Pet Sitting and Boarding in Chesapeake

Book trusted sitters and boarders

How it works

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Skip the kennel

Sittings take place at your home and boardings take place at your pet caregiver's home.

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Flexible transportation

All pet caregivers offer pick-up and drop-off for boarding services.

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Live updates

Your pet caregiver will send photos and videos throughout the service in addition to a thorough report card.

What is Wag!?

Wag! is the nation's fastest-growing network of pre-screened and insured pet sitters and dog walkers. In less than 15 minutes you can book a nearby dog sitter, daycare provider, or dog walker, who'll take complete care of your loved one - at their place or yours.

Book pet caregivers near you

“Your dog’s best friend when you can’t be there”

I am passionate about dogs and have raised and loved multiple medium to large breed dogs over the past 30 years. My current baby is an active 87 lb Rhodesian Ridgeback, the second Rhodesian I have raised from puppyhood. I tailor my level of effort to your dog’s needs and specialize in high energy dogs who enjoy a faster pace. I treat each of my dog clients as if they were my own and have a proven WAG! track record of being 100% reliable, giving above and beyond care to my clients on every walk.

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Top Pet Caregiver

Socially Distanced Pet Care

Specialties

Dog first aid and/or CPR, Can run with dogs, Oral medicine administration, Senior dog care, Special needs dog care, High energy dogs, Fast walker, Dogs who pull, Puppy care

My name is Anna. I am a mom of 4 kids, two of which are dogs ;) Beau my Goldendoodle and Ollie, my Maltipoo pup. I have always loved dogs. They are a big part of my life. I have been a dog owner for over 24 years and have helped dog owners care for , love , walk & play with their dogs while they are away . I am so excited to be part of the Wag team and look forward to helping you with your dog!!

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Dog Boarding in Chesapeake

If you believe that every dog deserves the chance to find a loving home and live a happy and healthy life, you’ll find plenty of friends in Chesapeake. This beautiful city boasts a diverse community of dog lovers and their furry friends, not to mention a number of excellent animal welfare organizations that do everything they can to help save and improve the lives of pets in need.

Chesapeake Humane Society has been promoting the welfare of animals in the region for more than four decades. Founded in 1972, this non-profit organization is funded entirely by private donations and does not receive any government support. It offers a wide range of services to help Chesapeake’s homeless pets, including spay and neuter programs, vaccination services, and providing countless volunteer hours to improve the lives of shelter pets.

With a slick media program advertising adoptable pets, it also hosts offsite adoption events to help match perfect pets with loving owners. The Chesapeake Humane Society operates towards the goal of helping pets and the people who love them find each other and stay together, and it makes a real difference in the lives of the region’s animals.

So, too, does Web of Life Animal Outreach, a non-profit, no-kill animal rescue organization founded in 2005. With a commitment to save injured, abused and neglected companion animals, Web of Life aims to find each pet a responsible owner who will remain dedicated to their furry friend for life. Its seven-acre companion animal sanctuary in Chesapeake houses dogs, cats, birds, livestock, and more, and is well worth a visit if you’re looking to adopt a new pet.

Upcoming Dog Friendly Events Chesapeake

Bark in the Park

48
Admission
$2.00

Month
October

Duration
12PM-5PM Sunday

Bark in the Park

48

Bark in the Park is a two-day annual pet-acular that celebrates our furry friends and raises essential funds for the Chesapeake Humane Society. The fun kicks off on Saturday with the 5k Doggy Dash and 1-mile Puppy Trot, where you and your pooch can enjoy some fresh air, exercise, and wonderful company. This is followed by a paw-some Sunday pet festival, held at Chesapeake City Park - rain, hail, or shine. Highlights include a Radar Run, doggy demonstrations, canine contests, food trucks, live entertainment, and stacks of pet product vendors. It’s the society’s largest fundraiser of the year, so get on down and lend your support!

VBSPCA Mutt Masquerade

36
Admission
$35.00

Month
October

Duration
9am to 1pm

VBSPCA Mutt Masquerade

36

Grab your dog, grab your leash, and hit the beach! The VBSPCA Mutt Masquerade is held every October and always draws a huge crowd of active animal lovers. Held in nearby Virginia Beach to benefit the Virginia Beach SPCA, this doggy dash features a 5K run/walk and a 1-mile pack walk. You can compete at whatever pace you want and cute costumes are encouraged, with a canine costume contest sandwiched between the 5K and 1-mile events. There are also plenty of vendors selling a range of pet products and services, so the event promises a day full of dog-friendly fun for you and your pooch!

Pucks and Paws

24
Admission
$5.00

Duration
7pm to 9:30pm

Pucks and Paws

24

Want to take in all the thrills, spills, and fast-paced entertainment of a hockey game with your dog by your side? Then Pucks and Paws is the event for you! On several selected nights throughout the season, the Norfolk Admirals invite all dog lovers to bring their furry friends along to watch all the action. Held to benefit the Chesapeake Humane Society and a number of other local animal shelters, these regular nights are a paw-fect way to enjoy a fun night out with your pet and socialize with other animal lovers! Pet tickets cost $5, so why not treat your dog to a night on the ice?

Mutt Strut

12
Admission
FREE!

Month
May

Duration
11am to 4pm

Mutt Strut

12

The Suffolk Humane Society has been helping Suffolk’s abandoned and unwanted animals since 2007. Each year, it holds a massive Mutt Strut Dog Walk and Festival to raise the funds it needs to continue helping homeless pets. Held in Bennett’s Creek Park, this paw-some fundraiser sees dog lovers and their furry friends move their paws and feet for a very good cause. There’s plenty of other pet-friendly activities to enjoy on the day as well, with heaps of pet product vendors, tasty treats, live entertainment, and more! It’s good old-fashioned fun for the whole family and your attendance will help animals in need enjoy a second chance at life.

World of Pets Expo

0
Admission
$9.00

Month
February

Duration
2PM to 8PM Daily

World of Pets Expo

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Love pets and animals of all shapes and sizes? The World of Pets Expo promises heaps of fun, informative, and educational experiences to suit any animal lover! Held in February at the Hampton Roads Convention Center, the expo features more dog-friendly experiences than you can wag a tail at. Highlights include dock jumping demonstrations, pet talent and fashion contests, pet care advice, a parade of breeds, and an extensive range of pet products and services on display. Well-socialized, leashed pets are more than welcome to come along and join in the fun, so get your pooch ready for a weekend exploring the world of pets.

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