House Sitting Fairlee
Find a loving house sitter to watch over your pets and your home.

Fairlee, Find top rated house sitting
About: Welcome to C & L’s Cozy Dog Retreat I have 2 pups, Chip & Lucy, ages 11 & 8, that I have raised from puppies. Many of my friends have dogs, and they frequently come over. I also enjoy riding horses when I can. I have experience working with anxious dogs & dogs in shelters also (as a volunteer). I love taking dogs for walks, playing with them, & give them attention. I limit the number of dogs I take at any given time so each pup gets lots of individual attention. You can see some of the dogs I have walked/played with in my profile pictures. I’m frequently in the Chestertown area and am more than happy to help with your pet-sitting needs. I offer drop-off and pick-up for your pups' boarding. I am available 24/7, Monday-Friday. I accept boarding and doggie daycare on a limited basis. Please message me if you are interested. This ensures I can give each pet the attention they need while ensuring safety. I am also happy to do multiple check-ins a day while your friend stays in their familiar home. I have a fenced yard and 2 friendly dogs. I can also kennel your dog if needed. A meet-and-greet with the dogs would be required before any overnight stays with us. Also, proof of immunizations.
“Maranda was fantastic. I really can’t say enough positive things about our experience with her. She was quick to learn and work with the idiosyncrasies of our two cats, took care of our house which was immaculate when we returned and communicated with us while away as much/or as little as we requested. She is very personable, respectful and responsive.”

“Michael was great with our herd. We have three pups, each with their own nuances. Michael stayed with them for a long weekend and kept us updated on their health and happiness. He was very accommodating with their needs and helped with their anxiety, and ours. We’d be glad to have him back and I think our dogs would be glad to have him back, too!”
About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.
About: I’ve been a devoted dog owner for 10 years, and I’m passionate about both dogs and staying active. As a schoolteacher, I’m excited to continue doing what I love while earning extra income to help pay off my student loans and purchase supplies for my classroom. I can walk dogs Monday through Friday after 3:30 pm. If you’re running late and need someone to help out in a pinch, I'm happy to assist. I’m available on Saturday and Sunday to walk your furry friend three times a day, or more if needed. Our dog is incredibly spoiled and loved. Whenever I come home, she brings me her ball, and we play fetch before anything else. She is groomed monthly, walked several times daily, and receives constant attention. When we have salmon, we cook her a plain fillet, which she loves.
About: I have hands-on experience caring for my own dogs, Koda and Eddie. Koda is a Cane Corso puppy, which has helped me learn the importance of patience, consistency, positive reinforcement, and proper exercise. I make sure my pups receive plenty of love, attention, playtime, and daily care while keeping their safety and comfort a priority. I understand that every dog has a unique personality and needs, and I would treat every pet in my care like family! 🐶❤️ Pet care is something I enjoy and make time for in my daily schedule. I strive to be flexible, dependable, and attentive to each pet’s needs, ensuring they receive plenty of exercise, attention, and care. I communicate with pet parents to coordinate schedules and make sure every pup gets the time, love, and attention they deserve! 🐾 I prioritize safety, patience, and trust when caring for every pet. I make sure each animal feels comfortable, loved, and secure while following the owner’s instructions and respecting each pet’s unique needs. I believe in keeping open communication with pet parents, providing regular updates, and creating a safe, welcoming environment where both pets and their owners can feel confident and at ease. My goal is to treat every pet like family! 🐾❤️
“Terry was absolutely Amazing!! She took great care of our 2 fur babies, sending photos and videos daily to update us on how they were doing while we were away. I was very anxious to leave our 2 cats with someone new, as our previous pet/house sitter is no longer in the business and we had not used someone new in many years, I have put off traveling due to this, much to my husband's dismay. I can say I was so relieved while away to see how great Terry was with our pets. I also think when we got home our house was cleaner than when we left! Terry did a fabulous job, she went above and beyond and now I'm ready to travel more feeling comfortable that we have found our new pet caretaker! I cannot recommend her enough!!”

About: Hello everyone! I am an animal lover, I grew up around animals all my life. Our furry friends are extended family members. I hope you entrust me with your furry loved ones. I am currently an active college student, but I have somewhat situated myself with a work-life balance. I am available and flexible for weekdays and weekends! I currently have a kitten almost a year old. Having him has taught me patience, and having complete responsibility. Milo is my profile picture! I feel as though I am completely up to any challenge, I hope I can help with your furry loved ones!
About: Before joining Rover I mainly provided my services through word of mouth. I have experience with providing basic medical care for dogs and cats, and training experience including potty training and easing separation anxiety. I have vast experience and knowledge on various breeds and their specific needs, and really just love being able to have the time and availability to be able to provide these services. They say a dog is a man’s best friend, but in my case, a dog has always been a woman’s best friend! I offer dog sitting, walking, training and boarding at my home as well. I am brand new to the app but I do have plenty of references and want to make all owners feel just as comfortable as I want to ensure their pets will feel with me! I currently work a part-time job from my home, so I have a flexible schedule and able to meet any needs your pet has. I am available everyday, all hours mainly, and can accommodate you and your pets schedule! In my home all pets are welcome. I have plenty of walking trails and a back yard for pets that stay at my home. I typically will customize the walks, food, bathing etc depending on the needs of the pet and what works best for them and the owner.

About: Hello furry parents! My name is Lily and I’m excited to support you and your family. I have worked with all dog breeds and all ages through fostering. I am currently in my training certification program to provide proper education to you and your puppers. I am an online student looking to spend my free time with amazing pets. My top priority is to give all animals time and love. Whether it’s giving a long walk, using my dog park at my complex or administering medication, I’m your girl! When I would care for your pets, it’s all about the greeting. I would love to make sure your pets are as comfortable with you as for me! If you’d love me to help them learn tricks, feel free to request!
“Heather was absolutely fantastic! She was extremely communicative from start to finish and has such a warm, positive personality. Our Boston Terrier, Lukin, is usually very anxious, but he did great with her — which says a lot! She took wonderful care of both him and our house while we were away. We really appreciated her updates and photos which kept us at ease. I can’t recommend Heather enough — she’s truly awesome and we will definitely be booking her again!”

About: I grew up with dogs and have always considered them part of the family. Until last year, I cared for my own dog, Tank, who passed away at 14. Caring for him through his senior years taught me the value of patience, close observation, and keeping a pet’s routine as comfortable and consistent as possible. Tank occasionally had seizures, which gave me firsthand experience remaining calm, reducing stimulation, helping keep a dog safe from injury, and closely monitoring them while following an owner’s or veterinarian’s instructions. I understand that every pet has their own needs, personality, routines, and comfort level. I’ve also dog sat for family members and truly enjoy making sure their pets receive dependable care, affection, exercise, and companionship while they are away. I’m detail-oriented and will follow your instructions closely. Feeding schedules, walking routines, medications, and house rules to favorite toys, training cues, and any special needs, your pet will feel safe, loved, and cared for in your absence. I work part-time as a caregiver for a person with a disability, a role that has strengthened my patience, reliability, and attention to individual routines and needs. Because my schedule is flexible, I can accommodate a wide range of pet-care routines, visit times, and scheduling needs. Whether I’m caring for your pet in my home or yours, I focus on keeping their routine safe, comfortable, and as familiar as possible. At my home, I have a yard available for regular bathroom breaks and a small park nearby for daily walks, exercise, and fresh air. I do not have any pets living with me full-time. From time to time, I care for my mother’s friendly French Bulldog, Vinny, who enjoys being around other dogs. I will always communicate in advance if another dog may be present and will make sure introductions are handled slowly, safely, and according to your pet’s comfort level. In a client’s home, I will follow your instructions closely regarding feeding, walks, playtime, medications, house rules, and any special routines or needs. My goal is to provide dependable, detail-oriented care that helps your pet feel secure and well cared for while you are away.
About: I mostly took care of my dog and my sisters dog growing up. She has relied on me to walk, feed, and bathe her dog while she was away on business trips and vacations. I would love to help you too. I currently work full time, but there will be plenty of time after work and on weekends to play with and take care of your dog. I have a fenced yard and a friendly dog to keep your fur baby company. I can easily crate your dog if need be. We will all get along just fine.
The median cost per night for house sitting in Fairlee is $50
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.
How to book house sitting

1. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for house sitting - Fairlee
Select a filter and find qualifying sitters offering house sitting.Sitters in Fairlee average 4 repeat house sitting clients
FAQs for House Sitting - Fairlee
Frequently asked questions about Rover
As of October 2026, there are 2,612 sitters on Rover offering House Sitting across Fairlee. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Fairlee walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Fairlee maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Fairlee choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Fairlee. On Rover:
- 90% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 96% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

