
Condo vacation rentals in Chesapeake
Find and book unique condos on Airbnb
Quick stats about condo rentals in Chesapeake

Total vacation rentals
Explore 40 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$10,461 GYD per night before taxes and fees

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

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake vacation 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
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.

Ocean & Bay Views - Newly Renovated! Local Family!
Just steps away from the sand, "Carolina on My Mind" is a 2b/2ba oceanside condo at the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. You'll enjoy a private patio with both Ocean and Back Bay views. The condo features a large open-concept living space, and a fully equipped gourmet kitchen, and high end finishes. 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!

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

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.

Beach Bungalow on the Boardwalk
If you are looking for convenience, comfort, and a pleasant experience than Beach Bungalow on the Boardwalk is for you. We are located only a block from the beach and boardwalk, and there is no shortage of restaurants and entertainment in the area. Our condo has been completely renovated with all new furniture. We know you will enjoy your experience and look forward to being your host.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Sandbridge Beach - DeepSeaSide Retreat

Clean, Calm, Contemporary home mins from Beach

Oceanfront Condo with Spectacular Beach View

* Modern Victorian 2 bdr, 1 bath, eat in kitchen

2BD/2BA Villa across Currituck Beach Lighthouse

Dolphin Beach condo-amazing view and indoor pool

Paradise Cove

Boardwalk Oceanfront Studio near Top Dining
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Bay Breeze At Ocean View Beach Home

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

Ocean Bliss: Cozy Apt Retreat(D)

Enjoy Sea Life! Steps to the Beach!

Oyster & Pearl Beautiful New Single Level Condo

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

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

3BR 2nd-Floor | Pool | Ocean Views | Gym

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

2BD2BA Condo w/Pool2Blocks2Beach

No Shoes Retreat

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Off The Hook-Luxury Cottage - Heart of Corolla!

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

The White Pearl A Modern 3 Bed w/Private Hot Tub!
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$23,014 GYD | G$23,014 GYD | G$22,804 GYD | G$22,386 GYD | G$21,968 GYD | G$21,340 GYD | G$21,131 GYD | G$21,549 GYD | G$22,804 GYD | G$21,549 GYD | G$22,595 GYD | G$21,758 GYD |
| 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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- Condo rentals Virginia
- Condo rentals United States
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Cape Charles Beachfront
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- First Landing Beach
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- Colonial Williamsburg's Merchants Square
- Hampton University
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- Regent University
- Old Dominion University
- Currituck Club
- Currituck Beach Lighthouse
- Virginia Living History Museum




