Vacation rentals in Chesapeake Beach

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Top-rated vacation rentals in Chesapeake Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Virginia Beach
The Seaglass Cottage by the Chesapeake Bay
The Seaglass Cottage by the Bay is located in the charming & beautiful neighborhood of Ocean Park just a quick 5-10 minutes stroll to the Chesapeake Bay beach. Our vintage beach house from the 1940’s has been fully remodeled and decorated in local art and beach décor. There are beautiful live oaks on the property and 3 private parking spaces for you and some first-come-first-serve street parking in front of the house. Easy load in with a ramp into the house and a mudroom for all your beach toys.
Apr 21 – 28
$272 per night
4.98 out of 5 average rating, 134 reviews
Guest favorite
Home in Virginia Beach
Play by the bay beach house,
Fantastic beach home with 3 bdrms and 3 baths. Renovated Dec2020 Great views of the Chesapeake Bay from the LR and deck. Just steps away from the beach access. Updated with SS appliances. First floor has Living room-dining rm combo with vaulted ceilings, kitchen, bdrm and bathrm. Second floor has 2 bdrms and 2 private baths . TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill. Washer-dryer. ONLY ROOM FOR 2 REGULAR SIZE CARS/SUVS IN DRIVEWAY PLUS FREE ON STREET PARKING.
Oct 26 – Nov 2
$275 per night
4.99 out of 5 average rating, 154 reviews
Guest favorite
Guest suite in Virginia Beach
Enjoy your little slice of heaven in Chics Beach!
UNIT WAS RENOVATED 11/21- UPDATED FROM 1 BDRM TO 2. 5 min walk to Chic's beach. Avoid the crowds and live with the locals! Surrounded by amazing restaurants, bars, coffee shops, and even an urban winery. We are a convenient 15 min ride from the tourist Oceanfront but you will have plenty to do in our relaxed beach town. This is a guest apartment attached to my home .The motto of Chic's Beach is "No Bad Days". Come see for yourself!
Jun 23 – 30
$193 per night
4.93 out of 5 average rating, 180 reviews

Popular amenities for Chesapeake Beach vacation rentals

Other great vacation rentals in Chesapeake Beach

Guest favorite
Guest suite in Virginia Beach
Virginia Beach 2 King BR apt 100 feet from beach
Dec 6 – 13
$159 per night
4.86 out of 5 average rating, 286 reviews
Guest favorite
Apartment in Sandbridge
Works4Me: A Sandbridge Beach Getaway
Apr 9 – 16
$209 per night
5.0 out of 5 average rating, 233 reviews
Guest favorite
Guest suite in Virginia Beach
Rest A’Shore-Virginia Beach
Apr 19 – 26
$96 per night
4.91 out of 5 average rating, 195 reviews
Guest favorite
Home in Virginia Beach
Water Oaks at Chic's Beach
Aug 12 – 19
$350 per night
4.95 out of 5 average rating, 100 reviews
Guest favorite
Condo in Virginia Beach
Chic's Beach Rental and Fishing
May 15 – 22
$427 per night
4.98 out of 5 average rating, 195 reviews
Guest favorite
Townhouse in Virginia Beach
Charming 3 BR / 3.5 BA with a Private Backyard
Dec 21 – 28
$186 per night
4.91 out of 5 average rating, 108 reviews
Guest favorite
Home in Virginia Beach
Steps to Beach At Chics Beach! Spacious + Clean!
Jul 29 – Aug 5
$596 per night
4.94 out of 5 average rating, 139 reviews
Guest favorite
Townhouse in Virginia Beach
Beach Livin' by the Chesapeake Bay - VA Beach
May 19 – 26
$275 per night
4.91 out of 5 average rating, 100 reviews
Guest favorite
Guest suite in Norfolk
Beachfront Exclusive Bay front Suite
May 7 – 14
$152 per night
4.93 out of 5 average rating, 490 reviews
Guest favorite
Townhouse in Virginia Beach
Chicks Beach Getaway large yard 500 yards to Beach
Nov 4 – 11
$232 per night
4.79 out of 5 average rating, 172 reviews
Guest favorite
Cottage in Virginia Beach
Carriage House at the Historic Church Point Manor
Jul 2 – 9
$514 per night
4.96 out of 5 average rating, 107 reviews
Guest favorite
Guest suite in Virginia Beach
Quiet Neighborhood 7 Miles From the Beaches
Jul 5 – 12
$76 per night
4.89 out of 5 average rating, 538 reviews

Destinations to explore