Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

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

2.0 star property
Chesapeake
The price is NZ$568
includes taxes & fees
15 Nov - 16 Nov
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.
The price is NZ$390
includes taxes & fees
25 Nov - 26 Nov
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Studio | Free Breakfast. Indoor Pool & Hot Tub

Chesapeake
Studio | 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.
The price is NZ$323
includes taxes & fees
30 Nov - 1 Dec
Great Studio | Pool & Hot Tub. Your Next Vacation

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

Chesapeake
The price is NZ$320
includes taxes & fees
23 Nov - 24 Nov
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
The price is NZ$322
includes taxes & fees
23 Nov - 24 Nov
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Chesapeake
The price is NZ$301
includes taxes & fees
30 Nov - 1 Dec
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

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.
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.
The price is NZ$710
includes taxes & fees
21 Nov - 22 Nov
Luxurious RV

OV Mosaic - Topaz Suite

East Ocean View
10.0 out of 10, Exceptional, (2)
"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.
The price is NZ$472
includes taxes & fees
16 Nov - 17 Nov
OV Mosaic - Topaz Suite

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.
The price is NZ$578
includes taxes & fees
23 Nov - 24 Nov
Sojourn's Harborage Coral Suite

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
The price is NZ$442
includes taxes & fees
16 Nov - 17 Nov
Ice Ice Baby Downtown Newport News

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.
The price is NZ$485
includes taxes & fees
24 Nov - 25 Nov
Cabin in the Woods, Pet Friendly

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.
The price is NZ$266
includes taxes & fees
24 Nov - 25 Nov
Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

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.
The price is NZ$578
includes taxes & fees
13 Nov - 14 Nov
Comfortable & Private 2 Bedrm Cottage w/ King bed.

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.
Sojourn's Harborage S

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.
The price is NZ$396
includes taxes & fees
13 Nov - 14 Nov
Knot Three- Balcony View of ICW- Dog Friendly!

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

Portsmouth
9.6 out of 10, Exceptional, (4)
"Great little home away from home. Came to visit my granddaughter that's in the Navy. Nice place to just sit and play games and visit. Couldn't get in at first but the owners answered the phone and took care of it right away. Would definitely stay here again!"
United States
Anonymous traveller
The price is NZ$465
includes taxes & fees
24 Nov - 25 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

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.
The price is NZ$569
includes taxes & fees
13 Nov - 14 Nov
Sojourn's Harborage Pelican Suite Near
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 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$182 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?

The Art Door only minutes from beach: This holiday home rental outside of Chesapeake comes with air conditioning so that you can feel at home during your trip.

How many holiday rentals are there in Chesapeake?

Expedia has 38 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.