Chesapeake Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Chesapeake vacation rentals

Terrace/patio

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, (47 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is ￥27,495
￥49,965 total
includes taxes & fees
Jun 9 - Jun 10
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Pool

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 ￥36,932
￥48,531 total
includes taxes & fees
Jun 11 - Jun 12
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Living area

Central Chesapeake Stay Near Mall, Trails & parks

Central Chesapeake Stay Near Mall, Trails & parks
Greenbrier
Central Chesapeake Stay Near Mall, Trails & parks
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is ￥34,662
￥44,635 total
includes taxes & fees
Jun 30 - Jul 1
Studio | Free Breakfast. Indoor Pool & Hot Tub.
Pool

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 ￥33,148
￥43,444 total
includes taxes & fees
Jun 11 - Jun 12
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is ￥34,662
￥45,003 total
includes taxes & fees
Jun 23 - Jun 24
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is ￥35,326
￥46,500 total
includes taxes & fees
Jun 23 - Jun 24
Studio | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

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 ￥35,485
￥46,142 total
includes taxes & fees
Jun 7 - Jun 8
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool

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 ￥32,996
￥43,086 total
includes taxes & fees
Jun 18 - Jun 19
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

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 ￥32,851
￥43,297 total
includes taxes & fees
Jun 7 - Jun 8
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Terrace/patio

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (80 reviews)
"The stay was great. We loved walking around the neighborhood at sunset to see the view over the water. We would definitely stay here again. "
United States
Maddi S.
The price is ￥31,930
￥64,115 total
includes taxes & fees
Jun 4 - Jun 5
Comfortable Beach Trailer Home
Dining

Luxurious RV

Luxurious RV
Sandbridge
8.4 out of 10, Very Good, (18 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is ￥31,930
￥63,371 total
includes taxes & fees
Jun 23 - Jun 24
Luxurious RV
House, Smoking | Private kitchen

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is ￥27,794
￥53,388 total
includes taxes & fees
Jun 8 - Jun 9
The Speakeasy Downtown Newport News
Outdoor dining

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 ￥21,736
￥44,129 total
includes taxes & fees
Jun 4 - Jun 5
Knot Three- Balcony View of ICW- Dog Friendly!
Smart TV, fireplace

Comfort near the water and University

Comfort near the water and University
Elizabeth city
8.0 out of 10, Very Good, (7 reviews)
"Everything was wonderful"
United States
Marc
The price is ￥13,596
￥47,536 total
includes taxes & fees
Jun 8 - Jun 9
Comfort near the water and University
Smart TV, DVD player

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.6 out of 10, Exceptional, (21 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is ￥18,679
￥53,722 total
includes taxes & fees
Jun 4 - Jun 5
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Dining

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 ￥12,788
￥41,990 total
includes taxes & fees
Jun 16 - Jun 17
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Shower, bidet

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (4 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
The price is ￥12,932
￥29,671 total
includes taxes & fees
Jun 4 - Jun 5
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (82 reviews)
"Very clean and modern room at a very reasonable price. We will definitely stay there again if we are in that area."
United States
Scott
The price is ￥18,998
￥21,817 total
includes taxes & fees
Jun 18 - Jun 19
stayAPT Suites Suffolk-Chesapeake
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Hotel Reviews

YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

10/10 Excellent
"Very nice, new hotel. Staff was extremely friendly and helpful. Snack shop in the lobby was incredibly well stocked and complimentary coffee always available was great. We really loved the small fenced dog run on the property. Restaurants and shopping really nearby. 100% recommend."
Tara 3-night trip
Posted 3 hours ago
YourSpace Hotels Chesapeake

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake
  • Use the map to find apartments and other holiday homes in the Chesapeake neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Chesapeake Arboretum, 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?

Ultimate Vacation Home: This highly rated vacation home rental in Chesapeake is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. 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.

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 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.