House Sitting in Winterport

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

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Top rated Winterport house sitters

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

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Sitter Profile Image: Shaun M.
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Shaun M.
Star Sitter
from
$100
per night
5.0 out of 5 stars
55 reviews
15 repeat clients
30 years of experience
Hampden, ME, 04444

I was very nervous to leave my 4 month old puppy for the first time overnight. Shaun came for a meet and greet first which eased my nerves. She did a great job with a very high energy puppy. I came home to a tuckered out boy, which is always welcome! The house was just as I left it. I will definitely be using Shaun again.

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Jennifer W.
Sitter Profile Image: Jessica B.
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Jessica B.
from
$50
per night
5.0 out of 5 stars
4 reviews
20 years of experience
Bucksport, ME, 04416

Jessica wa wonderful with all my dogs you can tell she really cares gave me updates she is such a joy

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Cindy D.
Sitter Profile Image: Glendon Y.
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Glendon Y.
Star Sitter
from
$75
per night
5.0 out of 5 stars
61 reviews
15 repeat clients
25 years of experience
Brewer, ME, 04412

Glendon is so GREAT !!!! He has helped us so many times and we would never think of not having him watch our dogs, who absolutely ADORE him! We trust Glendon with our home and beloved dogs and wholeheartedly recommend him to EVERYONE !! Thank you GLENDON !

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Joseph B.
Sitter Profile Image: Sydney J.
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Sydney J.
from
$50
per night
5.0 out of 5 stars
16 reviews
8 repeat clients
10 years of experience
Hampden, ME, 04444

Thank you for taking such great care of Pep! Always quick to respond and communicates well when we are away. Pepper seems happy and well cared for when we get home!! Thank you!

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Alison G.
Sitter Profile Image: William W.
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William W.
from
$52
per night
4.5 out of 5 stars
8 reviews
2 repeat clients
11 years of experience
Bangor, ME, 04401

William went above and beyond and sent many photos! Highly recommend again!

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Lina S.
Sitter Profile Image: Emma N.
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Emma N.
from
$30
per night
4.6 out of 5 stars
11 reviews
5 repeat clients
5 years of experience
Brewer, ME, 04412

Emma did a fantastic job taking care of our dog and cat over a 1.5 week period. Our house was also well looked over while we were away on vacation. On top of that, she is a wonderful caring person and easy to work with.

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Sarah L.
Sitter Profile Image: Madison O.
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Madison O.
from
$45
per night
5.0 out of 5 stars
3 reviews
5 years of experience
04402

As soon as we met Madison we felt so comfortable. She was so kind and loving to our dear dog Angel and was flexible with our unique scheduling needs. I loved the photo updates and reports. I could tell that Angel was happy and well cared for while we were away. We are so grateful for Madison!

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Luann M.
Sitter Profile Image: Taylor W.
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Taylor W.
Star Sitter
from
$75
per night
5.0 out of 5 stars
67 reviews
20 repeat clients
10 years of experience
Winterport, ME, 04496

Taylor was a great sitter for our two pups! She came and did the meet and greet promptly and clicked with our dogs right away. She arrived on time, spent the day with them, and kept the house neat and tidy. She kept us updated with pictures and our dogs seemed very well taken care of. Will definitely book with her again!

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Sarah B.
Sitter Profile Image: Joseph S.
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Joseph S.
from
$40
per night
5.0 out of 5 stars
175 reviews
66 repeat clients
12 years of experience
Hampden, ME, 04444

I can’t say enough. My Scout had not been boarded or to daycare during COVID and was an anxious and nervous dog in strange places. He visited Joey Doggo twice for daycare and was totally comfortable on day two. I had no concerns when we left for five days. I got lots of updates and photos and it was clear he was happy and getting lots of love! What more could you ask for I would highly recommend. Joey and Nieves will love you dog like their own❤️

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Karen L.
Sitter Profile Image: Alison M.
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Alison M.
from
$50
per night
5.0 out of 5 stars
20 reviews
5 repeat clients
60 years of experience
Searsport, ME, 04974

Alison was very conscientious and thorough in staying with my two Cavaliers. They were VERY happy pups while she stayed with them! She kept me informed about how they were doing, which allowed me to relax while I was gone. She also left my home in excellent condition—i never would have known anyone was here! I highly recommend Alison.

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Kim W.
Sitter Profile Image: Amber B.
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Amber B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
30 years of experience
Brewer, ME, 04412

About: I grew up on a farm with horses, pigs, sheep, cows, a dog and a cat. I particpated at a young age taking care of them (feeding, brushing, removing manure). Throughout my life I have had personal pets as well as helped care for pets of family and friends. I currently work full-time remotely M-F 8:00am-5:00pm. I also have a 9 year old son. I am typically available weekday evenings after work and weekends. I have a runner that extends from the side entrance of my house to my detached garage with a partially fenced backyard. I live in a safe neighborhood and have great neighbors. Three of my neighbors on my street work for the police department.

Sitter Profile Image: Jessica R.
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Jessica R.
Star Sitter
from
$63
per night
5.0 out of 5 stars
22 reviews
6 repeat clients
30 years of experience
Bucksport, ME, 04416

Our little dog was in the best of hands with Jessica. She kept us updated with how he was doing, stayed attentive to his needs throughout the weekend, and offered a safe, comfortable indoor and outdoor space to explore. Highly recommend!

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Anne E.
Sitter Profile Image: Libby N.
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Libby N.
from
$40
per night
4.9 out of 5 stars
69 reviews
11 repeat clients
10 years of experience
Winterport, ME, 04496

Thank you Libby! Great communication all around and our pups were in a great mood when we got home. She sent pictures throughout the day and will definitely use Libby again!

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daniel c.
Sitter Profile Image: Shmerl B.
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Shmerl B.
from
$45
per night
5.0 out of 5 stars
33 reviews
16 repeat clients
30 years of experience
Brewer, ME, 04412

Molly was wonderful, enthusiastic, great with my 8 year old lab who is obsessed with frisbee and her dog, Leon, was a gem. Highly recommend her.

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Kate M.
Sitter Profile Image: Jasmine S.
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Jasmine S.
from
$250
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
25 years of experience
Prospect, ME, 04981

About: I am always the first to be called when a friend needs doggy daycare or house sitting with dogs, cats, and often other animals. I’ve fostered and found homes for rescues internationally and domestically. I’ve worked for a doggy daycare where I was responsible for 50-70 dogs with a crew of 2-4 people. I also spent a few months off and on taking care of 10-22 huskies while part of the herd were sled racing. I’m comfortable with dogs of all sizes and enjoy seeing all of their unique personalities. I’ve loved animals since I was small. We always had cats when I was little, as well as ducks, chickens, guinea pigs, rabbits, my turtle boy China B, parakeets, and a Senegal parrot foster. I was surprised with a rescue dog when I was 10, Hemingway. It was an amazing experience and I helped train Hemmy to be a service dog for my grandmother who was visually impaired. Winter rates are now $250/day for basic overnights, includes 3 pets. Will adjust include extra rates accordingly to animals and household needs. I’m self employed and have the flexibility to set my daily schedule around your animals needs and regular routine. Lots of scritches, play time and love are part of my commitment to your pets. I am available for short and long walks (depending on your animals needs and ability), playtime, companionship, love and affection, meals and snacks as well as monitoring medication if needed.

Sitter Profile Image: Richard A.
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Richard A.
from
$40
per night
5.0 out of 5 stars
1 review
6 years of experience
Swanville, ME, 04915

Richard was great with my two girls Sadie, the great Pyrenees and Stella, the fluffy cat. He communicated great and sent pictures and took great care of the house. I definitely plan to book Richard again.

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Laurie P.
Sitter Profile Image: Elizabeth B.
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Elizabeth B.
from
$80
per night
4.7 out of 5 stars
16 reviews
5 repeat clients
5 years of experience
Bangor, ME, 04401

About: $20 off your first booking with me! With code ELIZAD92501 I've cared for different animals most of my life. I enjoy walking and I'm very good with them, they usually like me quite well. I've had pet cats, dogs, mice, birds, Guinea pigs, rabbits, fish, chickens and others. They've always been a big part of my life. I'm very attentive and empathetic and love to know everything ahead of time and I always send regular updates and photos. My boyfriend and I live together and he often enjoys helping care for them. He's is very kind hearted and loving and just all around a great guy I'm at home full time right now, I live next to a park with a walking trail and many side streets where I and other people regularly walk their dogs. If I'm not at home my boyfriend is and vice versa. I always make sure my pets have fresh food and water / clean bowls. Water change 3× a day. I like to make sure that they have their food and water station all set up, and their bed and toys set out right after they come in the door so they feel at home. I also note care details down and keep everything in mind. I send updates regularly and lots of photos. I'm attentive and empathetic too! Having an animal next to me while I'm having family time makes my place feel cozy and homey ❤️ I always double check with the owner about what their pets can and can't have and I also know a lot about what's good and bad for them.

Sitter Profile Image: Cailen A.
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Cailen A.
from
$45
per night
7 years of experience
Bangor, ME, 04401

About: Hello! My name is Cailen and I am currently a Veterinary Assistant. I also have years of experience working at an animal shelter. I am reliable, patient, and passionate about animals. I can guarantee that I will take care of every pet as if they were my own! Growing up, I had a big beautiful dog named Mac. In my early adulthood, I have adopted/rescued a few cats named Nora, Baby, Liza, Mikey and Slater. I now have a sweet cat named Wanda. Over the last five years, I have frequently pet/home sat for friends and co-workers. I love both dogs and cats very much, and would be happy to work with either or both. I would love to chat with you about your pet(s) and their needs! I have a fixed schedule at work. I have availability before and after work, along with the 3 days off every week, Tuesday and the weekend. I care for my clients pets as if they are my own. I want to keep your pets as happy as possible while they are in my care. For dogs, I am comfortable doing walks/hikes and outdoor play. For cats, I will keep their areas clean and am willing to spend extra time to let them adjust to me and feel comfortable.

Sitter Profile Image: brian w.
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brian w.
from
$50
per night
35 years of experience
Belfast, ME, 04915

About: I have had dogs since !0 and cats since 6. Have to admit I am more of a Dog guy though Cats Tolerate me. (Joke)... I have trained several dogs in my life two of which I worked with Sarah Hodgson who wrote "puppies for Dummies". Learned so much from her about dogs and found myself helping many of my family and friends over the years train their dogs. I am knowledgeable and am exited to learn more about each every one of my clients Fur babies. I promise you that I will learn I can about your special family member to give them the staycation that they deserve. I work as a teacher so I am able to do over nights, though I am not able to do mid day bathroom breaks. The dogs that I care for must be able to go 8 hours for a bathroom break. I will of course be taking them out before I leave for work and go directly home from school to relieve them. I have a my sweet dog under voice command, a small fenced in area and take for walks. I do not provide boarding. when I am sitting she stays with family or if requested is incredible with other dogs and children. she goes with me anywhere. though she is old enough now that she never feels left out staying with family. (haha)

Sitter Profile Image: Ashley B.
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Ashley B.
from
$50
per night
5.0 out of 5 stars
10 reviews
6 repeat clients
10 years of experience
Belfast, ME, 04915

Ashley came over to visit Donnie prior to and then took amazing care of him! She even came over to feed him breakfast the morning after as we were running a touch late.

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Luke F.
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Over 36
pet parents in Winterport have booked house sitting

Winterport pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

We had a wonderful experience during our week away. It gave us so much peace of mind knowing our pets were able to stay in their own home and keep their normal routines while we were gone. Jessica was communicative, and clearly cared about our pets as if they were her own. We received regular updates and photos, which made it easy to relax and enjoy our trip. When we returned home, the animals were happy and well cared for, and the house was just as clean and organized as when we left. We’re extremely grateful for the thoughtful care and attention Jessica gave our pets and our home. I would absolutely recommend Jessica to anyone looking for a trustworthy and responsible sitter!

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Jordan Z.
House Sitting
5.0 out of 5 stars

Chloe is truly the most conscientious, capable, and kind Rover sitter we could have ever asked for. She stayed with our beloved hound dog for 7 days while we were across the country and we were able to enjoy our trip knowing that he was in her care. She was so attentive, communicated daily updates consistently and timely, including adorable photos of all the snuggling and walking time they were getting together. We will use Chloe every single time we have to be away and will do so with complete confidence that our boy will be in the best possible care there is. Thank you Chloe for everything. Maple is so grateful and so are we!!

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Kelly O.
House Sitting
5.0 out of 5 stars

Della was amazing! She took excellent care of our dog and chickens while we were away. It’s obvious that she truly cares about animals and was very considerate of our home space in and outdoors. Great communication and beautiful picture updates made us feel comfortable being away from our pets. 10/10 recommend Della!

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Sharon U.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Winterport is $50

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 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 Winterport 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 Winterport on Rover as of Mar 2026 was about $50 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 Winterport 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 Mar 2026, there are 108 house sitters in Winterport. 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, 94% of Winterport house sitters respond in under an hour.

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 Winterport.

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. Winterport 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.