A golf course, a large building complex, and a marina by a river.

Chesapeake Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chesapeake vacation rentals

A living room with a sofa, armchair, glass coffee table, fireplace, and a television.

1. Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
10.0 out of 10, Exceptional, (1 review)
"Very clean and had all the essentials. Great location near a a beautiful lake"
United States
Erin K.
$391 nightly
The price is $437
Oct 19 - Oct 20
Total with taxes and fees
Nyakio Suite - Chesapeake
A living room with a sofa, armchair, coffee table, and fireplace.

2. Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
$475 nightly
The price is $548
Oct 21 - Oct 22
Total with taxes and fees
Nyakio Suite
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

3. Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
$147 nightly
The price is $169
Nov 1 - Nov 2
Total with taxes and fees
Great Studio | Pool & Hot Tub. Your Next Vacation
A spacious living area with a kitchen island, a fireplace, and a staircase leading to an upper level.

4. Hike, Beach & Explore! Family Home in Chesapeake

Hike, Beach & Explore! Family Home in Chesapeake
2.0 star property
Chesapeake
$542 nightly
The price is $625
Oct 18 - Oct 19
Total with taxes and fees
Hike, Beach & Explore! Family Home in Chesapeake
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

5. King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
$163 nightly
The price is $188
Nov 15 - Nov 16
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

6. 3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
$256 nightly
The price is $296
Oct 21 - Oct 22
Total with taxes and fees
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A two-story house with a front porch, a garage, and a well-maintained lawn.

7. Hike, Beach & Explore! Family Home in Chesapeake

Hike, Beach & Explore! Family Home in Chesapeake
Chesapeake
$528 nightly
The price is $609
Oct 18 - Oct 19
Total with taxes and fees
Hike, Beach & Explore! Family Home in Chesapeake
A living room with a brown sofa, a matching armchair, a wooden coffee table, a TV on a wooden stand, and two lamps.

8. Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
Chesapeake
9.4 out of 10, Exceptional, (8 reviews)
"The condo is nice, clean and very roomy. We love the stay and very convenient. The hotel provides breakfast it’s great!!"
United States
Linh T.
$306 nightly
The price is $351
Nov 15 - Nov 16
Total with taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

9. King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
$162 nightly
The price is $187
Nov 15 - Nov 16
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

10. Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Chesapeake
8.0 out of 10, Very good, (5 reviews)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
$179 nightly
The price is $206
Nov 15 - Nov 16
Total with taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

11. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
$266 nightly
The price is $306
Oct 24 - Oct 25
Total with taxes and fees
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
A modern courtyard with white furniture, a central seating area, and a small lawn.

12. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (111 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
$119 nightly
The price is $137
Oct 19 - Oct 20
Total with taxes and fees
stayAPT Suites Suffolk-Chesapeake
An outdoor seating area with wicker furniture and orange Adirondack chairs.

13. Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,442 reviews)
"Great stay"
United States
Nancy
$190 nightly
The price is $221
Nov 16 - Nov 17
Total with taxes and fees
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

14. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.4 out of 10, Exceptional, (29 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
$96 nightly
The price is $113
Nov 17 - Nov 18
Total with taxes and fees
stayAPT Suites Hampton
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

15. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
$536 nightly
The price is $619
Nov 5 - Nov 6
Total with taxes and fees
Centrally Located Hampton Roads Home w/ Game Room!
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

16. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.8 out of 10, Excellent, (13 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
$207 nightly
The price is $240
Oct 18 - Oct 19
Total with taxes and fees
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A living room with a sectional sofa, a round ottoman, a globe on a shelf, and artwork on the walls.

17. Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
Portsmouth
9.2 out of 10, Wonderful, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
$301 nightly
The price is $349
Oct 18 - Oct 19
Total with taxes and fees
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

18. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
$226 nightly
The price is $263
Oct 20 - Oct 21
Total with taxes and fees
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A narrow brick pathway flanked by two houses with siding.

19. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (16 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
$162 nightly
The price is $189
Oct 21 - Oct 22
Total with taxes and fees
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

20. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
$576 nightly
The price is $665
Oct 18 - Oct 19
Total with taxes and fees
Wooded Wonderland
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

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"Perfect"
Thu Ha 2-night trip
Posted 4 hours ago
Hyatt Place Virginia Beach / Oceanfront

Find out more about Chesapeake

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 $103 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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Broadmoor Play Area, 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?

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom: This vacation home rental outside of Chesapeake is located on the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals are there in Chesapeake?

Expedia has 36 vacation 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 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.