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 $165
CA $343 total
includes taxes & fees
Feb 11 - Feb 12
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 $167
CA $224 total
includes taxes & fees
Feb 22 - Feb 23
Great Studio | Pool & Hot Tub. Your Next Vacation

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 $193
CA $254 total
includes taxes & fees
Feb 22 - Feb 23
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is CA $167
CA $224 total
includes taxes & fees
Feb 22 - Feb 23
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 $167
CA $224 total
includes taxes & fees
Feb 22 - Feb 23
Studio | Free Breakfast. Indoor Pool & Hot Tub

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
10.0 out of 10, Exceptional, (1 review)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is CA $178
CA $236 total
includes taxes & fees
Feb 22 - Feb 23
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

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 $193
CA $254 total
includes taxes & fees
Feb 22 - Feb 23
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (80 reviews)
"There were three of us staying there, and we couldn't have been more comfortable and enjoyed the stay more. Loved the space! Loved the area! A great place for a vacation!"
United States
Joseph V.
The price is CA $274
CA $547 total
includes taxes & fees
Feb 28 - Mar 1
Comfortable Beach Trailer Home

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very good, (17 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is CA $274
CA $546 total
includes taxes & fees
Feb 8 - Feb 9
Luxurious RV

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)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is CA $138
CA $404 total
includes taxes & fees
Feb 23 - Feb 24
Comfortable & Private 2 Bedrm Cottage w/ King bed.

OV Mosaic - Topaz Suite

OV Mosaic - Topaz Suite
East Ocean View
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay in Norfolk, Virginia, at OV. The room was very clean, exactly as described, and just a very short walk to the beach. We brought our dog, and the area was perfect for walks and relaxing. Communication with the property manager was excellent, and the location couldn’t have been better. Would definitely stay again!"
United States
Jose V.
OV Mosaic - Topaz Suite

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, (105 reviews)
"The rooms were very clean and be was comfortable!"
United States
CYMANDYE V.
The price is CA $137
CA $317 total
includes taxes & fees
Feb 9 - Feb 10
The Art Door Duplex only minutes from beach

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is CA $134
CA $344 total
includes taxes & fees
Feb 8 - Feb 9
The Speakeasy Downtown Newport News

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
Willoughby Spit
10.0 out of 10, Exceptional, (2 reviews)
"very friendly host! very patient with me on day of check in, made sure we had everything we needed & more !"
United States
Shydymond B.
The price is CA $82
CA $130 total
includes taxes & fees
Feb 22 - Feb 23
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

Cozy Bay Cottage private backyard blocks from beach!

Cozy Bay Cottage private backyard blocks from beach!
Bayview
9.0 out of 10, Wonderful, (43 reviews)
"Beautiful home! Spacious and very clean! Short walk to the beach! And very close to Virginia Beach board walk! Highly recommend for all!"
United States
Elizabeth B.
The price is CA $245
CA $504 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Bay Cottage private backyard blocks from beach!

OV Mosaic - River Suite

OV Mosaic - River Suite
East Ocean View
9.2 out of 10, Wonderful, (7 reviews)
"Great place and cool area"
United States
Matt W.
OV Mosaic - River Suite

Sojourn's Harborage unit 6

Sojourn's Harborage unit 6
East Ocean View
9.2 out of 10, Wonderful, (5 reviews)
"Very comfortable - beds were soft, sheets were great and water pressure was nice. There was a problem with city drains so the parking lot was flooded a couple nights, which caused a lot of dirt to be tracked into the unit, but this wasn't a problem with the rental. Location was close to everything we needed."
United States
Ronald K.
The price is CA $101
CA $471 total
includes taxes & fees
Feb 10 - Feb 11
Sojourn's Harborage unit 6

Water Front Delight on the Bay

Water Front Delight on the Bay
Willoughby Spit
7.8 out of 10, Good, (25 reviews)
"Everything was very nice really enjoyed "
United States
Deborah B.
The price is CA $136
CA $488 total
includes taxes & fees
Feb 28 - Mar 1
Water Front Delight on the Bay

OV Mosaic - Coconut Suite

OV Mosaic - Coconut Suite
East Ocean View
9.6 out of 10, Exceptional, (7 reviews)
"Great location. Fit our needs perfectly. Highly recommend."
United States
Wendy A.
OV Mosaic - Coconut Suite

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 $111
CA $254 total
includes taxes & fees
Feb 10 - Feb 11
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 Bryant Farms Park, 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 40 vacation rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Bryant Farms Park and Broadmoor Play Area, whereas Oak Grove Lake Park and Chesapeake Arboretum are a couple of great spots to enjoy the outdoors. Greenbrier Mall and Chesapeake Conference Center are other places to visit while you're in town.

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.