Chesapeake Vacation Rentals

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Our top choices for Chesapeake vacation rentals

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

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (43 reviews)
"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"
United States
Tabitha P.
The price is CA $239
CA $436 total
includes taxes & fees
Mar 31 - Apr 1
3-bedroom home away from home in fabulous Chesapeake, Virginia.

Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
The price is CA $157
CA $211 total
includes taxes & fees
Mar 15 - Mar 16
Great Studio | Pool & Hot Tub. Your Next Vacation

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

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
The price is CA $212
CA $278 total
includes taxes & fees
Mar 15 - Mar 16
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is CA $189
CA $249 total
includes taxes & fees
Mar 15 - Mar 16
Studio | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is CA $157
CA $211 total
includes taxes & fees
Mar 15 - Mar 16
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is CA $224
CA $296 total
includes taxes & fees
Apr 5 - Apr 6
Studio | Free Breakfast. Indoor Pool & Hot Tub.

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

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
The price is CA $231
CA $303 total
includes taxes & fees
Apr 2 - Apr 3
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

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

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is CA $171
CA $228 total
includes taxes & fees
Mar 15 - Mar 16
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

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

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Chesapeake
8.0 out of 10, Very good, (4 reviews)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
The price is CA $194
CA $256 total
includes taxes & fees
Mar 15 - Mar 16
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
9.6 out of 10, Exceptional, (5 reviews)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is CA $143
CA $324 total
includes taxes & fees
Mar 10 - Mar 11
Knot Three- Balcony View of ICW- Dog Friendly!

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Northeast Virginia Beach
9.6 out of 10, Exceptional, (108 reviews)
"The rooms were very clean and be was comfortable!"
United States
CYMANDYE V.
The price is CA $136
CA $315 total
includes taxes & fees
Mar 12 - Mar 13
The Art Door Duplex only minutes from beach

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.8 out of 10, Exceptional, (17 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is CA $138
CA $400 total
includes taxes & fees
Mar 19 - Mar 20
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
10.0 out of 10, Exceptional, (2 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is CA $144
CA $369 total
includes taxes & fees
Mar 10 - Mar 11
Ice Ice Baby Downtown Newport News

2 king beds -2nd fl walk 2 beach apt3

2 king beds -2nd fl walk 2 beach apt3
East Ocean View
10.0 out of 10, Exceptional, (2 reviews)
"Clean and perfect for our family stay. The apartment had everything we needed to be comfortable. "
United States
Kelly D.
The price is CA $113
CA $403 total
includes taxes & fees
Mar 11 - Mar 12
2 king beds -2nd fl walk 2 beach apt3

Wild Horses - 4x4 Beach - Quiet & Cozy

Wild Horses - 4x4 Beach - Quiet & Cozy
Corolla
The price is CA $217
CA $537 total
includes taxes & fees
Mar 10 - Mar 11
Wild Horses - 4x4 Beach - Quiet & Cozy

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.0 out of 10, Wonderful, (37 reviews)
"Beautiful place, beautiful location "
United States
rocco m.
The price is CA $163
CA $371 total
includes taxes & fees
Mar 11 - Mar 12
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Large cozy private room

Large cozy private room
Marshall
The price is CA $133
CA $217 total
includes taxes & fees
Mar 10 - Mar 11
Large cozy private room

Knot Two- Balcony View of ICW- Dog Friendly

Knot Two- Balcony View of ICW- Dog Friendly
Coinjock
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed our stay nice and piece full and enjoyable watching the boats coming up and down the international water way"
United States
Jennifer S.
The price is CA $128
CA $302 total
includes taxes & fees
Mar 10 - Mar 11
Knot Two- Balcony View of ICW- Dog Friendly

Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Willoughby Spit
8.6 out of 10, Excellent, (7 reviews)
"Cute little bungalow on the beach. Beautiful sunrises. Location is great. Very clean. Has everything you need!!! The pier is a 2 min walk. "
United States
Virginia T.
The price is CA $134
CA $311 total
includes taxes & fees
Mar 10 - Mar 11
Beachfront Bungalow w/ BEST Location in Ocean View!

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is CA $110
CA $252 total
includes taxes & fees
Mar 15 - Mar 16
Private 1 Bed Apt - Historic Olde Towne Portsmouth
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.

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?

The Art Door Duplex only minutes from beach: This vacation home rental outside of Chesapeake comes with air-conditioning so you can feel at home during your trip.

How many vacation rentals are there in Chesapeake?

Expedia has 41 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 Lake Drummond and Chesapeake City 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.