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

Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chesapeake vacation rentals

A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

1. 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.
$137 nightly
The price is $157
Oct 25 - Oct 26
Total with taxes and fees
Great Studio | Pool & Hot Tub. Your Next Vacation
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

2. 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
$146 nightly
The price is $168
Oct 25 - Oct 26
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
A living room with a sofa, armchair, coffee table, and fireplace.

3. Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
$521 nightly
The price is $601
Oct 4 - Oct 5
Total with taxes and fees
Nyakio Suite
A living room with a sofa, armchair, glass coffee table, fireplace, and a television.

4. Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
$403 nightly
The price is $449
Oct 4 - Oct 5
Total with taxes and fees
Nyakio Suite - Chesapeake
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

5. 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, (55 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
$249 nightly
The price is $289
Oct 5 - Oct 6
Total with taxes and fees
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

6. Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
10.0 out of 10, Exceptional, (1 review)
$136 nightly
The price is $156
Oct 25 - Oct 26
Total with taxes and fees
Studio | Free Breakfast. Indoor Pool & Hot Tub
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

7. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
$149 nightly
The price is $171
Oct 4 - Oct 5
Total with taxes and fees
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

8. Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
$136 nightly
The price is $156
Oct 25 - Oct 26
Total with taxes and fees
Studio | Free Breakfast. Indoor Pool & Hot Tub.
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

9. 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.
$146 nightly
The price is $168
Oct 25 - Oct 26
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
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.
$158 nightly
The price is $182
Oct 25 - Oct 26
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. 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.
$276 nightly
The price is $317
Oct 25 - Oct 26
Total with taxes and fees
Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!
A living room with a sectional sofa, a round ottoman, a globe on a shelf, and artwork on the walls.

12. Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.2 out of 10, Wonderful, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
$292 nightly
The price is $339
Oct 3 - Oct 4
Total with taxes and fees
Comfortable & Private 2 Bedrm Cottage w/ King bed.
A modern courtyard with white furniture, a central seating area, and a small lawn.

13. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (106 reviews)
"This property was like a home away from home. Rooms were spacious and location was good. Host was very friendly."
United States
Karen
$119 nightly
The price is $137
Oct 12 - Oct 13
Total with taxes and fees
stayAPT Suites Suffolk-Chesapeake
A narrow brick pathway flanked by two houses with siding.

14. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
$159 nightly
The price is $186
Sep 28 - Sep 29
Total with taxes and fees
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

15. 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)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
$229 nightly
The price is $266
Oct 20 - Oct 21
Total with taxes and fees
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
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, (12 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
$188 nightly
The price is $219
Sep 28 - Sep 29
Total with taxes and fees
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A glass-top table with two cushioned chairs on a wooden deck, a vase with red flowers, and a brick wall.

17. Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.0 out of 10, Wonderful, (55 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
$230 nightly
The price is $268
Sep 28 - Sep 29
Total with taxes and fees
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

18. Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (30 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
$240 nightly
The price is $279
Sep 28 - Sep 29
Total with taxes and fees
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A modern kitchen with white cabinets, a built-in oven, and a dining area with a gray sofa and a table.

19. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (6 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
$245 nightly
The price is $280
Oct 3 - Oct 4
Total with taxes and fees
Guesthouse in ideal location with private entrance
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

20. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (20 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
$119 nightly
The price is $139
Sep 28 - Sep 29
Total with taxes and fees
stayAPT Suites Hampton
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

Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

8/10 Good
"I liked being by the pier. Parking felt safe. Staff was around and always assisted. Balcony was fun"
Brian 2-night trip
Posted 1 hour ago
Sandcastle Resort On The Beach

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 $98 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.