A beach at sunset with a pier extending into the water.

Chesapeake Vacation Rentals

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Dates

November 2026

December 2026

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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

Chesapeake

Patricia M.

$138 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

2. Entire Home in Chesapeake, Virginia

Chesapeake

$552 nightly

Nov 23 - Nov 24

Total with taxes and fees

3. 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

4. Entire Home in Chesapeake, Virginia

Chesapeake

$531 nightly

Nov 23 - Nov 24

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.

$244 nightly

Nov 16 - Nov 17

Total with taxes and fees

6. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Chesapeake

$209 nightly

Nov 28 - Nov 29

Total with taxes and fees

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

Chesapeake

$139 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

Chesapeake

$150 nightly

Nov 29 - Nov 30

Total with taxes and fees

9. 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

10. 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.

11. stayAPT Suites Suffolk-Chesapeake

Suffolk

Tarina

$119 nightly

Nov 9 - Nov 10

Total with taxes and fees

12. stayAPT Suites Hampton

Coliseum Central

Wakeelah

$108 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

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

Portsmouth

Coachmeech Gaming O.

$216 nightly

Nov 20 - Nov 21

Total with taxes and fees

A bedroom with a bed, bedside lamps, a ceiling fan, a window with curtains, a door, and a trash can.

14. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Portsmouth

Mark D.

$154 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a beige sofa, a green armchair, and a white armchair. There is a large plant, a wooden floor, and a ceiling vent.

15. Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

Portsmouth

Ryan H.

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

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

Portsmouth

Ronnie B.

$293 nightly

Nov 7 - Nov 8

Total with taxes and fees

An outdoor patio with wooden furniture, a fire pit, and a covered area with a view of the surrounding landscape.

17. Sojourn's Harborage | Pet-Friendly

East Ocean View

Antonio R.

$235 nightly

Dec 1 - Dec 2

Total with taxes and fees

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!!

Portsmouth

Niya w.

$245 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

19. Angie's Guest Cottage

Northeast Virginia Beach

Cheryl

$88 nightly

Nov 8 - Nov 9

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.

20. Guesthouse in ideal location with private entrance

Suffolk

Audrey J.

$246 nightly

Nov 7 - Nov 8

Total with taxes and fees

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Find vacation rentals that suit your style

Top Chesapeake Hotel Reviews

An outdoor patio area with seating, a fire pit, and a covered dining area.

Home2 Suites By Hilton Virginia Beach Princess Anne

Virginia Beach

10/10 Excellent

Kera

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

An indoor swimming pool with clear water, tiled walls, and a wooden floor.

Hampton Inn Newport News-Yorktown

Central Newport News

10/10 Excellent

Vicki

A beachside balcony with lounge chairs and a view of the ocean.

Hyatt Place Virginia Beach / Oceanfront

Northeast Virginia Beach

10/10 Excellent

My recent stay at the Hyatt Place Virginia Beach Oceanfront from July 13 to 16 was nothing short of spectacular! This hotel truly set the bar high for all future stays. From the moment we arrived, we were greeted with exceptional service, particularly the valet team, which was incredibly efficient and accommodating. The rain limited our outdoor activities, but we didn’t mind one bit because the comfort of our room made it an enjoyable stay. One of the highlights of our mornings was...

Adrian

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 hotel room with a large bed, a TV, a desk with drawers, a suitcase, and a view of a shopping center.

Hyatt Place Virginia Beach Town Center

Northwest

10/10 Excellent

neil

A modern interior with a central art installation, white walls, and a reflective floor.

Glass Light Hotel & Gallery, Autograph Collection

Downtown Norfolk

10/10 Excellent

Diondra

An indoor swimming pool with a view of the beach at night.

Embassy Suites by Hilton Virginia Beach Oceanfront Resort

Northeast Virginia Beach

10/10 Excellent

My husband and I needed a long weekend and VA beach is always our choice. This was our first time staying at Embassy Suites Oceanfront, and we were pleasantly surprised! A brand-new hotel on the best side of the beach with an extra clean room, and the tasty buffet breakfast and good reception drinks are included in the costs. If you take a winter getaway, be sure to take a bathing suit to enjoy the heated indoor pool. Outside has plenty of year-round chairs and even a fire-pit. This property is...

Angela

A hot tub with a view of the ocean through large windows.

Coastal Hotel and Suites Virginia Beach Oceanfront

Northeast Virginia Beach

10/10 Excellent

Patricia

A modern restaurant with a bar area, seating arrangements, and a counter with a menu display.

Courtyard by Marriott Suffolk Chesapeake

Suffolk

10/10 Excellent

Malcolm

An outdoor seating area with stone walls, a fire pit, and green chairs.

Home2 Suites by Hilton Norfolk Airport

Norfolk

10/10 Excellent

This was our first time staying in a Home 2 Suites and we were pleasantly surprised. The property was in beautiful condition. The staff was extremely friendly and welcoming. The room was immaculate and the bed was one of the most comfortable we have ever experienced. Even the pillows were ones we would like to buy. I highly recommend this hotel, especially for anyone flying in or out of Norfolk Airport.

Steven

A spacious lobby with a central reception area, large potted plants, and a wooden floor.

Hilton Garden Inn Newport News

Central Newport News

10/10 Excellent

This property was very clean and comfortable. I stayed for 2 nights, and I will definitely stay again. The hotel was walking distance to restaurants and grocery stores. The hotel was minutes away from shopping. The front desk staff was courteous and inviting. I stay in hotels often, and am very meticulous.....this one will not disappoint! Another plus is that NO PETS were allowed. I have really really bad allergies and sensitive skin. I cannot stay in places where pets are allowed.

Lisa

An outdoor seating area with a fire pit, wicker furniture, and string lights.

Hyatt Place Hampton Convention Center

Coliseum Central

10/10 Excellent

Tanya

A balcony with two blue chairs and a small table, overlooking a beach with a railing and ocean view.

Holiday Inn Express & Suites VA Beach Oceanfront by IHG

Northeast Virginia Beach

10/10 Excellent

Starlett

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 $126 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

Bundle & Save

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Upfront pricing

Check prices for these dates

Our top choices for Chesapeake vacation rentals

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

2. Entire Home in Chesapeake, Virginia

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

4. Entire Home in Chesapeake, Virginia

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

6. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

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

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

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

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

11. stayAPT Suites Suffolk-Chesapeake

12. stayAPT Suites Hampton

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

14. Private 1 Bed Apt - Historic Olde Towne Portsmouth

15. Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

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

17. Sojourn's Harborage | Pet-Friendly

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

19. Angie's Guest Cottage

20. Guesthouse in ideal location with private entrance

Find vacation rentals that suit your style

Top Chesapeake Hotel Reviews

Home2 Suites By Hilton Virginia Beach Princess Anne

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?

Explore a world of travel with Expedia