Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1151)
"We love staying here everyone is very helpful and it’s right in the middle of the boardwalk "
The price is NZ$366
includes taxes & fees
20 Oct - 21 Oct
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1434)
"The hotel and staff were excellent. Even housekeeping were friendly and professional. I love this hotel. I come every year with my family. "
The price is NZ$288
includes taxes & fees
28 Oct - 29 Oct
The Ocean Key Virginia Beach Resort

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1470)
"My stay at the atrium was well, very nice staff and helpful with all my needs. "
The price is NZ$263
includes taxes & fees
12 Oct - 13 Oct
The Atrium Resort, Virginia Beach by Vacatia

Four Sails Resort

4.0 star property
7.6 out of 10, Good, (43)
"It was peaceful"
The price is NZ$277
includes taxes & fees
5 Oct - 6 Oct
Four Sails Resort

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (224)
"Central location to boardwalk music venues. Friendly staff, clean, quiet. "
The price is NZ$170
includes taxes & fees
28 Sept - 29 Sept
Angie's Guest Cottage

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (46)
"Nice cozy place to go with your family "
The price is NZ$237
includes taxes & fees
30 Sept - 1 Oct
stayAPT Suites Suffolk-Chesapeake

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

9.8 out of 10, Exceptional, (107)
"We really enjoyed the area, the property, & the ease of communication with the host. Would highly recommend! "
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

9.8 out of 10, Exceptional, (182)
"This house was perfect for my family. The location was beautiful "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

9.6 out of 10, Exceptional, (63)
"Beautiful home!!! Very well kept and clean. The location was everything you can dream of! Wild horses seen daily, gorgeous beach, great pool!!! Thank you for sharing your home with us!"
Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom

Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

9.6 out of 10, Exceptional, (123)
"We stayed at Lightly Salted last week; my family of five [2 adults, 3 kids (11, 5, 1)]and out close friends family of three [2 adults, 1 kid (3)]. "
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach

Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

10.0 out of 10, Exceptional, (81)
"Great place to stay with family. Was very clean and well kept. We didn't have much sunshine, but we had a great stay! Host was great and house was like advertised."
Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

8.4 out of 10, Very good, (21)
"I visited the Outer Banks with my daughters and honestly the stay was amazing, the views, house, location this place had it all. "
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.

Oceanfront House on the beach at Croatan

8.0 out of 10, Very good, (117)
"Wonderful location with uncrowded beach! House is large enough to meet the needs of multiple families with plenty of space to hang out too! Host responds quickly to solve problems. Many parts of the house are beautiful and others need some cosmetic updates, but it was perfect for us!"
Oceanfront House on the beach at Croatan

10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

9.4 out of 10, Exceptional, (104)
"We had 18 people ranging in age 7-68 years old staying and you could not tell. The house was so big and was able to accommodate everyone. Less than 5 min walk to the beach and 5 min drive to amusement/ water park. The host was great communicating and answering questions. Oh I forgot to mention one elevator!!!!"
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

9.8 out of 10, Exceptional, (50)
"The house was what we needed for our family. Even though on busy street, great location with easy beach access and great pool. House had everything we needed."
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

Loft Space Minutes from Beach

5.2 out of 10, (5)
"Location was good in terms of what we needed and property provided all necessary household things you would need to clean the place. However, owner was not and still is not responsive. Refrigerator did not work. A/C did not work. Lock on door was loose. Backyard had massive camping trailer through it. Save your money."
Loft Space Minutes from Beach

OceanFront Row,Private Pool,New Hottub,Sleeps 16,PetFriendly,Beachfront&Updates!

9.4 out of 10, Exceptional, (34)
"The ocean views from this house are breathtaking. Each morning began with sipping coffee and overlooking the ocean view complete with dolphin sightings daily. We had 3 families of 4 with us so it was nice that each bedroom came with its own bathroom. The kiddos LOVED the pool and hot tub. The adults loved walking the beach. The host was very friendly and answered my messages quickly. We had a wonderful vacation."
OceanFront Row,Private Pool,New Hottub,Sleeps 16,PetFriendly,Beachfront&Updates!

Cozy Room • Near Dam Neck Base & Beach Access

9.4 out of 10, Exceptional, (3)
"The room was cozy and despite other guests staying in the other rooms everything felt secure, quiet, and comfortable. "
The price is NZ$256
includes taxes & fees
6 Oct - 7 Oct
Cozy Room • Near Dam Neck Base & Beach Access

Inviting oceanfront home with amazing views, private pool & deck

8.4 out of 10, Very good, (39)
"Property is in a great location. Ocean views and having the beach so close was nice. The kitchen is fully stocked they even have a crockpot, which wasn't in the listing but helped us feed a group of 17. The only thing missing was the ball for the foosball game. "
Inviting oceanfront home with amazing views, private pool & deck

Luxurious RV

8.6 out of 10, Excellent, (13)
"Upon arriving it was dark & I was having a hard time finding the residence. I gave the host a call & he was very friendly and helpful, was able to find it right after speaking with him. The RV is super cute, very relaxing view in the back."
The price is NZ$692
includes taxes & fees
28 Sept - 29 Sept
Luxurious RV
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

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$170 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.

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 Oak Grove Lake Park and Chesapeake City 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.