Chesapeake Vacation Rentals

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Vacation Rentals in Chesapeake

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very Good, (1426)
"My family has a really great time and stay"
The Atrium Resort, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1416)
"10/10 staying here again "
The price is ¥13,427
¥24,206 total
includes taxes & fees
Sep 1 - Sep 2
The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very Good, (1119)
"My family truly enjoyed our stay! Would definitely stay here again. "
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Four Sails Resort

3.5 star property
7.4 out of 10, Good, (38)
"Great balcony with a great view"
Four Sails Resort

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (221)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
The price is ¥11,020
¥14,405 total
includes taxes & fees
Sep 14 - Sep 15
Angie's Guest Cottage

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (35)
"Excellent hotel. I will definitely stay there again. "
The price is ¥17,523
¥20,123 total
includes taxes & fees
Sep 1 - Sep 2
stayAPT Suites Suffolk-Chesapeake

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

9.8 out of 10, Exceptional, (178)
"This house was perfect for my family. The location was beautiful "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

8.4 out of 10, Very Good, (21)
"I visited the Outer Banks with my daughters and honestly the stay was amazing, the views, house, location this place had it all. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

Loft Space Minutes from Beach

5.0 out of 10, (4)
"Overall the stay was good but they have a roach problem which in my opinion is very disgusting and would make me want to not stay here ever again. They also during our stay did not have functioning AC and just had a bunch of fans and a small mobile AC unit in the downstairs. Other than these two things it’s a very nice place and in a good convenient spot. "
Loft Space Minutes from Beach

10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

9.4 out of 10, Exceptional, (102)
"Lots of space and the third floor is a great place to hang out with a big group. Ocean is a quick walk away. But lots of things that we were expecting to be functional did not work. Upon arrival we were sent a message documenting a list of things that were broken, which was disappointing. The hot tub also turned out to be out of order. Still a good stay for a big group, but some love needs to be put into the house. "
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

9.8 out of 10, Exceptional, (48)
"Wonderful trip with an awesome house. Very quiet and the house is beautiful. Lots of room. Thank you so much."
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

9.6 out of 10, Exceptional, (121)
"We stayed at Lightly Salted last week; my family of five [2 adults, 3 kids (11, 5, 1)]and out close friends family of three [2 adults, 1 kid (3)]. "
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Nautical Dream, redecorated oceanfront home with incredible views and decks

10.0 out of 10, Exceptional, (12)
"Wonderful location, generous floor plan."
Nautical Dream, redecorated oceanfront home with incredible views and decks

Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

9.4 out of 10, Exceptional, (22)
"As listed close to everything and made our stay very easy. Communication with owner was easy and all questions we had were answered."
The price is ¥25,769
¥63,119 total
includes taxes & fees
Sep 1 - Sep 2
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub

9.8 out of 10, Exceptional, (140)
"The house was beautiful, clean and plenty of room for all our guest! The view was amazing! "
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub

Luxurious RV

8.2 out of 10, Very Good, (10)
"Upon arriving it was dark & I was having a hard time finding the residence. I gave the host a call & he was very friendly and helpful, was able to find it right after speaking with him. The RV is super cute, very relaxing view in the back."
The price is ¥29,450
¥59,136 total
includes taxes & fees
Aug 17 - Aug 18
Luxurious RV

Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach

9.6 out of 10, Exceptional, (118)
"Great location and accomadations"
Horse Inn Around: Pet Friendly-so bring the whole family! Just 3 mins to beach

Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

4.0 star property
7.4 out of 10, Good, (42)
"First want to start off by saying the house is as described actually better then the photos online led us to believe. It's an older house but was clean and decorated beautifully. For the money, description, and space you get staying in this home I would definatley recomend you staying here. It's not a 5 star luxury resort, but I gave 5 stars for the house being it was better then what we expected. Our family enjoyed our stay."
The price is ¥18,774
¥54,060 total
includes taxes & fees
Sep 2 - Sep 3
Home Near Towncenter | Minutes from Beaches | Central to Hamptonroads

Cozy 1-bedroom apartment in amazing Virginia Beach with WiFi, AC

10.0 out of 10, Exceptional, (1)
"It’s very nice place for small family members and quiet. We will definitely return next time and recommend for friends and family to check this out for affordable prices that can easily excepted. The owner very helpful and friendly. "
The price is ¥18,406
¥36,532 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 1-bedroom apartment in amazing Virginia Beach with WiFi, AC

Glamping your way-close to beach in Virginia Beach with AC

Glamping your way-close to beach in Virginia Beach with AC
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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Top Chesapeake Hotel Reviews

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Broadmoor Play Area, or you can go with a more remote option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Chesapeake. While you're in the area, you can also enjoy the top-notch restaurants and live music.

What are some of the best vacation home rentals in Chesapeake?

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi: This vacation home rental outside of Chesapeake is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Chesapeake?

Expedia has 35 vacation rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Broadmoor Play Area and Parkview Play Area, whereas Chesapeake City Park and Crestwood Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Naval Station Norfolk and Sandbridge Beach.

What’s a vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.