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Top Holiday Rentals in Chesapeake

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1454)
"Clean, spacious, short walk to beach, nice staff, I will be back definitely "
The price is £121
includes taxes & fees
1 Oct - 2 Oct
The Atrium Resort, Virginia Beach by Vacatia

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1423)
"10/10 staying here again "
The price is £137
includes taxes & fees
1 Oct - 2 Oct
The Ocean Key Virginia Beach Resort

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1129)
"My family truly enjoyed our stay! Would definitely stay here again. "
The price is £156
includes taxes & fees
1 Oct - 2 Oct
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (221)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
The price is £72
includes taxes & fees
14 Sept - 15 Sept
Angie's Guest Cottage

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (42)
"Parking was tiny but can be navigated carefully "
The price is £146
includes taxes & fees
15 Sept - 16 Sept
Four Sails Resort

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.6 out of 10, Exceptional, (41)
"Nice cozy place to go with your family "
The price is £99
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, (105)
"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.

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

9.8 out of 10, Exceptional, (180)
"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)
"It was a great place to stay!!! We had a great time."
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, (121)
"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

Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

10.0 out of 10, Exceptional, (152)
"We had a week long trip together at a wonderful spot that allowed a group of 10 ranging in age from 3 1/2 to 62 plenty of room to get together and still have space to separate when some quiet time was needed."
Last minute stays available! Great deals! Ocean views 8bdrm, 6bath pool!

Oceanfront House on the beach at Croatan

8.0 out of 10, Very good, (113)
"We loved being able to access the beach so easily. There are windows and deck seating that need to be replaced, and we were surprised that we had to rent our own linens, but our siblings and families enjoyed the open layout and functional kitchen. "
Oceanfront House on the beach at Croatan

Luxurious RV

8.4 out of 10, Very good, (11)
"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 £303
includes taxes & fees
3 Sept - 4 Sept
Luxurious RV

OceanFront Row,on Beach,PrivatePool,Hottub,Sleeps 16,Pet Friendly, Plus Updates!

9.4 out of 10, Exceptional, (33)
"This house was perfect for our family vacation. We loved that we had a pool and a hot tub with the beach right there. It gave our big group many options for entertainment. We enjoyed our week and the host was very responsive and helpful. "
OceanFront Row,on Beach,PrivatePool,Hottub,Sleeps 16,Pet Friendly, Plus Updates!

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.

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

9.4 out of 10, Exceptional, (103)
"Lots of space and the third floor is a great place to hang out with a big group. Ocean is a quick walk away. But lots of things that we were expecting to be functional did not work. Upon arrival we were sent a message documenting a list of things that were broken, which was disappointing. The hot tub also turned out to be out of order. Still a good stay for a big group, but some love needs to be put into the house. "
10Bd/10Ba Large Beach Home, Indoor Pool In Virginia Beach

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

10.0 out of 10, Exceptional, (80)
"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

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

9.8 out of 10, Exceptional, (50)
"this was such a beautiful home. everything was updated and very pretty and homey. tons of room for our large family with extra room with the pool house. easy walking distance to the beach and local market. loved the kitchen with the large table for the whole family with the high chair included. kitchen was well stocked with everything you would need. loved the extra fridge for more space. Beds were super comfortable and everyone had their own bathroom ensuite. would highly recommend this...
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony

The Art Door only minutes from beach

9.8 out of 10, Exceptional, (89)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The price is £173
includes taxes & fees
3 Sept - 4 Sept
The Art Door only minutes from 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
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, apart-hotels, 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 £72 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?

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 37 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.