
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 €44 per night before taxes and fees

Verified guest reviews
Over 1,110 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 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 Aerotheater
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.
4.99 out of 5 average rating, 178 reviews
Oceanfront Loft: Free Parking & 1 Block from Beach
Welcome to your stylish coastal retreat at the Virginia Beach Oceanfront, a thoughtfully designed 285 sq. ft. one-bedroom apartment just steps from the beach, boardwalk, dining, entertainment, and everything that makes Virginia Beach one of the East Coast’s favorite vacation destinations. This bright and modern condo combines comfort, convenience, and an unbeatable location in the heart of Virginia Beach Oceanfront. "Guest Favorite" for those looking for an easy, relaxing VA Beach getaway.
4.9 out of 5 average rating, 131 reviews
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!
4.93 out of 5 average rating, 130 reviews
VB Boardwalk Getaway (2b2ba) - Long or short term!
Located a block and a half from the lively Virginia Beach boardwalk, our condo is in the perfect spot for an East Coast beach getaway! I love catching the sunrise over the ocean and following it up with a trip to Parlor Doughnuts, right around the corner. There is a keypad at the main entrance of the building as well as one for our individual unit, so you won't need a key. The pool can be enjoyed between Memorial Day and Labor Day. We've lived here for a year - ask me for any recommendations!
4.79 out of 5 average rating, 107 reviews
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.
4.94 out of 5 average rating, 139 reviews
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!
4.92 out of 5 average rating, 399 reviews
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.
4.84 out of 5 average rating, 225 reviews
Beach Chic Condo 1 Block from Boardwalk
If a get-away is what you need, then simply "My Beach Hideout’ is what you want. Completely renovated 2 Bedroom/1 Bath condo a short one-block walk from the oceanfront. Enjoy a stylish, relaxed coastal-vibe experience. Perfectly comfortable for 4 guests or a solo long-business stay. Dining, nightlife, entertainment, events, VB boardwalk & shops all within walking distance. Immaculate condo has queen bed + TV in both bedrooms, living room, stocked kitchen, bath + parking.
4.96 out of 5 average rating, 133 reviews
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.
4.86 out of 5 average rating, 279 reviews
2 Bedroom Beach Condo Block Off Boardwalk
Come enjoy everything Virginia Beach has to offer. Our newly renovated condo has all of the comforts of home perfect for families. Bedroom 1 has a king size bed, bedroom 2 has a queen size bed, and Living room has sofa that pulls out into a full size sofa bed. TVs in all rooms. 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.
4.9 out of 5 average rating, 345 reviews
Cher's Place @ The Beach
Relax with the whole family at this peaceful place to stay in Sandbridge! This property is ON the beach (unit itself is not facing the ocean) with access to 3 pools, a gym, local restaurants and much more! As you can see, guests LOVE my place! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! ** I am currently replacing furniture and bedding so pics may not match perfectly. Need more room?? See my other property!
4.93 out of 5 average rating, 106 reviews
2 Bedroom Condo ONE Block from the Oceanfront
Come enjoy a Virginia Beach vacation ONE block from the oceanfront and boardwalk. Our 2 bedroom condo accommodates 4 adults and is also perfect for families. Bedroom 1 has a queen size bed and bedroom 2 has a king size bed. There is also a pull out sofa bed in the living room. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family.
4.92 out of 5 average rating, 349 reviewsPopular amenities for Chesapeake condo rentals
Weekly condo rentals

Good Vibes at the Beach
4.85 out of 5 average rating, 128 reviews
Cozy 1 Bd condo, 1 block from the beach!
4.89 out of 5 average rating, 116 reviews
Oceanfront Penthouse
4.86 out of 5 average rating, 157 reviews
Condo living just steps from the sand
4.87 out of 5 average rating, 142 reviews
VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
4.96 out of 5 average rating, 199 reviews
Oceanfront, beach, boardwalk, fun, dolphin, sunris
4.86 out of 5 average rating, 170 reviews
Paradise at the Beach
4.98 out of 5 average rating, 121 reviews
Beachfront Condo/ Pool/ Surfing/ Fishing / EW 1202
4.92 out of 5 average rating, 37 reviewsPet-friendly condo rentals

*Mid/Long Term Rental* Cozy Home at Mary Roberts
4.88 out of 5 average rating, 201 reviews
August Suite | Beach | Balcony | Fire Pit
4.76 out of 5 average rating, 74 reviews
Bay Breeze At Ocean View Beach Home
4.8 out of 5 average rating, 55 reviews
Hampton Condo Near Buckroe Beach | Dogs OK
4.77 out of 5 average rating, 123 reviews
Ocean Bliss: Cozy Apt Retreat(D)
5.0 out of 5 average rating, 29 reviews
Trendy 2024 Seaside Retreat
4.79 out of 5 average rating, 156 reviews
* Modern Victorian 2 bdr, 1 bath, eat in kitchen
4.95 out of 5 average rating, 110 reviews
Entire apartment in Chesapeake, Virginia
4.93 out of 5 average rating, 14 reviewsCondo rentals with a pool

Oceanfront Gem VaB Studio Exceptional Views
4.89 out of 5 average rating, 276 reviews
New Renovated-Beach & Boardwalk at Your Door &Pool
4.85 out of 5 average rating, 177 reviews
Oceanfront Condo with Spectacular Beach View
4.9 out of 5 average rating, 116 reviews
Beachfront Oasis
4.89 out of 5 average rating, 27 reviews
Beach Luxury Beachfront
4.94 out of 5 average rating, 83 reviews
Seas The Day of Virginia Beach
4.86 out of 5 average rating, 71 reviews
Spacious 2BR/2BA Condo | 1.5 Blocks to Oceanfront
4.96 out of 5 average rating, 45 reviews
Beach Studio - Oceanside, Pool, Boardwalk, Bikes
4.9 out of 5 average rating, 49 reviewsWhen is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €90 | €97 | €97 | €106 | €106 | €107 | €88 | €90 | €95 | €90 | €94 | €91 |
| 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 |
Destinations to explore
- New York Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Myrtle Beach Vacation rentals
- Charlotte Vacation rentals
- Ocean City Vacation rentals
- North Myrtle Beach Vacation rentals
- Virginia Beach Vacation rentals
- Raleigh Vacation rentals
- Jersey City Vacation rentals
- Wilmington Vacation rentals
- Newark Vacation rentals
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with beach access Chesapeake
- Beach house rentals Chesapeake
- Rentals with a kayak Chesapeake
- Cottage rentals Chesapeake
- Rentals with pools Chesapeake
- Family-friendly rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- House rentals Chesapeake
- Rentals with breakfast Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Townhouse rentals Chesapeake
- Beachfront rentals Chesapeake
- Waterfront rentals Chesapeake
- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Buckroe Beach
- Carova Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- Regent University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- The Mariners' Museum
- The Military Aviation Museum
- Back Bay National Wildlife Refuge-N
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University





