Dog Boarding Windermere
Find a loving dog sitter to watch your dog overnight at your sitter's home.

Over 136 pet parents in Windermere have booked dog boarding
Windermere, 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.

“Bunny has made another family at Charmaine’s place. He made loads of friends and we found him squeaky clean when we picked him up. Charmaine is our go to if we going out of town ever again.”

“Nathan was wonderful, excellent communication, lots of photos and treated my dog like one of his own. My dog had such a great time during his stay he barely registered that I was home after 10 days away. Will definitely use Nathan again next time I travel! So grateful to have someone I don’t have to worry leaving my kiddo with.”

“My sweet dog had a wonderful time with Carolyn. I received daily pictures so I knew she was having a good time. And Carolyn was proactive in communicating with me when my pup’s food was low. I wouldn’t hesitate to recommend Carolyn to others except she doesn’t need my help! Her past reviews speak volumes.”

“Sheena took great care of my dog, Uno. She handled introductions between Uno and her own dog really well. She updated me with photos, and Uno looked like he was having a great time. It was clear he was in good hands and well cared for. I’d definitely recommend Sheena to anyone looking for a reliable and attentive dog sitter.”

“Lorena was great. This was Tuesday's first time staying with someone new and it worked out really well. Lorena and her family made her feel comfortable. Lorena was very responsive, flexible and understanding!”

“He was so kind and took wonderful care of my dog! Made sure everything was talked through before I left him overnight, I had no doubt my dog was going to be taken good care of.”


“Sitter was super nice, place is super clean and has a backyard for dogs to play. She took great care of my dog he seemed happy in all the pics and when I picked him up. I’m glad to find a sitter I trust!”


“Isabella was so so great with our dog, Benji! She kept us updated on how he was each day and really went the extra mile with making sure Benji was comfortable. Really appreciate the great care and I wouldn’t think twice about leaving my dog with her again ! ❤️”

“Joyce is so great! She helped me out in a bind when I needed a last minute sitter while at work. She has a GREAT backyard space that is perfect for dogs to run and play. She is very laid back and easy to work with. She sent me updates throughout the day as well that were adorable. Thank you SO much for all that you do! We would love to use you again!”

“Margaret and Tony gave us the rare gift of peace of mind. From the moment we met them, it was clear how much they genuinely care for animals. They were wonderful with our two dogs—patient, affectionate, and attentive to their routines. While we were out of the country, they kept us updated and made sure our pups felt safe and loved. We came home to dogs who were content, relaxed, and clearly well cared for. We couldn’t ask for better sitters.”

“Paige took great care of Griffin, our senior Schnauzer. She was easy to work with, responded quickly to questions and sent pics so we could see how our pup was doing. She is very trustworthy and a great sitter. Thank you! Brad”

“Ziyan took such great care of our Sadie while we were away! She made sure that Sadie was comfortable with her dog prior to the stay and sent daily updates and pictures, even taking her on hikes and runs. We truly felt like she treated Sadie like a member of her family and would love to have her watch Sadie again!”

“Tianci took good care of Bagel! I enjoyed the shared Google photo album very much as they walked Bagel around the city and kindly also took him to the treat store.”

“Talia was wonderful with my nervous little guy and very understanding of how to manage his anxieties. He was definitely also put more at ease by having sweet Miss Cedar as a buddy and mentor. I was very grateful for the updates, quick communication, and knowing he was in very capable hands. I’d love to be able to board Xavi with Talia again in the future!”

“Kathryn & Mark are the best! They keep me updated on everything, and took the best care of our Remi! Definitely would recommend using them for the best doggy care🩷🩷”

“I have been using Rover for years now, and I can confidently say that Maiko is the BEST Rover dog sitter I've ever had and I will try every time to secure a stay with her for my mini bernedoodle, Trixie, in the future. Maiko only sits for one dog at a time, is a dog lover and former dog owner herself (who sadly lost her own pup about a year ago), a near-professional photographer who sent us the best photos of Trixie we have ever had(!), and her two young children adored and were so good with Trixie as well. Maiko is superb all-around, with communicating (asked us of her own volition how Trixie handled fireworks, as she watched Trixie over 7/4 holiday), with caring (Trixie so obviously grew so fond of Maiko and her family, with photos of her nestling against them all!). Trixie came home to us in great spirits, relaxed and happy, which has not been our experience often in the past with Rovers who watch multiple dogs at a time. Maiko is the BEST!”

“Wow Alexa and her family go above and beyond in making sure your fur baby is well taken care of, and that you are thoroughly communicated with every step of the way. Truly, she is an exceptional sitter, and Stella came home well-rested, comfortable, and anxiety free (rare for her!!!). Expectations entirely exceeded!! Thank you!!”

The median cost per night for dog boarding in Windermere is $60
Dog parents share their Rover experiences - Windermere
Carolyn is very friendly, attentive and responsive. She sent multiple pictures daily which I really appreciated. Our dog, Sully, is an only-dog so he really enjoyed having other dogs to play with and going to the park. Carolyn is a dog lover who has a dog-friendly home and lifestyle. I wont hesitate to book another stay for Sully when the time comes!

Juno had such a great time staying with Wen Yi and her family! They were great at communicating and working with us to accommodate her needs. We received so many updates, we never had to worry about how she was doing, which is very rare among sitters we’ve used.

Pam was fantastic! My Maxie loved her immediately, so glad I was referred to her! I had been stressing out, but after meeting Pam I felt much more at ease! I’m sure we will be coming back, Max would be thrilled to see her again and all the friends he made! He was very well taken care of!

We had such a great experience with Joyce! She was incredibly friendly, communicative, and kept us updated throughout Lola’s entire stay. She was very reassuring and made us feel confident that Lola was in great hands, which gave us so much peace of mind while we were away.

Sheena provided a caring and attentive environment for my dog. She sent photos to me during the trip so I could see that my pooch was doing well. Sheena is clearly a dog lover and took the time to do a "meet and greet" at the dog park one day--so we could see if our two dogs would get along. She also allowed me to bring my dog over to our place before my trip so he could sniff around and get a feel for where he would be staying.

Xinhui is great! Our dog takes time to warm up to new people. Over the course of a few days our dog allowed Xinhui and her partner to pet her, which was a big milestone! Xinhui shared daily updates including photos and videos. We could enjoy our vacation in peace knowing that our dog was well.

Marina, Bret and Georgia took wonderful care of Bronny again. They kept up with his routine without missing a beat and sent photo updates that always made our day. They’re also incredibly responsive whenever we reach out. It’s such a relief knowing we have sitters we can count on for Bronny. Can’t recommend them enough!

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
Book and pay through Rover’s secured platform—no cash or checks required.
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. Search
Browse profiles of sitters near you who offer dog boarding
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform















