Chesapeake Holiday Rentals, Virginia: Private House Rentals

Our top choices for Chesapeake hotels

Hampton Inn & Suites Chesapeake-Square Mall

Chesapeake

Carol

฿3,776 total

includes taxes & fees

2 Jun - 3 Jun

YourSpace Hotels Chesapeake

Western Branch North

Katie

฿5,478 total

includes taxes & fees

31 May - 1 Jun

Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

Dung

฿4,320 total

includes taxes & fees

7 Jun - 8 Jun

TRU by Hilton Chesapeake, VA

Greenbrier

Ernestina

฿4,416 total

includes taxes & fees

31 May - 1 Jun

Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

Joy

฿4,576 total

includes taxes & fees

21 Jun - 22 Jun

American Inn Chesapeake – Portsmouth

Chesapeake

Victoria

฿2,467 total

includes taxes & fees

1 Jun - 2 Jun

Days Inn by Wyndham Chesapeake

Chesapeake

Roberto Said

฿2,598 total

includes taxes & fees

31 May - 1 Jun

Comfort Suites Chesapeake - Norfolk

Greenbrier

Lewis

฿4,576 total

includes taxes & fees

28 May - 29 May

Standard Double Room, 2 Double Beds, Smoking | Bathroom | Combined shower/bathtub, towels

Bowers Hill Inn

Chesapeake

James

฿2,435 total

includes taxes & fees

2 Jun - 3 Jun

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

Candlewood Suites Chesapeake by IHG

Western Branch North

Cornelio

฿3,937 total

includes taxes & fees

21 Jun - 22 Jun

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Greenbrier

Ben

฿4,812 total

includes taxes & fees

31 May - 1 Jun

Wingate by Wyndham Chesapeake

Chesapeake

Brenda

฿4,463 total

includes taxes & fees

31 May - 1 Jun

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

Francelis

฿4,402 total

includes taxes & fees

28 May - 29 May

Fairfield Inn and Suites By Marriott Chesapeake

Greenbrier

Patricia

฿4,699 total

includes taxes & fees

31 May - 1 Jun

Holiday Inn Express Chesapeake - Norfolk by IHG

Chesapeake

Selena

฿5,068 total

includes taxes & fees

31 May - 1 Jun

Deluxe Double Room | Individually furnished, free WiFi, bed sheets

STUDIOS & SUITES 4 LESS CHESAPEAKE

South Norfolk

Tiara

฿2,704 total

includes taxes & fees

28 May - 29 May

Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

Naesha

฿5,215 total

includes taxes & fees

7 Jun - 8 Jun

Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

deshawn

฿3,782 total

includes taxes & fees

31 May - 1 Jun

Suite, 1 King Bed, Non Smoking, Hot Tub, Kitchenette | Desk, iron/ironing board, free WiFi, bed sheets

Sleep Inn & Suites Chesapeake - Portsmouth

Chesapeake

"The particular amenities I was looking for fell far short of expectation. This site claimed recently renovated. It advertised buffet breakfast and hot tub. Room furniture was well worn and showed corrosion on metal fixtures,handles and supports. Breakfast by industry standards was continental not buffet as advertised. The hot tub didn't work properly, no jet timer and on second night wasn't even warm. Doors to access side entrances and pool were not secure, any person could enter building and...

James

฿3,244 total

includes taxes & fees

31 May - 1 Jun

Hyatt Place Chesapeake

Greenbrier

Diahann

฿5,177 total

includes taxes & fees

21 Jun - 22 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 Deep Creek Park and The Crossings at Deep Creek Shopping Center.

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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

Coastal Hotel and Suites Virginia Beach Oceanfront

10/10 Excellent

"Breakfast it was very good so the entire hotel, definitely we will come back Thanks"

Schooner Inn

8/10 Good

"We experienced an upstairs leak in our room. We were given a lame excuse as to why their was leak from maintenance and that there was nothing they could do to keep it from happening. We were moved to another room after the incident occurred twice within hours of each other. It was a bigger room with a bigger bathroom. We finished our vacation with no more problems. The front desk people were good... the maintenance staff is pretty much a joke. Great beach and boardwalk view. And free parking with many happy hour spots within walking distance."

Hyatt House Virginia Beach / Oceanfront

4/10 Poor

"My family and I travel to Virginia Beach every year this is the first time we stayed at the Hyatt. We got there early our room wasn’t ready, which is understandable. When we got to our room, the bathroom room was not locking, and the balcony had a huge gap, I have a five year old so i wasn’t comfortable at all with my kids going on the balcony. We called the front desk, spoke to Mike the manager, they sent someone up to fix the bathroom, they saw the balcony took pictures and gave us 50% off the room stay. The next day, close to midnight, we saw a roach crawling by the bed, we saw a second one on the wall, we caught it and took a picture and call the front desk immediately. It was midnight, some of the kids were sleeping had to wake them up, pack all the bags and move to another room. Honestly at that point I didn’t want to stay at the hotel at all. The guy at the front desk name was Ralph, he was really nice to us, customer service was on point. The next day spoke to the manager Mike, he said he could only give us 50% off again. Honestly I don’t expect our stay to be free but I feel like we should have been compensated more, we found a roach, that’s disgusting for such a high end hotel. I felt like they could have offered more than that. I would never stay here again."

Wingate by Wyndham Chesapeake

6/10 Okay

"Book a king size bedroom was given a two double bedroom and charge for the state of a king size bedroom. Rooms are not cleaned on the daily basis, but towels is replenished. Overall, the staff was nice and accommodating. The hotel inside and out was fairly clean. The hot tub could not be used. The pool is not open until 1 PM and close at 10 PM. The walls of extremely thin. The breakfast was better than most places I’ve been."

Ocean Resort

6/10 Okay

"The stay was just okay. There was no room cleaning during our entire five-day stay. Management claimed they are still following COVID-19 protocols, meaning we had to replace our own towels and empty our own trash. Additionally, there was an unknown man sleeping on the lobby couch on Monday between 5:00 AM and 8:00 AM, and it was unclear if he belonged to the staff. This raised some safety concerns."

More cheap stays in Chesapeake

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy Chesapeake VA

฿2,294

฿2,704 total

28 May - 29 May

includes taxes & fees

7/10 Good! (820 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 STUDIOS & SUITES 4 LESS CHESAPEAKE and YourSpace Hotels 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?

SpringHill Suites by Marriott Chesapeake Greenbrier is a hotel with an indoor pool and free breakfast, and it's a top choice on Expedia for families. Other good options for your family trip include Delta Hotels by Marriott Chesapeake Norfolk and Days Inn by Wyndham Chesapeake. Also, attractions such as Broadmoor Play Area and Parkview 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 Naval Station Norfolk and Sandbridge Beach. In Chesapeake, there are 115 hotels and other accommodation options to choose from. Find out more about Chesapeake.

What are the top places to visit in Chesapeake?

The natural setting is picturesque, namely the beaches, and places to see include: Chesapeake City Park, Lake Drummond and Oak Grove Lake Park. Additionally, you'll find Naval Station Norfolk and Sandbridge Beach 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

Hampton Inn & Suites Chesapeake-Square Mall

YourSpace Hotels Chesapeake

Fairfield Inn & Suites by Marriott Chesapeake Suffolk

TRU by Hilton Chesapeake, VA

Holiday Inn Express Hotel & Suites Chesapeake by IHG

American Inn Chesapeake – Portsmouth

Days Inn by Wyndham Chesapeake

Comfort Suites Chesapeake - Norfolk

Bowers Hill Inn

Candlewood Suites Chesapeake by IHG

Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Wingate by Wyndham Chesapeake

SpringHill Suites by Marriott Chesapeake Greenbrier

Fairfield Inn and Suites By Marriott Chesapeake

Holiday Inn Express Chesapeake - Norfolk by IHG

STUDIOS & SUITES 4 LESS CHESAPEAKE

Delta Hotels by Marriott Chesapeake Norfolk

Comfort Inn & Suites Chesapeake - Portsmouth

Sleep Inn & Suites Chesapeake - Portsmouth

Hyatt Place Chesapeake

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

Coastal Hotel and Suites Virginia Beach Oceanfront

More cheap stays in Chesapeake

STUDIOS & SUITES 4 LESS CHESAPEAKE

Frequently asked questions

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