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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake condo rentals
Weekly condo rentals
Condo in Virginia Beach
4.91 out of 5 average rating, 116 reviewsWalk to beach BEAUTIFUL 2BR 1BA condo
Jan 20 – 27
Condo in Virginia Beach
4.84 out of 5 average rating, 239 reviewsBeautiful Beachfront Condo
Sep 27 – Oct 4
Condo in Virginia Beach
4.79 out of 5 average rating, 121 reviewsBeach Bliss Oasis
Jan 11 – 18
Condo in Virginia Beach
4.8 out of 5 average rating, 163 reviewsRetreat By the Sea Full Kitchen 1 St. to the Ocean
Jan 13 – 20
Condo in Williamsburg
4.81 out of 5 average rating, 100 reviewsBook a Piece of History at Kingsmill Williamsburg
Jul 3 – 10
Condo in Virginia Beach
4.85 out of 5 average rating, 92 reviewsBeach Bungalow on the Boardwalk
Oct 25 – Nov 1
Condo in Williamsburg
4.96 out of 5 average rating, 52 reviewsComfy 1BR w pond view Kingsmill
Oct 18 – 25
Condo in Virginia Beach
4.96 out of 5 average rating, 25 reviewsTropical 2BR Condo Getaway 1 Block from the Beach!
Jul 8 – 15
Pet-friendly condo rentals
Condo in Chesapeake
5.0 out of 5 average rating, 5 reviews2BR Condo in Chesapeake - Western Branch
Jul 5 – 12
Condo in Moyock
5.0 out of 5 average rating, 13 reviewsBrand New Townhome - Family and Dog Friendly
Jan 14 – 21
Condo in Norfolk
4.98 out of 5 average rating, 61 reviewsBeachfront Getaway, Pet Friendly, Mermaid Suite
Aug 26 – Sep 2
Condo in Hampton
4.9 out of 5 average rating, 72 reviewsCozy & Fun Hampton Condo- WIFI & W/D!
Mar 3 – 10
Condo in Norfolk
5.0 out of 5 average rating, 22 reviewsBeachfront Condo; Amazing views (1 bedrm, 1 bath)
Apr 19 – 26
Condo in Williamsburg
5.0 out of 5 average rating, 82 reviewsWalk to beach, lovely 2bdr 2ba by lake, Kingsmill
Mar 1 – 8
Condo in Norfolk
4.85 out of 5 average rating, 48 reviewslovely condo near chesapeake bay
Aug 30 – Sep 6
Condo in Virginia Beach
4.89 out of 5 average rating, 235 reviewsCoastal Coral - Oceanfront
Jul 24 – 31
Condo rentals with a pool
Condo in Virginia Beach
4.92 out of 5 average rating, 66 reviewsOceanfront/Boardwalk Complex, Beach, Pool, Balcony
Dec 11 – 18
Condo in Virginia Beach
4.98 out of 5 average rating, 54 reviews2BD/2BR Beachfront Condo Near Wildlife Refuge
Jul 28 – Aug 4
Condo in Virginia Beach
4.86 out of 5 average rating, 37 reviewsOcean front best beach, boardwalk, dolphins!
Oct 26 – Nov 2
Condo in Virginia Beach
4.89 out of 5 average rating, 57 reviews❤️Penthouse By The Sea❤️Huge Home w/ Amazing Views
Oct 16 – 23
Condo in Virginia Beach
5.0 out of 5 average rating, 3 reviewsSojourn | Southern Dunes | Sleeps 6
Sep 13 – 20
Condo in Virginia Beach
4.89 out of 5 average rating, 36 reviewsVA Beach Retreat! Quiet and perfect for families!
Mar 24 – 31
Condo in Virginia Beach
4.82 out of 5 average rating, 11 reviews1 BR/Kitchen w/Balcony, Beach Quarters Oceanfront
Jun 15 – 22
Condo in Williamsburg
4.83 out of 5 average rating, 6 reviewsGreensprings Vacation Resort 2br suite, Friday che
Oct 25 – Nov 1
Quick stats about condo rentals in Chesapeake
Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1K reviews
Nightly prices starting at
R928 ZAR before taxes and fees
Destinations to explore
- Outer Banks Vacation rentals
- Virginia Beach Vacation rentals
- Richmond Vacation rentals
- Norfolk Vacation rentals
- Williamsburg Vacation rentals
- Nags Head Vacation rentals
- Myrtle Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Condo rentals Outer Banks
- Condo rentals Virginia Beach
- Beach condo rentals Virginia Beach
- Condo rentals Virginia
- Condo rentals Richmond
- Private suite rentals Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- Waterfront rentals Chesapeake
- House rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with pools Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with outdoor seating Chesapeake
- Townhouse rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Family-friendly rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Apartment rentals Chesapeake
- Rentals with a home theater Chesapeake
- Monthly Rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a washer and dryer Chesapeake
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom