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Top rated Chilmark house sitters
“Leaving our elderly dog, Lulu, with Eva was like leaving her with a family member. She is by far the best and most trusted sitter we have EVER had. Special feeding instructions and care instructions were no problem for Eva. If you’re looking for a fantastic, attentive sitter, look no further. Thank you, Eva!!”
“Stephanie is so responsive and has made great friends with our fur babies. She’ll send us updates and photos whenever we ask. She’s definitely our go to sitter!”
“Meredith was great with my two pups! — 13-year-old German Shepherd who had emergency surgery the day prior and 10-week-old English Cream Retriever who is very high energy and not yet potty trained. Meredith watched my pups in my home while I was away at work. I was updated hourly with photos. She was a pro at taking care of my puppy and followed my instructions to the tee. She even gave my senior pup her pain medication when she seemed uncomfortable. Both my pups were very happy when I returned. I will definitely be using Meredith again in the future!”
“Kim was wonderful watching our two dogs over night! She was extremely diligent and took great care of them and kept us updated. We will happily use Kim again and recommend her for your pet sitting needs!”
About: I bring high-energy, all-terrain enthusiasm to every pet I care for! Whether I’m biking, swimming, running, walking, rollerblading, or scootering, I stay active so your dog can too. I’ve worked with pups of all ages—from playful puppies to mellow seniors—and tailor each walk or visit to fit their pace and personality. Pets aren’t just cared for, they’re engaged and uplifted. Let’s turn walk time into mission time! I work from home full-time, which means I’m always nearby and flexible. Pet care fits naturally into my day—I schedule walks, playtime, and snuggles around my work. I treat every pet like family—whether they're with me or I'm visiting their home. I have a fenced yard for safe outdoor time and two friendly dogs for social play. I follow any special instructions you provide and can crate your pup if needed. Clean spaces, constant supervision, and a whole lot of love ensure your pet’s comfort and security.
About: I have been working part time at the vets office for two years, taking care of boarded animals. I see a large variety of pets weekly, as I am a kennel attendant. I meet dogs and cats of all ages and breeds all the time. I have always had a special connection with animals. I stopped eating meat when I was six years old because I learned the chickens on the farm were what chicken nuggets are made of. I’ve grown up helping out at farms, as I’ve always had a drive to help animals to the best of my ability. I’ve been watching pets for the past three years and I have never met a dog that didn’t end up liking me by the end of the day! My entire life is based around animals, as I have my own pets and I’m a full-time pet sitter. I truly spend more time with pets than people, and I enjoy it. I take great pride in caring for pets, whether in my own home or others'. I go above and beyond to ensure they feel safe, loved, and comfortable, providing them with personalized attention and care. From maintaining their routines to offering plenty of playtime and cuddles, I make sure their environment is stress-free and enjoyable. Whether it's administering medications or ensuring they have all the comforts they need, I treat each pet as if they were my own, always striving to exceed expectations! I do not take any dogs with even the slightest aggression towards other animals into my home.
About: I have been dog sitting friends and family animals since college. I am devoted to animals and their wellbeing! Whether big or small I love all of them. I have experience dog sitting, cat sitting. I have three birds, a cockatiel, and two parakeets. I have had dogs of my own growing up, small, medium, and large sized. I have also grown up riding horses and caring for them as well. I love any animal, no matter the kind. I work full time Mondays to Fridays 8:30am-4pm I am willing to take care of your animals when I get out of work. I have an open availability for weekend days. I would go to your home and care for your animal/animals! I would provide them with food, water, bathroom breaks, and if they require any special medication.
“Morgan was a wonderful dog sitter. She offered to arrive early, was perfect with our two dogs and sent us pictures throughout the evening. We will definitely book her again in the future.”
“Alyssa was amazing with my pets. She went above and beyond what was asked. Mini (lab mix) is not a dog that warms up quickly to others and Alyssa didn’t give up on her. I do believe they are finally friends. I will be a repeat client and won’t hesitate to use Alyssa again.”
About: I have periodically taken care of pets all of my life. A roommate of mine had a lab, Lola, and we lived together for 3 years. I knew her from when she was a puppy. I also have other friends now who have dogs and I often care for them. My partner's family also has a scottie, and my relatives have both doodles and labs that I take care of often. I just left my corporate job and am taking some time off while I study for both my school teaching and pilates teaching certification exams. I mostly have an open schedule. Happy to follow whatever environment you wish for your pet. I am careful about closing doors slowly/not opening them all the way/not leaving them open to ensure security.
“Rachel did a wonderful job caring for Meloni the month I was away. She was kind, considerate, and made sure to update me when anything seemed slightly amiss with him. Highly recommend.”
“I can't even begin to describe how grateful I am for Jessica taking care of my two buds. They loved her and were very well cared for. My anxieties about leaving them behind were also quelled by plentiful pictures and updates.”
“Daniel did a wonderful job house sitting for our rescue pup. She felt immediately comfortable with him and they had a blast. We would be lucky to have Daniel take care of her again!”
About: I have been a pet sitter for the last 10 years, working for neighbors as well as for the families I was nannying for. I am committed to the dogs I am caring for and I will treat them as if they are my own. I currently work in a hotel and taking care of animals in my free time would be work that I am very passionate about. I am happy to take the dogs on walks, or host in your home. I currently work part time so I would love to fill my free time caring for animals. I spend most nights on long walks so it would be great to have a companion to keep me company. I am very responsible and trustworthy. I would treat your dog and your home as if it is my own. I am happy to feed, play, walk, go to the beach, or anything that will make the pets happy.
About: Animals have always been part of my life. When I was younger I had a Yorkshire Terrier, I had to look after her every day, and when she had puppies I cared for them until they grew up. I currently have a Boston Terrier and an Australian Shepherd but they live in my Guatemala home, I used to take them for walks in the park and often to the beach or to volcanoes. When I was living in Guatemala I helped take care of a blind dog by assisting with the food, walks, and by watching him. I have taken care many times of my friend's dogs, I play with them and take them for walks. I love dogs and all kinds of animals, I would love to take care of your pet!
About: People have trusted me to take care of their pets for decades. As a positive rewards trainer-in-training, I provide excellent, loving care to puppies, kittens, senior pets and all stages between. I have certifications in animal behavior and I can administer medication if necessary (depending on the patient's temperament). My services are limited to Martha's Vineyard. Depending on your needs, I can make most days and times work. Feel free to ask for what you need and we can discuss further. I cannot bring other pets into my own home, but I can spend nights at yours and/or housesit. I will follow your instructions to the letter, I will respect your privacy, I will bring no one but myself, and I will leave everything exactly how you left it.
About: Beyond being a dog owner myself to my beloved rescue Jordi, I've also taken more dog sitting jobs than I can count. I LOVE dogs! I like to go the extra mile by taking dogs on extra long walks and adventures, always administering their medication at the correct time, giving dogs extra love and cuddles, and always keeping the house super neat and tidy. I already walk my own dog twice a day, and he loves walking with a friend! If you need a drop in visit or occasional help with a dog walk, it's already a part of my routine. Of course I do not need to bring my own dog, but if your dog enjoys the companionship of other dogs, it could be a great option! I am not allowed to have any more pets other than my own where I am currently living so I will not be able to board your dog, only house sit. Thanks for understanding.
About: I love dogs and as a certified dog trainer have the experience and knowledge to bring joy and fun to your loved pet's time with me. I'm a retired cattle farmer and a professional dog trainer. I'm now a full-time columnist and author living on Martha's Vineyard. I'd love to spend quality time with your pets as I finish my third book. I give each pet individual attention and love. Since I work from home, I'll be with your pet most of the time I'm pet sitting.
About: Having accumulated over 15 years of experience in pet care, I've developed a deep understanding and comfort in tending to pets of all ages, from sprightly youngsters to wise seniors, each with their unique set of needs and requirements. This extensive tenure has equipped me with the skills and adaptability to cater to diverse situations, ensuring every pet's well-being and happiness, regardless of their stage in life or specific care necessities. My schedule is highly adaptable; working from home allows me to cater to your pet's needs. I accommodate walks or bathroom breaks based on your preferences. I'd love to walk your pet in the woods or on a bike trail, maybe play ball at the park. I provide in-house care, prioritizing your pet's comfort and respecting your home.
About: I have years of pet care from having pets in my family. I have done overnight sitting and regular dog walks. I live an active lifestyle and live to bring pets with me on long walks. I am available all day Friday's and Saturday's. I work until 4 all other days and can do check ins or walks after work. If you need any overnights I am happy to do so any time of the week. I give pets my full attention and care. They are my priority. I can adjust to whatever the pet or owner needs. I have experience with preparing raw food for dogs as well.
Loving house sitters in your neighborhood
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Éva R.
Star Sitter
“Leaving our elderly dog, Lulu, with Eva was like leaving her with a family member. She is by far the best and most trusted sitter we have EVER had. Special feeding instructions and care instructions were no problem for Eva. If you’re looking for a fantastic, attentive sitter, look no further. Thank you, Eva!!”
Stephanie B.
“Stephanie is so responsive and has made great friends with our fur babies. She’ll send us updates and photos whenever we ask. She’s definitely our go to sitter!”
Meredith B.
“Meredith was great with my two pups! — 13-year-old German Shepherd who had emergency surgery the day prior and 10-week-old English Cream Retriever who is very high energy and not yet potty trained. Meredith watched my pups in my home while I was away at work. I was updated hourly with photos. She was a pro at taking care of my puppy and followed my instructions to the tee. She even gave my senior pup her pain medication when she seemed uncomfortable. Both my pups were very happy when I returned. I will definitely be using Meredith again in the future!”
Kim G.
“Kim was wonderful watching our two dogs over night! She was extremely diligent and took great care of them and kept us updated. We will happily use Kim again and recommend her for your pet sitting needs!”
Alexandru G.
“Alex is the kind of person animals just trust. He’s calm, gentle, and super reliable. Someone you’d feel completely at ease leaving your pet with. He’s great at communicating and just a solid, responsible human all around. Highly recommend!”
Ruby S.
About: I have been working part time at the vets office for two years, taking care of boarded animals. I see a large variety of pets weekly, as I am a kennel attendant. I meet dogs and cats of all ages and breeds all the time. I have always had a special connection with animals. I stopped eating meat when I was six years old because I learned the chickens on the farm were what chicken nuggets are made of. I’ve grown up helping out at farms, as I’ve always had a drive to help animals to the best of my ability. I’ve been watching pets for the past three years and I have never met a dog that didn’t end up liking me by the end of the day! My entire life is based around animals, as I have my own pets and I’m a full-time pet sitter. I truly spend more time with pets than people, and I enjoy it. I take great pride in caring for pets, whether in my own home or others'. I go above and beyond to ensure they feel safe, loved, and comfortable, providing them with personalized attention and care. From maintaining their routines to offering plenty of playtime and cuddles, I make sure their environment is stress-free and enjoyable. Whether it's administering medications or ensuring they have all the comforts they need, I treat each pet as if they were my own, always striving to exceed expectations! I do not take any dogs with even the slightest aggression towards other animals into my home.
Carissa L.
“Hello, my name is Hope I work as a canine coach at a doggy daycare and have a degree in veterinary health care. I have known Carissa since 2015 and I can confidently say they are very responsible and caring with animals. She’s has already gotten experience in taking care of other peoples pets. They have all been happy with the care received.”
Morgan B.
“Morgan was a wonderful dog sitter. She offered to arrive early, was perfect with our two dogs and sent us pictures throughout the evening. We will definitely book her again in the future.”
Alyssa P.
“Alyssa was amazing with my pets. She went above and beyond what was asked. Mini (lab mix) is not a dog that warms up quickly to others and Alyssa didn’t give up on her. I do believe they are finally friends. I will be a repeat client and won’t hesitate to use Alyssa again.”
Katherine B.
“Katherine has been fantastic to my pup Chester! Extremely reliable and responsible, she has always been on top of the schedules we set. My dog has grown to really like her, getting very excited whenever he sees Katherine. Could not recommend highly enough.”
Rachel C.
“Rachel did a wonderful job caring for Meloni the month I was away. She was kind, considerate, and made sure to update me when anything seemed slightly amiss with him. Highly recommend.”
Jessica V.
“I can't even begin to describe how grateful I am for Jessica taking care of my two buds. They loved her and were very well cared for. My anxieties about leaving them behind were also quelled by plentiful pictures and updates.”
Daniel V.
“Daniel did a wonderful job house sitting for our rescue pup. She felt immediately comfortable with him and they had a blast. We would be lucky to have Daniel take care of her again!”
Lexi G.
“Lexi is an amazing dog sitter. Always on time, helps with anything I need & flexible with my schedule. She loves & cares for my dog as her own. My dog highly recommends her!”
Daniella A.
“Daniella is a lovely and caring person when it comes to dog sitting. She always takes fantastic care of her pets, and without a doubt, she will even do a better job with your pets. I would trust Daniella to take care of your pets!”
Jennifer Z.
“Jennifer seems to really enjoy dogs and is very attentive and responsible when tending to them. She’s careful to ensure they get enough exercise during her daily walks by transitioning from walking to running as her dog’s needs and interests change. Letting anyone take care of your dog is as important as tending to your children and I do think she’ll take great care of them.”
Lucy B.
“Lucy was our primary dog sitter for two years. During that time she was compassionate and caring toward our two Jack Russells. Lucy followed our instructions and was excellent about reaching out if she had any questions or concerns. I would highly recommend Lucy as a pet sitter. You and your pets will be very happy!”
Carole S.
“I recommend Carole for an animal care situation. I would not hesitate to ask her to care for my dogs and cats (and horses, too), Over the past 25 or more years she has animal sat my animal family many times. My dogs are rescued and some had difficult issues (both mental and physical). Her care and love is at same level I would give them.”
Blossom P.
“Blossom cared for my family’s elderly chihuahua many times. We always had peace of mind knowing that Tiki was in such good hands! Blossom is an excellent communicator, detail-oriented, and most importantly, has a heart of gold. You’ll be lucky to work with her!”
Cecilia T.
“Cecilia is a top-notch pet and house sitter. She is respectful of how we keep the house, keeps everything neat and organized, and is very personable with pets and enjoys walking them. You can feel safe knowing your pets and home are in good hands.”
Over 2 pet parents in Chilmark have booked house sitting
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets 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 house sitting in Chilmark is $66
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 house 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.
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chilmark on Rover as of Aug 2025 was about $66 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Aug 2025, there are 184 house sitters in Chilmark. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Chilmark house sitters respond in under an hour.
House sitters in Chilmark have an average of 17 years of experience. This can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Chilmark.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chilmark house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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