the Beach at all times of the year. Multiple restaurants of all types surrounding this location and a large Harris Teeter grocery store only steps away. Come enjoy the Beach Life where music and arts are abundant. Primary booking guest must be at least 21 yrs old

Spacious Captain’s Beach Suite Near Rudee Inlet
Take advantage of the seasonal rates plan a winter escape to the beach! Don’t miss all the wonderful holiday activities to include the holiday lights, holiday parade & more! This spacious beautifully decorated 2-bedroom (each with ensuite baths) condo is near Rudee Inlet and all oceanfront activities. Walk across the street & relax on the beach, dine at great restaurants, walk under the bridge next to the city parking lot to enjoy all the water activities that originate from Rudee Inlet.

2 Bedroom Condo One Block from the Oceanfront!
Our newly renovated 2 bedroom condo ONE block from the boardwalk accommodates 6 people and is also perfect for families. Each bedroom has a flat screen TV; one with a queen bed and the other with a king bed. There is also a pull out sofa bed in the living room along with a large TV. This is a 2nd floor unit with one designated parking spot. Plenty to do for the whole family with the beach, boardwalk, shopping, restaurants, amusement parks, and many more activities all within walking distance.

2 bedroom condo with oceanfront one block away!
Come enjoy everything Virginia Beach has to offer. Our cozy condo has all of the comforts of home and is perfect for families and accommodates 6 adults. Bedroom 1 has a king size bed w/TV, bedroom 2 has a queen size bed w/TV and the living room has a sofa that pulls out into a full size sofa bed w/TV. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach!

Beach Bliss Oasis • Walk to Ocean & Boardwalk
Stylish beach retreat just blocks from the ocean & boardwalk 🌊 Walk to the Virginia Beach Convention Center (3 blocks), top restaurants, and local attractions. Perfectly located for a relaxing getaway with everything you need just steps away. Please note: This is a multi-level home with multiple flights of stairs inside the property. Guests will need to use stairs to access different areas of the home, including the bedrooms. This may not be ideal for guests with mobility concerns.

2 Bedroom Stylish Kingsmill condo
Located in the beautiful Kingsmill resort, this charming two bedrooms, two baths condo with stunning seasonal views over the pond is only a few minutes away from CW, Busch Gardens, water country, William and Maryand other Williamsburg attractions. All Kingsmill amenities are not included as they are strictly for Kingsmill residents Guests have access to the Spa and to the Mill Coffee House which is within walking distance from the condo and serves breakfast and lunch every day..

Cozy 1 Bd condo, 1 block from the beach!
Your family will be close to everything when you stay at this centrally-located, cozy condo. 1 bedroom, 1 bath just a block off the beach. Queen bed in master and pull out couch and futon in living room. (comfortably sleeps 4, could sleep up to 6) Cute, fully equipped kitchen and dining area for 2. Walking distance to the popular board walk and beach, restaurants, bars, shopping and nearby activities and attractions. Perfect for a couples get away or a small family stay!

Ocean Escape
Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Community pool area, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Beach Condo Block Off Oceanfront!
Come enjoy everything Virginia Beach has to offer. Our condo has all of the comforts of home perfect for families. Bedroom has a king size bed and living room has sofa that pulls out into a full size sofa bed. TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do and you can walk to the beach in 3 minutes or less! Come have a relaxing and fun vacation at the beach.

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
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

Vibe District • Walk to Beach • Parking • Sleeps 6
Stay in the heart of Virginia Beach's Vibe Creative District—just a short walk to the beach and Boardwalk 🌊 Enjoy Atlantic Park, which is home to year-round surfing, along with The Dome concert venue and numerous new restaurants—all within two blocks. The Virginia Beach Sportsplex is also nearby. This 3-story condo offers a fully equipped kitchen, in-unit laundry, and a comfortable layout—perfect for families, small groups, or a fun coastal getaway.
Popular amenities for Chesapeake apartment rentals
Weekly apartment rentals

Beach Luxury Beachfront

Life’s A Beach

2BD/2BA Villa across Currituck Beach Lighthouse

River Breeze Condo @ Kingsmill

Oceanfront Condo with Balcony & Pool

Paradise Cove

Boardwalk Oceanfront Studio near Top Dining

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym
Pet-friendly apartment rentals

Bay Breeze At Ocean View Beach Home

Kingsmill 1bed/1ba on Golf Course 9th Fairway

Ocean Breeze: New Condo Steps to the Beach

Walk to beach lovely 2/2 in "Kingsmill on James"

OceansideLuxuryCondo*Walk2Beach*Pool*Pets*NoStairs

Ocean Bliss: Cozy Apt Retreat(D)

Oyster & Pearl Beautiful New Single Level Condo

Comfy cozy condo for four and so much more!
Apartment rentals with a pool

Sandbridge Beach - DeepSeaSide Retreat

Oceanfront Condo with Spectacular Beach View

Oceanfront Gem VaB Studio Exceptional Views

Enjoy Sea Life! Steps to the Beach!

Dolphin Beach condo-amazing view and indoor pool

Lewis Villa | 2 Min Walk to Beach + Heated Pool

Seas The Day of Virginia Beach

VB Boardwalk Getaway (2b2ba) - Long or short term!
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $131 SGD | $141 SGD | $141 SGD | $136 SGD | $134 SGD | $130 SGD | $129 SGD | $131 SGD | $139 SGD | $131 SGD | $137 SGD | $132 SGD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
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- Apartment rentals Virginia
- Apartment rentals United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- Cape Charles Beachfront
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Hampton University
- First Landing Beach
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Town Point Park
- Regent University
- Old Dominion University
- Virginia Living History Museum
- Currituck Club
- Currituck Beach Lighthouse





