Chesapeake Vacation Rentals from $125: Search Short-Term Rentals

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Our top choices for Chesapeake vacation rentals

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

1. Entire Home in Chesapeake, Virginia

Chesapeake

$552 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

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

Chesapeake

Patricia M.

$123 nightly

Dec 6 - Dec 7

Total with taxes and fees

3. Entire Home in Chesapeake, Virginia

Chesapeake

$508 nightly

Nov 23 - Nov 24

Total with taxes and fees

4. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Chesapeake

$150 nightly

Nov 29 - Nov 30

Total with taxes and fees

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.

Chesapeake

James W.

$237 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Chesapeake

$139 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

Chesapeake

Tony H.

$139 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

Chesapeake

$142 nightly

Nov 22 - Nov 23

Total with taxes and fees

9. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Chesapeake

$209 nightly

Nov 28 - Nov 29

Total with taxes and fees

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

Chesapeake

Ariel G.

$150 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

Chesapeake

Linh T.

$299 nightly

Nov 29 - Nov 30

Total with taxes and fees

A modern courtyard with white furniture, a central seating area, and a small lawn.

12. stayAPT Suites Suffolk-Chesapeake

Suffolk

Tarina

$119 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern living room with a wooden coffee table, a large white orchid, and a flat-screen TV.

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

Portsmouth

Ronnie B.

$286 nightly

Nov 9 - Nov 10

Total with taxes and fees

A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

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

Portsmouth

Coachmeech Gaming O.

$210 nightly

Nov 20 - Nov 21

Total with taxes and fees

A narrow brick pathway flanked by two houses with siding.

15. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Portsmouth

Mark D.

$150 nightly

Nov 12 - Nov 13

Total with taxes and fees

16. stayAPT Suites Hampton

Coliseum Central

Wakeelah

$107 nightly

Nov 9 - Nov 10

Total with taxes and fees

A kitchen with granite countertops, stainless steel appliances, and black bar stools.

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

Portsmouth

Niya w.

$238 nightly

Dec 1 - Dec 2

Total with taxes and fees

A poolside area with a covered seating area, a pool, and a white fence.

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

Portsmouth

Kimberly

$192 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Suffolk

Audrey J.

$246 nightly

Nov 8 - Nov 9

Total with taxes and fees

A two-story house with a white porch, a red door, and a small Christmas tree.

20. Angie's Guest Cottage

Northeast Virginia Beach

Cheryl

$88 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top Chesapeake Hotel Reviews

A modern interior with a green wall, a neon sign, and a variety of seating arrangements including tables and chairs.

Fairfield Inn & Suites by Marriott Virginia Beach Town Center

North Central

10/10 Excellent

Maggie

A modern kitchen with a central island, bar stools, pendant lighting, and a large wall-mounted artwork.

Fairfield Inn and Suites By Marriott Chesapeake

Greenbrier

10/10 Excellent

Nadiya

A Holiday Inn Express hotel with a covered entrance, outdoor lighting, and a landscaped area with plants.

Holiday Inn Express Chesapeake - Norfolk by IHG

Chesapeake

10/10 Excellent

Lisa

An outdoor patio area with tables and chairs, string lights, and a canopy.

Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

10/10 Excellent

Shanon

A modern lounge area with seating, tables, and hanging lights.

TRU by Hilton Chesapeake, VA

Greenbrier

10/10 Excellent

Lilli

An outdoor patio area with stone walls, a brick floor, and outdoor furniture.

Staybridge Suites Chesapeake by IHG

Chesapeake

10/10 Excellent

Anonymous traveler

A workspace with two computers, a printer, and two black leather chairs.

Hampton Inn Norfolk/Chesapeake (Greenbrier Area)

Chesapeake

10/10 Excellent

I was coming to Chesapeake from a long drive from Upstate NY. I was very tired and found the hotel online with hotels.com. I booked it using my phone, then used GPS to find the hotel. I just wanted to go to sleep. When I arrived, I found out that my reservation was inserted for the next day and I couldn't check in until after 3 pm. Well it was around 5 am and all I wanted to do was lay down. The front desk clerk allowed me to check in anyway and later on, I was given a late check-out. So in all,...

Esther

An outdoor patio area with brick walls, a fire pit, and outdoor furniture.

Residence Inn by Marriott Chesapeake Greenbrier

Greenbrier

10/10 Excellent

alicia

An outdoor patio area with stone walls, outdoor furniture, and string lights.

Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

10/10 Excellent

Deborah

A modern restaurant with a central bar area, multiple seating options including high tables and bar stools, and a flat-screen TV mounted on a wooden panel.

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

10/10 Excellent

Jamie

A hotel room with a bed, a desk with a chair, a sofa, a TV, and a window with curtains.

Candlewood Suites Chesapeake/Suffolk by IHG

Western Branch North

10/10 Excellent

Max

A hotel lobby with a reception desk, seating area, and dining tables.

Wingate by Wyndham Chesapeake

Chesapeake

10/10 Excellent

Kelly

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 $125 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 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.

Chesapeake Vacation Rentals

Check prices for these dates

Our top choices for Chesapeake vacation rentals

1. Entire Home in Chesapeake, Virginia

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

3. Entire Home in Chesapeake, Virginia

4. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

5. 3-bedroom home away from home in fabulous Chesapeake, Virginia.

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

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

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

9. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

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

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

12. stayAPT Suites Suffolk-Chesapeake

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

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

15. Private 1 Bed Apt - Historic Olde Towne Portsmouth

16. stayAPT Suites Hampton

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

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

19. Guesthouse in ideal location with private entrance

20. Angie's Guest Cottage

Find vacation rentals that suit your style

Top Chesapeake Hotel Reviews

Fairfield Inn & Suites by Marriott Virginia Beach Town Center

10/10 Excellent

Find out more about Chesapeake

Everything you need to know about Chesapeake vacation rentals

Chesapeake vacation rentals: An excellent choice for every season

How to find incredible deals on Chesapeake rentals

Frequently Asked Questions

Are there vacation rentals in Chesapeake?

What are some of the best vacation home rentals in Chesapeake?

How many vacation rentals are there in Chesapeake?

What’s there to see and do in Chesapeake?

What’s a vacation rental in Chesapeake like?

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