A golf course, a large building complex, and a marina by a river.

Chesapeake Vacation Rentals

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Our top choices for Chesapeake vacation rentals

1. Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
Nyakio Suite

2. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (113 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is CA $167
CA $191 total
includes taxes & fees
Nov 23 - Nov 24
stayAPT Suites Suffolk-Chesapeake

3. Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,447 reviews)
"Great stay"
United States
Nancy
The price is CA $185
CA $296 total
includes taxes & fees
Nov 6 - Nov 7
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.0 out of 10, Wonderful, (32 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is CA $142
CA $166 total
includes taxes & fees
Nov 2 - Nov 3
stayAPT Suites Hampton

5. The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort
3.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (1,687 reviews)
"The room was nice and spacious. The hot tub wasn't working. Overall a great place to stay."
United States
Sharon
The price is CA $126
CA $148 total
includes taxes & fees
Oct 28 - Oct 29
The Ocean Key Virginia Beach Resort

6. Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.4 out of 10, Very good, (250 reviews)
"Not a top of the line hotel, but it was clean, good location, and it served our needs. We would definitely stay here again."
United States
Cheryl
The price is CA $111
CA $144 total
includes taxes & fees
Oct 26 - Oct 27
Angie's Guest Cottage

7. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
Centrally Located Hampton Roads Home w/ Game Room!

8. Private Virginia Beach Escape w/ Pool & Fire Pit!

Private Virginia Beach Escape w/ Pool & Fire Pit!
3.5 star property
Virginia Beach
The price is CA $297
CA $738 total
includes taxes & fees
Oct 26 - Oct 27
Private Virginia Beach Escape w/ Pool & Fire Pit!
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

Find out more about Chesapeake

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chesapeake. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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?

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom: This vacation home rental outside of Chesapeake is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Chesapeake?

Expedia has 36 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 Oak Grove Lake 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.