Dog Boarding Winchester
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 44 pet parents in Winchester have booked dog boarding
Winchester, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: Hello!! I have two cats a beautiful Red Calico and a Siamese Mix as well as a Bordercollie Mix puppy. I have grown up with cats and dogs and would love the chance to help out the community! I am currently working part-time in this economy its hard to make it on one income, so why not do something you enjoy on the side? I have an enclosed back porch that all animals enjoy! My cats have a inside door to go in and out as they please and puppies go out for supervised play time.
“My cat Willow had such a great time! I loved getting pictures everyday to see how she was doing. She was cared for so well! I’m so glad there’s someone close by that I can trust to help out with my animals!!”
“Shannon is great! Her and her dog Goose are very welcoming. They were able to give my doggo the best time while I was away. It's hard to leave your dog behind on a trip but it's a lot easier when you know they are in good hands. She gave me great pictures and videos so I could be at ease while I was away.”
“my dog was happy and healthy after I picked him up. Ana was very communicative throughout the boarding period and sent me daily pictures which I used to wait for. My dog seemed to get a lot of outdoor times, walks, and playtimes with other dogs. I also opted for the bathing service. He came back looking fresh and his coat was very well taken care of. definitely recommend her!”
“Everything was great with Shakia! She took great care to understand Rosie's needs, and made sure to communicate with me. I especially loved that Rosie got a couple of walks in the country. I fully expect to book with Shakia again!”
“This was the first time I have used Victoria’s service. When I was dropping off my Bassets with her, I immediately sensed the friendliness presence with her and her family. The dogs were comfortable and happy. She sent me pictures yesterday. Was very friendly today. I will be booking with her again.”
About: I have had pets my whole life. I am very active and love playing with and walking your babies. I have had the privilege to watch many fur babies in the Winchester, Tullahoma and Manchester area. I have lived in Tullahoma for a year, with my two dogs. All 5 of my children are now out of the house. I am not working, teaching or Coaching. Therefor I have a lot of time. My only commitments are when I go watch my kids play Lacrosse at their Colleges. My husband travels so I thought this would be a fun way to make some side cash and new friends. I have a fenced yard and will accept crated dogs too. I have opened my home to overnight pets. At your home, I get on the floor and play with the fur babies and go for walks.
“Patrick was awesome for taking Whiskey last minute. I am a nervous fur baby mom. So I like a lot of pictures and updates, Patrick did communicate everyday, but sometimes later in the day. He has a sweet fur baby that Whiskey loved playing with. Patrick was very sweet and playful with my high energy Bel Mal.”
“Jenna was great! Milo really had a wonderful time with her and she said he even did well with her cat(s). She’s responsive, attentive and loving with her care for fur babies. Will be rebooking with her again!”
“Jodi was amazing with our puppy Bennie! It was our first time boarding him and she alleviated all nerves. She sent multiple updates and wonderful photos. He even got sick for the first time and she helped him through it while we were away. She is wonderful and Bennie loves her! Will definitely book Jodi again!!”
“I had a bit of a last second same day emergency with my pet sitting plans, and Christina agreed to watch my pup same day! It's always a bit nerve wracking leaving your pup in a new place for a weekend but Christina eased those worries immediately. Very good communication, sends lots of updates and My pup Maddux had the time of her life. I will definitely use Christina everytime I go out of town from now on and happy to have found Maddux's new sitter. Very easy drop off and pick up. Thanks Christina.”
“Stephanie really brought out my dog’s personality! T had the time of her life and I knew she was in good, qualified hands. I even learned a thing or two. I would definitely recommend Stephanie and will be back next year. *such cute photos too :)”
About: I have cared for dogs, cats, snakes and hamsters of multiple breeds/sizes for friends overseas. No special training but self taugh crate trainer and have worked primarily with puppies/kittens I work from 8am-4pm four to five days a week. Mornings i make sure pets have food/water and their first potty break. If needed, I come home from 11am-1pm to let dogs out again. I have a big backyard that i am able to fence off for play. Crated pets will stay in my spare bedroom or living room. I prefer to let pets roam and not be crated all day.
“Haley and her Family are outstanding providers. My little guy obviously got all the love and attention as if he were with me. (No doubt MORE so than he is accustomed to) :D My buddy felt right at home the moment he walked in. Making me feel comfortable with leaving him with Haley and her Family. I am appreciative and thankful to have found Haley on such short notice. Dude misses you all and thank you again for taking care of my Buddy.”
About: I have had dogs in my house since I was born and love all animals. I have experience in walking and sitting dogs and cats from the animal shelter as well, so I am comfortable with all shapes and sizes. I am a seasonal worker so I move around and often have crazy jobs. Pet care is something I love to do for fun, and a bit extra cash. If you book with me, you and your baby will be my top priority! I will make sure they get walked and fed while giving them a bunch of hugs and kisses! If your area is safe to take them out, I enjoy taking them for walks or playing out back with their favorite toys.
“Kayleigh was fantastic to work with. Excellent communication and flexibility. Our golden retriever Chipper had the time of his life staying with the other dogs, too. Overall a great experience. Thanks Kayleigh!”
The median cost per night for dog boarding in Winchester is $39
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- 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.
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Popular requests for dog boarding - Winchester
Select a filter and find qualifying sitters offering dog boarding.Sitters in Winchester average 5 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 $43.07 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 44 sitters on Rover offering Dog Boarding across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter 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.
Sitters may also include daily walks in the neighborhood during your dog's boarding stay. You can also request photo and message updates throughout so you can see which local 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 TN 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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