Dog Boarding in South Windham, CT
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Top rated South Windham dog boarders

“Bailey loves visiting Brittany and family!!! Never EVER worry about his care So many photos of Bailey’s antics. Always know what he’s up to because of her amazing communication He becomes an instant member of their family. Absolutely the best sitter!”


“As first time puppy parents and first time Rover users it was extremely difficult to leave our pup with anyone else. Suzanne made the entire process extremely easy and comfortable for us. From the booking and flexible arrangements to a slew of happy pictures of our puppy Eloise smiling and playing with her and her family made us feel extremely comfortable in our decision and allowed us the peace of mind to enjoy our getaway. We will not hesitate to use Suzanne again for any of our boarding needs in the future. Thank you Suzanne for loving up on our pup for us!”


“We’ve had Kristin watch our dogs every time we go away for two years and would never book with anyone else. She is amazing. Takes amazing care of them, sends photos and updates and is great at communication and flexibility. I could not recommend her more.”


“Jessica is very caring and attentive! She kept me in the loop by sending pics and updates every day. My dogs seemed very calm when I picked them up, which isn't always the case with different dog care providers. I'm really happy with how the experience went and I'm sure my dogs will spend time with her (and Calvin) again!”


“Jackson had a realy great time at Autum’s house. I highly recommand her care for your sweet pets because she his just the best. Jackson could fun crée in the fonce yard with her dog MIEL who is sweet has honney. She send us pictures almost every day and my dog was very confortable and secure with her. Tanks again for ta King care of Jackson ❤️”


“Our dogs stayed with Coy for 9 days over the April vacation. They seemed to have an amazing time. We were updated about them with videos and texts about the dogs. Coy was very knowledgeable about my texas heeler and has given me some helpful tips for her training and the overall health of our dogs. I highly recommend Coy”


“Stephen was phenomenal with our pup!! Extremely communicative and friendly. We got multiple photos and videos each day! He took him on walks every morning and let him play with all the tennis balls he could find! This was our dogs first time staying with someone other than family and it seemed like a vacation - we were afraid he wouldn’t want to come home. Highly recommend Stephen and we will definitely use his dog sitting services the next time we go away.”


“Hope's stay with Erica and Thomas left her exhausted and happy. I have never seen my dog look sad when I picked her up from somewhere but she was definitely not ready to leave them. It was obvious through her demeanor and how the kids came running down from school just to give her a hug goodbye that she was well cared for during her stay. I would absolutely recommend them to anyone looking for a great family to leave their dog with and will be leaving Hope with them again soon.”


“Thank you sooooo much for taking care of my Willow! You and your family did a wonderful job with her over night visit. I am so blessed to have found you. This is a super family and I would love have them care for my sweet dog anytime. Our communication was fabulous and the photos you shared are so appreciated THANK YOU❤️”


“I do not know where to START! There are no words no describe how grateful we are for Albert and Amanda! They are LIFE SAVERS! We were away out of the country for vacation and had an unfortunate situation where our current sitter could not handle our puppy Buddy! We had very little reception and Rover was amazing finding Buddy a new home! I believe that everything happens for reason and we are more than happy to have met Albert and Amanda! We literally have a new dog! They took the time to go over tips and tricks on how to train him! A new leash for him at no cost to us! We are beyond satisfied with this stay! We will be returning weekly for Doggy Day Care! God bless guys!! Than you again!!!”


“Laura was so wonderful! She made our family and our pup so comfortable and sent pictures and updates throughout our trip. We were so happy knowing that our dog got to be part of Laura’s family while we were away. We’d highly recommend Laura!”


“We had the pleasure of having Kristin watch our two dogs for the first time, and we couldn’t be more pleased with the experience!! We were a bit nervous leaving them for the first time, but she made it so easy and reassuring. From the thoughtful updates and pictures, to the way she made our dogs feel comfortable and cared for, we could tell she genuinely loves animals. It was such a relief to know they were in good hands! We came back to happy pups! We’ll definitely be booking again in the future. We highly recommend!!”


“We went on a 16 day trip out of the country and we knew Marley was in safe and caring hands. We got regular videos which reassured us he was happy and having a great time with the other dogs. The best review was when we were eating at an outdoor restaurant patio and suddenly he started to wag his tail like crazy! I was trying to think of who would cause that type of reaction, and it was Shannon and her husband! We will definitely be going back to Shannon.”



“This is the second time I have used Andrea G. and once again it was a fantastic experience. I received daily updates via text which included pictures and even a video of my beautiful Shilo having the time of her life! It's never easy to leave a beloved pet, but Andrea and Rover.com make it as comfortable as possible and I won't hesitate to use them again.”


About: I have been taking care of dogs for 4 years and I'm excited to continue my pet sitting journey on rover. I look forward to meeting your dog and treating them like part of the family! I am home full time so I can always be with your pet. I can do morning drop off any time after 7 and pick up at whatever time you need. I have a large yard with a 100ft dog runner. However if you or your dog are uncomfortable with the runner let me know and I can leash for bathroom breaks instead.

“Karen kept me informed and communicated promptly. My dog absolutely loved his stay and would recommend Karen for anyone looking for someone to watch your beloved pets.”



“Husky approved! Our 4 year old, Skye, was happy and content having had plenty of exercise time while we were away. We recommend Ricky and will be calling again ourselves. Great yard space, easy communication.”


“I appreciated that Shelby was willing to do a meet and greet with our dogs on such a short notice. I ended up having to cancel last minute but she was very communicative, attentive, and I’d definitely look to book with her again!”

Loving dog boarding sitters in your neighborhood
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Brittany W.Star Sitter

“Bailey loves visiting Brittany and family!!! Never EVER worry about his care So many photos of Bailey’s antics. Always know what he’s up to because of her amazing communication He becomes an instant member of their family. Absolutely the best sitter!”


Suzanne B.
Star Sitter


“As first time puppy parents and first time Rover users it was extremely difficult to leave our pup with anyone else. Suzanne made the entire process extremely easy and comfortable for us. From the booking and flexible arrangements to a slew of happy pictures of our puppy Eloise smiling and playing with her and her family made us feel extremely comfortable in our decision and allowed us the peace of mind to enjoy our getaway. We will not hesitate to use Suzanne again for any of our boarding needs in the future. Thank you Suzanne for loving up on our pup for us!”


Kristin T.Star Sitter

“We’ve had Kristin watch our dogs every time we go away for two years and would never book with anyone else. She is amazing. Takes amazing care of them, sends photos and updates and is great at communication and flexibility. I could not recommend her more.”


Jessica C.Star Sitter

“Jessica is very caring and attentive! She kept me in the loop by sending pics and updates every day. My dogs seemed very calm when I picked them up, which isn't always the case with different dog care providers. I'm really happy with how the experience went and I'm sure my dogs will spend time with her (and Calvin) again!”


AUTUMN H.Star Sitter

“Jackson had a realy great time at Autum’s house. I highly recommand her care for your sweet pets because she his just the best. Jackson could fun crée in the fonce yard with her dog MIEL who is sweet has honney. She send us pictures almost every day and my dog was very confortable and secure with her. Tanks again for ta King care of Jackson ❤️”


Coy G.

“Our dogs stayed with Coy for 9 days over the April vacation. They seemed to have an amazing time. We were updated about them with videos and texts about the dogs. Coy was very knowledgeable about my texas heeler and has given me some helpful tips for her training and the overall health of our dogs. I highly recommend Coy”


Stephen S.
Star Sitter


“Stephen was phenomenal with our pup!! Extremely communicative and friendly. We got multiple photos and videos each day! He took him on walks every morning and let him play with all the tennis balls he could find! This was our dogs first time staying with someone other than family and it seemed like a vacation - we were afraid he wouldn’t want to come home. Highly recommend Stephen and we will definitely use his dog sitting services the next time we go away.”


Erica & Thomas C.Star Sitter

“Hope's stay with Erica and Thomas left her exhausted and happy. I have never seen my dog look sad when I picked her up from somewhere but she was definitely not ready to leave them. It was obvious through her demeanor and how the kids came running down from school just to give her a hug goodbye that she was well cared for during her stay. I would absolutely recommend them to anyone looking for a great family to leave their dog with and will be leaving Hope with them again soon.”


Elizabeth A.Star Sitter

“Thank you sooooo much for taking care of my Willow! You and your family did a wonderful job with her over night visit. I am so blessed to have found you. This is a super family and I would love have them care for my sweet dog anytime. Our communication was fabulous and the photos you shared are so appreciated THANK YOU❤️”


Albert L.
Star Sitter


“I do not know where to START! There are no words no describe how grateful we are for Albert and Amanda! They are LIFE SAVERS! We were away out of the country for vacation and had an unfortunate situation where our current sitter could not handle our puppy Buddy! We had very little reception and Rover was amazing finding Buddy a new home! I believe that everything happens for reason and we are more than happy to have met Albert and Amanda! We literally have a new dog! They took the time to go over tips and tricks on how to train him! A new leash for him at no cost to us! We are beyond satisfied with this stay! We will be returning weekly for Doggy Day Care! God bless guys!! Than you again!!!”


Laura G.Star Sitter

“Laura was so wonderful! She made our family and our pup so comfortable and sent pictures and updates throughout our trip. We were so happy knowing that our dog got to be part of Laura’s family while we were away. We’d highly recommend Laura!”


ROSMERY P.

“Seems my dog Kimee had a great time at her sitter . Very friendly sitter .”


Serenity H.

“Serenity took great care of my dog, Kasey. She sent me photos of him daily and he came back as happy as when I left him. 10/10 recommend working with her.”


Kristin S.
Star Sitter


“We had the pleasure of having Kristin watch our two dogs for the first time, and we couldn’t be more pleased with the experience!! We were a bit nervous leaving them for the first time, but she made it so easy and reassuring. From the thoughtful updates and pictures, to the way she made our dogs feel comfortable and cared for, we could tell she genuinely loves animals. It was such a relief to know they were in good hands! We came back to happy pups! We’ll definitely be booking again in the future. We highly recommend!!”


Shannon C.Star Sitter

“We went on a 16 day trip out of the country and we knew Marley was in safe and caring hands. We got regular videos which reassured us he was happy and having a great time with the other dogs. The best review was when we were eating at an outdoor restaurant patio and suddenly he started to wag his tail like crazy! I was trying to think of who would cause that type of reaction, and it was Shannon and her husband! We will definitely be going back to Shannon.”




Andrea G.


“This is the second time I have used Andrea G. and once again it was a fantastic experience. I received daily updates via text which included pictures and even a video of my beautiful Shilo having the time of her life! It's never easy to leave a beloved pet, but Andrea and Rover.com make it as comfortable as possible and I won't hesitate to use them again.”


Cecelia P.
“Cece has watched my dog before and is very attentive and caring. They always made sure my dog was happy and cared for at all times!!”


Karen F.Star Sitter

“Karen kept me informed and communicated promptly. My dog absolutely loved his stay and would recommend Karen for anyone looking for someone to watch your beloved pets.”




Ricky R.Star Sitter

“Husky approved! Our 4 year old, Skye, was happy and content having had plenty of exercise time while we were away. We recommend Ricky and will be calling again ourselves. Great yard space, easy communication.”


Shelby A.


“I appreciated that Shelby was willing to do a meet and greet with our dogs on such a short notice. I ended up having to cancel last minute but she was very communicative, attentive, and I’d definitely look to book with her again!”
South Windham dog parents share their Rover experiences
Popular requests near you
Select a filter and find qualifying South 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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away3. 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 South Windham is $50
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 South Windham average 11 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 275 sitters provided dog boarding in South 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, 87% of South Windham dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in South Windham have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 11 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 South Windham.
Rover makes it easy to find South 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 275 dog boarding sitters in South Windham on Rover, so you’re sure to find the perfect match for your dog! In South Windham, 100% of sitters offer daily exercise, 100% offer medication administration, and 94% 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.
