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Top rated Chilmark house sitters
“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!”
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.
“Jess dog/house sat for me last week and she was absolutely amazing! I think my dogs want to live with Jess (and Matt) now, to be honest. :) She was highly communicative, sent a ton of pictures, and kept my pups totally entertained. Couldn't recommend Jess more highly for house/dog sitting and dog walking!”
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.
“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.”
“Jessica did a great job house sitting for us and taking care of our three dogs and bunny while we were gone for the weekend. She sent lots of pictures and left our house so clean! Would love to have her house sit again”
“Daniel did an awesome job caring for Lucy and Captain while staying at our house for an extra long weekend. We would absolutely recommend him! It was a pleasure to return home to two happy pups.”
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: 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: 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: 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: 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
Search Results
Éva R.
Star Sitter
“Eva was so helpful and flexible with scheduling and she really connected with my dog and sent photos showing how he was doing! Highly recommend her.”
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! I especially appreciated that she understands the complexity and beauty of rescue pups. Our little girl took to her right away!”
Alexandru G.
“Alex is someone whom I would recommend to watch or care for their pet without a second thought. He is fantastic around all types of animals, especially dogs and cats, and has been a pet owner for many decades. Alex has rescued multiple pets which is a testament to his deep, authentic, and genuine love for and care for animals. He is extremely respectful, responsible, reliable, and has the highest ethical integrity and character of any pet sitter I have ever worked with. He always shows up on time, asks thoughtful questions, is honest, trustworthy, and I have never had a single concern or problem working with him. He is also just a fantastic, great, and down-to-earth guy. If you are looking for a pet sitter who understands and takes the job seriously, and has experience and a natural inclination towards working with animals, look no further. I have had multiple 10/10 experiences with him, and actively recommend him to all my friends and family. And I have met his pets, and it is clear they are extremely happy well taken care for. Your pet is in excellent hands with Alex.”
Jessica T.Star Sitter
“Jess dog/house sat for me last week and she was absolutely amazing! I think my dogs want to live with Jess (and Matt) now, to be honest. :) She was highly communicative, sent a ton of pictures, and kept my pups totally entertained. Couldn't recommend Jess more highly for house/dog sitting and dog walking!”
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.
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.
“I'd highly recommend Katherine as a pet sitter - she did a great job when she took amazing care of my little baby, who can be pretty needy and high maintenance at times. She was patient, attentive, and went above and beyond to make sure my pet felt comfortable and loved. I trust her completely and know she’ll provide the best care for any animal!!”
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.
“Jessica did a great job house sitting for us and taking care of our three dogs and bunny while we were gone for the weekend. She sent lots of pictures and left our house so clean! Would love to have her house sit again”
Daniel V.
“Daniel did an awesome job caring for Lucy and Captain while staying at our house for an extra long weekend. We would absolutely recommend him! It was a pleasure to return home to two happy pups.”
Daniella A.
“I've known Daniella since we were in middle school, she has always loved and cared for animals. Daniella has always had pets, she had some parrots, a green iguana called Iggy and a dog named Sasha. Daniella worked some time at the national zoo of Guatemala as a volunteer where she learned a lot on taking care of animals and also teached us at school several tips on how to take care of our pets. Several times when I traveled she would take care of my two dogs, and everytime i texted her to see how they where doing she would answer back with a picture of my dogs and she would walk with them and give them treats. Daniella is an excellent pet owner with her dog Sasha, she has trained her and likes to walk her outside her apartment. I totally recommend Daniella as a dog sitter because I can assure you your dog will be with a loving and caring pet sitter, she is a responsible student and friend, and mostly she has a great time taking care of pets.”
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!”
Lucy B.
“I have known Lucy for well over a decade and she is a loving, responsible, playful, attentive, active dog sitter! She connects deeply with them and is a very fun puppy playmate! I have seen her interact with dogs of many ages, sizes and breeds with ease and confidence.”
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.”
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 is incredibly dependable and attentive as a pet caregiver. She eliminates all stress related to animal care. She is an excellent communicator and quickly learns routines, making her exceptional at providing optimal care. Her compassion for animals makes her an obvious choice! There’s no one more I trust with my pets.”
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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