Best Resorts in Chesapeake

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Compare 92 Resorts in Chesapeake with updated reviews, rates, and availability.

Exterior
Beautiful Oceanfront 2 bedroom luxury suite at Oceanaire Resort, upscale resort
10.0 out of 10, Exceptional, (1)
"We had a great stay and couldn't be more pleased with this Oceanaire property. Our condo we stayed in was perfect for my family. Plenty of space, with very pretty views of the ocean and the rooms were spotless. Very well maintained units. They have four pools, two outdoor, one indoor for everyone to enjoy and one indoor adult only pool. The pools outdoors get very crowded and you should obtain a seat early in the morning to ensure a spot. The adult only indoor pool/hot tub is beautiful and...
Beautiful Oceanfront 2 bedroom luxury suite at Oceanaire Resort, upscale resort
Indoor pool
Four Sails Resort Oceanfront condo with 2 Oceanfront Balconies
10.0 out of 10, Exceptional, (1)
"Super easy rental and check in process, clean property with great view of the ocean. Overall, a great experience."
Four Sails Resort Oceanfront condo with 2 Oceanfront Balconies
Property grounds
Ocean Beach Club Resort a Hilton Oceanfront Resort with 2 Oceanfront Balconies!
10.0 out of 10, Exceptional, (1)
"This was a great family vacation. So relaxing and so easy to have a great family vacation. I do wish the TVs were S mart TVs."
Ocean Beach Club Resort a Hilton Oceanfront Resort with 2 Oceanfront Balconies!
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Exterior
Celebrate July 4th at Ocean Sands, Virginia Beach, Virginia
10.0 out of 10, Exceptional, (1)
"I booked the rental well in advance and the process went very smoothly from start to finish. My family and I had great time at this prime beach location. Thanks again."
Celebrate July 4th at Ocean Sands, Virginia Beach, Virginia
Property grounds
Hilton - Ocean Beach Club Resort condo with Oceanfront & Oceanview Balconies!
10.0 out of 10, Exceptional, (1)
"Everything was just as described. The only thing that would make it better is some type of breakfast at the hotel."
Hilton - Ocean Beach Club Resort condo with Oceanfront & Oceanview Balconies!
Full-size fridge, microwave, stovetop, dishwasher
Ocean Key Resort 2br sleeps 6 with Oceanview balcony!
10.0 out of 10, Exceptional, (1)
"East access to the beach. Art classes for kids and easy access to everything"
Ocean Key Resort 2br sleeps 6 with Oceanview balcony!
TV
Ocean Key Resort next to Rudee Inlet
9.0 out of 10, Wonderful, (74)
"Was in town for the NCAA Indoor Track and Field Championships at the Virginia Beach Sports complex. Ocean Key Resort is less than 2 miles from the complex. It's in a great location and within walking distance of several restaurants and shops. The resort itself was very clean with a nice indoor pool and hot tub. Would definitely stay here again."
The price is $189
$302 total
includes taxes & fees
May 20 - May 21
Ocean Key Resort next to Rudee Inlet
On the beach, beach towels
Ocean Beach Club and Oceanaire is the nicest resort in Virginia Beach - 4 stars
9.0 out of 10, Wonderful, (2)
"The whole experience was fantastic. The pools were great and the beach right across the bike path. The room was tidy with dishes for four. The view from the bedroom window and balcony is flawless."
The price is $289
$431 total
includes taxes & fees
May 19 - May 20
Ocean Beach Club and Oceanaire is the nicest resort in Virginia Beach - 4 stars
Property grounds
Ocean Sands Resort Oceanfront condo with Oceanfront Balcony!
9.0 out of 10, Wonderful, (2)
"Easy working with realtor."
Ocean Sands Resort Oceanfront condo with Oceanfront Balcony!
Exterior
Ocean Sands Resort with a nice Oceanfront Balcony
8.8 out of 10, Excellent, (66)
"Great stay"
Ocean Sands Resort with a nice Oceanfront Balcony
Balcony
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
8.8 out of 10, Excellent, (16)
"The check-in is so easy. The room was very clean with plenty of storage. The kitchen was stocked with everything you need. If you find you need anything, the 24/7 staff will get it for you. Already want to return."
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
Property grounds
Beach Quarters Resort Oceanfront condo with Oceanfront balcony!
8.8 out of 10, Excellent, (3)
"We had a great stay! They also had a cool feature that we could just text them when we needed something. They also had full size Shampoo and body wash hanging in the shower that smelled awesome! And lotion near the sink! Their elevators are a little slow, but that was the only pain we had. Thank you!"
Beach Quarters Resort Oceanfront condo with Oceanfront balcony!
Property grounds
Ocean Sands Resort with a nice Oceanfront Balcony
8.6 out of 10, Excellent, (98)
"Great stay great property near every thing you need."
Ocean Sands Resort with a nice Oceanfront Balcony
Balcony
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
8.4 out of 10, Very Good, (15)
"Walking distance to shops and restaurants. Love the ground level, perfect with teens that want to stay on the go! Greatly enjoyed our stay and will be back!!"
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
Exterior
Ocean Key Resort
8.0 out of 10, Very Good, (32)
"Worked great for our family of four. Right next to the beach. Definitely would recommend."
Ocean Key Resort
Full-size fridge, microwave, stovetop, dishwasher
Ocean Key Resort Directly Across the Street from Beach with Balcony!
8.0 out of 10, Very Good, (2)
"This property was great! Exactly what we hoped for!"
Ocean Key Resort Directly Across the Street from Beach with Balcony!
Property grounds
Ocean Sands Resort Oceanfront condo with Oceanfront Balconies!!
8.0 out of 10, Very Good, (1)
"Our stay was nice. The view is absolutely fantastic. The location is great and right in the middle of all the street entertainment. The only reson i knock a star off is because parking is not the greatest, especially if you have a bigger vehicle and when we first walked in the room, it wasnt the cleanest. I had read other reviews and took some cleaning supplies of my own. I recleaned the bathroom myself but other then that everything is great. If you plan using the coffee pot, clean it out...
Ocean Sands Resort Oceanfront condo with Oceanfront Balconies!!
Balcony
Barclay Towers Resort Oceanfront Units with Oceanfront Balcony
7.8 out of 10, Good, (11)
"Perfect size space for a quick trip"
Barclay Towers Resort Oceanfront Units with Oceanfront Balcony
Beach
Ocean Key Resort
7.0 out of 10, Good, (7)
"It met my expectations. My only concerns were the internet - it was hesitant/buffering quite a bit. I also noticed there were no knives for slicing fruit/veggies or meat -only table/butter knives. But overall my stay was pleasant with a great view of the ocean and super convenient to restaurants and shops. The check in/out process was easy and the staff was able to answer/assist with any questions I had. I am definitely considering staying here in the future."
Ocean Key Resort
Property grounds
Beach Quarters Resort Oceanfront condo with 2 oceanfront balconies!
2.0 out of 10, (1)
"To much to type , feel free to call me"
Beach Quarters Resort Oceanfront condo with 2 oceanfront balconies!
Don't see what you're looking for?
See all available properties in Chesapeake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Chesapeake

Beach
Beach Condo 2 Min Walk From The Beach
9.2 out of 10, Wonderful, (91)
"This condo was absolutely fabulous. It is literally 2 minute walk to the beach access. The rooms were comfortable and I've never stayed at a Vrbo with such an impressively stocked kitchen. The host responded quickly and answered all our questions. They were also very responsive. It was a lovely stay."
Beach Condo 2 Min Walk From The Beach
Interior
The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very Good, (1077)
"The property staff was very nice and tentative to our needs during our stay. We had an issue with our room and they changed our room that was more suitable."
The price is $108
$178 total
includes taxes & fees
May 29 - May 30
The Atrium Resort by VSA Resorts
Exterior
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very Good, (1269)
"View was immaculate. Room was accommodating. Some major amenities were not available during entire duration of stay (wi fi) and some ice machines. The ocean view made it worth the stay."
The price is $122
$199 total
includes taxes & fees
May 16 - May 17
The Ocean Sands Resort by VSA Resorts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chesapeake Resorts information

Number of reviews
332
Accommodation
92 Resorts
Lowest Price
$189
Highest Price
$289

Frequently asked questions

What is Chesapeake like for a resort vacation?
Longing for a relaxing getaway? Treat yourself to all the comforts and luxuries of a resort, where you can find everything you need for your vacation from convenient dining options to activities and entertainment. Browse the resort options in the area and discover the right one for you, whether you picture yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.
What's the best resort for my stay in Chesapeake?
Our top-rated resorts around Chesapeake: Ocean Key Resort next to Rudee Inlet - Beach resort, 5-minute walk from Virginia Beach Boardwalk. 18 mi (29 km) from Chesapeake. Features a water park, a fitness center, and concierge services. Ocean Sands Resort with a nice Oceanfront Balcony - Beach resort steps from Virginia Beach Boardwalk. 18.2 mi (29.2 km) from Chesapeake. Has a water park, a sauna, and a fitness center. Ocean Sands Resort with a nice Oceanfront Balcony - Beach resort steps from Virginia Beach Boardwalk. 18.2 mi (29.2 km) from Chesapeake. Access to a water park, a sauna, and a fitness center.
What can I do in Chesapeake?
Travelers love exploring the beaches in Chesapeake, and come here for shopping and other popular activities. Grab your golf clubs for a game at Cahoon Plantation Golf Course and Chesapeake Golf Club, or head to Greenbrier Mall and Chesapeake Square Mall for some retail therapy. Naval Station Norfolk and Sandbridge Beach are a couple additional top attractions in the area.
What's the seasonal weather like in Chesapeake?
The hottest months are usually July and August with an average temp of 77°F, while the coldest months are January and February with an average of 45°F. Average annual precipitation for Chesapeake is 54 inches.
What's the best way to get to and around Chesapeake?
Fly into Norfolk Intl. Airport (ORF), which is located 10.1 mi (16.3 km) away from the heart of the city. Otherwise, look for flights into Newport News - Williamsburg Intl. Airport (PHF), which is 27.6 mi (44.5 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.

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