Best Resorts in Chesapeake

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 108 Resorts in Chesapeake with updated reviews, rates, and availability.

Hilton Virginia Beach Oceanfront
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Hilton Virginia Beach Oceanfront

4.0 star property
8.2 out of 10, Very Good, (1002)
"Great place to stay in"
The price is $214
includes taxes & fees
$183 per night
May 26 - May 27
Hilton Virginia Beach Oceanfront
Embassy Suites by Hilton Virginia Beach Oceanfront Resort
Indoor pool, seasonal outdoor pool

Embassy Suites by Hilton Virginia Beach Oceanfront Resort

3.5 star property
9.2 out of 10, Wonderful, (357)
"Beautiful, well maintained, staff was great. "
The price is $280
includes taxes & fees
$242 per night
May 11 - May 12
Embassy Suites by Hilton Virginia Beach Oceanfront Resort
Ocean Sands Resort with a nice Oceanfront Balcony
Exterior

Ocean Sands Resort with a nice Oceanfront Balcony

8.6 out of 10, Excellent, (84)
"Good place to stay"
Ocean Sands Resort with a nice Oceanfront Balcony
Ocean Key Resort next to Rudee Inlet
Interior

Ocean Key Resort next to Rudee Inlet

9.0 out of 10, Wonderful, (79)
"Excellent location and great service all around"
Ocean Key Resort next to Rudee Inlet
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
Spa

Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio

8.6 out of 10, Excellent, (20)
"Room was clean"
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
Ocean Key Resort
Exterior

Ocean Key Resort

8.0 out of 10, Very Good, (39)
"We've stayed here numerous times. Rooms are clean and well appointed. Great location for us. Only one working elevator the last 2 stays."
Ocean Key Resort
1BR 1BA sleeps four on Atlantic Ave near Rudee Inlet
Pool

1BR 1BA sleeps four on Atlantic Ave near Rudee Inlet

2.0 star property
9.2 out of 10, Wonderful, (5)
"The location and the accommodation was beautiful and very modern."
1BR 1BA sleeps four on Atlantic Ave near Rudee Inlet
Ocean Sands Resort with a nice Oceanfront Balcony
Property grounds

Ocean Sands Resort with a nice Oceanfront Balcony

8.6 out of 10, Excellent, (109)
"Parking was an adventure "
Ocean Sands Resort with a nice Oceanfront Balcony
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
Spa

Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio

9.0 out of 10, Wonderful, (18)
"We love staying here! The staff is friendly and it is a very laid back place! We come and go as we please! We love the ocean front view!!"
Barclay Towers Resort Oceanfront Unit with Oceanfront Balcony or Oceanview Patio
Barclay Towers Resort Oceanfront Units with Oceanfront Balcony
Spa

Barclay Towers Resort Oceanfront Units with Oceanfront Balcony

8.0 out of 10, Very Good, (12)
"Perfect size space for a quick trip"
Barclay Towers Resort Oceanfront Units with Oceanfront Balcony
Beautiful Oceanfront 2 bedroom luxury suite at Oceanaire Resort, upscale resort
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
Barclay Towers Resort Oceanfront Unit with Full Oceanfront Balcony
Spa

Barclay Towers Resort Oceanfront Unit with Full Oceanfront Balcony

10.0 out of 10, Exceptional, (2)
"The property was clean as expected and the view was fantastic. Staff was very nice and always helpful. A great stay."
Barclay Towers Resort Oceanfront Unit with Full Oceanfront Balcony
The Colony Condominiums Oceanfront Unit with Amazing Oceanfront Balcony
Property grounds

The Colony Condominiums Oceanfront Unit with Amazing Oceanfront Balcony

9.6 out of 10, Exceptional, (5)
"Place was great. Very clean, friendly staff and ocean front. What more do you need. Also a great location near shops and restaurants."
The Colony Condominiums Oceanfront Unit with Amazing Oceanfront Balcony
Beach Quarters Resort Oceanfront condo with Oceanfront balcony!
On the beach

Beach Quarters Resort Oceanfront condo with Oceanfront balcony!

9.0 out of 10, Wonderful, (4)
"We enjoyed our stay,the location was perfect. Can't wait to go back next year."
Beach Quarters Resort Oceanfront condo with Oceanfront balcony!
The Colony Condominiums Oceanfront Unit with Amazing Oceanfront Balcony
Property grounds

The Colony Condominiums Oceanfront Unit with Amazing Oceanfront Balcony

9.0 out of 10, Wonderful, (2)
"Great place to stay. Convenient to everything and just as advertised. Second time staying here and will definitely consider for further stays."
The Colony Condominiums Oceanfront Unit with Amazing Oceanfront Balcony
Boardwalk Villas Oceanfront Resort Oceanfront condo with Oceanfront Balcony!
Indoor pool, a heated pool

Boardwalk Villas Oceanfront Resort Oceanfront condo with Oceanfront Balcony!

Boardwalk Villas Oceanfront Resort Oceanfront condo with Oceanfront Balcony!
Beach Quarters Resort Oceanfront condo with 2 oceanfront balconies!
On the beach

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!
Hilton Oceanaire Resort Escape – Oceanfront Bliss with Dual Oceanview Balconies!
Indoor pool, outdoor pool

Hilton Oceanaire Resort Escape – Oceanfront Bliss with Dual Oceanview Balconies!

8.0 out of 10, Very Good, (1)
"The space in the rooms worked out perfectly. There were some minor blemishes associated with the rooms: a moldy shower curtain, one of the pieces of trim falling off, the one balcony missing chairs, and the doors to get in and the ones for the adjoining room all stuck really badly. The only other inconvenience was not having enough elevators. I loved the view and the playground on the beach right in front of the hotel. The pools were perfect. The front desk associates, along with the rest of...
Hilton Oceanaire Resort Escape – Oceanfront Bliss with Dual Oceanview Balconies!
Four Sails Resort Oceanfront condo with Oceanfront & City View Balconies
Indoor pool

Four Sails Resort Oceanfront condo with Oceanfront & City View Balconies

Four Sails Resort Oceanfront condo with Oceanfront & City View Balconies
Celebrate July 4th at Ocean Sands, Virginia Beach, Virginia
On the beach

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
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.
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Other property types in Chesapeake

The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1317)
"Would love to visit again. Maybe longer next time! "
The price is $162
includes taxes & fees
$139 per night
May 13 - May 14
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Exterior

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1047)
"very nice place"
The price is $162
includes taxes & fees
$139 per night
May 27 - May 28
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very Good, (1324)
"Location is great close to beach nice places to eat nearby."
The price is $152
includes taxes & fees
$131 per night
May 13 - May 14
The Atrium Resort, Virginia Beach by Vacatia
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.

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: Hilton Virginia Beach Oceanfront - Beach resort, 5-minute walk from Virginia Beach Boardwalk. 18.2 mi (29.3 km) from Chesapeake. Features 3 bars, a seasonal outdoor pool, and a health club. Highly rated for its great location. Embassy Suites by Hilton Virginia Beach Oceanfront Resort - Spa resort, 5-minute walk from Virginia Beach Boardwalk. 18.3 mi (29.5 km) from Chesapeake. Has 2 restaurants, a full-service spa, and a seasonal outdoor pool. Ocean Key Resort next to Rudee Inlet - Beach resort, 5-minute walk from Virginia Beach Boardwalk. 18 mi (29 km) from Chesapeake. Enjoy the water park, 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. Amenities include 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.