House Sitting in Winthrop

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

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Top rated Winthrop house sitters

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
94 reviews
32 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: Audrie C.
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Audrie C.
Star Sitter
$73
total per night
5.0 out of 5 stars
11 reviews
2 repeat clients
8 years of experience
Winthrop, MA, 02152

Audrie stayed with my kitty for a few days and she was absolutely wonderful. She is super sweet and communicated well, sending pictures everyday. I would definitely use her again!!

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Elizabeth M.
Sitter Profile Image: Arshneel K.
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Arshneel K.
$89
total per night
5.0 out of 5 stars
54 reviews
17 repeat clients
8 years of experience
Boston, MA, 02110

Arshneel was so great with Rhubarb! She sent updates with photos and videos (which we love!) and was communicative about Rhubarb. We asked ahead of time the best way to care for Rhubarb given the heat wave which we really appreciated. We came home to a very clean apartment and happy dog, and would definitely book with her again!

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Kelsey P.
Sitter Profile Image: Lauren B.
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Lauren B.
$89
total per night
5.0 out of 5 stars
28 reviews
5 repeat clients
10 years of experience
Boston, MA, 02129

Jean and Tom L. House sitting - August 15, 2025 Five Stars. Lauren was outstanding. She took exceptional care of Our Bischone, Rosie. It was the first time we had a non-family member watch our dog. Rosie is very skittish and anxious around people she does not know. However, Lauren took great care to set Rosie at ease. We highly recommend Lauren and are planning to book her again.

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

Alexandra stayed with our 6 month old pup, Ray, for two days while we visited the Cape. Ray has an abundance of energy and, given his young age, requires a lot of time outdoors on walks and exploring. Alexandra was accessible, easy to talk to, and very committed to keeping us looped in via text (updates, pictures, and videos). We were grateful that Alexandra came over for short visits twice prior to coming to stay with Ray. This way, he was already a bit familiar with her and so were we. We feel very fortunate to have connected with her and plan to use her services again in the future. Would highly recommend her to family, friends, and people in our community.

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Rachele Elizabeth W.
Sitter Profile Image: Anastasia C.
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Anastasia C.
$55
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
East Boston, Boston, MA, 02128

Anastasia responded to my booking with less than an 24 hour notice. She immediately responded and made time to meet my pup Clem within an hour of booking! She was very communicative while I was away and made sure to send lots of updates throughout her stay. She’s dog and human approved!!

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Kristian B.
Sitter Profile Image: Volkan E.
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Volkan E.
$117
total per night
5.0 out of 5 stars
62 reviews
15 repeat clients
20 years of experience
Boston, MA, 02129

Volkan took great care of our anxious senior pup. He shared updates and photos that put us at ease while we were away. And he left our house cleaner than it was when he arrived!

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Isaiah O.
Sitter Profile Image: Haowen S.
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Haowen S.
Star Sitter
$100
total per night
5.0 out of 5 stars
135 reviews
41 repeat clients
13 years of experience
Everett, MA, 02149

Haowen is the best! He took amazing care of our yellow lab, taking him for many long walks, playing frisbee, and cuddling with him on cold December nights. I know all this because he sent me dozens of pictures every day for the whole week he was at our house. He left the house in perfect condition and even watered the plants. He even emailed in the middle of the night when our lab had some leg pain. Highly recommended!

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Cyrus V.
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 fantastic! I had only ever left my cat, Rajah, with close friends or family so I was so so nervous to hire someone. Jennifer put my mind at ease immediately. She was so communicative and kept me updated several times/day with his behavior, meals, sleep habits, and litter box cleanings. I know Rajah had a great time! She gave him a ton of attention, which is exactly what he needs. Jennifer left the apartment in great shape when she left, so it made my life so easy and stress free when I came home from a busy work trip. I would absolutely love to have her back to watch Raj again!

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Marissa
Sitter Profile Image: Skylar A.
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Skylar A.
Star Sitter
$139
total per night
5.0 out of 5 stars
30 reviews
12 repeat clients
17 years of experience
Boston, MA, 02129

We loved Skylar! She was friendly and playful with our puppy while providing frequent potty breaks to prevent accidents in the house during his potty training experience. Would definitely use her again!

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Allie H.
Sitter Profile Image: Sergio M.
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Sergio M.
$89
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
East Boston, Boston, MA, 02128

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.
Sitter Profile Image: Eryn B.
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Eryn B.
$73
total per night
4.7 out of 5 stars
45 reviews
26 repeat clients
20 years of experience
Boston, MA, 02129

Eryn did an amazing job with my Cooper who is a nut job! He has a lot of anxiety and it was the first time I left him alone with a stranger, but she accommodated all of his special needs and sent lots of updates.

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Gem M.
Sitter Profile Image: Andrew T.
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Andrew T.
Star Sitter
$84
total per night
5.0 out of 5 stars
160 reviews
56 repeat clients
15 years of experience
Medford, MA, 02155

Andrew was fantastic. He sat for Cooper at our place for 4 days and did a great job caring for our pup, administering meds, and taking care of the house. Thanks!

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Tom & Tony A.
Sitter Profile Image: Fahad S.
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Fahad S.
Star Sitter
$89
total per night
5.0 out of 5 stars
218 reviews
58 repeat clients
14 years of experience
Malden, MA, 02148

Fahad did a great job house sitting for me while I was out of town. He took care of my senior cat and senior dog very well. I received lots of photos and constant communication.

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Ryan R.
Sitter Profile Image: Kirsten R.
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Kirsten R.
$45
total per night
10 years of experience
Winthrop, MA, 02152

About: I have been an animal lover since I was a kid. Though I cannot afford my own dog right now, I am always looking to hang out with dogs any chance I can get! My roommate has a Bernese Mountain Dog who is the most mellow, sweetest pup ever (she is 8 months old). I assist in feeding her, walking her, playing with her, and just keeping her company as my roommates schedule is more demanding than mine. I love going for long walks, (or runs), playing fetch, and just keeping dogs company. I think I am a great candidate due to my experience with animals and my love for them. I am excited for the day that I can provide a home to my own dog!

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

Kristina went above and beyond taking care of my senior dog Jazzy. She sent lots of photos and updates everyday. When we met before booking, she took notes during our conversation, which demonstrated how she is a detail oriented person. I left her a 2-3 page document with instructions about Jazzy’s routine and my apartment. She followed the instructions very closely and everything went perfectly! It was a huge relief to know Jazzy was in the care of an amazing person while I was away. For anyone with senior dogs, you can be assured that Kristina will give your pup the care they need (but for dogs of all ages too)! ☺️🐾 I would certainly hook her again!

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Ariana C.
Sitter Profile Image: Shantae Mcdonald
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Shantae Mcdonald
$67
total per night
5.0 out of 5 stars
34 reviews
16 repeat clients
10 years of experience
Chelsea, MA, 02150

Shantae is great. She took very good care of my little doggie. She is also very responsible and followed all the instructions I provided pertaining to the dog. I fully recommend her.

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Nans M.
Sitter Profile Image: Masiel P.
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Masiel P.
Star Sitter
$134
total per night
5.0 out of 5 stars
55 reviews
23 repeat clients
5 years of experience
East Cambridge, Cambridge, MA, 02141

Masiel was friendly and came over a few days before the booking to meet our dog. She got along well with our dog and took him for several walks. She kept us updated with photos and videos. She also kept the house clean. We would definitely book her again. Thank you!

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Marissa L.
Sitter Profile Image: Destinee M.
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Destinee M.
$73
total per night
5.0 out of 5 stars
10 reviews
4 repeat clients
3 years of experience
Revere, MA, 02151

Destinee was wonderful with Brutus. She sent me pictures so I could see he was happy and cared for. She also left my house just as it was before she came. Would highly recommend her for your fur babies!

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Heather S.
Sitter Profile Image: Layla M.
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Layla M.
$84
total per night
5.0 out of 5 stars
5 reviews
2 repeat clients
2 years of experience
Saugus, MA, 01906

About: I am a college student who majors in Biomedical Sciences and plans to attend veterinary school after graduation. I have always had a love for animals, especially dogs, since I was young, and have helped care for my own dog since childhood. My passion for animal care has been my motivation to pursue a future in veterinary medicine. Along with caring for my own dogs, I have had experience with dog sitting and dog walking. I am comfortable caring for dogs of all sizes and personalities while making sure they are happy, safe, active, and well cared for. I am currently a college student home for summer break, and I am looking for part-time work. I am available almost every day until August 1st. I will be home again for Thanksgiving break, winter break, and spring break. When caring for pets in my client's home, I would follow the pet's normal routine and follow any additional instructions my client has left me while playing and caring for their pet.

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Over 196
pet parents in Winthrop have booked house sitting

Winthrop pet parents share their Rover experiences

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5.0 out of 5 stars

Trin is so good with my puppy! So attentive, always sends me updates, and I can tell my puppy really likes staying with Trin. Def will continue to book with her!

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Emily R.
House Sitting
5.0 out of 5 stars

Emily was great! She was very communicative, flexible on timing, and sent lots of photos. Would hire her again in a minute!

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Allie C.
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

Skylar was great! It seems like our dog got super attached and was missing her when she was leaving. Great updates too. Definitely would recommend Skylar and will be booking in the future.

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Taner K.
House Sitting
5.0 out of 5 stars

Melissa was awesome! She’s a professional and I could tell she had a lot of experience. She came by for a brief meet and greet before her stay and my dog immediately took a liking to her. I came home to a happy puppy! I will happily reach out to Melissa again in the future

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Sonia B.
House Sitting
5.0 out of 5 stars

As always Amy took excellent care of our senior dog roux! We especially appreciate the updates and how she cares for Roux as her own.

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Nicholson D.
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

Maddie is always amazing, and my boys definitely didn't listen when I told them to be good for her but she loves them anyway! As always, flexible , communicative, and caring. Thank you so much, Maddie!

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Holly T.
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
5.0 out of 5 stars

Ari is such a trustworthy pet sitter! Super responsive and kind. We’d trust her with our pets and she is very attentive, loving, and knowledgeable. 10/10 sitter!

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Ashlyn P.
House Sitting
5.0 out of 5 stars

Heaven is absolutely fantastic. My dogs love her, and one of them was an abused rescue dog, so she is very nervous of new people. She loved Heaven right away. My two pugs also instantly felt comfortable with her and she gave them lots of cuddles. We went to Europe for a long time so it was important to is to really trust someone. Out digs have very complicated diets and daily medications. Heaven handled all of that perfectly. She is professional, kind and a great communicator. She is an Awesome pet sitter, and trustworthy in the home.

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Amanda C.
House Sitting
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  1. 1. Search

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  2. 2. Meet & Greet

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  3. 3. Book & Pay

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The median cost per night for house sitting in Winthrop is $60

Why Choose Rover?

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  • Reservation protection

    It doesn’t happen often, but if your house 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.

Sitters in Winthrop average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winthrop on Rover as of Jun 2026 was about $60 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Winthrop house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 6,350 house sitters in Winthrop. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 84% of Winthrop house sitters respond in under an hour.

House sitters in Winthrop have an average of 14 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winthrop.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winthrop house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.