Chesapeake Vacation Rentals

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Vacation Rentals in Chesapeake

Interior
The Atrium Resort by VSA Resorts
3.5 star property
8.2 out of 10, Very Good, (1092)
"It was a great environment. Not too far off the beach and awesome polite staff. Only downfall is 1 elevator"
The price is $122
$194 total
includes taxes & fees
Jun 2 - Jun 3
The Atrium Resort by VSA Resorts
Exterior
The Ocean Sands Resort by VSA Resorts
3.0 star property
8.0 out of 10, Very Good, (1286)
"Property staff are excellent! Close to (walkable) to several restaurants, shops, attractions, etc. "
The price is $191
$279 total
includes taxes & fees
Jun 12 - Jun 13
The Ocean Sands Resort by VSA Resorts
Indoor pool
The Ocean Key Resort by VSA Resorts
3.0 star property
7.6 out of 10, Good, (1134)
"It was a good experience "
The price is $169
$254 total
includes taxes & fees
May 30 - May 31
The Ocean Key Resort by VSA Resorts
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Beach
Beach Condo 2 Min Walk From The Beach
9.2 out of 10, Wonderful, (92)
"2min walk was th best! The house was fun!! Sunrise and sunset on th beach was incredible! Would definitely recommend and go again to this same place!"
Beach Condo 2 Min Walk From 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
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 17 - Jun 18
The Art Door only minutes from beach
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
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 $79
$224 total
includes taxes & fees
May 30 - May 31
Cozy Suite at the Beach
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
On the beach, sun loungers, beach towels
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
10.0 out of 10, Exceptional, (68)
"Stayed 6 nights. Very quaint and cozy studio. Located in a nice location. Sitting on the lawn in the morning having coffee and watching the dolphins was perfect. Any questions we had was answered immediately.. The building is older as someone mentioned but well maintained. Pool was cleaned every morning. Hope to return someday"
The price is $212
$384 total
includes taxes & fees
Jun 22 - Jun 23
Virginia Beach Oceanfront Studio, Lawn, Boardwalk, Pool, Beach
Property entrance
Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, (178)
"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 $89
$114 total
includes taxes & fees
May 30 - May 31
Angie's Guest Cottage
Private kitchen
Lovely 4-bedroom open concept home 8mins from oceanfront
2.6 out of 10, (4)
"Full size bed bedroom no box spring support- just a mattress on springs.. when layed on, it is not level- Also, the floor board connecting the carpet and flooring broken in half. Needs to be repaired. Ceiling fan moves but has a loud noise that sounds like sharpening knives sound! Ceiling wired smoke detector is missing only wires hanging out of ceiling. Thermostat did not adjust. Could not adjust the temperature in the house because thermostat was not working. Carey replied and said he could...
Lovely 4-bedroom open concept home 8mins from oceanfront
Beach nearby, sun loungers
Great Location ! 1 Short Block To The Boardwalk.
9.6 out of 10, Exceptional, (206)
"Location excellent.Walking distance convenient. Quiet complex. Only drawback is narrow parking lot."
The price is $275
$528 total
includes taxes & fees
Jun 9 - Jun 10
Great Location ! 1 Short Block To The Boardwalk.
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
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."
Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR 1.5 Bath
Sun loungers, beach towels
Norfolk Beach Cottage Rental
9.0 out of 10, Wonderful, (229)
"two downstairs bedrooms and one upstairs made the accommodations great for us. Easy access to the beach, grocery store, and restaurants was very convenient. Host was very helpful and responsive. Thank you!"
The price is $199
$396 total
includes taxes & fees
May 30 - May 31
Norfolk Beach Cottage Rental
Beach nearby, sun loungers
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
9.0 out of 10, Wonderful, (48)
"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 $199
$357 total
includes taxes & fees
May 30 - May 31
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Terrace/patio
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
9.6 out of 10, Exceptional, (81)
"Perfect spot and great access to the beach. I plan on booking here again."
Cozy Ocean-Side Cottage @ Peaceful North End of Virginia Beach
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
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 $229
$396 total
includes taxes & fees
May 31 - Jun 1
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
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

Suite, 1 King Bed with Sofa bed | Individually decorated, individually furnished, desk, laptop workspace
Comfort Suites Chesapeake - Norfolk
2.5 star property
8.2 out of 10, Very Good, (1002)
"The only thing I would mention, I’m sorry to say, negatively, is the does to the rooms were very heard to close. You had to pull with all your might until it slammed shut. At any part of the day, who cares? At 6am you hear people trying to shut their doors. All the slamming. Other than that, everything, including breakfast was great. "
The price is $118
$137 total
includes taxes & fees
Jun 5 - Jun 6
Comfort Suites Chesapeake - Norfolk
Lobby lounge
Wingate by Wyndham Chesapeake
2.5 star property
8.0 out of 10, Very Good, (1000)
"Zakir is the best. Polite, friendly, helpful, and accommodating. "
The price is $143
$166 total
includes taxes & fees
May 30 - May 31
Wingate by Wyndham 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, (814)
"the staff was very helpful, checking in and out was simple, the hotel was keep very clean, would go back "
The price is $125
$145 total
includes taxes & fees
Jun 9 - Jun 10
Fairfield Inn and Suites By Marriott 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.

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 $79 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 Chesapeake City 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

Schooner Inn

Schooner Inn

5/5 Excellent
"Great property for taking your family to the beach. "
A verified traveler stayed at Schooner Inn
Posted 8 hours ago
Schooner Inn