Dog Boarding Winchester

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Over 806
pet parents in Winchester have booked dog boarding

Winchester, Find top rated dog boarding

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Frank &  Saleha B.
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Frank & Saleha B.
$46
total per night
5.0 out of 5 stars
102 reviews
34 repeat clients
20 years of experience
Menifee, CA, 92584

Saleha & Frank took such good care of our dog. We very much appreciated the pictures they sent of our dog throughout the day. I would highly recommend them.

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Shelley D.
Sitter Profile Image: Stephanie R.
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Stephanie R.
$49
total per night
5.0 out of 5 stars
86 reviews
15 repeat clients
15 years of experience
Menifee, CA, 92584

Stephanie was incredible and was exactly what my female lab and our family needed. We recently had to put our elder pitbull down and suddenly leave town so we needed to board our female lab. Stephanie, her family were incredibly gracious to open their home as well as keep us up-to-date while we are out of country more than twice a day with videos and pictures and just reassurance. Thank you again Stephanie.

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Michael C.
Sitter Profile Image: Edgar & Denise M.
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Edgar & Denise M.
$55
total per night
4.9 out of 5 stars
66 reviews
25 repeat clients
14 years of experience
Hemet, CA, 92544

Our dog had such a good time with Edgar and Denise! He went on twice daily walks, lounged on the couch and got treats from their daughter! The daily pics and videos were awesome and helped us to relax on our trip knowing he was in good hands!!! We will definitely have Edgar and Denise watch our guy again!

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Kristin R.
Sitter Profile Image: Kimberly C.
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Kimberly C.
$56
total per night
5.0 out of 5 stars
23 reviews
4 repeat clients
26 years of experience
Menifee, CA, 92584

As a first time cat owner, we (my husband and I) were very unsettled about leaving her with a complete stranger. We needn't have worried. Kimberly was truly the "cat whisperer" for both my cat and us. Kimberly sent pictures communicated with us every day. We really can't thank her enough. She even trimmed Lollipop's nails!

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Danette M.
Sitter Profile Image: Rachel G.
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Rachel G.
$77
total per night
5.0 out of 5 stars
24 reviews
8 repeat clients
20 years of experience
Moreno Valley, CA, 92551

Rachel was absolutely amazing with my two pugs, Roxy and Kobe! This was my first time leaving them with a dog sitter, so I was naturally a little nervous, but she made the entire experience completely stress-free. Her communication was outstanding from start to finish. She always responded quickly to my messages, kept me updated on how my dogs were doing, and sent me plenty of pictures, which gave me so much peace of mind while I was away. Anytime I had a question, she answered right away and made sure I knew how Roxy and Kobe were doing. Before their stay, we met in person, and I also got to meet her adorable Golden Retriever, Chubbs. He is such a sweet and friendly dog, and Roxy and Kobe got along so well with him. It was comforting to know they were in such a welcoming environment. Rachel is kind, caring, professional, and truly loves the dogs she watches. I felt completely comfortable leaving Roxy and Kobe with her, and I wouldn’t hesitate to book with her again. I highly recommend Rachel to anyone looking for a trustworthy, reliable, and attentive dog sitter. Thank you, Rachel, for taking such wonderful care of Roxy and Kobe!

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Sabrina R.
Sitter Profile Image: Delaney B.
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Delaney B.
$56
total per night
5.0 out of 5 stars
16 reviews
5 repeat clients
14 years of experience
Menifee, CA, 92584

Always grateful for Delaney & her family, I never have to worry while out Coco is with them because I know they love her just as much as we do And Coco loves them and their fur babies!

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Irene W.
Sitter Profile Image: Tammi (Shigtastic) B.
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Tammi (Shigtastic) B.
$45
total per night
5.0 out of 5 stars
29 reviews
9 repeat clients
38 years of experience
Winchester, CA, 92596

Tammi’s the best! We have a Malinois that we needed help with. Our girl, Nymeria, can be a handful as a high energy, high drive pup. It’s pretty tough to find someone who understands her and we feel we got lucky finding Tammi. She did some training with her and helped us address behavioral issues. She communicates very well with us and is happy to answer any questions. We’ve definitely noticed the progress in Nymeria when it comes to jumping on people, waiting for direction, and how to behave/play with other dogs. She also loves playing with Tammis pup Ollie and usually comes home very tired. We’re definitely going to continue to book with Tammi.

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Jess F.
Sitter Profile Image: Jenny D.
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Jenny D.
$52
total per night
5.0 out of 5 stars
192 reviews
44 repeat clients
40 years of experience
Menifee, CA, 92584

We left our baby Toby with Jenny for 5 days. Jenny would send us photos everyday of Toby and update us on how he was doing. She is simply the best! Toby bonded with her and her son Charlie and had a really fun stay. I can't thank her enough for taking such great care of our Toby. She will definitely be the one we trust with him the next time we need a sitter. Thank you Jenny :)

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Nicole M.
Sitter Profile Image: Breeanna A.
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Breeanna A.
$67
total per night
5.0 out of 5 stars
33 reviews
9 repeat clients
6 years of experience
Hemet, CA, 92545

Maverique is young and very large. She loves people and other dogs, but is also excitable when entering a new situation. Breanna handled her very well and I am very pleased with her services.

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Ron G.
Sitter Profile Image: demelia r.
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demelia r.
$56
total per night
5.0 out of 5 stars
17 reviews
3 repeat clients
15 years of experience
menifee, CA, 92586

Super thankful for how well Demelia cared for my dog while I was away! The photo and video updates were such a nice touch—I could tell my fur baby was having a great time. I came back to a happy, relaxed dog. Will definitely book again.

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Mariejoy G.
Sitter Profile Image: Sandra B.
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Sandra B.
$56
total per night
5.0 out of 5 stars
7 reviews
3 repeat clients
50 years of experience
Menifee, CA, 92585

Fantastic! Made sure our pup was comfortable, fed and cared for. This was our first time using rover so we weren’t sure what to expect but Sandra made it such a great experience. She gave daily updates with pictures which was very comforting. When we came to pick up our pup he was not stressed at all and seemed very happy—which says it all.

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Kirsten K.
Sitter Profile Image: Luzi M.
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Luzi M.
$100
total per night
4.9 out of 5 stars
38 reviews
14 repeat clients
35 years of experience
Lake Elsinore, CA, 92532

Another wonderful stay with Luzi and her husband. Finn is treated like family when he stays there. Finn is nervous around most people but he is excited when we go drop him off with Luzi! Love all the updates and pictures of our pup while we are away! So thankful for a great sitter!

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Tara S.
Sitter Profile Image: Robert A.
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Robert A.
$56
total per night
5.0 out of 5 stars
121 reviews
29 repeat clients
25 years of experience
Murrieta, CA, 92563

We needed a last minute booking and thankfully Robert was able to take us, our dog LOVED her stay! Robert is such a sweetheart, and so is his family. My dog also made a new boyfriend and had tons of fun playing with Chief! The pictures were adorable, and some of them were even professional quality (I’m going to print one and hang it on our wall)! We definitely won’t hesitate to book with him again!

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Tam H.
Sitter Profile Image: Sahar S.
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Sahar S.
$39
total per night
4.9 out of 5 stars
60 reviews
13 repeat clients
18 years of experience
Murrieta, CA, 92563

Sahar was wondering! Very communicative and sent lot of updates which made me feel very comfortable with leaving my cat in her care. She also accepted my cat at last notice, just the day before.

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Yasmine N.
Sitter Profile Image: Angelica K.
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Angelica K.
$33
total per night
5.0 out of 5 stars
13 reviews
2 repeat clients
15 years of experience
Wildomar, CA, 92595

The best experience I’ve ever had on Rover. Excellent communication took care of my dog like he was family. Sent multiple pictures and videos without asking. Unbelievably good communication. I think my dog thought it was a vacation. He didn’t wanna come home. I cannot her more highly. Awesome experience.

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Scott M.
Sitter Profile Image: Rachelle F.
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Rachelle F.
$74
total per night
5.0 out of 5 stars
254 reviews
57 repeat clients
33 years of experience
Murrieta, CA, 92562

We had such a great experience with Rachelle! From the start, she cared a lot about our dog. We got regular updates and photos, which gave us total peace of mind while we were away. Our dog was happy, well-cared for, and comfortable which is always a great sign. We wouldn’t hesitate to book her again and highly recommend Rachelle to anyone looking for a trustworthy, kind, and attentive dog sitter. I’m very happy we chose Rachelle! 😊

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Maribel G.
Sitter Profile Image: Chad Z.
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Chad Z.
$38
total per night
5.0 out of 5 stars
2 reviews
5 years of experience
Murrieta, CA, 92563

Very sweet family that treated my pet as part of the family. Chad is great at communication and giving updates. Highly recommend to others.

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Nelson S.
Sitter Profile Image: Marisa C.
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Marisa C.
$43
total per night
5 years of experience
Menifee, CA, 92584

About: I've been working with animals for 5 years, and as of right now I am now currently working at a general practice animal hospital. I currently work full time, four days a week with 10 hours shifts, and I receive my work schedule a month in advance. I’m generally available on my days off, after work and on Sundays. I’m also able to bring pets to my work (if need be). I understand that every pet and family has different needs, so I’m always willing to do my best to accommodate special scheduling requests whenever possible. Even if a date or time doesn’t appear available on my calendar, please feel free to reach out and ask! I may be able to adjust my schedule or make arrangements that work for you and your pet. My goal is to provide dependable, and attentive care while making things as convenient as possible for both you and your pet. I treat every pet in my care as if they were part of my own family. I want them to feel safe, comfortable, and loved while they’re with me. I enjoy spending quality time with them, whether that means relaxing at home, playing outside, going for walks, or visiting the park for some exercise. I also work as a veterinary assistant, which has given me hands on experience caring for pets with a variety of medical and special care needs. I’m comfortable administering medications as directed, including oral and injectable medications, as well as providing subcutaneous fluids and other routine supportive care when appropriate. I always follow each pet parent’s instructions and routine as closely as possible, including feeding schedules, medications, exercise and any special care needs. Most importantly, I make sure every pet receives plenty of attention, affection, and supervision while in my care.

Sitter Profile Image: Tashia H.
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Tashia H.
$54
total per night
5.0 out of 5 stars
11 reviews
3 repeat clients
13 years of experience
Hemet, CA, 92545

I’m happy I made the choice of leaving my baby Georgie with Tasha. She was a great at communicating, and sending me pics and videos. I would definitely leave him with her again. Thank you Tasha.

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Sabrina S.
Sitter Profile Image: Edith H.
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Edith H.
$56
total per night
4.7 out of 5 stars
15 reviews
3 repeat clients
5 years of experience
Beaumont, CA, 92223

Edith was so responsive the whole time she watched our maple girl. We loved having maple stay with her and would recommend her to anyone in the area !! :)

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Kelsea M.
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The median cost per night for dog boarding in Winchester is $56

Dog parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

So happy I found them for our dogs. We've had terrible experiences with boarding facilities in the past. So this is the first time trying Rover. What a blessing! Our dogs were treated with utmost care. They had a yard to run and play in and kids. It was just what our dogs needed. Treated like a family member. I would highly recommend to anybody that is looking for high quality care for their pups.

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Mindy B.
Boarding
5.0 out of 5 stars

Jennifer was amazing! Very communicative and took such great care of our pup. Such a kind person and we’re so grateful to have found her on Rover. Highly recommend!!

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Adrian O.
Boarding
5.0 out of 5 stars

Casey is great. She’s watched my pup twice now, and both times he is very well taken care of. She responds right away, is very accommodating. 10 out of 10 recommend every time.

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Chase R.
Boarding
5.0 out of 5 stars

Tammi was awesome! She took great care of my Koko Bean. She was very attentive, professional, and super nice. My pup was super happy when I picked her up, so I know she was well taken care of. Thank you Tammi! We’ll definitely use her service again in the near future.

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Erika D.
Boarding
5.0 out of 5 stars

Jessica took very good care of our puppy, Po. She was attentive and caring, made sure we felt like he was in the best of hands. We loved the videos and pictures she sent us every day.

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Sarah L.
Boarding
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

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

  • World-class support

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

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding
  2. 2. Meet In Person

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Popular requests for dog boarding - Winchester

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Sitters in Winchester average 12
repeat dog boarding clients

FAQs for Dog Boarding - Winchester

Frequently asked questions about Rover

The average cost for Dog Boarding in Winchester on Rover is $44.4 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .

As of September 2026, there are 1,680 sitters on Rover offering Dog Boarding across Winchester. Enter your ZIP code to see which available sitters are closest to your home.

Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.

95% of Winchester sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Winchester landmarks or neighborhoods your dog is enjoying.

If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Winchester home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Winchester.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Winchester sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in CA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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