TOP Family-Friendly Hotels in Chesapeake, VA for 2026

Check availability on Chesapeake Family-Friendly Hotels

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Our top choices for Chesapeake family-friendly hotels

Days Inn by Wyndham Chesapeake

Chesapeake

Create a memorable family holiday where kids enjoy free breakfast and comfy rooms with cots available at this convenient motel.

฿2,598 total

includes taxes & fees

31 May - 1 Jun

TRU by Hilton Chesapeake, VA

Greenbrier

฿4,416 total

includes taxes & fees

31 May - 1 Jun

Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

฿3,782 total

includes taxes & fees

31 May - 1 Jun

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

STUDIOS & SUITES 4 LESS CHESAPEAKE

South Norfolk

฿2,704 total

includes taxes & fees

31 May - 1 Jun

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

Create a vibrant family splash zone at SpringHill Suites with indoor pool, children's games, and quick access to USS Wisconsin.

฿4,402 total

includes taxes & fees

28 May - 29 May

Standard Studio, 2 Double Beds, Non Smoking, Kitchen | Desk, iron/ironing board, free WiFi, bed sheets

WoodSpring Suites Chesapeake - Norfolk South

Greenbrier

฿3,411 total

includes taxes & fees

28 May - 29 May

Holiday Inn Express Chesapeake - Norfolk by IHG

Chesapeake

฿4,501 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

฿3,244 total

includes taxes & fees

31 May - 1 Jun

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Choose what matters most at family-friendly hotels in Chesapeake

Breakfast included

Pool

Family-friendly hotels with free breakfast in Chesapeake

Holiday Inn Express Chesapeake - Norfolk by IHG

Chesapeake

฿4,501 total

includes taxes & fees

31 May - 1 Jun

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

฿4,402 total

includes taxes & fees

28 May - 29 May

Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

฿5,215 total

includes taxes & fees

7 Jun - 8 Jun

Comfort Suites Chesapeake - Norfolk

Greenbrier

฿4,734 total

includes taxes & fees

31 May - 1 Jun

Sleep Inn & Suites Chesapeake - Portsmouth

Chesapeake

฿3,244 total

includes taxes & fees

31 May - 1 Jun

Residence Inn by Marriott Chesapeake Greenbrier

Greenbrier

฿5,591 total

includes taxes & fees

31 May - 1 Jun

WoodSpring Suites Chesapeake - Norfolk South

Greenbrier

฿3,411 total

includes taxes & fees

28 May - 29 May

View all properties

Family-friendly hotels with pools in Chesapeake

Holiday Inn Express Chesapeake - Norfolk by IHG

Chesapeake

฿4,501 total

includes taxes & fees

31 May - 1 Jun

SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

฿4,402 total

includes taxes & fees

28 May - 29 May

Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

฿5,215 total

includes taxes & fees

7 Jun - 8 Jun

Comfort Suites Chesapeake - Norfolk

Greenbrier

฿4,734 total

includes taxes & fees

31 May - 1 Jun

Residence Inn by Marriott Chesapeake Greenbrier

Greenbrier

฿5,591 total

includes taxes & fees

31 May - 1 Jun

Sleep Inn & Suites Chesapeake - Portsmouth

Chesapeake

฿3,244 total

includes taxes & fees

31 May - 1 Jun

Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

฿3,782 total

includes taxes & fees

31 May - 1 Jun

View all properties

Top Chesapeake Hotel Reviews

Hilton Virginia Beach Oceanfront

10/10 Excellent

"Friendly"

Coastal Hotel and Suites Virginia Beach Oceanfront

10/10 Excellent

"A one hour early check-in is usually doable by the staff in most instances, mainly during the week. Weekends gets harder as the hotel really fills up. All rooms are oceanfront with a great view right on the boardwalk. Room size is much better than most hotels. Rooms are comfortable and clean. Staff is friendly and most helpful. A great place to stay when visiting Virginia Beach by yourself, with a loved one, or with your whole family."

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."

Frequently asked questions

What's Chesapeake like for family-friendly holidays?

The destination of Chesapeake is a great choice if you've been thinking about a holiday with your children. The beaches, sporting events and theatres are just a few things that make this an attractive place for families. Take to the air and fly into Norfolk, VA (ORF-Norfolk Intl.), which is located 10.1 mi (16.3 km) from the city centre.

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 choices for your child-friendly holiday include Delta Hotels by Marriott Chesapeake Norfolk and Days Inn by Wyndham Chesapeake.

When's the best time to book a family-friendly holiday 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.

What's there to see and do with your family in Chesapeake?

Greenbrier Mall, Chesapeake Square Mall and Dominion Marketplace are interesting attractions that you and your family will enjoy exploring while you are staying in Chesapeake. Make sure that you have plenty of time to take in activities in the area such as Naval Station Norfolk and Sandbridge Beach.

Search Family-Friendly Hotels in Chesapeake

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Check availability on Chesapeake Family-Friendly Hotels

Our top choices for Chesapeake family-friendly hotels

Days Inn by Wyndham Chesapeake

TRU by Hilton Chesapeake, VA

Comfort Inn & Suites Chesapeake - Portsmouth

STUDIOS & SUITES 4 LESS CHESAPEAKE

SpringHill Suites by Marriott Chesapeake Greenbrier

WoodSpring Suites Chesapeake - Norfolk South

Holiday Inn Express Chesapeake - Norfolk by IHG

Sleep Inn & Suites Chesapeake - Portsmouth

Delta Hotels by Marriott Chesapeake Norfolk

Aloft by Marriott Chesapeake

Choose what matters most at family-friendly hotels in Chesapeake

Family-friendly hotels with free breakfast in Chesapeake

Holiday Inn Express Chesapeake - Norfolk by IHG

Family-friendly hotels with pools in Chesapeake

Holiday Inn Express Chesapeake - Norfolk by IHG

Top Chesapeake Hotel Reviews

Hilton Virginia Beach Oceanfront

Frequently asked questions

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