Dog Boarding in Chilmark, MA
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Chilmark dog boarders
“Ruby was wonderful with our dog, Moose. We were able to leave town and not worry about him. She also sent us some great photos and videos of Moose playing with other dogs in her care. I highly recommend her!”
“Katherine was great watching our dog for a long weekend! She was very accommodating when we had a last minute change of plans and sent lots of pictures keeping us in the loop.”
“Our dog, Emmy, stayed with Shannon for three nights and wow-what a great experience! I felt an instant sense of calm entering her home. Shannon and her partner welcomed Emmy as if she was their own. In only a few days, they both formed a close bond with her, as well as quickly familiarized themselves with Emmy’s quirky behavior. Shannon was able to manage Emmy’s medication and food preferences along with her anxious tendencies and hostile reactions to other dogs. We will definitely be rebooking with Shannon!”
“I had never left my 14 week old pug puppy with anyone before but I was very afraid to leave him alone all day while I was in my sister’s wedding . Out of town and not sure where the best place was, I read reviews and found Julia ! She made it so easy! I got photo and video updates and i could see my pup was having a blast! If I’m ever on the cape again I’d absolutely use Julia. Great experience for me and I know Sandor gad fun too!”
About: As a recent college graduate working remotely from home, I’m looking for a dog fix while also helping those who need a break! I’ve grown up with a Chocolate Lab and a Rat Terrier which gave me various experience with little dogs and big dogs. Unfortunately they are not with us anymore which made me want to pick this up on the side! Remote every week day, except Wednesdays. Will be able to give care at any point in day/night except for my 30 minute meetings 3x per week. I have a big room in my office where the dog can play while I work, they will never be alone. The room has lots of natural sunlight and leads into a big backyard!
About: *Martha’s Vineyard Only* I have had pets of all kinds for as far back as I can remember. I currently have a very loving, sweet, energetic and playful dog of my own, Lola. She is 10 years old and enjoys playing with new friends! I am knowledgable and caring and will provide your dog with lots of love and care! I am comfortable caring for dogs of any size and breed as well as administering medication (oral, injections, eye and ear drops and topicals). I currently work part time from home so I am flexible and available throughout the day to tend to and care for pets in my care I have a fenced in yard, but don’t leave dogs unattended in the yard. I have a dog of my own to provide your dog with companionship and a playmate while they stay with us! A crate is not required but I’m happy to set yours up if it makes your dog comfortable. I can provide care for potty trained dogs, though I am comfortable with and have experience with senior dogs who require diapers.
“Marcia did an excellent job taking care of Tuka! I could tell he was very comfortable with her and her family both when I left him and picked him up. Loved all the pictures she sent! We will definitely use her again!”
“I can’t express how grateful I am that we Kathleen. It was the perfect environment for my dog. She and her very nice family took such good care of him that he felt at home. She also sent us many updates and photos so I knew he was happy and safe. I highly recommend her and would rebook! Thank you so much to Kathleen and family because of your great care I didn’t have to worry about him at all!”
About: I've grown up with dogs of all breeds and sizes, and caring for them has always been a big part of my life. From being the go-to dog walker in my neighborhood to watching friends’ pets while they’re away, I’ve handled everything from high-energy pups to sweet senior dogs. I make sure every dog feels safe, happy, and well looked after. I work remotely during the summer, so my schedule is super flexible. That means I can easily fit walks, check-ins, or overnight stays into my day and give your pet plenty of attention. My home is pet-friendly, with a fully fenced yard for safe outdoor time. I also have a laid-back senior dog who gets along great with other dogs.
“Taylor and Ryan were both amazing. Their adorable, wonderful puppers were so good as well. Our Daisy had the time of her life and we felt so comfortable leaving her there. Taylor has more than enough space for our girl to get her exercise, get lots of loving and feel right at home. She came back with no issues at all. Taylor is definitely our go to! Thank you so much again!”
“Maria was wonderful! Very communicative. A beautiful fenced in yard and two lovely dogs who quickly became my dogs best friends. I think he may have had the best day of his life. ?”
“Sam and his wife took incredible care of our dog - he is an anxious rescue who loves exercise. Sam took him on long walks every day and was very responsive to texts. I could tell when we picked up our dog that he had a mini vacation of his own. I highly recommend him!!”
“Austin was great. This was my first time ever boarding my four-year-old American bully. She does have some anxiety and stress issues. He was Fantastic with her from the start and made it easy for me to start the booking right from the beginning I would definitely recommend him. He kept me updated throughout her stay, which was a full three days and answered any concerns and questions I had along the way. I will definitely book again with Austin.”
About: I have had dogs for most of my life. I just love them! I have experience caring for young dogs and seniors and will treat your dog as if it is my own. I currently work from home so my schedule is flexible. I enjoy being outside taking walks and playing with them as much as they enjoy. If I am staying in your home or your dog is staying in my home, I will follow your dog's current routine. I will do my best to keep your pet comfortable and you stress free knowing they are being well cared for.
“Megan food a great job with our one year old springer pup. Megan was flexible, communicative and kind. I would use her again in a heartbeat. She watched out fog and did an overnight.”
“Lana had a great weekend while we were away! It was clear she remembered staying there even though it had been a few years. Grateful to have a place for Lana to stay when we’re out of town where she will be safe and cared for.”
“Fantastic dog sitter! She is compassionate and takes fantastic care of your pet. My dog was happy and comfortable the entire time she was away and the level of care is even better than a professional facility. She even sends daily pictures and videos and that is great when missing your pup. Next time I need to leave my dog I will definitely be sending her back over Nathalias!!”
“Adrienne took great care of Stella! I could tell Stella was very comfortable with her. Adrienne was super easy to work with and flexible with our crazy travel schedule. Highly recommended for overnight stays, Stella will definitely be staying with her again!”
Loving dog boarding sitters in your neighborhood
Search Results
Ruby S.
“Ruby was wonderful with our dog, Moose. We were able to leave town and not worry about him. She also sent us some great photos and videos of Moose playing with other dogs in her care. I highly recommend her!”
Katherine B.
“Katherine was great watching our dog for a long weekend! She was very accommodating when we had a last minute change of plans and sent lots of pictures keeping us in the loop.”
Shannon H.
“Our dog, Emmy, stayed with Shannon for three nights and wow-what a great experience! I felt an instant sense of calm entering her home. Shannon and her partner welcomed Emmy as if she was their own. In only a few days, they both formed a close bond with her, as well as quickly familiarized themselves with Emmy’s quirky behavior. Shannon was able to manage Emmy’s medication and food preferences along with her anxious tendencies and hostile reactions to other dogs. We will definitely be rebooking with Shannon!”
Julia & Bryan M.
Star Sitter
“I had never left my 14 week old pug puppy with anyone before but I was very afraid to leave him alone all day while I was in my sister’s wedding . Out of town and not sure where the best place was, I read reviews and found Julia ! She made it so easy! I got photo and video updates and i could see my pup was having a blast! If I’m ever on the cape again I’d absolutely use Julia. Great experience for me and I know Sandor gad fun too!”
Thomas S.
“Tommy is a caring young man who loves animals. He has experience caring for multiple dogs of his own and is very responsible and conscientious. He would make an excellent pet caregiver!”
Kayla J.
“Kayla has watched many of my pets throughout the years and is someone I trust with them without question. She is compassionate and provides them with endless love in my absence. With Kayla, I know that my beloved animals were in the best of hands.”
Marcia S.Star Sitter
“Marcia did an excellent job taking care of Tuka! I could tell he was very comfortable with her and her family both when I left him and picked him up. Loved all the pictures she sent! We will definitely use her again!”
Kathleen W.Star Sitter
“I can’t express how grateful I am that we Kathleen. It was the perfect environment for my dog. She and her very nice family took such good care of him that he felt at home. She also sent us many updates and photos so I knew he was happy and safe. I highly recommend her and would rebook! Thank you so much to Kathleen and family because of your great care I didn’t have to worry about him at all!”
Maggie M.
About: I've grown up with dogs of all breeds and sizes, and caring for them has always been a big part of my life. From being the go-to dog walker in my neighborhood to watching friends’ pets while they’re away, I’ve handled everything from high-energy pups to sweet senior dogs. I make sure every dog feels safe, happy, and well looked after. I work remotely during the summer, so my schedule is super flexible. That means I can easily fit walks, check-ins, or overnight stays into my day and give your pet plenty of attention. My home is pet-friendly, with a fully fenced yard for safe outdoor time. I also have a laid-back senior dog who gets along great with other dogs.
Taylor C.Star Sitter
“Taylor and Ryan were both amazing. Their adorable, wonderful puppers were so good as well. Our Daisy had the time of her life and we felt so comfortable leaving her there. Taylor has more than enough space for our girl to get her exercise, get lots of loving and feel right at home. She came back with no issues at all. Taylor is definitely our go to! Thank you so much again!”
Maria C.Star Sitter
“Maria was wonderful! Very communicative. A beautiful fenced in yard and two lovely dogs who quickly became my dogs best friends. I think he may have had the best day of his life. ?”
Sam M.Star Sitter
“Sam and his wife took incredible care of our dog - he is an anxious rescue who loves exercise. Sam took him on long walks every day and was very responsive to texts. I could tell when we picked up our dog that he had a mini vacation of his own. I highly recommend him!!”
Rachel R.
“Rachel and Andrew were great watching Rocket overnight. Rocket got lots of walks and was well cared for. Would highly recommend!”
Austin C.
“Austin was great. This was my first time ever boarding my four-year-old American bully. She does have some anxiety and stress issues. He was Fantastic with her from the start and made it easy for me to start the booking right from the beginning I would definitely recommend him. He kept me updated throughout her stay, which was a full three days and answered any concerns and questions I had along the way. I will definitely book again with Austin.”
Kim G.
“Kim has been a constant "go to" for looking after my oder dog. She is first, incredibly compassionate & a TRUE dog lover. She is more responsible & reliable than anyone I know. My dog adores her and the tail wags as soon as she walks in. Be it a need to let him out & for a walk or to look after or a few days, I could to ask for anyone more reliable than Kim. I simply have no reservations or worries when he is in her care.”
Megan W.Star Sitter
“Megan food a great job with our one year old springer pup. Megan was flexible, communicative and kind. I would use her again in a heartbeat. She watched out fog and did an overnight.”
Mike L.
“Lana had a great weekend while we were away! It was clear she remembered staying there even though it had been a few years. Grateful to have a place for Lana to stay when we’re out of town where she will be safe and cared for.”
Nathalia P.
“Fantastic dog sitter! She is compassionate and takes fantastic care of your pet. My dog was happy and comfortable the entire time she was away and the level of care is even better than a professional facility. She even sends daily pictures and videos and that is great when missing your pup. Next time I need to leave my dog I will definitely be sending her back over Nathalias!!”
Rebekah C.
“Rebekah was great. Flexible with pick up/ drop off times, shared updates/photos, and my dog seemed to enjoy being there. 10/10 would recommend!”
Adrienne H.
“Adrienne took great care of Stella! I could tell Stella was very comfortable with her. Adrienne was super easy to work with and flexible with our crazy travel schedule. Highly recommended for overnight stays, Stella will definitely be staying with her again!”
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?
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.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 103 sitters provided dog boarding in Chilmark. 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, 94% of Chilmark dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chilmark have an average of 17 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 Chilmark.
Rover makes it easy to find Chilmark 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 103 dog boarding sitters in Chilmark on Rover, so you’re sure to find the perfect match for your dog! In Chilmark, 100% of sitters offer daily exercise, 91% offer medication administration, and 82% 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.
Connect anywhere with the Rover app
