
Condo vacation rentals in Chesapeake
Find and book unique condos on Airbnb
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

Oceanfront, beach, boardwalk, fun, dolphin, sunris
Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

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.

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!

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!

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.

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.

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

Life’s A Beach

Pacific Paradise

Newly Renovated Condo in Virginia Beach, Virginia

OceanSands Oceanfront AquariumChairsBikes

Just a block from beach

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

Shadowlawn Villas II, Suite I, close to surf park

Cozy 2BR Condo in Williamsburg
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Bay Breeze At Ocean View Beach Home

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

Ocean Bliss: Cozy Apt Retreat(D)

Enjoy Sea Life! Steps to the Beach!

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Comfy cozy condo for four and so much more!

Wonderful & tranquil beach retreat: 2BR/2BA Condo.
Condo rentals with a pool

Beach Luxury Beachfront

Sandbridge Beach - DeepSeaSide Retreat

Dog Friendly Luxury Condo, Walk to the Beach

Oceanfront Gem VaB Studio Exceptional Views

2BD/2BA Villa across Currituck Beach Lighthouse

Dolphin Beach condo-amazing view and indoor pool

Oceanfront Condo with Balcony & Pool

Paradise Cove
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $142 CAD | $153 CAD | $153 CAD | $147 CAD | $144 CAD | $140 CAD | $139 CAD | $142 CAD | $150 CAD | $142 CAD | $149 CAD | $143 CAD |
| 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 vacation rentals
Explore 40 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at $69 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Chesapeake vacation 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 Cinemark Chesapeake Square
Destinations to explore
- Norfolk Vacation rentals
- New York City Vacation rentals
- Washington Vacation rentals
- Myrtle Beach Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Outer Banks Vacation rentals
- Charlotte Vacation rentals
- Ocean City Vacation rentals
- Cape Fear River Vacation rentals
- Jersey City Vacation rentals
- Rentals with outdoor seating Chesapeake
- Family-friendly rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Waterfront rentals Chesapeake
- Rentals with pools Chesapeake
- House rentals Chesapeake
- Cottage rentals Chesapeake
- Rentals with a washer and dryer Chesapeake
- Rentals with a firepit Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a kayak Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Beachfront rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with breakfast Chesapeake
- Beach house rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with beach access Chesapeake
- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Nauticus
- Kiptopeke Beach
- First Landing Beach
- Currituck Beach Lighthouse
- Neptune's Park
- Regent University
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- Virginia Living History Museum
- Currituck Club





