Dog Boarding in Windham, ME
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Top rated Windham dog boarders
“Cindy was amazing with our dog Loki! We felt so much more comfortable leaving him with her than we ever have at a traditional boarding facility. From the start, she was super flexible—when our travel plans changed last minute, she was totally accommodating and easy to work with. Communication was on point the entire time. Cindy sent us regular updates, including photos and videos, which gave us so much peace of mind. It was clear Loki was having a great time—he had dog buddies to play with, was allowed on the couch (which he loved), and genuinely looked happy and relaxed in every update. Not only did she treat Loki like one of her own, but her home is also lovely and the backyard was perfect for him to run around and play. That made a huge difference for us knowing he had space to enjoy himself. We couldn’t be happier with our experience and will absolutely book with Cindy again in the future. Highly recommend!”
“Our pup is a sensitive, nervous guy. Marna made sure he felt loved and at home. I could tell he was having fun with her family through the photos she sent. She filled us in each day and sent photos. 🤩 Will definitely use Marna again!”
“Great stay for Miss Louise who has been exhausted sleeping on me since she got home. She loves seeing Elisabeth and her very sweet crew of dogs!”
“This is the third time we have left our pup with Jennifer. She does a great job of sending daily (twice daily) updates and photos. We know Max is well cared for and well loved when he stays there. He loves Maya as well!”
“We are so grateful to have found Kelly! She took such wonderful care of our dog while we were away, treating him like part of her own family. Communication was excellent — we received regular updates with photos that put us completely at ease. It was clear from the moment we met Kelly that she genuinely loves animals and has a real gift for connecting with them. Our dog came home happy, relaxed, and clearly well-loved. We couldn’t have asked for a better experience and would absolutely trust Kelly again for future stays!”
“Christina did a great job with Crosby. I trusted that he was well cared for and got lots of love and attention. Normally a very stressed out dog, he seemed very relaxed when I picked him up. We'll definitely use her again in the future.”
“Molly did a great job with our dog, Watson! Watson is an anxious boy, but in no time I received a picture of him asleep, cuddling on their couch. We'd be happy to work with Molly again!”
“It felt so good to know that my pup was having a good time at Heidi’s thanks to all the adorable pictures and videos she sent throughout the week. It’s like he was on his own vacation 😎”
“Benny was sad for 2 days after I brought him home from his "vacation"!! I think he had more fun at Vicky's than I had in Mexico! I'm sure he can't wait until the next time I go away; I hope she'll be available again. As we drove away from her house, he stared out the window and whined! He almost never whines! Her dog and mine played for days straight until their energy ran out. She has a fantastic fenced backyard and plenty of dog toys (all of which Benny promptly pulled out during our meet-n-greet). She also sends photo updates while you're gone, which were so cute. Awesome experience! Hope we can do it again.”
“Claudia and Jason were an absolute lifesaver. We needed a last minute sitter while visiting Maine and they came through. Drop off was a breeze and I knew Chase was in good hands. Regular updates including photos reassured myself and the kids that Chase was doing well. I can’t thank them enough and I can honestly attest that your dog is in good hands with them. I would absolutely without hesitation use them again if we’re in town.”
“Our pup had an amazing time! He seemed right at home and we had great communication throughout his stay. We would definitely reach out again if we need a sitter in the future!”
“Amy was great with my two Bernedoodles. I had a lot of anxiety leaving them and she made sure to send lots of pics that made me feel better. She was great at communicating and I would definitely board my dogs with her again.”
“This was our second time leaving Pepper with Sarah, and our longest time away from her since we adopted her. Sarah did a great job communicating with us throughout our week away, sending pictures and videos and keeping us posted on how Pepper was doing. Pepper can be a bit nervous at times but it is obvious she had a great time at Sarah's house and Sarah made her feel at ease. Sarah is a great sitter who I'd recommend to anyone!”
About: I've always had dogs in my life, and I think they deserve to be treated with love, patience & spoiled too! I'm comfortable with teacup-sized to the biggest dogs. I have a lab named Penne who loves to welcome new friends into our home! I work from home, so I have plenty of time to give pups all the love they need during their stay. I usually walk Penne 3x a day in Deering Oaks & let her run around the fenced-in yard if the weather is nice. For puppies I can do more-frequent runs! I am generous with treats, happy to have pets on furniture, and love to give pups love. I understand the concern with leaving your pup behind during work or a trip all too well, so I'm happy to give regular updates & pictures!
“Viva is an amazing Dog Sitter. She took care of a relatively elderly dog with lots of medication’s beautifully with excellent communication and I plan to work with her again many thanks.”
“We couldn’t have had a better experience with Kathleen B. She welcomed our dog into her family for the weekend and cared for him like he was her own. I highly recommend Kathleen B. I look forward to having her watch our dog again in the future.”
“I had a family emergency come up and needed quick assistance. Kristian was very patient with my last minute arrangements and thoughtful and took wonderful care of my dog Moe! He was very happy to join her on all of her day to day activities and lounge in her yard. Thank you again Kristian!”
“Our pup Maggie had a wonderful time staying at Anne's house while we were away for the weekend!! She enjoyed the great backyard and time playing with Anne's sweet dogs, and got lots of pets and attention from Anne and her husband. We could tell she was having a great time from all the adorable pics we got! Maggie gives her stay at Anne's a 5 star review! :)”
“Audrey took great care of Apollo. We will definitely board Apollo with Audrey again. She was very experienced and had a good plan on how to introduce Apollo to her sweet little dog. She sent lots of pictures and updates! We were very happy and he ate all his meals so he felt very happy as well!”
Loving dog boarding sitters in your neighborhood
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Cindy T.Star Sitter
“Cindy was amazing with our dog Loki! We felt so much more comfortable leaving him with her than we ever have at a traditional boarding facility. From the start, she was super flexible—when our travel plans changed last minute, she was totally accommodating and easy to work with. Communication was on point the entire time. Cindy sent us regular updates, including photos and videos, which gave us so much peace of mind. It was clear Loki was having a great time—he had dog buddies to play with, was allowed on the couch (which he loved), and genuinely looked happy and relaxed in every update. Not only did she treat Loki like one of her own, but her home is also lovely and the backyard was perfect for him to run around and play. That made a huge difference for us knowing he had space to enjoy himself. We couldn’t be happier with our experience and will absolutely book with Cindy again in the future. Highly recommend!”
Marna A.Star Sitter
“Our pup is a sensitive, nervous guy. Marna made sure he felt loved and at home. I could tell he was having fun with her family through the photos she sent. She filled us in each day and sent photos. 🤩 Will definitely use Marna again!”
Elisabeth K.
“Great stay for Miss Louise who has been exhausted sleeping on me since she got home. She loves seeing Elisabeth and her very sweet crew of dogs!”
Jennifer B.
“This is the third time we have left our pup with Jennifer. She does a great job of sending daily (twice daily) updates and photos. We know Max is well cared for and well loved when he stays there. He loves Maya as well!”
Kelly D.Star Sitter
“We are so grateful to have found Kelly! She took such wonderful care of our dog while we were away, treating him like part of her own family. Communication was excellent — we received regular updates with photos that put us completely at ease. It was clear from the moment we met Kelly that she genuinely loves animals and has a real gift for connecting with them. Our dog came home happy, relaxed, and clearly well-loved. We couldn’t have asked for a better experience and would absolutely trust Kelly again for future stays!”
Christina R.Star Sitter
“Christina did a great job with Crosby. I trusted that he was well cared for and got lots of love and attention. Normally a very stressed out dog, he seemed very relaxed when I picked him up. We'll definitely use her again in the future.”
Molly & Ricky W.Star Sitter
“Molly did a great job with our dog, Watson! Watson is an anxious boy, but in no time I received a picture of him asleep, cuddling on their couch. We'd be happy to work with Molly again!”
Heidi A.Star Sitter
“It felt so good to know that my pup was having a good time at Heidi’s thanks to all the adorable pictures and videos she sent throughout the week. It’s like he was on his own vacation 😎”
Vicky P.
Star Sitter
“Benny was sad for 2 days after I brought him home from his "vacation"!! I think he had more fun at Vicky's than I had in Mexico! I'm sure he can't wait until the next time I go away; I hope she'll be available again. As we drove away from her house, he stared out the window and whined! He almost never whines! Her dog and mine played for days straight until their energy ran out. She has a fantastic fenced backyard and plenty of dog toys (all of which Benny promptly pulled out during our meet-n-greet). She also sends photo updates while you're gone, which were so cute. Awesome experience! Hope we can do it again.”
Claudia & Jason M.
“Claudia and Jason were an absolute lifesaver. We needed a last minute sitter while visiting Maine and they came through. Drop off was a breeze and I knew Chase was in good hands. Regular updates including photos reassured myself and the kids that Chase was doing well. I can’t thank them enough and I can honestly attest that your dog is in good hands with them. I would absolutely without hesitation use them again if we’re in town.”
Kyle & Mariah H.
“Our pup had an amazing time! He seemed right at home and we had great communication throughout his stay. We would definitely reach out again if we need a sitter in the future!”
Amy Y.Star Sitter
“Amy was great with my two Bernedoodles. I had a lot of anxiety leaving them and she made sure to send lots of pics that made me feel better. She was great at communicating and I would definitely board my dogs with her again.”
Sarah C.Star Sitter
“This was our second time leaving Pepper with Sarah, and our longest time away from her since we adopted her. Sarah did a great job communicating with us throughout our week away, sending pictures and videos and keeping us posted on how Pepper was doing. Pepper can be a bit nervous at times but it is obvious she had a great time at Sarah's house and Sarah made her feel at ease. Sarah is a great sitter who I'd recommend to anyone!”
Alicia C.
“Alicia has had pets her entire life, and all of them lived long, happy, and healthy lives. She loves all dogs, and pats attention to what they like/listen to take care of them the way they are used to. She has dog sit for friends, and I can personally say she takes great care of our dog, Penne. She is constantly going above and beyond for her, and blows me out of the water consistently in exercising her, training her, or just generally making her feel happy and safe.”
Viva L.Star Sitter
“Viva is an amazing Dog Sitter. She took care of a relatively elderly dog with lots of medication’s beautifully with excellent communication and I plan to work with her again many thanks.”
Kathleen B.Star Sitter
“We couldn’t have had a better experience with Kathleen B. She welcomed our dog into her family for the weekend and cared for him like he was her own. I highly recommend Kathleen B. I look forward to having her watch our dog again in the future.”
Kristian N.Star Sitter
“I had a family emergency come up and needed quick assistance. Kristian was very patient with my last minute arrangements and thoughtful and took wonderful care of my dog Moe! He was very happy to join her on all of her day to day activities and lounge in her yard. Thank you again Kristian!”
Anne B.
“Our pup Maggie had a wonderful time staying at Anne's house while we were away for the weekend!! She enjoyed the great backyard and time playing with Anne's sweet dogs, and got lots of pets and attention from Anne and her husband. We could tell she was having a great time from all the adorable pics we got! Maggie gives her stay at Anne's a 5 star review! :)”
Audrey C.Star Sitter
“Audrey took great care of Apollo. We will definitely board Apollo with Audrey again. She was very experienced and had a good plan on how to introduce Apollo to her sweet little dog. She sent lots of pictures and updates! We were very happy and he ate all his meals so he felt very happy as well!”
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!
Why Choose Rover?
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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.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Windham is $63 per night, including service fees. Boarding your dog for one week typically costs $441. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Windham dog boarding rates can be found as low as $26 to as high as $72 per night.
As of Aug 2025, 247 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, 91% of Windham dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Windham have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 8 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 247 dog boarding sitters in Windham on Rover, so you’re sure to find the perfect match for your dog! In Windham, 100% of sitters offer daily exercise, 97% offer medication administration, and 100% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care 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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