Chesapeake Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Aug - 3 Aug
Tomorrow
3 Aug - 4 Aug
Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug

Holiday Rentals in Chesapeake

The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1418)
"My family has a really great time and stay"
The Atrium Resort, Virginia Beach by Vacatia
The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1408)
"Nice quiet hotel, very suitable for families with children. "
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1112)
"My family truly enjoyed our stay! Would definitely stay here again. "
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Angie's Guest Cottage
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (220)
"Very Cozy and near the beach, Staff is very courteous and friendly. "
The price is HK$622
HK$808 total
includes taxes & fees
1 Sept - 2 Sept
Angie's Guest Cottage
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (31)
"Great place to stay!"
The price is HK$934
HK$1,073 total
includes taxes & fees
1 Sept - 2 Sept
stayAPT Suites Suffolk-Chesapeake
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Smart TV, fireplace, video games, DVD player

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

9.8 out of 10, Exceptional, (176)
"Amazing house, great location! This house was perfect for our family vacation. The wild horses strolled by a few times and the owner was great on giving helpful tips on where to find the horses. Highly suggest this house if you want to have a once in a lifetime experience in the Outer Banks! "
FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi
Four Sails Resort
Indoor pool

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (37)
"Very nice place"
Four Sails Resort
Gorgeous 6BR house, Wild Horses, stunning views! Private parking. 4WD required.
Smart TV, video games, DVD player, video library

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

8.6 out of 10, Excellent, (19)
"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.
Loft Space Minutes from Beach
Exterior

Loft Space Minutes from Beach

5.4 out of 10, (3)
"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
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (102)
"Our family enjoyed the property rental at VA Beach. The owners responded "
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach
Nautical Dream, redecorated oceanfront home with incredible views and decks
On the beach

Nautical Dream, redecorated oceanfront home with incredible views and decks

10.0 out of 10, Exceptional, (12)
"Wonderful location, generous floor plan."
Nautical Dream, redecorated oceanfront home with incredible views and decks
Lightly Salted OBX, Beach front Luxury, Wild Horses, Pool, Hot Tub, 4x4 Beach
Smart TV, DVD player, books

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

9.6 out of 10, Exceptional, (119)
"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
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
Interior

Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home

9.4 out of 10, Exceptional, (22)
"As listed close to everything and made our stay very easy. Communication with owner was easy and all questions we had were answered."
The price is HK$2,473
HK$4,800 total
includes taxes & fees
7 Aug - 8 Aug
Lovely 2 bedroom condo walking distance to Beach Condominium - Entire home
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
On the beach, sun-loungers

Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub

9.8 out of 10, Exceptional, (139)
"The house was beautiful, clean and plenty of room for all our guest! The view was amazing! "
Newly Updated Beautiful 4BR Oceanfront Home with Pool & Hot Tub
Luxurious RV
Private kitchen

Luxurious RV

7.8 out of 10, Good, (8)
"Great location, the rv itself was ok, spacious, does the job for a beach weekend. a little overpriced for what you get. The pull out couches were not comfortable at all and there was not much provided. One roll of toilet paper, one trash bag. It would have been nice to have a sponge to wash dishes and some basic spices. Maybe a couple K cups for coffee. I would rent again."
The price is HK$1,570
HK$3,152 total
includes taxes & fees
4 Aug - 5 Aug
Luxurious RV
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse
Smart TV, fireplace, DVD player, books

OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse

9.8 out of 10, Exceptional, (46)
"Wonderful trip with an awesome house. Very quiet and the house is beautiful. Lots of room. Thank you so much."
OceanfrontOasis w/Breathtaking Views! Pool w/TikiBar.Hottub.Guesthouse
Glamping your way-close to beach in Virginia Beach with AC
1 bedroom

Glamping your way-close to beach in Virginia Beach with AC

Glamping your way-close to beach in Virginia Beach with AC
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
On the beach, beach towels

OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission

8.0 out of 10, Very good, (15)
"Loved the location and the avtivitoes/events in the neighborhood."
The price is HK$2,897
HK$4,638 total
includes taxes & fees
4 Aug - 5 Aug
OceanSands Oceanfront Free Bike & Chair Use Aquarium Admission
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Exterior

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

9.8 out of 10, Exceptional, (103)
"We stayed as a family for our spring break. House was clean, beds were comfortable, and location was great! The kids loved seeing wild horses right off the deck and we found more by driving around. We spent one day on the beach and that was a lot of fun. Weather was a bit chilly, but nothing we could control!"
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Charming Tiny Cottage
1 bedroom, WiFi, bed sheets

Charming Tiny Cottage

10.0 out of 10, Exceptional, (38)
"This place is very nice, very clean, modern, private. "
Charming Tiny Cottage
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.
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

Schooner Inn

Schooner Inn

10/10 Excellent
"This is not the fanciest hotel on the strip, but the location cannot be beat. It is at the very end of the boardwalk, so you can still walk to everything but also have a little more peace and quiet. Could use some upgrades, but the staff is friendly and my kids loved that the pool was 8’ deep at one end. Overall a very good value compared to the very pricey hotels nearby."
Jessica 4-night trip
Posted 13 hours ago
Schooner Inn

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?

FamilyMemoryMaker!,8 MASTERS,MovieRoom,OceanViews,Pool,HotTub,Grill,StarlinkWiFi: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Chesapeake?

Expedia has 35 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.