Chesapeake Vacation Rentals

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Find properties with these dates

Tonight
May 15 - May 16
Tomorrow
May 16 - May 17
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

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, (1077)
"The property staff was very nice and tentative to our needs during our stay. We had an issue with our room and they changed our room that was more suitable."
The price is $108
$178 total
includes taxes & fees
May 29 - May 30
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, (1269)
"View was immaculate. Room was accommodating. Some major amenities were not available during entire duration of stay (wi fi) and some ice machines. The ocean view made it worth the stay."
The price is $122
$199 total
includes taxes & fees
May 16 - May 17
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, (1122)
"The people at the front desk were very pleasant at each encounter with them. The room was nice except the bathtub/ shower needed some caulking "
The price is $115
$192 total
includes taxes & fees
May 16 - May 17
The Ocean Key Resort by VSA Resorts
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Beach Condo 2 Min Walk From The Beach
Beach
Beach Condo 2 Min Walk From The Beach
9.2 out of 10, Wonderful, (91)
"This condo was absolutely fabulous. It is literally 2 minute walk to the beach access. The rooms were comfortable and I've never stayed at a Vrbo with such an impressively stocked kitchen. The host responded quickly and answered all our questions. They were also very responsive. It was a lovely stay."
Beach Condo 2 Min Walk From The Beach
Beach Condo, Walk To The Beach
Beach | Beach nearby
Beach Condo, Walk To The Beach
9.4 out of 10, Exceptional, (40)
"The property owner felt like a longtime friend by the time our weekend was over. Super nice & welcoming. The place was perfect for what we needed. The shower was a little small but thats just bc we needed more. Its perfect for a small family stay. Thank you for allowing us to be there. You are awesome!"
Beach Condo, Walk To The Beach
The Art Door only minutes from beach
Property grounds
The Art Door only minutes from beach
9.8 out of 10, Exceptional, (36)
"This cute little apartment is the perfect getaway spot and pet friendly! It was super clean and smelled fantastic. The fenced in backyard is perfect to just sit out and enjoy the warm weather, and to be outside with your dog! The bathroom is a great size and beautiful! The bed was very comfortable and the linens and towels were great quality. The living room and kitchen was an added bonus, although we didn’t use it much. The host was very responsive and attentive to our needs, offering to adjust...
The price is $120
$258 total
includes taxes & fees
Jun 11 - Jun 12
The Art Door only minutes from 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, (39)
"Our family had a wonderful stay! We loved the remoteness of the house and the easy walk to the beach. The heated pool was perfect even though it was a chilly week. We can't wait to return!"
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)
"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
Cozy Suite at the Beach
On the beach, sun loungers
Cozy Suite at the Beach
8.4 out of 10, Very Good, (53)
"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 $149
$316 total
includes taxes & fees
May 16 - May 17
Cozy Suite at the Beach
Angie's Guest Cottage
Property entrance
Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, (177)
"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 $91
$117 total
includes taxes & fees
May 16 - May 17
Angie's Guest Cottage
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, (66)
"We love staying at the Oceans 2 Condos. This was our second time staying in this complex and love the pool and proximity to the boardwalk/beach. The studio was actually pretty spacious and allowed us to sit on the couch at night and still hear the waves crashing. It was a lovely getaway for our five year anniversary. We got to walk everywhere we wanted to go and the studio even has two bikes you could use to get around. I recommend this complex to anyone looking for a cozy getaway to the beach...
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
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, (204)
"This property was great. Perfect size and close to walk the boardwalk everyday. Loved it !"
The price is $275
$528 total
includes taxes & fees
Jun 9 - Jun 10
Great Location ! 1 Short Block To The Boardwalk.
Lovely 4-bedroom open concept home 8mins from oceanfront
Private kitchen
Lovely 4-bedroom open concept home 8mins from oceanfront
2.0 out of 10, (2)
"I am not sure where to begin. The water was shut off for non-payment and the host tried to say it was due to work. There were bugs. The dishwasher was full of dishes which may have been washed but were definitely not clean. The bathroom had used toothbrushes in a container on the counter. Someone had been on one of the beds prior to our check in. A pillow had blood on it. The couch had uses tissues under the pillows. I can go on! This property is completely misrepresented! If you are going to...
Lovely 4-bedroom open concept home 8mins from oceanfront
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)
"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."
The price is $179
$356 total
includes taxes & fees
May 16 - May 17
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
SPRING SPECIAL !!!Canal Front - Paddle Board
Smart TV, fireplace
SPRING SPECIAL !!!Canal Front - Paddle Board
9.8 out of 10, Exceptional, (30)
"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
9.0 out of 10, Wonderful, (226)
"This place was placed perfectly. Just across the street from a very nice peaceful beach access, as well as a large park for children and dogs. There was an exceptional farmers market on Saturday that had an immense variety of local product and food trucks. The hosts were very responsive and accommodating. My family and I stayed (Grandma 72 years old, aunts and cousins from 6years old to 37, and my mother 52 years old.) I would stay here again."
The price is $199
$396 total
includes taxes & fees
May 16 - May 17
Norfolk Beach Cottage Rental
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, (47)
"House was old (as described) and a bit shabby but very clean. Even a few minimal upgrades would improve it immensely. However the price was right and the location for that price was great! The fishing pier with the restaurant/bar at the end was a bonus. Beautiful beach to walk. The weather did not cooperate with us - we were a week too early but you can’t change the weather!"
The price is $159
$304 total
includes taxes & fees
May 16 - May 17
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Beach nearby
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
9.0 out of 10, Wonderful, (42)
"We have family in Norfolk! That would be a great rental in the summer months."
The price is $169
$317 total
includes taxes & fees
May 20 - May 21
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
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, (79)
"We are Senior Citizens that rent this property a couple times a year in the off season to visit our son and his family in Virginia Beach. The property is always clean and well kept. It is fully equipped with everything we need. All appliances and heating work well. The neighborhood is quiet and is only a 10 -15 minute drive to good restaurants on Shore Drive. We always enjoy our stay at this location near Fort Story."
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
Entire home on Bells Island in Currituck County NC
Outdoor dining
Entire home on Bells Island in Currituck County NC
10.0 out of 10, Exceptional, (3)
"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
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, (1002)
"This isn’t my first stay at this hotel. As always, the facility is clean, and the staff is very friendly. The spa tub is my favorite spot while the kids enjoy the indoor pool. We came here to celebrate Mother’s Day and a very happy momma I am!! Thank you!! "
The price is $127
$147 total
includes taxes & fees
May 16 - May 17
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, (807)
"Nice hotel, clean, very nice staff. Would stay again"
The price is $98
$114 total
includes taxes & fees
May 28 - May 29
Fairfield Inn and Suites By Marriott Chesapeake
Delta Hotels by Marriott Virginia Beach Waterfront
Seasonal outdoor pool
Delta Hotels by Marriott Virginia Beach Waterfront
4.0 star property
8.6 out of 10, Excellent, (964)
"Very clean and well put together "
The price is $159
$185 total
includes taxes & fees
May 19 - May 20
Delta Hotels by Marriott Virginia Beach Waterfront
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 $91 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 35 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 Naval Station Norfolk and Sandbridge 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

La Quinta Inn & Suites by Wyndham Virginia Beach

La Quinta Inn & Suites by Wyndham Virginia Beach

5/5 Excellent
"Pet friendly "
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Virginia Beach
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Virginia Beach