Dog Sitting Old Greenwich

Book a Old Greenwich dog sitter to watch your dog in your sitter’s home or yours.

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pet parents in Old Greenwich have booked dog sitting

Old Greenwich, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Cassidy M.
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Cassidy M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
90 reviews
33 repeat clients
6 years of experience
Downtown, Stamford, CT, 06905

Amazing! So appreciative of the quick visit, prompt replies, and the photo updates. The cats came to say hi which is a good sign, they usually hide the whole time. Thanks, will definitely reach out again.

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Mariel V.
Sitter Profile Image: Ziyi Y.
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Ziyi Y.
from
$20
per visit
1 repeat client
15 years of experience
Downtown, Stamford, CT, 06901

About: I’ve had animals my whole life, including dogs, cats, birds, and reptiles. I’ve trained multiple puppies, cared for senior dogs, and have years of experience looking after cats. I’m patient, detail-oriented, and always make sure each pet feels safe and loved. I currently work from home, so I have a flexible schedule for walks and drop-in visits throughout the day. At the moment, I’m not able to offer boarding, as my own pets may not adjust well to new animals in the home. My approach is calm and understanding. I like to respect each pet’s unique personality and habits. I don’t believe in being overly strict, but I always make sure they are safe, comfortable, and well cared for.

Sitter Profile Image: Karen P.
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Karen P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
22 reviews
6 repeat clients
30 years of experience
Greenwich, CT, 06830

About: Have many years of experience in caring for pets. Have had several kittens to cats in prior years, and more recently cared for our family dog from a 9 week old puppy to a happy long life of 17 years! I take care of family member's dog and cat while they are away. Have experience in caring for a senior dogs, from medicines to mobility support. Will provide loving, attentive and patient care for your pet. Happy to provide the excellent care your dog or cat deserves, so you can be away without worry! I am at home 4 days a week and available to take 24 hour care of your pet's needs. Always present to let them outside for breaks as needed in private secure backyard or on a walk. Love to go on walks for your dog's excercise! Will keep a close eye on your pet throughout the day. Able to provide special senior care to support your pet needs. Have a single home townhouse with private backyard. Handy when they need to go out briefly for breaks. Will always make sure your pet is secure on a leash while out. Dogs and cats can freely move around home and I ensure a clean and safe environment. Plenty of space but structured in that I can keep a close eye on them to know all is well with their needs.

Sitter Profile Image: Aaron G.
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Aaron G.
from
$20
per visit
4.9 out of 5 stars
73 reviews
42 repeat clients
10 years of experience
Downtown, Stamford, CT, 06905

Aaron has been an amazing sitter for my pets. I have an older lab and he has worked with him on several behavior issues and I see such a dramatic change in my dog! I highly recommend Aaron not only for pet sitting but training as well.

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Carrie W.
Sitter Profile Image: Jessica S.
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Jessica S.
from
$17
per visit
5.0 out of 5 stars
54 reviews
16 repeat clients
5 years of experience
Glenbrook, Stamford, CT, 06902

Jessica was so wonderful with our bunny Macho over the holidays! He even escaped before her first visit and she was able to lure him with blueberries safely back into his enclosure area while we were away. She is professional, communicated very well and lovely to work with! Thank you Jessica for making our holiday stress free and taking great care of Macho :)

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Amy C.
Sitter Profile Image: Avery C.
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Avery C.
from
$20
per visit
10 years of experience
South End, Stamford, CT, 06902

About: Hi! I’m a lifelong dog lover who has had dogs since I was little. Caring for dogs has always been a part of my life, and I understand how important it is to find someone you can trust with your furry family member. Whether your pup loves long walks, playtime, belly rubs, or just relaxing with a companion, I’m happy to provide the attention and care they need. I treat every dog as if they were my own and will make sure they feel safe, comfortable, and loved while you’re away. Pet care fits easily into my daily routine because I’ve always had dogs and genuinely enjoy spending time with them. I work a flexible schedule that allows me to make time for walks, playtime, feeding, and giving pets plenty of attention throughout the day. On weekends, I’m typically outdoors, going for walks, spending time with family, or relaxing at home, which makes it easy to incorporate extra pet care. I love having dogs around and enjoy making sure they feel comfortable, active, and cared for while their owners are away. I care for every pet as if they were my own. In my home, I make sure pets have a safe, comfortable environment with plenty of attention, exercise, playtime, and affection. I follow each pet’s normal routine as closely as possible, including feeding schedules, walks, medications, and any special instructions from their owner. In a client’s home, I respect both the pet’s routine and the owner’s space. I know many pets are most comfortable in their familiar environment, so I focus on keeping their schedule consistent, providing companionship, exercise, and lots of love while their owner is away.

Sitter Profile Image: Shawn S.
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Shawn S.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
66 reviews
23 repeat clients
35 years of experience
Port Chester, NY, 10573

Shawn is super thoughtful!!! He took the time to come visit the cats ahead of sitting to make sure we all get comfortable. He also takes the time to check in with you when unsure about the cats needs or behaviors, that was hugely appreciated! I will definitely reach out and o Shawn next time.

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Myriam M.
Sitter Profile Image: Jesse K.
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Jesse K.
from
$20
per visit
5.0 out of 5 stars
4 reviews
25 years of experience
Downtown, Stamford, CT, 06901

About: I've taken care of dogs since I was 7 years old and picked out the cutest black Lab/ border Collie mix named Memphis. Growing up with dogs and living with dogs has been such an important part of my life. My Mom even says I love dogs more than her! Friends have trusted me to take their dogs on walks, house-sit and just go over for some play-time. I'm currently working part-time on my next venture and can work from anywhere! This means my time is very flexible and can help out during all hours of the week. I consider myself a very caring and detail oriented person. I will care for your pets as if they were my own, per your instructions. I also pride myself on being a very clean individual and will take great care of your home.

Sitter Profile Image: Katie V.
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Katie V.
from
$25
per visit
5.0 out of 5 stars
92 reviews
26 repeat clients
7 years of experience
Stamford, CT, 06901

Katie was amazing all around. She did everything I asked and took great care of my cats. I was anxious about leaving them for 6 days but she made me comfortable and allowed me not to worry during my vacation.

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Daniella A.
Sitter Profile Image: Kenisha M.
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Kenisha M.
from
$40
per visit
5.0 out of 5 stars
47 reviews
8 repeat clients
5 years of experience
Downtown, Stamford, CT, 06902

Responsive, kind, and very easy to work with! I would not hesitate to book again with Kenisha.

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Aaron E.
Sitter Profile Image: Cinthia J.
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Cinthia J.
from
$35
per visit
5.0 out of 5 stars
43 reviews
16 repeat clients
15 years of experience
Cove-East Side, Stamford, CT, 06902

Personable, responsive and dependable. A good combination from a client perspective, and our 4-year old springer spaniel seemed to like the attention. Cinthia will be at the top of our list the next time we need help with the animals.

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Brian C.
Sitter Profile Image: Denise M.
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Denise M.
from
$20
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
15 years of experience
Downtown, Stamford, CT, 06902

About: Hi, I'm Denise and have worked in doggie daycare and pet sitting, including fostering for many years. My full time job pays my mortgage but caring for animals brings me joy. I am professional, polite, old school and give personalized attention to your pooch. I'm available super early weekday mornings, evenings and all day Saturday and Sunday. I currently work full time near home so I can easily get home for potty breaks. Pets will never be alone for more than 4 hours. I always am sure they are leashed before the door is open. While I do not have a fenced in yard, I'm an avid walker so your pets will surely get the steps in. I work a mile from home so mid day potty breaks are easy. I'm a big walker so pups get their exercise and lots of play time at home. I always keep the pups in my care away from other dogs and people for safety. I do not have a fenced in yard but have enough property for a late night quick pee and poop.

Sitter Profile Image: shannon p.
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shannon p.
from
$60
per visit
5.0 out of 5 stars
11 reviews
1 repeat client
1 year of experience
West Side, Stamford, CT, 06902

Perfect.

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Richard Adam S.
Sitter Profile Image: Penny S.
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Penny S.
from
$25
per visit
30 years of experience
Riverside, CT, 06878

About: I’ve had dogs growing up. As an adult I have had cats and dogs, many of whom had special needs. I have had two blind cats and cats and dogs with various chronic medical conditions. I also have a veterinary assistant certificate from Norwalk Community College and I have worked as a vet assistant. I am retired for now. This leaves me time to focus on your animals. I can do sleepovers as well as daily walks and home visits for cats. I cannot take pets in my home but can do walks and sleepovers in a clients home. If an owner has a fenced in yard and the dog likes going out in the yard I would go with the dog and not leave the dog unattended. If the dog is used to walks we would walk.

Sitter Profile Image: Yushin "Tina" P.
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Yushin "Tina" P.
from
$35
per visit
5.0 out of 5 stars
21 reviews
3 repeat clients
22 years of experience
Cove-East Side, Stamford, CT, 06902

About: Welcome, if you happened to find my page, I am offering many services for you loving pets. 1. Boarding, small breeds only. I have a big back yard, fenced, no harmful pesticides. Your fur babies can run around to their hearts content. I offered daily walk during boarding( weather permitting). 2. Drop in visit. I usually visit twice a day, staying one hour or more each time. Following the client' instruction on routines for your pet. Small, medium, and Large dogs are all welcome. 3. Day Care, usually 8 hours duration, your fur pal gets plenty of companionship from my dogs, on our laps, backyard and daily walks. Plenty cuddle time and what ever routine you prefer. Small breed only. 4.Walks: each walk is 30 min or 1 hour. if you need other service besides during that time just let me know. Small, medium, and Large dogs are all welcome. A little bit about myself, I live with husband and 2 fur babies. I have owned various size and breed of dogs since I was in elementry schools. Right now I have 3 small dogs( all were adopted), one is a senior and one is handicapped. They go out for walks at least 30 min per day in the parks, and I groom them myself. We trained them well and they dont beg by the table, they dont bark for no reasons, and they are well socialized. I am so grateful for able to take care them. One of the dog is 15 years old she got adopted by us at age 7, she came with anxiety issues. we retrained her to relieve herself outdoor, she learned fast, and she was rehabilitated into a wonderful, fun, loving dog. The handicapped one has a birth defects but he is the sweetest dog I ever owned, he is well behaved and very smart. I want to pour more time into taking care of these amazing pets, they are not just dogs, they are our family, companions and true friends I work as arts and craft teacher at elementry school (5 hours per week). I also teach 3 hours per week at the YMCA. I have ample time to take care of the dogs. At my home the dogs are being monitored with servalliace camera. I let them out every 2 -4 hours during the day if I am home. Our yard is fenced. They get 2 meals a day. some treats. I follow clients instruction on taking care of dogs.

Sitter Profile Image: Claire H.
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Claire H.
from
$20
per visit
5.0 out of 5 stars
6 reviews
13 years of experience
South End, Stamford, CT, 06902

Claire is amazing. She kept in touch throughout our weekend away, sending photos of Noodle and keeping us updated on what they were doing. She spent a lot of time with Noodle, taking her for walks and playing with her. Noodle loves her. Claire is very professional and you can tell she loves dogs. Don't hesitate to book her. She's great. We will definitely use her whenever we need a sitter for Noodle.

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Dean T.
Sitter Profile Image: Raquel A.
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Raquel A.
from
$30
per visit
5.0 out of 5 stars
10 reviews
1 repeat client
4 years of experience
Glenbrook, Stamford, CT, 06906

Raquel was great to our sweet Jackson! She was right on time, sent us lots of pictures and gave our boy lots of love! We will definitely be using her again!

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Connor E.
Sitter Profile Image: Sindy A.
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Sindy A.
from
$25
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
6 years of experience
Downtown, Stamford, CT, 06901

Sindy was GREAt! Friendly and Very responsive, flexible about timing and last minute needs! She sent us adorable pictures of Loki during her stay <3 We glad we met her and definitely recommend ;)

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Thaynara D.
Sitter Profile Image: Chris C.
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Chris C.
from
$27
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
15 years of experience
Greenwich, CT, 06830

About: Dogs have been my world for 15 years. I've worked in daycares, training facilities, grooming, shelters, and now I focus on providing reliable walks and personalized care. I offer neighborhood walks during the week, and on weekends I also offer 90 to 120 minute off-leash adventure hikes for the weekend warrior dogs that love to explore and need to burn off some energy! Every visit includes photos, updates, gps and plenty of attention! Dogs are what i do! And because this is what I do professionally, I’m able to provide consistent scheduling and care, building relationships with your pup! Almost any given day you can find me working with dogs of all sizes and energy levels! I primarily provide care through structured outdoor hikes rather than in-home services. When working in a client’s home, I follow all instructions closely, keep doors and gates secure, and maintain a calm, controlled environment.

Sitter Profile Image: Wendy R.
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Wendy R.
from
$20
per visit
5.0 out of 5 stars
26 reviews
15 repeat clients
2 years of experience
West Side, Stamford, CT, 06902

Wendy is super sweet and responsive to all of my messages ! She texts me pics and short videos & responds timely to all of my requests . She is attentive to my puppy even when the weather is a bit chilly and it’s mostly indoors apart from a potty break . I would book her again :)

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Rachel E.
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The median cost per visit for dog sitting in Old Greenwich is $25

Dog parents share their Rover experiences - Old Greenwich

1 / 1
5.0 out of 5 stars

Claire was amazing! She took so many videos of scout, and he looked like he was really comfortable with her and enjoying the pets! I will definitely use Claire again.

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Rebecca K.
Drop-In Visits
5.0 out of 5 stars

Maria was great with my dog. She came in at the last minute - she was so very responsive and communicative- providing happy pictures of their short time together. I will definitely be using her again! Many thanks Maria!

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Linda L.
Drop-In Visits
5.0 out of 5 stars

I am so happy with Rover and Aaron.I have complete piece of mind when I am away from my 17 year old dog with him .

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Kimberly M.
Drop-In Visits
5.0 out of 5 stars

Crystal is the best. She is excellent with Snow. She is the doggie whisperer. Crystal is my fur baby favorite. Professional,on time, and goes beyond expectations.

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Dina M.
Drop-In Visits
5.0 out of 5 stars

Stephanie always comes on time. She is caring for the dogs and has great communication skills. She is a top sitter for us.

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Cheryl W.
Drop-In Visits
5.0 out of 5 stars

Michelle took great care of my dog when I was away. She was on time, communicative and responsive when needed. I’d highly recommend her to other local pet parents.

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Natasha F.
Drop-In Visits
5.0 out of 5 stars

Kaitlyn was on time and so sweet with my Leo! He loved playing in the backyard with her for the afternoon!

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Corinne B.
Drop-In Visits
5.0 out of 5 stars

Annabel was on time and so great with my Leo! He had tons of fun running around in the backyard with her .

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Corinne B.
Drop-In Visits
5.0 out of 5 stars

Ali was perfect. Responsive communicator, kind spirit, and genuine affection for our puppy. Could not have had a more positive experience. Would highly recommend!

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Michael G.
Drop-In Visits
5.0 out of 5 stars

Maria was AMAZING! Our dog is really nervous around new people and she took such good care of him and made sure he had everything he needed. Will 100% rebook again

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Rebecca R.
Drop-In Visits
5.0 out of 5 stars

Daniela was great. We needed help and she accepted our request at last minute. Took great care of our dogs and was very responsive. Highly recommend.

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Kim F.
Drop-In Visits
5.0 out of 5 stars

Nicole is wonderful with my Atlas. She is always on time, communicative, and sends lots of pics. I was concerned that he might develop separation anxiety when I returned to work, but Nicole’s drop-ins keep him happy and engaged (the only separation anxiety is mine 😊). Her consistency and experience is helping him learn his manners (leash and potty etiquette) very well.

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Amanda B.
Drop-In Visits
5.0 out of 5 stars

Very dependable and reliable! Along with being respectful with the home, I completely trust Francisco to watch my 2 needy dogs.

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Steven Y.
Drop-In Visits
5.0 out of 5 stars

Carter is great with my dogs and is professional with his service! Very happy to have found him to care for them.

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susanne m.
Drop-In Visits
5.0 out of 5 stars

Emma has good communication skills. Hunter and Tucker reacted well, Brownie was shy and hiding. We look forward to working with her in the future.

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Cheryl W.
Drop-In Visits
5.0 out of 5 stars

Chris was great with my puppy! Very attentive to both my needs and my puppy’s needs during his visits. Great communication and photos to ease my nerves. I’m would highly recommend him for any of your pets needs!!

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Amanda E.
Drop-In Visits
5.0 out of 5 stars

Excellent: Reliable, caring, and responsible. Claire provided us with photos and updates while taking care of our dog. HIGHLY RECOMMEND!!!!!

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John M.
Drop-In Visits
5.0 out of 5 stars

Evelina was absolutely amazing with my Marley while I was away on a week-long cruise. From the start, she was professional, kind, and very communicative, which gave me real peace of mind. She sent regular updates and photos, and it was clear Marley was happy, comfortable, and well cared for the entire time. When I got back, Marley was relaxed, healthy, and clearly loved his time with her. Evelina truly treated him like her own. I couldn’t have asked for a better sitter and will definitely be booking with her again. Highly recommend Evelina to anyone looking for a trustworthy and caring Rover helper.

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Rafael Y.
Drop-In Visits
5.0 out of 5 stars

Nicole was really great! Our dog can be nervous around new people but he seemed to really like her. We felt confident she’d take good care of him.

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Rebecca R.
Drop-In Visits
5.0 out of 5 stars

Excellent! Ryan is super patient and kind!!! And he also help us clean the potty pads and refill the food. Thank you so much 😊 5 stars!!! Highly recommend.

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Yue L.
Drop-In Visits
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Popular requests for dog sitting - Old Greenwich

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Sitters in Old Greenwich average 6
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FAQs for Drop-In Visits - Old Greenwich

Frequently asked questions about Rover

The average cost for Dog Sitting in Old Greenwich on Rover is $22.2 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 18,084 sitters on Rover offering Dog Sitting across Old Greenwich. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Old Greenwich stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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!

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 Rover's Trust & Safety page .

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 Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Old Greenwich with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Old Greenwich. On Rover:

  • 89% of sitters can help with special care needs
  • 93% 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.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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