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
102 reviews
36 repeat clients
12 years of experience
Boston, MA, 02128

We're so grateful to Melissa for taking such good care of our wonderful but neurotic dog Birdie! Melissa is communicative, responsible, and clearly loves dogs. We would have her to sit for Birdie again anytime.

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Cornelius H.
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: Skylar A.
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Skylar A.
Star Sitter
$139
total per night
5.0 out of 5 stars
33 reviews
14 repeat clients
17 years of experience
Boston, MA, 02129

Skylar was excellent!! So communicative, came perfectly on-time and shared so many adorable pup-updates while we were away. Our dogs were very well take care of and we felt at ease with Skylar being with them. I would recommend her to ANYONE looking for a sitter. Thank you, Skylar!!

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Sally M.
Sitter Profile Image: Erica B.
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Erica B.
$90
total per night
5.0 out of 5 stars
41 reviews
18 repeat clients
10 years of experience
Medford, MA, 02155

Erica was amazing! She kept us updated on our pups the whole time we were away. We will definitely use her again and would recommend to a friend! :)

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Samantha F.
Sitter Profile Image: Kristina M.
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Kristina M.
Star Sitter
$106
total per night
5.0 out of 5 stars
97 reviews
22 repeat clients
34 years of experience
South End, Boston, MA, 02116

Kristina was great!! We had a sitter cancel last minute and consider ourselves VERY lucky that Kristina was available. She did an excellent job dog & house sitting and sent us detailed updates. We will absolutely book with her again!!

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Jodi H.
Sitter Profile Image: Danielle K.
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Danielle K.
Star Sitter
$50
total per night
5.0 out of 5 stars
13 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: Dayna D.
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Dayna D.
$56
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
1 year of experience
East Boston, Boston, MA, 02128

Dayna took great care of my dog while I was gone for a weekend! Super responsive whenever I reached out!

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Eileen D.
Sitter Profile Image: Emily S.
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Emily S.
$56
total per night
5.0 out of 5 stars
1 review
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: Elizabeth A.
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Elizabeth A.
Star Sitter
$111
total per night
5.0 out of 5 stars
31 reviews
10 repeat clients
20 years of experience
Jamaica Plain, Chelsea, MA, 02150

Liz is awesome! I had a lot of anxiety about leaving our puppy, since I work from home and I’m with her all the time. Liz came over to do a meet and greet with us, and she immediately put me at ease. Maisie loved her! Liz sent tons of photos and updates while she was at my house, and I would highly recommend her to anyone looking for a great pet sitter. Maisie got lots of outside play time, walks, and cuddles. She was also great with my four-year-old cats. Would definitely use Liz again!

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Ali B.
Sitter Profile Image: Bridget P.
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Bridget P.
Star Sitter
$139
total per night
5.0 out of 5 stars
151 reviews
34 repeat clients
35 years of experience
Quincy, MA, 02171

Bridget was exceptional! I couldn’t find a better word to describe how great she was with our two Jack Russell’s who both have personalities larger themselves. Bridget checked in daily with us without us having to ask for photos or an update during an overnight for our week vacation. She also took the extra step and took care of our houses. We highly recommend Bridget for anyone looking for a sitter for their babies, she is incredibly trustworthy!

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Jessica H.
Sitter Profile Image: Rachael B.
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Rachael B.
$78
total per night
5.0 out of 5 stars
51 reviews
16 repeat clients
5 years of experience
Somerville, MA, 02143

Rachael took great care of our house and dog Lyka for a long weekend. Lyka is looking forward to seeing Rachael again for a longer stay in October!

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

This was the first time I left Milo with a sitter, and it worked out beautifully. Andrew was great with the dog, communicated clearly and regularly with me before and while I was away, and left the house spotless. I'll definitely try to book him for future trips.

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Tom S.
Sitter Profile Image: Amanda K.
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Amanda K.
$67
total per night
13 years of experience
Medford, MA, 02155

About: My experience in pet care comes from regularly providing walking, sitting, and overnight care for the dogs of family members and close friends. This has allowed me to develop experience working with dogs of varying breeds, sizes, personalities, and exercise needs. In addition to routine walks and daily care, I have frequently stayed in clients' or friends' homes for extended periods while they travel, ensuring both their pets and property are cared for responsibly and attentively. I understand how important trust is when leaving your pet and home in someone else's care, and I take pride in being dependable, communicative, and attentive to every pet's and home's unique routine and needs. Pet care is my primary professional focus, which allows me to maintain a highly flexible and open schedule. Because I am not balancing pet care with another job, I am available to accommodate a wide range of client needs, including daytime walks, drop-in visits, overnight stays, and last-minute requests when possible. This flexibility enables me to provide reliable, attentive care and dedicate my time and energy to ensuring pets receive the attention, exercise, and companionship they need. At this time, I provide care exclusively in my clients' homes and do not offer boarding in my own home, as I already have multiple dogs at home and want to ensure every pet receives the safety and space they deserve. I offer services including dog walking, drop-in visits, pet sitting, and overnight stays. When caring for pets in their own environment, I focus on maintaining their normal routine, including feeding schedules, exercise, playtime, medication administration if needed, and plenty of companionship. My goal is to keep pets comfortable, safe, and stress-free while their owners are away, while also treating each client's home with the utmost respect and care.

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: Alexis G.
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Alexis G.
$84
total per night
5.0 out of 5 stars
6 reviews
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: Sara B.
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Sara B.
$89
total per night
5.0 out of 5 stars
21 reviews
10 repeat clients
10 years of experience
Allston-Brighton, Allston, MA, 02134

Sara was amazing! We were unsure if our puppy had accidentally ingested something the night prior. Sara was on top of it, giving us updates and communicating the whole time! I highly recommend her!

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Zane M.
Sitter Profile Image: Triin P.
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Triin P.
$95
total per night
5.0 out of 5 stars
4 reviews
1 repeat client
14 years of experience
Chelsea, MA, 02150

Triin was fantastic with our two dogs! It’s clear she took the time to really know them and their preferences. They were definitely well cared for while we were away. And she left our home very clean :) would 100% recommend trusting her with your pets!

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Darby H.
Sitter Profile Image: Lauren B.
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Lauren B.
$89
total per night
5.0 out of 5 stars
30 reviews
7 repeat clients
10 years of experience
Boston, MA, 02129

Lauren did a great job caring for my dogs and followed all instructions carefully. I was a little nervous since one of them is reactive, but she handled the situation really well. My apartment was left just as I left it, and I’d be happy to book with her again.

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Kimberly V.
Sitter Profile Image: Masiel P.
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Masiel P.
Star Sitter
$139
total per night
5.0 out of 5 stars
62 reviews
26 repeat clients
5 years of experience
East Cambridge, Cambridge, MA, 02141

Maisel was so great with our dogs, Tavish & Ellie. She took great care of them and they were happy as ever when we returned. She also took meticulous care of our home which she stayed in while we were gone. We’ll definitely book her again next time the need arises!

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Justin F.
Sitter Profile Image: Natalie J.
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Natalie J.
Star Sitter
$111
total per night
5.0 out of 5 stars
172 reviews
61 repeat clients
14 years of experience
Medford, MA, 02155

Natalie house sat this weekend for our recently rescued 7 1/2 yr old wheaten. She was both professional and compassionate. We were very pleased with her work and have already booked her for a week later in the year. It is with great confidence and pleasure that we recommend her to you

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Joe L.
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The median cost per night for house sitting in Winthrop is $63

Pet parents share their Rover experiences - Winthrop

1 / 1
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

Fifi had an ear infection and needed ear drops while I was away and Maddie did a great job taking care of her. She left my apartment very clean and tidy which I greatly appreciated as well. Very communicative and attentive, I recommend!!

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Mia M.
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

Emily was great - communicative, responsible, and took wonderful care of my cat (and house!). Would book her again!

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Rachele R.
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

Alicia was absolutely fantastic and outstanding! She took the time to meet Doxy and Sammie and was very comprehensive in reviewing all their routine needs and habits. She bonded very well with our dogs and sent us photos that made us smile, being reassured that they were in great hands. When I returned home, the dogs were very relaxed and happy. We are so thankful and appreciative to have Alicia’s help with dog sitting and highly recommend her without any reservations. She is truly the best! Thank you so much, Alicia, for taking great care of Doxy and Sammie!

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Anne L.
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
5.0 out of 5 stars

Samantha was amazing! We had a last minute cancellation the week before Christmas and Samantha was readily available for a quick meet and great and to watch our pets a few days later. She was communicative and my pets loved her!

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Paige B.
House Sitting
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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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for house sitting - Winthrop

Select a filter and find qualifying sitters offering house sitting.

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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