Chesapeake Vacation Rentals

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Vacation Rentals in Chesapeake

3-bedroom house in Chesapeake with workspace, ready-to-cook kitchen, and yard

2.0 star property
Chesapeake
$286 nightly
The price is $331
Nov 15 - Nov 16
Total with taxes and fees
3-bedroom house in Chesapeake with workspace, ready-to-cook kitchen, and yard

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

2.5 star property
Chesapeake
8.0 out of 10, Very Good, (4)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
$178 nightly
The price is $205
Nov 23 - Nov 24
Total with taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Chesapeake
$145 nightly
The price is $167
Dec 1 - Dec 2
Total with taxes and fees
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Great Studio | Pool & Hot Tub. Your Next Vacation

Chesapeake
10.0 out of 10, Exceptional, (3)
"Impressed with the whole experience. "
United States
Patricia M.
$155 nightly
The price is $178
Dec 1 - Dec 2
Total with taxes and fees
Great Studio | Pool & Hot Tub. Your Next Vacation

Studio | Free Breakfast. Indoor Pool & Hot Tub

Chesapeake
$145 nightly
The price is $167
Dec 1 - Dec 2
Total with taxes and fees
Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Chesapeake
$145 nightly
The price is $167
Dec 11 - Dec 12
Total with taxes and fees
Studio | Free Breakfast. Indoor Pool & Hot Tub.

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

Chesapeake
$153 nightly
The price is $176
Dec 1 - Dec 2
Total with taxes and fees
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!

Chesapeake
10.0 out of 10, Exceptional, (1)
"Property was fine, the pool just wasn't clean enough & it was crowded. "
United States
Kevin
$158 nightly
The price is $181
Dec 1 - Dec 2
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Comfortable Beach Trailer Home

Sandbridge
9.2 out of 10, Wonderful, (80)
"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.
$343 nightly
The price is $402
Nov 30 - Dec 1
Total with taxes and fees
Comfortable Beach Trailer Home

Luxurious RV

Sandbridge
8.4 out of 10, Very Good, (16)
"Exactly what we were expecting. Easy check-in and super convenient location. Definitely would stay again when we come back to the area."
United States
Travis H.
$341 nightly
The price is $399
Nov 15 - Nov 16
Total with taxes and fees
Luxurious RV

Ice Ice Baby Downtown Newport News

2.0 star property
Newport News
10.0 out of 10, Exceptional, (2)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
$203 nightly
The price is $237
Nov 16 - Nov 17
Total with taxes and fees
Ice Ice Baby Downtown Newport News

Sojourn's Harborage Coral Suite

2.0 star property
East Ocean View
10.0 out of 10, Exceptional, (2)
"The modern decor, cleanliness (comfortable bedding) and proximity to the beach was very nice. Unfortunately there was road construction right next to the property and parking was very tight. Units below us had odors that wafted up and loud music was played past midnight. Communicating with the manager seemed to be via AI and did not feel personal although they were responsive. Bath fixtures were coming off the wall and they had insect spraying scheduled during our stay which was not ideal but we...
United States
Carla D.
$320 nightly
The price is $341
Dec 2 - Dec 3
Total with taxes and fees
Sojourn's Harborage Coral Suite

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Portsmouth
10.0 out of 10, Exceptional, (15)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
$284 nightly
The price is $330
Nov 16 - Nov 17
Total with taxes and fees
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Cabin in the Woods, Pet Friendly

Shawboro
8.8 out of 10, Excellent, (23)
"quiet, remote cabin full of personality. Great if you want to be AWAY from people"
United States
Jamie F.
$243 nightly
The price is $274
Nov 24 - Nov 25
Total with taxes and fees
Cabin in the Woods, Pet Friendly

Knot Three- Balcony View of ICW- Dog Friendly!

Coinjock
9.6 out of 10, Exceptional, (4)
"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.
$198 nightly
The price is $223
Nov 15 - Nov 16
Total with taxes and fees
Knot Three- Balcony View of ICW- Dog Friendly!

Sojourn's Harborage S

2.0 star property
East Ocean View
10.0 out of 10, Exceptional, (2)
"I really enjoyed my stay. I would do it again "
United States
Joseph W.
$250 nightly
The price is $267
Nov 16 - Nov 17
Total with taxes and fees
Sojourn's Harborage S

Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

Cottage Park
7.8 out of 10, Good, (16)
"Check in was ok. The hot water heater was in the kitchen with exposed wire. The table was uneven it would rock up and down. There’s also mold or grease on the ceiling in the kitchen. a spaghetti noodle on the wall. Floor was not clean there was sand on the floor. Bathroom window would not lock. The best part was having a big TV to watch. We made due for 2 nights. "
United States
Wendy C.
$128 nightly
The price is $150
Nov 17 - Nov 18
Total with taxes and fees
Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

Sojourn's Harborage S

2.0 star property
East Ocean View
9.2 out of 10, Wonderful, (5)
"Our only problem with property was it was upstairs. I don't remember that being in the listing"
United States
Martha P.
$304 nightly
The price is $322
Nov 16 - Nov 17
Total with taxes and fees
Sojourn's Harborage S

Sojourn's Harborage Pelican Suite Near

2.0 star property
East Ocean View
10.0 out of 10, Exceptional, (1)
"The Sojourn team was very accommodating, proactive, and responsive in all our communications. They did a wonderful job."
United States
Bryce R.
$308 nightly
The price is $326
Nov 23 - Nov 24
Total with taxes and fees
Sojourn's Harborage Pelican Suite Near

Sojourn 1 BR Beach Home with Private Beach Access

Cottage Park
8.2 out of 10, Very Good, (20)
"Very clean and very nice, really nice kitchen and bath. Smallish bedroom but clean and comfortable, parking was tight. A few minutes walk to a beautiful beach. We would definitely come back! "
United States
Marla G.
$264 nightly
The price is $284
Nov 17 - Nov 18
Total with taxes and fees
Sojourn 1 BR Beach Home with Private Beach Access
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

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.

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 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 38 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.