House Sitting Winthrop

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

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Over 175
pet parents in Winthrop have booked house sitting

Winthrop, Find top rated house sitting

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Melissa R.
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Melissa R.
Star Sitter
$95
total per night
4.9 out of 5 stars
107 reviews
36 repeat clients
12 years of experience
Boston, MA, 02128

Melissa sat for my dog Hazel and our cat Sasha and was fantastic. Melissa is super professional, sweet, trustworthy, and it is clear she makes caring for your pet her priority. Hazel is a large, strong and reactive dog and Melissa handled her very well. I also get so nervous to leave the pets and Melissa was so reassuring and gave lots of updates and pictures. I will be re-booking Melissa in the future.

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Haley D.
Sitter Profile Image: Masiel P.
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Masiel P.
Star Sitter
$139
total per night
5.0 out of 5 stars
64 reviews
28 repeat clients
5 years of experience
East Cambridge, Cambridge, MA, 02141

Our first experience with Masiel was great. She was warm, friendly and had great energy. She was so loveable with my dog, Charlie. She sent photos and updates and kept my house very clean. We’re excited to use her again.

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Jasmin W.
Sitter Profile Image: Amy O.
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Amy O.
Star Sitter
$120
total per night
5.0 out of 5 stars
24 reviews
4 repeat clients
10 years of experience
Boston, MA, 02110

Amy was an amazing sitter! I felt completely at ease having her in my home with my dogs, who absolutely adored her. She kept me updated throughout their stay, sent lots of pictures, and even handled a tornado warning, making sure the dogs were safe and secure. I would highly recommend her and would happily have her sit again in the future!

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Esther N.
Sitter Profile Image: Emily S.
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Emily S.
$78
total per night
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Boston, MA, 02110

Emily was great house sitting my cat! She is very easy to work with, communicative, respectful, and sent me updates! Thank you so much for your help Emily. Will definitely be asking her to sit again!

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Sadie W.
Sitter Profile Image: Kristina M.
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Kristina M.
Star Sitter
$106
total per night
5.0 out of 5 stars
103 reviews
24 repeat clients
34 years of experience
South End, Boston, MA, 02116

Kristina did a fantastic job taking care of my 2 dogs and cat while I was away! Her detailed updates and myriad of adorable pics gave me confidence everyone was being very well taken care of while I was away. We'll definitely be booking Kristina again in the future

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Alyssa M.
Sitter Profile Image: Jennifer M.
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Jennifer M.
Star Sitter
$117
total per night
5.0 out of 5 stars
29 reviews
15 repeat clients
8 years of experience
East Boston, East Boston, MA, 02128

Jennifer was great! She communicated very efficiently, loved on my pups well, and sent great pictures! I will book her again 10/10! I wish I could give her more than 5 stars!

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Rebecca C.
Sitter Profile Image: Andrew T.
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Andrew T.
Star Sitter
$84
total per night
5.0 out of 5 stars
172 reviews
57 repeat clients
15 years of experience
Medford, MA, 02155

Andrew was great with Koji. He took good care of him, took him for walks, played with him & kept him entertained. Koji has some mobility issues and Andrew followed our directions carefully and kept Koji comfortable. He was also able to administer medications as needed. Will work with him again :)

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Sushrut K.
Sitter Profile Image: Haowen S.
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Haowen S.
Star Sitter
$100
total per night
5.0 out of 5 stars
180 reviews
59 repeat clients
13 years of experience
Everett, MA, 02149

Haowen was so communicative and kept us constantly up-to-date for our slow to warm dog. He was so loving and patient and gave our dog so much attention and care. Can’t wait to have him stay again!

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Ilana R.
Sitter Profile Image: Sasha P.
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Sasha P.
Star Sitter
$106
total per night
5.0 out of 5 stars
32 reviews
12 repeat clients
25 years of experience
Boston, MA, 02128

I’m afraid to leave this review because Sasha may have less availability in the future, not that I’m so influential…lol. However, I must say that my dogs, who have separation anxiety, took to Sasha like no other dog sitter we have had! The communication and engagement throughout her stay was excellent. We got pictures and feedback while she was with the dogs and she answered all our messages very quickly. I could tell by the pictures that our girls were very comfortable and happy and that means the world to us. Perhaps these empty nesters will actually get to go away for a weekend in the near future! Sasha welcomed my list of instructions and followed through and left our dogs and our home in great shape. I couldn’t be happier!

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Peter and Diane M.
Sitter Profile Image: arik a.
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arik a.
$62
total per night
5.0 out of 5 stars
23 reviews
5 repeat clients
13 years of experience
Boston, MA, 02127

Arik is the absolute best sitter and our pup is so lucky to have him! He always sends us updates, and we just know Bo has the most fun with him.

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Emily & Daniel M.
Sitter Profile Image: Alexandra L.
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Alexandra L.
$111
total per night
5.0 out of 5 stars
48 reviews
19 repeat clients
7 years of experience
Winthrop, MA, 02152

Alexandra did overnight sitting for us again and was very communicative and supportive to our pets' needs! We have an older cat with urinary struggles, and she was extremely attentive to the areas we requested and gave us great updates. Our pets love her and we are grateful to have a reliable, caring and responsible sitter while we travel!!

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Jeremy D.
Sitter Profile Image: Alexis G.
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Alexis G.
$84
total per night
5.0 out of 5 stars
8 reviews
1 repeat client
7 years of experience
Somerville, MA, 02145

It was so great having Alexis take care of our 5-month-old puppy for the weekend. She had tons of experience and he was in great hands. She kept him on a great schedule with lots of fun, play, and walks and sent updates and pictures morning and evening. He loved her. She also left the house in perfect condition. We would definitely love to hire her again.

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Laura O.
Sitter Profile Image: Josselyn J.
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Josselyn J.
$36
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
12 years of experience
Saugus, MA, 01906

Benny absolutely loves when Josselyn comes to spend the day with him! She is so great with him and I always know he's being taken care of, which means so much to us.

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Lauren W.
Sitter Profile Image: Julia L.
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Julia L.
$64
total per night
5.0 out of 5 stars
11 reviews
4 repeat clients
5 years of experience
Chelsea, MA, 02150

About: I always grew up with dogs and cats growing up and still now. I’ve always had a very good connection with animals especially dogs. B If it’s a week day I’m available for walks/visits & sittings. When it comes to boarding I have wider availability on the weekends. Hope this helps I have a dog and a cat they are 2 years and 11 years old they’re allowed on the furniture. They are are friendly but a little hesitant to newcomers but love attention.

Sitter Profile Image: Samantha N.
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Samantha N.
Star Sitter
$95
total per night
5.0 out of 5 stars
31 reviews
3 repeat clients
5 years of experience
Salem, MA, 01970

Sam was an amazing sitter for our 3 dogs and they loved her company so much. She watched the dogs while we had to travel far for a concert and she kept them loved and entertained until we returned. She is kind, sweet and clearly loves our dogs. She updated us with photos and kept us up to date frequently. We will hire her again without question!

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Aurelio D.
Sitter Profile Image: Stephanie D.
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Stephanie D.
$95
total per night
5.0 out of 5 stars
114 reviews
37 repeat clients
17 years of experience
Revere, MA, 02151

We absolutely love Stephanie, but not nearly as much as our pup does. He goes full Velcro-pittie whenever she stays with him and she always sends us the best photos and video updates. Top notch communication and care of our home, and most importantly of our boy. Can’t recommend her enough!

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Kristen T.
Sitter Profile Image: Camille P.
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Camille P.
$85
total per night
5.0 out of 5 stars
41 reviews
8 repeat clients
7 years of experience
Somerville, MA, 02145

Hi - Camille took care of our wonderful yellow lab, Ollie, and our house for a long weekend. She was amazing and I look forward to working with her again. She kept us well informed about what was happening, and when we had a question, she quickly got back in touch. She is another member of this wonderful Rover.com family. I am so happy that we found you all and Camille. Thank you, Tom

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Tom W.
Sitter Profile Image: Annaliese G.
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Annaliese G.
Star Sitter
$89
total per night
5.0 out of 5 stars
104 reviews
30 repeat clients
3 years of experience
Chelsea, MA, 02150

Sophie and my cats were happy and well cared for when I returned, and my home was left clean and tidy. Communication throughout the stay was good, and I also appreciated her willingness to be flexible while battling a cancelled flight incident during my travels. Overall, it was a positive experience.

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Merisa A.
Sitter Profile Image: Danielle K.
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Danielle K.
Star Sitter
$50
total per night
5.0 out of 5 stars
16 reviews
5 repeat clients
10 years of experience
Boston, MA, 02122

Danielle was great! She shared great updates and pics of kuzco while we were traveling and it was clear how much she cared about him being comfortable and having a good time with her!

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Bethany J.
Sitter Profile Image: Amy A.
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Amy A.
$77
total per night
5.0 out of 5 stars
48 reviews
15 repeat clients
7 years of experience
Boston, MA, 02115

Amy is trust worthy and responsible. She provided an excellent care for our little girl who is recovering after a surgery . We definitely will use her again.

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Rimma K.
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The median cost per night for house sitting in Winthrop is $63

Pet parents share their Rover experiences - Winthrop

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5.0 out of 5 stars

As always, my 2 angels didn't fail to make her stay eventful, but Maddie genuinely loves them, no matter what trouble they cause!

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Holly T.
House Sitting
5.0 out of 5 stars

We booked Alexandra last minute. The very next day she arrives at the agreed arrival time and my dog loved her. The entire time we were away she was open to communication and sent videos of she and my dog playing and on walks. She left our apartment exactly how we left it, with happy healthy pets.

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Grayson & Mark P.
House Sitting
5.0 out of 5 stars

Emily was so great! We came back to a happy dog and a clean house. She was super communicative over the course of her whole stay with our dog. She sent a lot of great updates and pictures. She took care of our home and our dog so well. We will definitely use her again!

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Alison B.
House Sitting
5.0 out of 5 stars

Alicia watched dog at my home while I was at my wedding, everyone who I usually have watch her was also at my wedding.She was so amazing, It felt so good knowing my dog was in such good hands. She sent so many pup dates and was just absolutely lovely. She stayed at my house and left it so clean and my dog was so happy and loved her so much!

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Sarah K.
House Sitting
5.0 out of 5 stars

Skylar was amazing with our dog. She sent us consistent updates, and we could tell Milo missed her after she left. She was super communicative and made us feel so at ease given our dog can be a little anxious at times.

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Courtney C.
House Sitting
5.0 out of 5 stars

Absolutely amazing dog/ house sitter! Shaun is VERY responsive and reliable; and provides real-time updates with pictures and videos. Apparently there was a coyote near our backyard when our dog was outside and he notified us immediately, picked up our dog and went inside. He's thoughtful, caring and left our house exactly as we left it for the weekend. We will absolutely use Shaun over and over again. We feel lucky to have found him. Thanks again Shaun!

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Scott R.
House Sitting
5.0 out of 5 stars

Sophie and my cats were happy and well cared for when I returned, and my home was left clean and tidy. Communication throughout the stay was good, and I also appreciated her willingness to be flexible while battling a cancelled flight incident during my travels. Overall, it was a positive experience.

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Merisa A.
House Sitting
5.0 out of 5 stars

Trin was absolutely wonderful with our Cavalier King Charles Spaniel, Zero! From our first meet & greet, she was kind, professional, and made us feel completely at ease. While we were away, she sent us regular updates and lots of photos, which meant so much to us. Zero looked happy, relaxed, and comfortable the entire time. When we got home, he was calm, content, and clearly very well cared for. She also took great care of our home, followed all of our instructions, and communicated with us throughout the stay. We truly felt that Zero was treated like one of her own. We couldn’t have asked for a better first Rover experience, and we would absolutely book with Trin again. Highly recommend her to anyone looking for a trustworthy, caring, and reliable sitter!

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Burçin S.
House Sitting
5.0 out of 5 stars

Melissa was awesome with my fur babies! She responded quickly and gives frequent updates and pictures. I plan on using her again!

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Lisa B.
House Sitting
5.0 out of 5 stars

We are so grateful to Amy for taking care of our pup while we are away. Her communication helps us navigate all the emotions of being away.

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Nicholson D.
House Sitting
5.0 out of 5 stars

Ian's dog sitting was excellent. He is really knowledgeable on dog behavior, and he's highly personable. My dog, Sully, loved him right away. Ian followed all my instructions and kept me updated as I requested. He also gave Sully lots of love, attention, and companionship-- ultimately going above and beyond regular dog sitting duties. He is my sitter again anytime for Sully in the future.

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Ana E.
House Sitting
5.0 out of 5 stars

Jennifer was amazing! She provided great updates throughout the day and I could tell from the pictures my needy & quirky pup was very comfortable around her!

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Chase G.
House Sitting
5.0 out of 5 stars

Sergio is always so amazing with Summer! We are so grateful he had time to come hangout with her while we went out for the night. He keeps you constantly updated and overall does such an amazing job! We will continue to book with him!

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Kayla C.
House Sitting
5.0 out of 5 stars

River was able to come and watch our dog for just the evening on semi short notice after he was recovering from surgery. As always she was prompt, communicative and dependable! Wally was so excited to see her and was snuggled up with her all night. Will always recommend her services to anyone looking to hire her!

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Jami W.
House Sitting
5.0 out of 5 stars

Colleen was amazing! She spent the weekend with our dog Sage. She sent plenty of updates with tons of pictures. I was a little nervous Sage wouldn't want us to come home. :) They went on lots of walks and did plenty of cuddling. I feel like my house just might have been cleaner than I left it. We are already scheduling our next getaway with Colleen!

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Rebecca M.
House Sitting
5.0 out of 5 stars

We’ve now booked with Audrie twice and she is truly a 10/10 sitter. She stays in our home with our cat and 1-year-old lab, and we always come back feeling like everything was in the best hands. She sends regular updates and photos, which gives us so much peace of mind while we’re away, and she’s great about flagging anything out of the ordinary right away. What really stands out is how intuitive and genuinely caring she is with animals. Our puppy actually went into heat the night we were coming home, and she stayed a few extra hours to comfort her and make sure everything was okay- that meant so much to us. You can just tell she truly loves what she does. As an added bonus, she leaves the house spotless, which is the best feeling after coming home from a trip. We feel so lucky to have found her and will absolutely continue booking with her!

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Dominique G.
House Sitting
5.0 out of 5 stars

Sophia is wonderful! Communicative, friendly, and was great with my giant dog and cat. She hunkered down with my pets during a massive blizzard and eased our minds during the storm while we were out of town. Thank you, Sophia!!

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Paige B.
House Sitting
5.0 out of 5 stars

Stephanie always takes amazing care of our pups and our house! She is reliable and extremely communicative and we trust her completely. She has become our go-to for sitting when we go away.

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Vanessa O.
House Sitting
5.0 out of 5 stars

Caroline took great care of my dog, Oliver, over the weekend and was a huge help! She took the time to go over Oliver’s needs with me and sent several picture updates during the visit. She was super flexible and easily adapted to changes. Highly recommend!

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Kaylee R.
House Sitting
5.0 out of 5 stars

Tracy is the best! Always goes above and beyond. She takes great care of my pups when I’m away or just gone for a longer period of the day. Highly recommend if you’re in need of a great pet sitter!!

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Melissa L.
House Sitting
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  • 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?

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  • 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.

Meet local sitters who will treat your pets like family

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    Browse profiles of sitters near you who offer house sitting
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Popular requests for house sitting - Winthrop

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Sitters in Winthrop average 4
repeat house sitting clients

FAQs for House Sitting - Winthrop

Frequently asked questions about Rover

The average cost for House Sitting in Winthrop on Rover is $42.8 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .

As of August 2026, there are 6,287 sitters on Rover offering House Sitting across Winthrop. 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 Winthrop 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 Winthrop 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 Winthrop 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 Rover Guarantee , 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 Rover's Trust & Safety page .

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 short introductory meeting between you, your pet, 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.

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.

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

  • 92% of sitters can help with special care needs
  • 97% 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.

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