Chesapeake Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Chesapeake

The Atrium Resort by VSA Resorts
Interior
The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very Good, 1,120 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 $144
$219 total
includes taxes & fees
Jun 17 - Jun 18
The Atrium Resort by VSA Resorts
The Ocean Sands Resort by VSA Resorts
Exterior
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very Good, 1,304 reviews
"the hotel is well located, close to everything."
The price is $199
$288 total
includes taxes & fees
Jun 17 - Jun 18
The Ocean Sands Resort by VSA Resorts
The Ocean Key Resort by VSA Resorts
Indoor pool
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 $225
$318 total
includes taxes & fees
Jun 17 - Jun 18
The Ocean Key Resort by VSA Resorts
Beach Condo, Walk To The Beach
Beach | Beach nearby
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
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
Property entrance
Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, 182 reviews
"One block from the ocean. I'm always happy with my stay here. Helpful staff and very accommodating. I look forward to next time!"
The price is $114
$143 total
includes taxes & fees
Jun 17 - Jun 18
Angie's Guest Cottage
The Art Door only minutes from beach
Property grounds
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 $149
$296 total
includes taxes & fees
Jun 17 - Jun 18
The Art Door only minutes from beach
Cozy Suite at the Beach
On the beach, sun loungers
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 $179
$354 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Suite at the Beach
Charming Carova Cottage on 4x4 beach, Heated Pool, Hot Tub, Close Beach Access
Outdoor pool, a heated pool
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
Fridge, microwave, oven, stovetop
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.
Beach nearby, sun loungers
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
On the beach, sun loungers, beach towels
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
Smart TV, fireplace
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
Norfolk Beach Cottage Rental
Sun loungers, beach towels
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 $199
$393 total
includes taxes & fees
Jun 30 - Jul 1
Norfolk Beach Cottage Rental
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Beach | On the beach, sun loungers
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
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Beach nearby, sun loungers
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 $299
$486 total
includes taxes & fees
Jun 18 - Jun 19
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Norfolk Oasis
3 bedrooms, desk, iron/ironing board, travel crib
Norfolk Oasis
9.2 out of 10, Wonderful, 11 reviews
"From the moment we walked in the door we were immediately greeted with the smell of freshly cleaned floors, linens, and counter tops. I was very impressed by the customer service of our hosts and the speed at which they responded to any of our questions. They were very kind and respectful as well. We were visiting from NY, and the house was pleasantly bigger than what we expected. They provided clean linens and basically everything we needed for the weekend. Will definitely recommend and stay...
Norfolk Oasis
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
Terrace/patio
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
Fridge, microwave, oven, stovetop
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
Property grounds
Skyview by the Sea
10.0 out of 10, Exceptional, 3 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
Don't see what you're looking for?
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
Lobby lounge
Wingate by Wyndham Chesapeake
2.5 star property
8.0 out of 10, Very Good, 1,003 reviews
"Great customer service "
The price is $169
$196 total
includes taxes & fees
Jun 17 - Jun 18
Wingate by Wyndham Chesapeake
Fairfield Inn and Suites By Marriott Chesapeake
Room, 1 King Bed | Desk, laptop workspace, blackout drapes, iron/ironing board
Fairfield Inn and Suites By Marriott Chesapeake
2.5 star property
8.8 out of 10, Excellent, 835 reviews
"I like the cleanliness of the hotel easy access to the hotel and the breakfast was really good and the breakfast was really good. Had to say that a second time because it was I enjoyed my stay."
The price is $125
$145 total
includes taxes & fees
Jun 30 - Jul 1
Fairfield Inn and Suites By Marriott Chesapeake
Schooner Inn
Superior Room, 1 King Bed, Ocean View, Oceanfront | Living area | TV
Schooner Inn
2.0 star property
8.8 out of 10, Excellent, 2,446 reviews
"Quiet and calm location"
The price is $170
$197 total
includes taxes & fees
Jul 8 - Jul 9
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesapeake vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesapeake in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $114 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake vacation 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 vacation.

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 vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Jillian's Billiards, or you can go with a more remote 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 vacation home rentals in Chesapeake?

The Atrium Resort by VSA Resorts: This vacation home rental outside of Chesapeake is located by the ocean and has an indoor pool, an arcade game 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 vacation rentals are there in Chesapeake?

Expedia has 33 vacation 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 like Virginia Beach Town Center and Veterans United Home Loans Amphitheater at Virginia Beach.

What’s a vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.

Recent reviews of Chesapeake properties
Expedia verified reviews

Schooner Inn

Schooner Inn

5/5 Excellent
"Quiet and calm location"
A verified traveler stayed at Schooner Inn
Posted 23 hours ago
Schooner Inn