Dog Boarding in Windham, VT
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Top rated Windham dog boarders
“I left my golden retriever with Briana for the weekend. She provided pictures, updates, and my dog was happy as can be during pickup. He played great with her dog and I will definitely use her again.”
“Nancy is so pleasant and kind. Watson came back happy and tired - all good signs! If we are ever in the area again, we would not hesitate to ask Nancy to watch Watson again. And what a view!!”
“I knew Winnie was in great hands right away. Hope made sure to ask all the right questions and played with our anxious puppy as we left so Winnie wouldn’t cry. Hope also went out of her way to drive two hours round trip so Winnie could be the flower girl in our wedding ceremony. It’s obvious how much she loves dogs and knows how to handle them.”
“Our pup has stayed with Ashley and her family twice now. Ashley is great! She sends sweet updates, photos, and videos if you want. My dog was so happy to see her he didn't even care that I was dropping him off. My dog likes kids and other dogs, so her household is all fun for him. They took great care of him, and we will use them again for sure!”
“Kate is sooo wonderful! It was my first time looking for a sitter and i was worried because I never left my dog with someone that’s not my family members or friends but my Bella took to her right away and gets so excited to see her. Kate is very responsive to texts and keeps me posted with photos I feel so much at ease knowing that my pup is well looked after. Thank you Kate for taking such a good care of my dog while I was away 🙏🏻”
“Pepper stayed with Laura for 3 nights while we went away. We felt at ease leaving her, knowing she would be well taken care of. We were not wrong. When we went to pick her up I could tell she had made a new friend and was comfortable with Laura. I am so thankful we picked Laura to take care of Pepper.❤️”
“It was our first time using Rover, and our first time leaving Juniper with someone who wasn't family, friend or vets - and we could not have been luckier to find Tara. She communicated well, sent plenty of pictures and updates and made everything flawless. We had to switch our drop-off time and she was so nice about it. Everything was simple and it all turned out great! I could not recommend her more!”
“Callie had a wonderful time and their dog Amber is her new best friend! Tom kept us up to date with plenty of pictures and we could see she was being well-cared for. She was "doggone" tired when she got home, which we appreciated!”
“Richard and Hope took great care of Betty; lots of outdoor time and playing with children. They obviously LOVE dogs and make them part of their family! If I’m back in their ar3a, Betty is definitely staying with them again!”
“Romeo seemed to have a good stay overnight with Elijah, Carson and their dogs and cats. I received photos and updates and Romeo seemed very tuckered out when he got home so I think he probably had lots of stimulation and fun. Thank you! We will be back!”
“Ringo had a great time. Kaylea communicated very well and her dogs enjoyed having our dog around. Kaylea send us some nice pictures and kept us updated on Ringo’s 3 night stay.”
“Letícia took excellent care of our dog for five nights while we were away. She sent many wonderful photos and videos of Jojo playing, running and looking so happy that it made it easier for us to enjoy our vacation.”
“Haley was absolutely amazing! She was able to accommodate us last minute, which was such a relief. From the very beginning, her communication was outstanding—she kept me updated regularly, which gave me so much confidence that my dog was happy and well cared for. Her own dog is super chill and friendly, and the welcoming atmosphere created by her other family members made my dog feel right at home. Even though I didn’t know Haley very well at first, her attentiveness and warm family setting made it clear my dog was in great hands. I highly recommend Haley to anyone looking for a trustworthy and caring sitter!”
“My pups had so much fun with Kaitlin and her son! The communication was prompt from the onset of booking our appointment and it was easy to coordinate drop off and get updates throughout their stay. Kaitlin made sure the pups got lots of time outside and they looked cozy cuddled up in her home. I would definitely recommend her to others!”
“Christine was taking care of our beagle Dexter while we were in the area attending an event. She has a lot of positive energy and is very compassionate and knowledgeable. Great communicator, what's a big plus! Our puppy had separation anxiety, but she engaged and calmed him down. We felt confident leaving Dexter in her house.”
“Mike and Laura are wonderful. You can immediately tell just how much they love animals and they treated our pup like he was their own. They kept us up to date the whole visit with lots of pictures and videos and made sure our dog had a great time. He got tons of exercise and play and they made sure he had a nice soft spot to snuggle down. Their property is also a great location with wide open fields and plenty of places to take a dog for good walks and sniffs. I'd highly recommend Mike and Laura and I know our dog will be looking forward to another visit with them in the future!”
“Danielle looked after our dog for a few days while we travelled. Without hesitation, I would recommend her and gladly use her services again. Danielle has a kind, positive nature. She was accommodating and our dog took to her immediately. She kept us updated, gave him lots of exercise and attention, and has a lovely location for a dog to have a holiday of their own. 5+ stars! Thanks Danielle.”
“DJ was excellent with my pup and I will definitely be keeping him in mind when booking in the future. He was very communicative and sent lots of updates as well as cute photos of their adventures. I highly recommend him to anyone looking for a responsible, caring sitter.”
Loving dog boarding sitters in your neighborhood
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Briana L.Star Sitter
“I left my golden retriever with Briana for the weekend. She provided pictures, updates, and my dog was happy as can be during pickup. He played great with her dog and I will definitely use her again.”
Nancy H.
“Nancy is so pleasant and kind. Watson came back happy and tired - all good signs! If we are ever in the area again, we would not hesitate to ask Nancy to watch Watson again. And what a view!!”
Hope R.Star Sitter
“I knew Winnie was in great hands right away. Hope made sure to ask all the right questions and played with our anxious puppy as we left so Winnie wouldn’t cry. Hope also went out of her way to drive two hours round trip so Winnie could be the flower girl in our wedding ceremony. It’s obvious how much she loves dogs and knows how to handle them.”
Ashley M.Star Sitter
“Our pup has stayed with Ashley and her family twice now. Ashley is great! She sends sweet updates, photos, and videos if you want. My dog was so happy to see her he didn't even care that I was dropping him off. My dog likes kids and other dogs, so her household is all fun for him. They took great care of him, and we will use them again for sure!”
Kate B.
“Kate is sooo wonderful! It was my first time looking for a sitter and i was worried because I never left my dog with someone that’s not my family members or friends but my Bella took to her right away and gets so excited to see her. Kate is very responsive to texts and keeps me posted with photos I feel so much at ease knowing that my pup is well looked after. Thank you Kate for taking such a good care of my dog while I was away 🙏🏻”
Kevin & Inez W.Star Sitter
“Great response time. Was grateful they were available on such short notice which I was not expecting. Sent pictures and kept me updated during my dog’s stay.”
Laura P.
Star Sitter
“Pepper stayed with Laura for 3 nights while we went away. We felt at ease leaving her, knowing she would be well taken care of. We were not wrong. When we went to pick her up I could tell she had made a new friend and was comfortable with Laura. I am so thankful we picked Laura to take care of Pepper.❤️”
Tara R.Star Sitter
“It was our first time using Rover, and our first time leaving Juniper with someone who wasn't family, friend or vets - and we could not have been luckier to find Tara. She communicated well, sent plenty of pictures and updates and made everything flawless. We had to switch our drop-off time and she was so nice about it. Everything was simple and it all turned out great! I could not recommend her more!”
Tom D.
“Callie had a wonderful time and their dog Amber is her new best friend! Tom kept us up to date with plenty of pictures and we could see she was being well-cared for. She was "doggone" tired when she got home, which we appreciated!”
Richard & Hope R.
“Richard and Hope took great care of Betty; lots of outdoor time and playing with children. They obviously LOVE dogs and make them part of their family! If I’m back in their ar3a, Betty is definitely staying with them again!”
Elijah & Carson H.
“Romeo seemed to have a good stay overnight with Elijah, Carson and their dogs and cats. I received photos and updates and Romeo seemed very tuckered out when he got home so I think he probably had lots of stimulation and fun. Thank you! We will be back!”
Kaylea N.Star Sitter
“Ringo had a great time. Kaylea communicated very well and her dogs enjoyed having our dog around. Kaylea send us some nice pictures and kept us updated on Ringo’s 3 night stay.”
Letícia B.
“Letícia took excellent care of our dog for five nights while we were away. She sent many wonderful photos and videos of Jojo playing, running and looking so happy that it made it easier for us to enjoy our vacation.”
Haley C.Star Sitter
“Haley was absolutely amazing! She was able to accommodate us last minute, which was such a relief. From the very beginning, her communication was outstanding—she kept me updated regularly, which gave me so much confidence that my dog was happy and well cared for. Her own dog is super chill and friendly, and the welcoming atmosphere created by her other family members made my dog feel right at home. Even though I didn’t know Haley very well at first, her attentiveness and warm family setting made it clear my dog was in great hands. I highly recommend Haley to anyone looking for a trustworthy and caring sitter!”
Kaitlin O.
“My pups had so much fun with Kaitlin and her son! The communication was prompt from the onset of booking our appointment and it was easy to coordinate drop off and get updates throughout their stay. Kaitlin made sure the pups got lots of time outside and they looked cozy cuddled up in her home. I would definitely recommend her to others!”
Sean O.
“Benji had a great time with Sean and his dog Elora! Sean sent pictures and updates during the two night stay and Benji came home very relaxed and seemed to have a great time. Thanks!”
Christine C.
“Christine was taking care of our beagle Dexter while we were in the area attending an event. She has a lot of positive energy and is very compassionate and knowledgeable. Great communicator, what's a big plus! Our puppy had separation anxiety, but she engaged and calmed him down. We felt confident leaving Dexter in her house.”
Mike & Laura O.
“Mike and Laura are wonderful. You can immediately tell just how much they love animals and they treated our pup like he was their own. They kept us up to date the whole visit with lots of pictures and videos and made sure our dog had a great time. He got tons of exercise and play and they made sure he had a nice soft spot to snuggle down. Their property is also a great location with wide open fields and plenty of places to take a dog for good walks and sniffs. I'd highly recommend Mike and Laura and I know our dog will be looking forward to another visit with them in the future!”
Danielle L.
“Danielle looked after our dog for a few days while we travelled. Without hesitation, I would recommend her and gladly use her services again. Danielle has a kind, positive nature. She was accommodating and our dog took to her immediately. She kept us updated, gave him lots of exercise and attention, and has a lovely location for a dog to have a holiday of their own. 5+ stars! Thanks Danielle.”
Donald C.
“DJ was excellent with my pup and I will definitely be keeping him in mind when booking in the future. He was very communicative and sent lots of updates as well as cute photos of their adventures. I highly recommend him to anyone looking for a responsible, caring sitter.”
Popular requests near you
Select a filter and find qualifying Windham sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
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 night for dog boarding in Windham is $60
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 boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Windham average 7 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 33 sitters provided dog boarding in Windham. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters 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, 95% of Windham dog boarding sitters respond in under an hour.
Dog boarding sitters with repeat customers have an average of 7 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 Windham.
Rover makes it easy to find Windham dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 33 dog boarding sitters in Windham on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding 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 dog boarding 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.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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