Chesapeake Vacation Rentals

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Our top choices for Chesapeake vacation rentals

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is CA $203
CA $265 total
includes taxes & fees
Apr 26 - Apr 27
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

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, (46 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is CA $240
CA $443 total
includes taxes & fees
May 6 - May 7
3-bedroom home away from home in fabulous Chesapeake, Virginia.

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 $216
CA $281 total
includes taxes & fees
Apr 26 - Apr 27
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

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 $181
CA $239 total
includes taxes & fees
Apr 26 - Apr 27
Great Studio | Pool & Hot Tub. Your Next Vacation

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is CA $181
CA $239 total
includes taxes & fees
Apr 26 - Apr 27
Studio | 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 $231
CA $302 total
includes taxes & fees
May 10 - May 11
Studio | Free Breakfast. Indoor Pool & Hot Tub

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 $252
CA $329 total
includes taxes & fees
May 10 - May 11
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

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 $227
CA $295 total
includes taxes & fees
May 10 - May 11
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

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)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
The price is CA $242
CA $314 total
includes taxes & fees
Apr 26 - Apr 27
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Your Tropical Oasis awaits in Hampton Roads Virginia

Your Tropical Oasis awaits in Hampton Roads Virginia
Portsmouth
The price is CA $273
CA $452 total
includes taxes & fees
Apr 28 - Apr 29
Your Tropical Oasis awaits in Hampton Roads Virginia

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 $273
CA $543 total
includes taxes & fees
Apr 25 - Apr 26
Luxurious RV

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.4 out of 10, Exceptional, (19 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is CA $136
CA $431 total
includes taxes & fees
Apr 26 - Apr 27
Comfortable & Private 2 Bedrm Cottage w/ King bed.

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is CA $156
CA $370 total
includes taxes & fees
Apr 26 - Apr 27
The Speakeasy Downtown Newport News

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, (111 reviews)
"Many restaurants and shopping nearby. Excellent place to stay."
United States
Daniel A.
The price is CA $137
CA $317 total
includes taxes & fees
Apr 28 - Apr 29
The Art Door Duplex only minutes from beach

Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is CA $132
CA $533 total
includes taxes & fees
Apr 28 - Apr 29
Sojourn | Coastal Cottage | 3 BR

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

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (4 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is CA $110
CA $363 total
includes taxes & fees
Apr 25 - Apr 26
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (283 reviews)
"Great location. Very close to the beach and a park. Great place for families. Large dining table worked great for us for Thanksgiving. "
United States
Cody H.
The price is CA $227
CA $555 total
includes taxes & fees
Apr 28 - Apr 29
Norfolk Beach Cottage Rental

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
Apr 28 - Apr 29
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (46 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is CA $178
CA $463 total
includes taxes & fees
Apr 28 - Apr 29
Cozy Beach Home in Oceanview

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

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (26 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is CA $137
CA $396 total
includes taxes & fees
Apr 26 - Apr 27
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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?

Octopus Oasis, HORSES/ Sea Turtles 4x4 a must Pets OK. Jacuzzi. Carova Beach: This vacation home rental outside of Chesapeake is located near the beach and has a patio, a hot tub, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chesapeake?

Expedia has 42 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 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 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.