
Condo holiday rentals in Chesapeake
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Top-rated condo rentals in Chesapeake
Guests agree: These condos 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.

3bd Sandbridge - Sunset Bay views! Newly Remodeled
Welcome to "Heels in the Sand", a 3bed-2bath luxury condo in the exclusive Sanctuary at False Cape, the only oceanfront complex at Sandbridge in Virginia Beach. Inside, there is space aplenty with a open-concept living area with Roku TV, a fully-stocked gourmet kitchen, high-end finishes & sleeping for 9! Two huge patios offer stunning views of the scenic Back Bay. Free access to all condo amenities, including free parking, 3 pools, grills, and a fitness center! Your beach vacation awaits!

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!

Paradise at the Beach
Our newly renovated condo has all of the comforts of home. Accommodates 6 adults or perfect for families. Bedroom #1 has a KING SUITE, with sliding glass door that leads to the pool. The pool is open from Memorial weekend til the end of September. Bedroom 2 has a Queen size bed and livingroom has a sofabed. Blackout curtains in both bedrooms. Cable TV and Wi-Fi in ALL rooms. Secured building. Outdoor shower and shared grill. Come have a relaxing and fun vacation at the beach.

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!

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

Beachfront Getaway, Pet Friendly, Mermaid Suite
Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Beach Luxury Beachfront

Life’s A Beach

2BD2BA Condo w/Pool2Blocks2Beach

2BD/2BA Villa across Currituck Beach Lighthouse

River Breeze Condo @ Kingsmill

Paradise Cove

Boardwalk Oceanfront Studio near Top Dining

Shadowlawn Villas II, Suite I, close to surf park
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Cozy & Fun Hampton Condo, WIFI & W/D! Dogs welcome

Ocean Breeze: New Condo Steps to the Beach

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

Oyster & Pearl Beautiful New Single Level Condo

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Wonderful & tranquil beach retreat: 2BR/2BA Condo.

*Mid/Long Term Rental* Cozy Home at Mary Roberts
Condo rentals with a pool

Sandbridge Beach - DeepSeaSide Retreat

Oceanfront Condo with Spectacular Beach View

Oceanfront Gem VaB Studio Exceptional Views

Family reunion? Here ya go! 8BDR/8BA sleeps 24!

3BDR 2 bath, Sleeps up to 8 Guests

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

Barefoot Bliss - Single Level Steps to the Beach

Bay Creek Blessed at The Fairways
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $188 NZD | $188 NZD | $186 NZD | $183 NZD | $179 NZD | $174 NZD | $173 NZD | $176 NZD | $186 NZD | $176 NZD | $185 NZD | $178 NZD |
| 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 |
Quick stats about condo rentals in Chesapeake

Total holiday rentals
Explore 40 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $85 NZD per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake holiday rentals include Wi-Fi 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 Cinemark Chesapeake Square
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- Condo rentals Virginia
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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
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- Colonial Williamsburg's Merchants Square
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- Town Point Park
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- Old Dominion University
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- Chrysler Hall
- Regent University




