Dog Boarding in Winter Harbor Haven

Your dog stays overnight at a reliable dog sitter's home whilst you're away

47 results for Dog Boarding in Winter Harbor Haven, VA

Sitter Profile Image

Omaira & Isaac Z.

(237)
54 repeat clients
from $30.00
per night

O&I was able to take in Beamer as last minute and a 10pm drop off/pickup request to due to work meeting. Just moved to the area and they made Beamer feel comfortable.

Sitter Profile Image

Jackie & Kevin K.

(112)
46 repeat clients
from $35.00
per night

I left Milo and teddy with Jackie and Kevin from 4/12/26-4/19/26. They treated my dogs very well and also kept me updated by sending me the pictures of my dogs. I can tell Milo and teddy were very relaxed and comfortable with them. I really appreciate them for taking care of my dogs and will definitely reach out to them again in the future.

Sitter Profile Image

Rodney M.

(75)
19 repeat clients
from $35.00
per night

Rodney was amazing! Plenty of pictures and updates twice a day. Took our pups on walks every day and they absolutely loved it. Will only be booking exclusively with Rodney in the future!

Sitter Profile Image

Amy J.

(10)
6 repeat clients
from $35.00
per night

Great communication with several texts/pics of our pup to let us know how she was settling in - went out of her way to make her a comfy bed and find her”babies” to snuggle at night ♥️

Sitter Profile Image

Shanae R.

(24)
11 repeat clients
from $30.00
per night

The absolute best! This was my fur baby’s first time away from home, first time being several days away from me and the family. Shenae is so personable, sent may pictures and videos and just understood how tough it was to be away. Typically my pup has separation anxiety just in leaving for work, and yet in all the videos his tail was wagging, he was excited and happy. He was playing with her fur baby’s Ash so well. I can’t rave enough! I’m so grateful I found her and to how well she cared for him.

Sitter Profile Image

Deemie B.

(52)
11 repeat clients
from $25.00
per night

Deemie was great! She took awesome care of my dog and sent updates along the way. She was super flexible with the drop off and pick up times as well! I would highly recommend and will definitely use her again for any pet sitting needs!

Sitter Profile Image

Monica P.

(46)
19 repeat clients
from $45.00
per night

I absolutely recommend Monica for all pet care needs. After a not-so-great boarding experience in the past we were very nervous to leave our dog anywhere but Monica’s gentle care and love for animals was immediately apparent and it put us at ease. She provides regular updates and is quick to respond. Our dog has been with Monica twice and just loves her and her pups as well. We will absolutely be rebooking again :)

Sitter Profile Image

Lyra & Scott H.

(224)
74 repeat clients
from $39.00
per night

Lyra and Scott did an amazing job caring for our dog! They were great communicators and sent pictures to let us know how much fun our dog was having. I highly recommend them!

Sitter Profile Image

Alexandra B.

(213)
141 repeat clients
from $50.00
per night

Awesome person and animal lover. Kept us posted on our dog on a daily basis without even asking. Very flexible on the days we needed her to look after our dog. Just a wonderful person overall.

Sitter Profile Image

Vianca A.

(15)
7 repeat clients
from $38.00
per night

Vianca and her family made my anxious little guy feel right at home. She was flexible, communicative, sent photos, and even went and purchased him more food when he ate through what we provided. Very grateful for her time and care.

Sitter Profile Image

Suzanne V.

(13)
2 repeat clients
from $34.00
per night

Suzanne and her family are amazing! I’ve booked with her multiple times, and always feel at ease leaving my dog knowing he’s in great hands. She’s also great at communication and frequent updates along with pictures. I plan to seek her out anytime I need a Rover.

Sitter Profile Image

Tyrah J.

(8)
1 repeat clients
from $28.00
per night

Tyrah is such a lifesaver, she was available for a last minute booking and my boys enjoyed their stay. Thank you again

Sitter Profile Image

Tameka B.

(49)
15 repeat clients
from $40.00
per night

Tameka was a wonderful pet sitter. My dog visited for the first time this week. Tameka’s dog was very friendly and ready to play with our dog at first sight. My dog enjoyed their fenced in back yard, during his overnight stay.

Sitter Profile Image

Heather A.

(51)
24 repeat clients
from $45.00
per night

Heather is a godsend. This was my first time leaving my 10 month old extremely high energy GSP/Springer puppy. And knowing he was with her, made it so much easier. She sent updates and pictures that were really appreciated. Heather is a wonderful dog sitter and I could tell how happy my puppy was that he enjoyed himself so much.

Sitter Profile Image

Jared L.

(82)
25 repeat clients
from $48.00
per night

Quincy had another incredible stay with Jared! I was surprised to see how excited she was driving to his house as this was only her second stay but she knew exactly where we were headed and was quite happy to see Jared. It is so great to know I have a place to leave my sweet girl with someone I trust and who treats her well and gives her lots of attention and love while I am away. Thank you again!!!

Sitter Profile Image

Ellie G.

(31)
9 repeat clients
from $60.00
per night

Ellie was so great with our dogs. She went above and beyond to take good care of them. Instead of leaving them at boarding- it was more like they went to camp. I will definitely be calling Ellie again.

Sitter Profile Image

Deidre Y.

(14)
3 repeat clients
from $40.00
per night

Ms.Deidr is a gentle patient lady who took great care of my cat Gabi while I was on a weeks vacation. We chatted like old friends and she gave me great tips. I plan to use her service again in October. I know Gabi will be spoiled and loved😻

Sitter Profile Image

Abagail C.

(6)
4 repeat clients
from $34.00
per night

Great sitter who really loves animals. Will definitely book again!!

Sitter Profile Image

Janel G.

(459)
228 repeat clients
from $35.00
per night

From the pictures I could tell my dogs were having so much fun. I thought they wouldn’t wanna come home. They absolutely love the other dogs. Highly recommend.

Sitter Profile Image

Maria G.

(24)
7 repeat clients
from $40.00
per night

Caring and experienced cat sitter. Maria was professional, attentive, detailed, and patient. She always sent me pictures and videos of my cat which I truly appreciated. I could tell my cat was in great hands.


Find Dog Boarding in Winter Harbor Haven

The alternative to dog boarding kennels

Are you looking for Dog Boarding in Winter Harbor Haven to take care of your beloved dog? You are in the right place! We currently have 47 experienced, loving and background-checked dog care specialists in Winter Harbor Haven. Our sitters offer a variety of pet services such as home dog boarding, dog walking and doggy daycare. Make an informed decision based on reviews, response rates and contact at least 3 approved Dog Boarding professionals. Your dog will be delighted to be looked after by our loving dog sitters.