Holiday Rentals in Chesapeake

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Holiday Rentals in Chesapeake

The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very good, 1,118 reviews
"Our suit was perfect. The bed was very comfortable! The location was an extra bonus. Staff were very helpful when our jey card wouldnt work."
The price is €205
includes taxes & fees
19 Jun - 20 Jun
The Atrium Resort by VSA Resorts
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very good, 1,302 reviews
"the hotel is well located, close to everything."
The price is €248
includes taxes & fees
18 Jun - 19 Jun
The Ocean Sands Resort by VSA Resorts
The Ocean Key Resort by VSA Resorts
3.0 star property
7.6 out of 10, Good, 1,152 reviews
"Great customer service especially considering how booked and busy they were."
The price is €272
includes taxes & fees
16 Jun - 17 Jun
The Ocean Key Resort by VSA Resorts
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Beach Condo, Walk To The Beach
9.4 out of 10, Exceptional, 42 reviews
"Very clean and maintained property!! The appliances are all brand new and state of art!! My 4 legged son enjoyed his stay as well especially being so close to his beach walks!! Make sure you obey dog beach laws!! We will definitely stay here again!!"
Beach Condo, Walk To The Beach
Beach Condo 2 Min Walk From The Beach
9.2 out of 10, Wonderful, 93 reviews
"Very nice condo had no issues. It was clean, in an area that was quiet, close to the beach and perfect for a weekend getaway for my sons wrestling tournament. The property manager was also very nice and easy to deal with!! My only thing thats not really a complaint but i wish it wasn't so expensive to bring our dog. Maybe do a small fee for ppl and ask for a refundable deposit and if nothing is destroyed or no big mess give the deposit back. Ppl love to bring their fur babies. But im not mad bc...
Beach Condo 2 Min Walk From The Beach
Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, 182 reviews
"Honestly the only negative was the tiny parking space but it's beachfront cottage. having parking included at all was nice. Friendly clean and close to everything"
The price is €134
includes taxes & fees
17 Jun - 18 Jun
Angie's Guest Cottage
The Art Door only minutes from beach
9.8 out of 10, Exceptional, 41 reviews
"Convenient location and great to have a private yard. Listing is accurate and I enjoyed the stay!! Thank you!"
The price is €283
includes taxes & fees
17 Jun - 18 Jun
The Art Door only minutes from beach
Cozy Suite at the Beach
8.4 out of 10, Very good, 53 reviews
"We had a great stay at this property for 3 nights. It is a perfect fit for two adults and a dog and was right around the corner from the ocean. The bed and bathtub were absolutely wonderful! I appreciated the communication from owners and had an easy, peaceful weekend. Thanks!"
The price is €337
includes taxes & fees
17 Jun - 18 Jun
Cozy Suite at the Beach
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
10.0 out of 10, Exceptional, 41 reviews
"We had a great time at splash of a lime. It was our first time on the 4x4 beach and we will be back after staying here."
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
9.8 out of 10, Exceptional, 30 reviews
"The house itself was nice, clean although slightly in need of updates in the kitchen."
Trendy home steps from beach access w/private outdoor pool, gas grill, balcony
Great Location ! 1 Short Block To The Boardwalk.
9.6 out of 10, Exceptional, 209 reviews
"Absolutely beautiful and amazing! We had all the perfect amenities right at our fingertips. The location was perfect. It was our first time to Virginia Beach and our first time using VRBO. So easy and accommodating."
Great Location ! 1 Short Block To The Boardwalk.
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
10.0 out of 10, Exceptional, 68 reviews
"I cannot say enough about our stay here. From the initial contact to our checkout, it was the most accommodating, guest-friendly experience we could have asked for. Instructions were simple and had no trouble settling in. The place was clean, comfortable and had everything we needed. They even added special touches to celebrate my girlfriend’s birthday, which was the reason for our trip. Easy access to bicycles, the boardwalk, as well as our own private area to sit by the beach and enjoy the...
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
SPRING SPECIAL !!!Canal Front - Paddle Board
9.8 out of 10, Exceptional, 30 reviews
"We had a great week. Kevin was great and help us out when we needed it."
SPRING SPECIAL !!!Canal Front - Paddle Board
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
8.4 out of 10, Very good, 37 reviews
"The ceiling was low, bathroom sink was clogged. Bathroom floor needs work. Property was clean and beds were comfortable. Loved being at the beach. They have a different Property i stayed at on an earlier date that was great. Although we didnt care for the mentioned things, the process was easy and the owners were good to deal with."
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Norfolk Beach Cottage Rental
9.2 out of 10, Wonderful, 232 reviews
"The house was cozy and a very welcoming respite after seventeen hours on the road. Communication with management was pleasant and easy. Most of the events and activities that we attended were relatively close by. It was just the two of us, but there was plenty of room for a family with kids."
The price is €377
includes taxes & fees
30 Jun - 1 Jul
Norfolk Beach Cottage Rental
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
9.0 out of 10, Wonderful, 48 reviews
"My husband booked this stay for myself and a friend for my birthday. It was a nice getaway for us to enjoy and this spot was perfect for our weekend. Thank you!"
The price is €464
includes taxes & fees
18 Jun - 19 Jun
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
9.6 out of 10, Exceptional, 82 reviews
"Enjoyed our first trip to Virginia Beach. Cottage was well equipped (especially the beach closet) and the perfect size for our group! Location and proximity to the beach was exactly as described."
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
Recently Remodeled Northend Home Just Steps From Beach With Pool Table
9.6 out of 10, Exceptional, 129 reviews
"The house was just as advertised. Nice and clean and the location is great. It’s close to all the hot spots at the beach but in a nice residential area so less congested. The beach access is a short walk and the beach was clean and not too crowded."
Recently Remodeled Northend Home Just Steps From Beach With Pool Table
Skyview by the Sea
10.0 out of 10, Exceptional, 2 reviews
"Everything was perfect. The house was as described - we love it! Communication with host was great! I hope to stay there again."
Skyview by the Sea
Entire home on Bells Island in Currituck County NC
10.0 out of 10, Exceptional, 3 reviews
"Excellent option for my duck hunting crew. Lots of space, outstanding kitchen with everything you need."
Entire home on Bells Island in Currituck County NC
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See all available properties in Chesapeake
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.

Other types of properties in Chesapeake you may be interested in

Wingate by Wyndham Chesapeake
2.5 star property
8.0 out of 10, Very good, 1,002 reviews
"Great customer service "
The price is €182
includes taxes & fees
26 Jun - 27 Jun
Wingate by Wyndham Chesapeake
Fairfield Inn and Suites By Marriott Chesapeake
2.5 star property
8.8 out of 10, Excellent, 834 reviews
"The employees were kind, friendly, and helpful. Checking in and out was simple. The daily breakfast was delicious! I appreciated that there were always breakfast staples there but that the "main dish" switched up from day to day. My bed was super comfortable. There was plenty of parking. The lobby was easy to access from either side of the building. The hotel was conveniently located near restaurants, gas stations, our conference location, and roads taking us to and from Virginia Beach."
The price is €135
includes taxes & fees
17 Jun - 18 Jun
Fairfield Inn and Suites By Marriott Chesapeake
Schooner Inn
2.0 star property
8.8 out of 10, Excellent, 2,442 reviews
"Stayed on the top level and was it was spectacular. The view was georgous and a great location if you are one to enjoy the sunrise and a quiet start to the day. The front desk, they were so helpful and the parking there was easy. Would stay there again. I do wish they accepted animals but I also understand not all hotels are able to accommodate them. Great place/ Great location. 👍 "
The price is €164
includes taxes & fees
18 Jun - 19 Jun
Schooner Inn
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.

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 €134 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 Jillian's Billiards, 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 Atrium Resort by VSA Resorts: This holiday home rental outside of Chesapeake is located by the ocean, and has an indoor pool, an arcade/games room and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Chesapeake?

Expedia has 33 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Great Dismal Swamp National Wildlife Refuge and Oak Grove Lake Park are a couple of scenic spots to enjoy the outdoors, whereas Portlock Galleries at SoNo is one of the cultural attractions. While in the area, you can also visit popular places such as Virginia Beach Town Center and Veterans United Home Loans Amphitheater at Virginia 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.

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