Chesapeake Vacation Rentals from CA $163: Short-Term Rentals for 2026

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Our top choices for Chesapeake vacation rentals

Nyakio Suite

Greenbrier

CA $921 total

includes taxes & fees

Jun 9 - Jun 10

3-bedroom home away from home in fabulous Chesapeake, Virginia.

Chesapeake

James W.

CA $516 total

includes taxes & fees

Jun 29 - Jun 30

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

Chesapeake

CA $416 total

includes taxes & fees

Jun 9 - Jun 10

Central Chesapeake Stay Near Mall, Trails & parks

Greenbrier

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Chesapeake

CA $411 total

includes taxes & fees

Jul 9 - Jul 10

Studio | Free Breakfast. Indoor Pool & Hot Tub

Chesapeake

CA $349 total

includes taxes & fees

Jun 30 - Jul 1

Great Studio | Pool & Hot Tub. Your Next Vacation

Chesapeake

Patricia M.

CA $326 total

includes taxes & fees

Jun 30 - Jul 1

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Chesapeake

Ariel G.

CA $388 total

includes taxes & fees

Jun 30 - Jul 1

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Top Chesapeake Hotel Reviews

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent

"The front desk clerk was impeccable, help with information i needed to get around and she gave me helpful information."

Wingate by Wyndham Chesapeake

6/10 Okay

"There was no phone in the room. I know we have cell phones, but in case of an emergency it would've been nice to have a land line. I didn't gave a remote to the tv. I went to the desk and the girl gave me 3 because she didn't know which one controled the tv in my room! The shampoo and conditioner were too small. I have long hair so they we were a joke. The refridgerator was sooo cold it froze my soda and when I opened it it shot all over and I had to clean it up! Other than this my stay was comfortable."

Marriott Virginia Beach Oceanfront Resort

8/10 Good

"Clean room and hotel overall. Polite staff at the front desk and cleaning team. This is one of the best properties Virginia Beach has to offer. On-site restaurant Tulu was a hit and miss we found. The female attendant at the beach offering chairs and umbrellas we found to be unnecessarily rude."

Schooner Inn

2/10 Terrible

"I was so embarrassed when I got there. I had planned a birthday weekend for my Girl friend and the place was atrocious. The bed was sunken in and old and squeaky. It smelled badly. There were roaches in the bathroom. The door to the room was hard to open and shut. The only good thing about my experience was the view of the beach. I will never ever ever ever go back to that hotel again. I advised anyone that reads this to NOT GO HERE UNLESS YOU HAVE NO OTHER CHOICE."

Comfort Suites Chesapeake - Norfolk

10/10 Excellent

"Upon check in, and until check out the staff was very friendly and accommodating. The hotel was clean, smelled good, and presentable. Our room was a chilly 69 deg. We asked for an additional blanket and got it quickly. Room was very spacious. Bed was comfortable. Hotel pillows are always too soft though. Breakfast was good, with a variety to choose from. Overall, we had an excellent stay. So far, one of our top choices, should we return to VA."

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

4/10 Poor

"The view was great right on the boardwalk. But they charged my card without me knowing it and they didn’t even know why. They were suppose to text me or let me know cause it happened on my last night they never did. It took four days to get my back account straightened back out. The pool was cold and full of sand where people came for the beach and jumped it. Never seen anyone cleaning it. Dirty bandaids were laying by the pool. Several of the brick around the pool were loss. They put a $250 deposit hold on your card and charge you $15 a day to park that isn’t included in your room. The door to the garage on your floor wasn’t working right. Instead of them fixing it they just left it unlocked."

Wyndham Virginia Beach Oceanfront

6/10 Okay

"Very over priced!! Carpets looked shabby, in room coffee is terrible but u can pay 4 bucks for Starbucks! No free breakfast, our dinner was 50 for one soup and a cold entree!!! Hot water iffy, wallpaper coming off walls. Internet spotty at best. Beds very comfortable though housekeeping was great!"

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 Riverwalk Parkway Park and Playground, 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?

Spacious 4-bedroom house in beautiful 4x4 area of Corolla with ocean views!: This vacation home rental outside of Chesapeake is located by the ocean and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Chesapeake?

Expedia has 39 vacation rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Riverwalk Parkway Park and Playground and Broadmoor Play Area, whereas Chesapeake City Park and Lake Drummond 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 Veterans United Home Loans Amphitheater at Virginia 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.

Chesapeake Vacation Rentals

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Check prices for these dates

Our top choices for Chesapeake vacation rentals

Nyakio Suite

3-bedroom home away from home in fabulous Chesapeake, Virginia.

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

Central Chesapeake Stay Near Mall, Trails & parks

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub

Great Studio | Pool & Hot Tub. Your Next Vacation

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Comfortable Beach Trailer Home

Luxurious RV

Knot Three- Balcony View of ICW- Dog Friendly!

Comfortable & Private 2 Bedrm Cottage w/ King bed.

The Speakeasy Downtown Newport News

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC

Beachfront Bungalow w/ BEST Location in Ocean View!

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Find vacation rentals that suit your style

Top Chesapeake Hotel Reviews

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Find out more about Chesapeake

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Frequently asked questions

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