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

Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chesapeake vacation rentals

Apartment, Balcony | Living area

1. Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
$486 nightly
The price is $561
Sep 21 - Sep 22
Total with taxes and fees
Nyakio Suite
Terrace/patio

2. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (105 reviews)
"This property was like a home away from home. Rooms were spacious and location was good. Host was very friendly."
United States
Karen
$119 nightly
The price is $137
Sep 30 - Oct 1
Total with taxes and fees
stayAPT Suites Suffolk-Chesapeake
Property grounds

3. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
10.0 out of 10, Exceptional, (15 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
$119 nightly
The price is $139
Sep 20 - Sep 21
Total with taxes and fees
stayAPT Suites Hampton
Beach nearby, beach shuttle

4. The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia
3.5 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,668 reviews)
"Great stay"
United States
Denitra LaStacia
$142 nightly
The price is $165
Oct 6 - Oct 7
Total with taxes and fees
The Atrium Resort, Virginia Beach by Vacatia
Indoor pool

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, (1,653 reviews)
"Staff was helpful"
United States
Keith
$131 nightly
The price is $152
Oct 1 - Oct 2
Total with taxes and fees
The Ocean Key Virginia Beach Resort
Terrace/patio

6. 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, (1,410 reviews)
"Wonderful family friendly hotel with beautiful ocean front view! Awesome balcony, great kitchenette and friendly staff. Will definitely be staying again!"
United States
craig
$184 nightly
The price is $214
Oct 18 - Oct 19
Total with taxes and fees
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Property entrance

7. Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.4 out of 10, Very good, (243 reviews)
"This was our second time staying there. Location is wonderful. Owners are very friendly and accommodating. And the price was unmatched. Make sure to bring plates, utensils and cups."
United States
Bret
$88 nightly
The price is $103
Oct 1 - Oct 2
Total with taxes and fees
Angie's Guest Cottage
Apartment (2 Bedrooms) | Interior

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

Private Virginia Beach Escape w/ Pool & Fire Pit!
3.5 star property
Virginia Beach
$403 nightly
The price is $465
Sep 21 - Sep 22
Total with taxes and fees
Private Virginia Beach Escape w/ Pool & Fire Pit!
House | 2 bedrooms

9. Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
$245 nightly
The price is $283
Sep 20 - Sep 21
Total with taxes and fees
Ice Ice Baby Downtown Newport News
Interior

10. 4BR Waterfront Penthouse Pool Views

4BR Waterfront Penthouse Pool Views
2.0 star property
Sandbridge
$687 nightly
The price is $792
Sep 20 - Sep 21
Total with taxes and fees
4BR Waterfront Penthouse Pool Views
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

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

8/10 Good
"The place was great. My only issue was our balcony overlooked part of the roof. That would be fine if the roof wasn’t covered in trash, clothing, etc."
Molly 1-night trip
Posted 1 hour ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find out more about Chesapeake

Everything you need to know about Chesapeake vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesapeake in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Chesapeake Arboretum, 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?

Sweetwater | Oceanfront | Private Outdoor Pool, Private Indoor Pool: This vacation home rental outside of Chesapeake is located on the beach and has an indoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind.

How many vacation rentals are there in Chesapeake?

Expedia has 37 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.