Doggy Day Care in Winter Harbor Haven

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

End
Search

Feel secure with ID-verified sitters and 25.000 € in eligible vet care. Learn about RoverProtect

Top rated Winter Harbor Haven doggy day care sitters

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 15% and taxes will apply.

1 / 1
Sitter Profile Image: Bryan S.
Verified Enhanced Background Check
Bryan S.
Star Sitter
from
$33
per day
4.9 out of 5 stars
52 reviews
24 repeat clients
40 years of experience
Hayes, VA, 23072

This family takes great care of our pup. When I pulled into the drive and Rosy recognized where we were, she was super excited! They love her and Rosy loves them right back!

Profile image
Andrea R.
Sitter Profile Image: Cheyanne B.
Verified Enhanced Background Check
Cheyanne B.
Star Sitter
from
$20
per day
4.9 out of 5 stars
139 reviews
49 repeat clients
15 years of experience
Newport News, VA, 23608

Cheyanne kept my Scooby for the holidays and not once ever made me feel like he wasn’t in good hands. She cared for our boy and kept us up to date on everything. So grateful for her services and will definitely rebook in the future!

Profile image
Monique H.
Sitter Profile Image: Alexis F.
Verified Enhanced Background Check
Alexis F.
Star Sitter
from
$30
per day
5.0 out of 5 stars
9 reviews
2 repeat clients
4 years of experience
Downtown, Hampton, VA, 23669

Alexis was super flexible and was great with my pup! She sent pictures and kept me updated. I would definitely book with her again.

Profile image
Alissa H.
Sitter Profile Image: Timerra L.
Verified Enhanced Background Check
Timerra L.
Star Sitter
from
$25
per day
5.0 out of 5 stars
41 reviews
15 repeat clients
25 years of experience
Mercury Central, Hampton, VA, 23666

Dani is an excellent sitter! She is very sweet and Ryder always comes home happy and tired. I love knowing my Ryder is being taken care of while im at work. Thank you!

Profile image
Victoria M.
Sitter Profile Image: Samantha T.
Verified Enhanced Background Check
Samantha T.
Star Sitter
from
$25
per day
5.0 out of 5 stars
72 reviews
14 repeat clients
1 year of experience
Newport news, VA, 23606

I could rave about how absolutely amazing Samantha was with my Khaleesi for hours, but I’ll keep it short for reading purposes. My dog Khaleesi is a high anxiety dog and does not do well with strangers and typically hides from them. Samantha had her during the day for 3 days, and from day 1 Khaleesi took right to her. It did take some warming up time, but Samantha kept me very updated and sent pictures throughout the day. By the end of the 3 days, Khaleesi was walking into Samantha’s house without hesitation and didn’t even turn around to look at me. Samantha is incredible and I highly recommend her!!!!

Profile image
Sara B.
Sitter Profile Image: Elisabeth F.
Verified Enhanced Background Check
Elisabeth F.
Star Sitter
from
$30
per day
4.9 out of 5 stars
194 reviews
58 repeat clients
20 years of experience
Hampton, VA, 23665

She's great! Really cared for our scared pups during their first time away from home. Definitely would use her again and recommend to anyone needing a caring and loving sitter for their fur babies.

Profile image
Amanda R.
Sitter Profile Image: Shawna B.
Verified Enhanced Background Check
Shawna B.
Star Sitter
from
$40
per day
5.0 out of 5 stars
78 reviews
26 repeat clients
20 years of experience
Newport News, VA, 23608

We had a great experience with Shawna! She took great care of our dog while we visited Busch Gardens for the day. We were provided videos and pics of her short stay, which was great!

Profile image
Michelle R.
Sitter Profile Image: Lauryn B.
Verified Enhanced Background Check
Lauryn B.
Star Sitter
from
$28
per day
5.0 out of 5 stars
46 reviews
16 repeat clients
12 years of experience
Newport News, VA, 23608

Very professional and caring.

Profile image
J1 gaming G.
Sitter Profile Image: Abigail L.
Verified Background Check
Abigail L.
from
$40
per day
5.0 out of 5 stars
170 reviews
51 repeat clients
35 years of experience
Gloucester, VA, 23061

Victor and Abigail were awesome and took extra steps to make sure our anxious pup had a great time. They sent us videos and pictures every day, which we really appreciated. After his first day in daycare, my dog was very excited to return on the following days. He seemed to really like the folks who took care of him and was nice and tired once I picked him up. Staying with these folks was definitely a mini vacation for my dog!

Profile image
Liz W.
Sitter Profile Image: Brandy G.
Verified Enhanced Background Check
Brandy G.
Star Sitter
from
$30
per day
5.0 out of 5 stars
105 reviews
38 repeat clients
30 years of experience
Buckroe, Hampton, VA, 23664

Brandy is an excellent dog sitter!!! I’m so grateful to have found her. She was quick to respond and immediately made me feel at ease. Milo went to her home for daycare and he did not want to leave! She played with him, took walks with him, and even did some obedience training. Milo came home tired and happy. She also sent photos and videos which always puts me at ease. I would highly recommend!

Profile image
Jessica S.
Sitter Profile Image: Ellie G.
Verified Enhanced Background Check
Ellie G.
from
$50
per day
5.0 out of 5 stars
29 reviews
8 repeat clients
20 years of experience
Locust Hill, VA, 23092

Ellie G. is a great communicator with photo updates. The daycare day went well and Annie O was introduced to Ellie’s chickens and I’m sure she wanted to get a little closer but Ellie was great keeping Annie away from them. Annie also met Ellie’s dog and it appears that they both made a new friend. The day was a success.

Profile image
Jacqueline E.
Sitter Profile Image: Tara M.
Verified Enhanced Background Check
Tara M.
from
$27
per day
5.0 out of 5 stars
4 reviews
1 repeat client
40 years of experience
Gloucester, VA, 23061

Tara was amazing with our fur babies ! She was very accommodating and kind ! Will definitely use her services every time we’re in the area 😊

Profile image
J D.
Sitter Profile Image: Michelle W.
Verified Background Check
Michelle W.
Star Sitter
from
$35
per day
4.9 out of 5 stars
484 reviews
180 repeat clients
25 years of experience
Yorktown, VA, 23692

I can't say enough good things about Michelle and her care of my Previous Demi! Demi loved going there! Michelle treated her like one of her own. I often have an unsure schedule and Michelle was so flexible and easy to work with. I wish I could take her with me to New Hampshire. But I will for sure use Rover to find my next sitter. I was extremely pleased with the whole process. Thank you so much!!

Profile image
Kat W.
Sitter Profile Image: Lynn P.
Verified Enhanced Background Check
Lynn P.
from
$45
per day
5.0 out of 5 stars
8 reviews
2 repeat clients
35 years of experience
Deltaville, VA, 23043

Lynn is very nice and kept me updated. Every so often she sent me pictures of Annie and their outings. Very communicative. I love that. We will definitely use Lynn again and will recommend her to friends. All in all it was a great day for Annie.

Profile image
Jacqueline E.
Sitter Profile Image: Renee W.
Verified Background Check
Renee W.
from
$50
per day
5.0 out of 5 stars
84 reviews
32 repeat clients
30 years of experience
Hudgins, VA, 23076

About: I am a lover of all animals. I currently have 4 goats, 10 pot bellied pigs, 5 cats. and 3 dogs and almost all of my pets are rescues. Your babies will get great care and attention when I visit or stay over. I will respect and abide by any rules you personally have regarding that. I work my full time job from home so your pet will get 24-hour care as well as lots of love and attention if over night stays are needed. I love going on walks with pets, and guarantee I can tire them out, even the most energetic of them by playing ball or any other thing they like. Plenty of time for play and walks. I can administer oral or injectable meds if needed. I know I am the perfect person to love and care for your pet while you are away. You can have the peace of mind knowing they are loved and cared for as if they were part of our family. I have spent my entire life around animals! My mother raised and bred Dobermans for many years and we took in rescue dogs as fosters. I also grew up around horses and other farm animals. I am comfortable with any breed so long as they are pet and people friendly. Since I personally have owned and currently own animals, I really understand the value of making them part of the family, not just a "pet" I look forward to hearing from you! I work full ti.e from home. Whereever there is wifi i can work which gives me lots of flexibility. I am able schedule around my calls easily. I spend time outside playing when applicable and allow for plenty of cuddle time. I often send pics so you will always see and know that your baby is doing fine.

Sitter Profile Image: Noelle L.
Verified Background Check
Noelle L.
from
$40
per day
5.0 out of 5 stars
75 reviews
20 repeat clients
15 years of experience
Magruder Area, Hampton, VA, 23666

I highly recommend Noelle. Our fur baby Max loves her. We have had no concerns leaving him with her for daycare and for an overnight. Max thinks he is apart of her family 😊

Profile image
Norvetta R.
Sitter Profile Image: Stephanie M.
Verified Background Check
Stephanie M.
Star Sitter
from
$55
per day
5.0 out of 5 stars
223 reviews
92 repeat clients
20 years of experience
Williamsburg, VA, 23188

Fantastic dog sitter. This is the third time Mazie has stayed with Stephanie. We were in town for my daughters Fife and Drum Performances and it was so nice to know Mazie was well taken care of. Highly recommend Stephanie.

Profile image
Jennifer H.
Sitter Profile Image: Sarah D.
Verified Enhanced Background Check
Sarah D.
Star Sitter
from
$40
per day
5.0 out of 5 stars
79 reviews
27 repeat clients
15 years of experience
Seaford, VA, 23696

Sarah did a fabulous job with Reno. He had fun, and she clearly loves having animals around so he felt welcome. She made me feel completely at ease leaving my precious pup for the day!

Profile image
Jim V.
Sitter Profile Image: Alyssa A.
Verified Enhanced Background Check
Alyssa A.
from
$40
per day
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
gloucester, VA, 23061

My dogs loved Alyssa and her puppy diesel. She took them for the day while we were sea kayaking. Would use again in a heart beat!

Profile image
Megan C.
Sitter Profile Image: Carolina S.
Verified Enhanced Background Check
Carolina S.
from
$35
per day
4.9 out of 5 stars
12 reviews
1 repeat client
20 years of experience
Gloucester, VA, 23061

this was a last minute and Caroline was very helpful to accommodate this and take care of our dog.

Profile image
Mike S.
1 / 1
View more sitters

Popular requests near you

Select a filter and find qualifying Winter Harbor Haven sitters!

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per day for doggy day care in Winter Harbor Haven is €30

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Winter Harbor Haven average 4
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Winter Harbor Haven on Rover as of Jun 2026 was about €30 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

As of Jun 2026, 185 sitters provided doggy day care in Winter Harbor Haven. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 89% of Winter Harbor Haven sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Winter Harbor Haven have an average of 18 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winter Harbor Haven.

Winter Harbor Haven doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Winter Harbor Haven sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 185 sitters offering doggy day care in Winter Harbor Haven on Rover, so you’re sure to find the perfect match for your dog! In Winter Harbor Haven, 100% of sitters offer daily exercise, 100% offer medication administration, and 90% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.