Chesapeake Holiday Rentals

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Check prices for these dates

Our top choices for Chesapeake holiday rentals

1. 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 NZ$271
includes taxes & fees
29 Nov - 30 Nov
Great Studio | Pool & Hot Tub. Your Next Vacation

2. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
The price is NZ$1,173
includes taxes & fees
29 Nov - 30 Nov
Entire Home in Chesapeake, Virginia

3. 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 NZ$296
includes taxes & fees
29 Nov - 30 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

4. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is NZ$1,090
includes taxes & fees
29 Nov - 30 Nov
Entire Home in Chesapeake, Virginia

5. 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, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is NZ$495
includes taxes & fees
16 Nov - 17 Nov
3-bedroom home away from home in fabulous Chesapeake, Virginia.

6. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is NZ$442
includes taxes & fees
27 Nov - 28 Nov
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

7. 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 NZ$320
includes taxes & fees
29 Nov - 30 Nov
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

8. 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 NZ$296
includes taxes & fees
29 Nov - 30 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

9. 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
7.8 out of 10, Good, (7 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
The price is NZ$320
includes taxes & fees
29 Nov - 30 Nov
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

10. Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is NZ$271
includes taxes & fees
29 Nov - 30 Nov
Studio | Free Breakfast. Indoor Pool & Hot Tub.

11. Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Chesapeake
9.4 out of 10, Exceptional, (8 reviews)
"The condo is nice, clean and very roomy. We love the stay and very convenient. The hotel provides breakfast it’s great!!"
United States
Linh T.
The price is NZ$626
includes taxes & fees
29 Nov - 30 Nov
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

12. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (119 reviews)
"Room was clean, very nice and quiet property. Loved staying here and will recommend anyone who visits the area"
United States
olivia
The price is NZ$247
includes taxes & fees
23 Nov - 24 Nov
stayAPT Suites Suffolk-Chesapeake

13. 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
9.4 out of 10, Exceptional, (10 reviews)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
The price is NZ$455
includes taxes & fees
20 Nov - 21 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

14. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (21 reviews)
"As described, clean, comfortable, and convenient! Will look to stay here again next time in the area."
United States
Mark D.
The price is NZ$311
includes taxes & fees
16 Nov - 17 Nov
Private 1 Bed Apt - Historic Olde Towne Portsmouth

15. Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
Portsmouth
9.2 out of 10, Wonderful, (29 reviews)
"We really enjoyed our stay! The house was cozy and the perfect size for the three of us. While we didn't do any cooking, the kitchen appeared to have everything you would need. The shower had great hot water, which was nice after a long day. The neighborhood was quiet and peaceful, and there were several good restaurants nearby, making it easy to grab a meal. We'd definitely stay here again!"
United States
Allan S.
The price is NZ$617
includes taxes & fees
16 Nov - 17 Nov
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

16. 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, (33 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 NZ$492
includes taxes & fees
30 Nov - 1 Dec
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

17. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (42 reviews)
"Great stay! Will be staying again!"
United States
Wakeelah
The price is NZ$239
includes taxes & fees
16 Nov - 17 Nov
stayAPT Suites Hampton

18. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (7 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
The price is NZ$521
includes taxes & fees
16 Nov - 17 Nov
Guesthouse in ideal location with private entrance

19. The SEA-renity 11 cozy apartment across from the beach

The SEA-renity 11 cozy apartment across from the beach
Cottage Line
The price is NZ$180
includes taxes & fees
7 Dec - 8 Dec
The SEA-renity 11 cozy apartment across from the beach

20. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.8 out of 10, Excellent, (13 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
The price is NZ$426
includes taxes & fees
1 Dec - 2 Dec
Charming 1-bedroom in-law suite with functional kitchen in pleasant 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.

Find holiday rentals that suit your style

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as NZ$238 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday 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 holiday.

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 holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Broadmoor Play Area, or you can select a more secluded 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 holiday rentals that Chesapeake has to offer?

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with an arcade/games room and 1 hot tub.

How many holiday rentals are there in Chesapeake?

Expedia has 36 holiday 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 such as Naval Station Norfolk and Sandbridge Beach.

What’s a holiday rental in Chesapeake like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for small groups.