Chesapeake Holiday Rentals, Virginia: Private House Rentals

Our top choices for Chesapeake hotels

1. Hampton Inn & Suites Chesapeake-Square Mall

Chesapeake

Carol

฿3,782 total

includes taxes & fees

29 Jun - 30 Jun

2. Holiday Inn Express Chesapeake - Norfolk by IHG

Chesapeake

Kiara

฿4,771 total

includes taxes & fees

5 Jul - 6 Jul

3. TRU by Hilton Chesapeake, VA

Greenbrier

Betty Jo

฿4,611 total

includes taxes & fees

28 Jun - 29 Jun

4. Hyatt Studios Chesapeake

Greenbrier

฿5,333 total

includes taxes & fees

1 Jul - 2 Jul

5. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

Richard

฿4,047 total

includes taxes & fees

29 Jun - 30 Jun

6. SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

Russell

฿4,272 total

includes taxes & fees

28 Jun - 29 Jun

7. Hyatt Place Chesapeake

Greenbrier

Diahann

฿5,147 total

includes taxes & fees

28 Jun - 29 Jun

8. Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

Christopher

฿5,223 total

includes taxes & fees

21 Jun - 22 Jun

9. Aloft by Marriott Chesapeake

Greenbrier

Monica

฿4,846 total

includes taxes & fees

5 Jul - 6 Jul

10. Comfort Suites Chesapeake - Norfolk

Greenbrier

Robert

฿5,435 total

includes taxes & fees

28 Jun - 29 Jun

11. Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Greenbrier

Kathy

฿5,282 total

includes taxes & fees

21 Jun - 22 Jun

12. Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

Danette Lady

฿5,147 total

includes taxes & fees

1 Jul - 2 Jul

13. American Inn Chesapeake – Portsmouth

Chesapeake

B.F

฿2,619 total

includes taxes & fees

16 Jun - 17 Jun

Standard Suite, 1 Queen Bed with Sofa bed, Non Smoking, Kitchen | 1 bedroom, premium bedding, desk, laptop workspace

14. YourSpace Hotels Chesapeake

Western Branch North

Mark

฿4,853 total

includes taxes & fees

6 Jul - 7 Jul

15. Fairfield Inn and Suites By Marriott Chesapeake

Greenbrier

oliver

฿5,226 total

includes taxes & fees

29 Jun - 30 Jun

16. Wingate by Wyndham Chesapeake

Chesapeake

Justine

฿4,613 total

includes taxes & fees

1 Jul - 2 Jul

17. Days Inn by Wyndham Chesapeake

Chesapeake

Roberto Said

฿2,538 total

includes taxes & fees

21 Jun - 22 Jun

Desk, laptop workspace, blackout curtains, iron/ironing board

18. Candlewood Suites Chesapeake by IHG

Western Branch North

Cornelio

฿4,093 total

includes taxes & fees

21 Jun - 22 Jun

19. Courtyard by Marriott Chesapeake

Greenbrier

matthew

฿4,395 total

includes taxes & fees

28 Jun - 29 Jun

20. Bowers Hill Inn

Chesapeake

James

฿2,619 total

includes taxes & fees

16 Jun - 17 Jun

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Where to stay in Chesapeake

Find the best Chesapeake areas for the activities you enjoy most.

Greenbrier

Greenbrier combines suburban comfort with retail convenience in this family-friendly Chesapeake area. Greenbrier Mall anchors the area with department stores and speciality shops alongside tree-lined residential streets. Parks and green spaces like Chesapeake Arboretum offer peaceful breaks from shopping. Explore Chesapeake City Park's walking trails or visit Oak Grove Lake Park for outdoor recreation. Chain restaurants and familiar stores line Greenbrier Parkway in typical American strip mall fashion. With limited public transit, having a car makes it easier to discover this authentic slice of suburban America.

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scenes around chesapeak bay virginia beach

Great Bridge

Great Bridge offers a peaceful suburban retreat where Revolutionary War history meets waterfront tranquility. The area surrounds the scenic Intracoastal Waterway, with tree-lined streets leading to waterside parks and fishing piers. History buffs will appreciate the Great Bridge Battlefield & Waterways Museum commemorating a key Revolutionary War battle. Stroll along Elizabeth River's peaceful banks or enjoy a round at Chesapeake Golf Club. The family-friendly area features convenient shopping centers and casual seafood restaurants specialising in Chesapeake Bay delicacies. Though limited in public transit, the welcoming community provides an authentic glimpse into suburban American life.

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Aerial panorama of Chesapeake Bay Bridge Tunnel at sunset. CBBT is a 17.6-mile bridge tunnel that crosses the mouth of the Chesapeake Bay.

Western Branch North

Western Branch North offers a peaceful family-oriented residential retreat just outside Chesapeake's urban core. This welcoming area features tree-lined streets with colonial-style homes and manicured lawns. Travellers will appreciate the authentic suburban American experience without tourist crowds. The area provides easy access to Chesapeake Square Mall and Bowlero Western Branch for entertainment options. Nearby Elizabeth River natural areas offer opportunities for hiking, fishing, and kayaking. With affordable dining at casual eateries and comfortable holiday rentals, Western Branch North serves as an excellent base for budget-conscious travellers exploring the region.

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South Norfolk

South Norfolk blends historic charm with quiet suburban living. The tree-lined streets showcase early 20th-century Craftsman bungalows and Colonial Revival homes with inviting front porches. Visitors can explore the restored railway station and vintage shopfronts along Chesapeake Avenue. The area offers a genuine small-town Southern experience. Local diners serve comfort food while antique shops house unique regional treasures. Community parks provide peaceful retreats under towering pines, perfect for travellers seeking authentic local character away from tourist crowds.

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Deep Creek South

While visiting Deep Creek South, you might make a stop by sights like The Crossings at Deep Creek Shopping Center and Deep Creek Park.

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Stay near popular Chesapeake attractions

Greenbrier Mall

4.2/5 (837 reviews)

This regional shopping centre features over 100 stores and eateries, plus a Cinema Café for dining during films. Families enjoy the supervised soft play area and convenient amenities while shopping.

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Learn more about Chesapeake

Explore the Great Dismal Swamp's boardwalk trails where kayakers glide past cypress trees and wildlife thrives. The Chesapeake Arboretum's 48 acres of forests and gardens offer peaceful hiking, while nearby waterfront restaurants serve the bay's famous blue crabs.

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Top Chesapeake Hotel Reviews

Hilton Virginia Beach Oceanfront

10/10 Excellent

"clean room, great beach view"

Hampton Inn Virginia Beach-Oceanfront South

10/10 Excellent

"My family and i took a short 48 hour weekend trip to Virginia Beach. This was my first time ever going to Virginia Beach as well as my toddlers first experience of the beach. We had a wonderful stay at the Hampton inn. The rooms were clean but of course i still did my own additional cleaning however i did not find anything outrageously dirty. The breakfast was ok, we mainly had waffles and cereal every morning. Overall i give the hotel a 9/10. The indoor pool was the only thing we did not like. We will be staying here again in the future"

More cheap stays in Chesapeake

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy Chesapeake VA

฿2,068

฿2,444 total

22 Jun - 23 Jun

includes taxes & fees

7.2/10 Good! (837 reviews)

Frequently asked questions

Where is the best place for a stay in Chesapeake?

Based on our traveller data, Wingate by Wyndham Chesapeake is one of the top choices for your stay. This hotel offers free breakfast and an indoor pool. Other good options for your trip include Comfort Suites Chesapeake - Norfolk and STUDIOS & SUITES 4 LESS CHESAPEAKE. See all available top hotels, or vacation rentals in Chesapeake.

If I need to cancel my hotel reservation in Chesapeake, will I receive a refund?

Yes! You'll find that most hotel reservations are fully refundable if you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chesapeake.

What's the best family accommodation in Chesapeake?

Delta Hotels by Marriott Chesapeake Norfolk is a hotel with an indoor pool and a restaurant, and it's a top choice on Expedia for families. Other good options for your family trip include SpringHill Suites by Marriott Chesapeake Greenbrier and Days Inn by Wyndham Chesapeake. Also, attractions such as Riverwalk Parkway Park and Playground and Broadmoor Play Area are fun for children of all ages. Find more child-friendly accommodations in Chesapeake.

What's the best LGBTQ-friendly accommodation in Chesapeake?

Red Roof Inn Chesapeake Conference Center is a top LGBTQ-friendly hotel, and features free Wi-Fi and flat-screen TVs. Delta Hotels by Marriott Chesapeake Norfolk and Hyatt Place Chesapeake are other good choices for your stay. See all available hotels listed as LGBTQ-friendly in Chesapeake.

What's the best dog-friendly place to stay in Chesapeake?

YourSpace Hotels Chesapeake is a top dog-friendly hotel, and offers a 24-hour fitness centre along with in-room kitchens for its human guests. Other good options for you and your pet include Aloft by Marriott Chesapeake and TRU by Hilton Chesapeake, VA. See more pet-friendly hotel accommodations in Chesapeake.

What are some hotels with pools in Chesapeake?

Comfort Suites Chesapeake - Norfolk is a top hotel with a seasonal outdoor pool, free buffet breakfast and free WiFi. Hyatt Place Chesapeake is an additional hotel with an on-site pool. View all hotels with pools in Chesapeake.

What is staying in Chesapeake like?

Couples looking to get away will find a romantic atmosphere in Chesapeake, and visitors give high marks for the shopping, top-notch restaurants and beaches. This city also attracts tourists with its live music, theatres and sporting events. Top sights around the area include Sandbridge Beach and Naval Station Norfolk. In Chesapeake, there are 116 hotels and other accommodation options to choose from. Find out more about Chesapeake.

What are the top places to visit in Chesapeake?

Favorite family attractions include Riverwalk Parkway Park and Playground and Jillian's Billiards. The natural setting is picturesque, namely the beaches, and places to see include: Chesapeake City Park, Dismal Swamp Canal and Lake Drummond. Additionally, you'll find Sandbridge Beach and Naval Station Norfolk in the area. Take a look at what more there is to see and do in Expedia's Chesapeake guide.

What's the seasonal weather in Chesapeake?

The hottest months are usually July and August, with an average temperature of 25°C, while the coldest months are January and February, with an average of 7°C. Average annual precipitation for Chesapeake is 1359 mm.

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Our top choices for Chesapeake hotels

1. Hampton Inn & Suites Chesapeake-Square Mall

2. Holiday Inn Express Chesapeake - Norfolk by IHG

3. TRU by Hilton Chesapeake, VA

4. Hyatt Studios Chesapeake

5. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

6. SpringHill Suites by Marriott Chesapeake Greenbrier

7. Hyatt Place Chesapeake

8. Delta Hotels by Marriott Chesapeake Norfolk

9. Aloft by Marriott Chesapeake

10. Comfort Suites Chesapeake - Norfolk

11. Hampton Inn & Suites Chesapeake-Battlefield Blvd.

12. Holiday Inn Express Hotel & Suites Chesapeake by IHG

13. American Inn Chesapeake – Portsmouth

14. YourSpace Hotels Chesapeake

15. Fairfield Inn and Suites By Marriott Chesapeake

16. Wingate by Wyndham Chesapeake

17. Days Inn by Wyndham Chesapeake

18. Candlewood Suites Chesapeake by IHG

19. Courtyard by Marriott Chesapeake

20. Bowers Hill Inn

Where to stay in Chesapeake

Greenbrier

Great Bridge

Western Branch North

South Norfolk

Deep Creek South

Stay near popular Chesapeake attractions

Greenbrier Mall

Learn more about Chesapeake

Top Chesapeake Hotel Reviews

Hilton Virginia Beach Oceanfront

More cheap stays in Chesapeake

STUDIOS & SUITES 4 LESS CHESAPEAKE

Frequently asked questions

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