House Sitting Old Greenwich
Find a loving house sitter to watch over your pets and your home.
Over 12 pet parents in Old Greenwich have booked house sitting
Old Greenwich, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“We were fortunate to have Dana house sit for us on relatively short notice. She watched our 13 year old dog and 2 cats. We received updates and came home to some happy pets and a tidy house.”
“Nicole was great with Sky and Sid! She was super communicative, asked great questions, and sent us lots of updates and photos throughout the day. It was such a comfort knowing they were well cared for. Would definitely recommend!”
“Claire is absolutely the best dog sitter you could find. We came home from an extended trip to find out senior dog calm and happy after Claire’s overnight stays at our home. Claire sent photos, videos and text updates daily which were lovely and reassuring.”
“Dagmar was our house-sitter for a weekend and we couldn’t be happier with the experience. She took excellent care of our dog and cat and the house was just as we left it. I wouldn’t hesitate to recommend her services.”
“Anastasia is the best! I'm new to the area and was very anxious about leaving my pets. Anastasia put me at ease from the moment we met. My pets were immediately drawn to her and she showed them an incredible amount of care and love. She's an excellent communicator and sent me regular updates to let me know they were ok while I was gone. She was very flexible with my schedule and overall just a joy to get to know. I highly recommend Anastasia!”
About: I’ve been caring for pets for years and have experience with both dogs and cats. I’m comfortable with feeding, walks, playtime, cleaning up after pets, and giving them lots of love and attention. I’ve also helped care for my family dog for 6 years and have experience caring for cats. I treat every pet like they’re my own and always make sure they feel safe, comfortable, and cared for while you’re away. 🐾💗 I work full-time during the week, but I’m available for pet care in the evenings after work and on weekends. I’m happy to work around your schedule and provide your pets with plenty of attention, playtime, and care while you’re away. I want every pet to feel safe, comfortable, and cared for while they’re with me. I have experience caring for both dogs and cats and will follow your pet’s routine, including feeding, walks, playtime, and any special instructions you provide. 🐾
“Annabelle was an excellent match for my 15 year old Spaniel. She was conscientious, neat and tidy (she stayed overnight), reliable and trustworthy. My dog’s age brings challenges (vision and hearing issues) yet Annabelle never skipped a beat. I was nervous about leaving my dog with a stranger but it worked fine.”
“Laura took our 3 year old Corgi Jack into her home and did an incredible job taking care of him. She is so responsive and a natural with dogs. She treated him like her own and sent us updates and pictures several times a day. She is very active and took Jack on long walks and even introduced him successfully to another dog he became friends with while we were away. We will trust Laura with all of our dog sitting needs in the future and would recommend her to anyone!”
About: I have always had pets growing up as a child and now my love has grown even more. My experience in Pet Care is from having my own pets and caring for friends and family. I deal a lot with active dogs since I have two Siberian husky of my own and a Mutt mix. Im currently working part time-usually available every mornings, mid day depending on the week, weekends available all day once booked in advance sometimes flexible if booked late, and definitely available overnight at anytime. I can do anywhere in Greenwich, Stamford, Darien, Norwalk, Westport and Southport. I will treat your furry pets as they are like mine. I will communicate with you- if the dogs need extra attention, medicine, more walks, take them to their favorite place I will do it. I will always be transparent with you. I want your pets to not be stress when you leave the house - I will be another best friend that they can play with.
About: I have cared for dogs my entire life and have experience with dogs of different ages and needs. I am dependable, attentive, and passionate about animal care. I enjoy spending time with dogs and ensuring they feel safe, comfortable, and well cared for. I currently work from home so I have a lot of free time. Why not spend time with furry friends! It’s also a great opportunity to take a breather and get fresh air during daily dog walks. When caring for pets in a client's home, I ensure that their daily routines are maintained to keep them comfortable and stress-free. I also make sure the home remains clean and secure while providing pets with plenty of attention, affection, and companionship. I am attentive to each pet's individual needs and committed to creating a safe, loving environment while their owners are away.
“If you want to leave your dogs with someone and never worry at all about their mental well-being, their feeding needs, their exercise then you need to hire Jesse as your sitter. He's taken my care of my dogs for many days and I will say there is no better. Not only were my dogs, completely relaxed and happy, but my house was also immaculate and every instruction was followed to the tee, including the complicated medical things that one of my dog needs to have followed. Jesse is all around the best I've had!”
“I cannot recommend Melanie enough. She looked after our senior dog while we were on an extended trip overseas. I received numerous photographs of him looking healthy, happy and loved, and his affection for her was obvious on our return home. Melanie kept our house immaculate and also maintained good contact with us while we were away. She is extremely responsive to emails, punctual, and has an excellent work ethic. I felt extremely comfortable while away knowing Chessie was in her care. THANK YOU!!!!”
“Raquel was more than we could have hoped for. She is kind and professional, caring for our two dogs for five days/four nights at our home. She sent so many photos of them eating, playing, and sleeping, and kept in communication with us the entire time. She is perfect! FIVE STARS!!!!!”
About: Since growing up, I have always had family dogs. I have always walked and watched my own dogs, as well as friends and family. Since returning home from Upstate NY, Im looking to get back into spending time with animals. I am a full time teacher, so my availability is afternoons, and all weekends! I am generally available from around 4pm until late at night, and any time on the weekends. If there are vacations or days off from a school calendar, I also can work around those. I treat all my clients homes with the utmost respect. i am there for one job and one job only, and I know that. I will make sure my clients inside and outside is just as they have found it. I treat my clients with the love I would give to my own fur babies!!
“Kelly was excellent with our new puppy and took care of him so well! She is very experienced and is reliable, responsive, and even kept us updated on how our puppy was doing. We had to go out at last minute and she was so accommodating. We will definitely be working with Kelly again!”
About: Hi, I’m Ashley — I have nearly 25 years of hands-on experience in dog training, behavioral rehabilitation, rescue work, fostering, structured socialization, and canine management. I specialize in highly individualized, trainer-led care for dogs requiring structure, reinforcement, enrichment, confidence building, and real-world behavioral development. My approach goes far beyond standard daycare or pet sitting — dogs in my care receive consistent structure, guidance, and reinforcement throughout the day in a calm, highly managed environment. I’m fully insured and based in the beautiful Westover neighborhood of Stamford, CT on a private 2-acre property with secure outdoor space, structured walking routes, and training equipment used for confidence-building and behavioral development. Note: all prices are starting. SCHEDULE I provide private trainer-led care focused on structure, enrichment, behavioral reinforcement, and real-world manners — not standard daycare. Dogs in my program receive hands-on guidance, individualized attention, and consistent routines throughout the day in a calm, highly managed environment. Services include: • Structured Day Training & Care • Intensive Day Training • Private Training • In-Home Training • Board & Train Programs • Boarding • Drop-Ins Please reach out to schedule a Meet & Greet so we can determine the best fit for your dog. SAFETY, TRUST & ENVIRONMENT Your dog’s safety, comfort, and structure come first. I intentionally keep my program limited-capacity so every dog receives close supervision and individualized attention. Dogs are either expected to already have structure and manners, or they are actively trained to develop them while under my care. I’m fully insured and based on a private 2-acre property in Westover, Stamford with secure outdoor space, structured walking routes, and a calm home environment.
The median cost per night for house sitting in Old Greenwich is $60
Pet parents share their Rover experiences - Old Greenwich
Allison did a great job taking care of our senior dog, Bob Barker. It was our first time working with someone through Rover, and very happy we did. She stopped by to meet him before our trip and walk through his routine, then communicated with us during the trip. Bob and the house were in great shape and we look forward to booking with Allison again this month when we're out of town for another weekend.
After a last minute cancellation Crystal came in like a super hero! She had valid concerns with our older girl and worked with us via messenges to make sure she eats. Handled all the extra care of 3 dogs and one with many health issues. Had a few other thing pop up and she handled like a pro. 10/10 would recommend and if needed I will get her again!!!
Janine was the BEST! She took excellent care of the dogs - she genuinely loves dogs. I hate to leave my dogs with anyone, but they are so happy with Janine it made my trip possible. I didn’t worry for a second. She also took excellent care of the house. I will only ever leave them with Janine from now on.
Nicole did an amazing job at watching our dog Georgi overnight in our home. It was our first time leaving him overnight and we felt completely comfortable and at ease knowing Nicole was there with him. She communicated a lot throughout her time in our home with how things were going and included many pictures. She was polite to our space and kept it clean when she left. We would definitely recommend her and will be rebooking in the future!
Matt cared for my 10 month-old puppy this past weekend, and was absolutely incredible. He was kind, communicative, punctual, and took great care of my (high energy!) pup and of our home. I highly recommend working with Matt if you’re looking for someone to look after your furry friend. He’s wonderful!
Leca once again took excellent care of our cat and home. Our shy girl warmed up SO quickly thanks to Leca’s cat whisperer energy and therefore was able to enjoy lots of pets, brushing sessions, and playtime. Leca went above and beyond by watering our outdoor plants every day so our tomatoes didn’t die in the hot and humid weather. She is all-around an excellent sitter whom we recommend highly!
Emma was fantastic to work with from start to finish. We came home to find the house exactly as we left it, and she sent plenty of updates with pictures throughout our stay, which gave us so much peace of mind. She was incredibly responsive and responsible the entire time. We had zero hesitation leaving our girls in her care, and it was clear they made a new friend — they were so happy with her. Highly recommend!
I am simply amazed at the care that Chris gave to my 2 havanese dogs and 2 kitty’s. It was beyond my expectations. Not only is he a fabulous person himself but he takes care of not only your pets but your home as well. Five stars does not explain his level of service. 10000 out of 10. Chris is truly one of a kind. He is simply fantastic ❤️
Hallie is THE BEST! This is my second year in a row that Hallie has taken care of my cat, Kimchi. She is extremely thorough, timely, and detailed with her updates and care. Having Hallie taking care of Kimchi is PRICELESS- I can really enjoy my vacation knowing that Hallie is taking excellent care. Thank you Hallie!
If you want to leave your dogs with someone and never worry at all about their mental well-being, their feeding needs, their exercise then you need to hire Jesse as your sitter. He's taken my care of my dogs for many days and I will say there is no better. Not only were my dogs, completely relaxed and happy, but my house was also immaculate and every instruction was followed to the tee, including the complicated medical things that one of my dog needs to have followed. Jesse is all around the best I've had!
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 - Old Greenwich
Select a filter and find qualifying sitters offering house sitting.Sitters in Old Greenwich average 3 repeat house sitting clients
FAQs for House Sitting - Old Greenwich
Frequently asked questions about Rover
The average cost of House Sitting in Old Greenwich on Rover is $48 per night as of October 2026. Most bookings cost between $44 and $76 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 13,031 sitters on Rover offering House Sitting across Old Greenwich. 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 Old Greenwich 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 Old Greenwich 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.
<b>Tip:</b> 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 Old Greenwich 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 Old Greenwich. On Rover:
- 86% of sitters can help with special care needs
- 90% can help with giving oral medications or injections
- 95% 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.
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