House Sitting Windsor

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

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Over 2
pet parents in Windsor have booked house sitting

Windsor, Find top rated house sitting

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: Sarah W.
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Sarah W.
from
$60
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
5 years of experience
Augusta, ME, 04330

Sarah was wonderful! She and our pup were fast friends and we appreciated the photo updates! Would highly recommend!

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Amanda M.
Sitter Profile Image: Liseli M.
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Liseli M.
from
$82
per night
4.9 out of 5 stars
46 reviews
13 repeat clients
4 years of experience
South China, ME, 04358

Liseli is amazing with our big dog, Tycho. He gets really excited when he sees her. I felt very comfortable with Liseli staying in our home and taking care of our little buddies.

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Ashley V.
Sitter Profile Image: Stephanie B.
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Stephanie B.
Star Sitter
from
$68
per night
4.9 out of 5 stars
36 reviews
8 repeat clients
7 years of experience
Damariscotta, ME, 04543

Stephanie was great! She was a huge help when another sitter cancelled last minute. She took great care of our dog and home and communicated well through the experience. We would definitely re-book with her if ever needed! Thank you, Stephanie!

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Whitney A.
Sitter Profile Image: Erin D.
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Erin D.
from
$55
per night
4.9 out of 5 stars
21 reviews
5 repeat clients
30 years of experience
Benton, ME, 04901

Highly recommend Erin for your critter care!! 11/10!!! She watched out 2 dogs, cat, chickens, and house for a week and a half and did such an amazing job. She was very communicative, giving us updates every night. She left the house cleaner than when we left and just did such a good job with our animals. We will absolutely be having Erin help us again and you should too!!

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Emily P.
Sitter Profile Image: Esther B.
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Esther B.
from
$50
per night
5.0 out of 5 stars
2 reviews
2 repeat clients
4 years of experience
Gardiner, ME, 04345

Esther loved on my pets and kept my home in good order. We loved her!

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Amy S.
Sitter Profile Image: Carla V.
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Carla V.
Star Sitter
from
$70
per night
4.9 out of 5 stars
44 reviews
8 repeat clients
5 years of experience
Waterville, ME, 04901

Carla is the best! She sat for our four dogs, including a needy Italian Greyhound. She is super experienced with dogs and treats them like her own. Great communication too. Thank you Carla!

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Rebecca S.
Sitter Profile Image: Katharine D.
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Katharine D.
from
$75
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Randolph, ME, 04346

About: I’ve never not had a pet in my house hold, owning cats, dogs, and even lizards and hamsters over the years. Growing up I also pet sat for birds, snakes, dogs, cats, and fish as well as worked on a horse farm for two summers. My own personal dog is a senior lad at the age of 14 years and have a kitten at home. Ive worked with puppies, adult dogs, and senior pups, kitten and full grown cats. I love to spend time playing and petting them (if thats what they want) and will do my best to love them a fraction of what you do to keep them happy while you’re away! I work in Portland until 4pm every week day and get back to the area around 5. I would be free to care for your pets from around 5:30pm-6:20am. I can feed, walk, brush, pet, and/or play with any of the animals you may have tailoring to whatever best suits their needs, I am an animal lover and want to best support the critters in any way I can in your absence.

Sitter Profile Image: Wendy J.
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Wendy J.
from
$30
per night
5.0 out of 5 stars
3 reviews
30 years of experience
Randolph, ME, 04346

Wendy did a great job with my pup,Buddy! She even stayed later to make sure he wasn’t alone! Very nice, our whole family liked her tight off! She also sent me a great picture of Buddy, he looked very content! She also was available on short notice, as my son surprised me with a visit! Thanks again Wendy! Definitely will be booking you in the near future!

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Wendy B.
Sitter Profile Image: Ascher t.
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Ascher t.
from
$30
per night
25 years of experience
Vassalboro, ME, 04989

About: Hi! I’m a lifelong animal lover with experience caring for a wide range of pets, including dogs, cats, and horses. Growing up around animals has given me a deep understanding of their needs, personalities, and behaviors. I’m attentive, patient, and committed to making sure every pet feels safe, comfortable, and loved while you’re away. Whether it’s going for walks, playtime, or just providing companionship, I treat every animal as if they were my own. I’m also experienced in administering medications and can confidently follow any specific care instructions to ensure your pet stays happy and healthy. You can count on me to provide reliable, compassionate care and plenty of updates so you have peace of mind while you’re away! Pet care fits naturally into my routine, especially during evenings and weekends when I’m most available. I make it a priority to be there for pets when their owners are busy, traveling, or just need an extra hand after a long day. I’m consistently available for evening drop-in visits, making sure pets are fed, exercised, and given plenty of attention and companionship before settling in for the night. On weekends, I have even more flexibility and can accommodate multiple visits, extended care, or last-minute bookings. Caring for animals is something I truly enjoy, so I build my schedule around giving them the time, consistency, and care they deserve. I tailor my care based on each pet’s needs and the service requested, whether I’m in my home or yours. My goal is always to keep pets comfortable, safe, and as close to their normal routine as possible. In a client’s home, I focus on maintaining your pet’s usual schedule feeding, walks, playtime, and any special care instructions so they feel secure in their familiar environment. I keep things clean and organized, and I’m respectful of your space while making sure your pet gets plenty of attention, affection, and exercise. I also provide regular updates and photos so you always know how your pet is doing. If caring for pets in my home, I provide a calm, safe, and pet-friendly environment where they’ll receive lots of supervision, love, and attention. I make sure they have a comfortable place to relax, consistent potty breaks, and plenty of playtime. I’m attentive to details and experienced in administering medications if needed, and I’m always mindful of each pet’s personality, energy level, and comfort. My priority is making sure every pet feels happy, safe, and well cared for while you’re away.

Sitter Profile Image: Jedan S.
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Jedan S.
from
$86
per night
5.0 out of 5 stars
5 reviews
1 repeat client
13 years of experience
Winslow, ME, 04901

Jedan is amazing!!! She stayed at our house for about a week and cared for (and spoiled!) Kimmie as if she were her own, buying her toys/treats and even cooking for her. She kept us constantly updated with messages and photos and was extremely respectful. Looking forward to booking her again!

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Laurie G.
Sitter Profile Image: Christi C.
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Christi C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
20 years of experience
Whitefield, ME, 04353

Christi was a terrific house/pet sitter for us. She sent daily updates of activities and pictures of our cat, Lucy, and young golden retriever, Pepper. Pepper is a bit of a handful and Christi spent a lot of time with her on walks, car rides and clicker training. We really appreciated her efforts. The daily communications reassured us that our pets were in good hands. It was nice to see how Lucy snuggled right up to her. We were greeted by happy pets on our return and a tidy house. We highly recommend Christi for a pet sitter.

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Linda & Jim M.
Sitter Profile Image: Chloe S.
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Chloe S.
from
$30
per night
6 years of experience
Augusta, ME, 04330

About: I have experience with animals from Great Danes to Fancy rats. I have training experience as well with things such as potty training, walking etiquette, and a few show tricks. I have college classes in the afternoons but my mornings and nights are wide open on weekdays. As for weekends its just dependent on the day so I'll need advanced notice. I have a small yard, and within a quarter mile from the nearest park. I can give potty breaks ever hour if need be, and I'm great at matching an animals energy level.

Sitter Profile Image: Paige C.
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Paige C.
from
$40
per night
5.0 out of 5 stars
27 reviews
3 repeat clients
7 years of experience
Manchester, ME, 04351

Paige is a life saver!!! I’m able to go away w no stress while she takes excellent care of my fuzzy ones! So thankful for Rover, and for Paige’s four years of helping me head out for work and vacation!!!

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Rachel B.
Sitter Profile Image: Candi W.
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Candi W.
from
$85
per night
5.0 out of 5 stars
6 reviews
1 repeat client
15 years of experience
Bristol, ME, 04539

Candi was great to work with. This was my first time being apart from Zoey since I adopted her a year ago. Candi took time to get to know Zoey and bond with her enough that I felt comfortable leaving Zoey in her care. It was a great weight off my mind to know that Zoey would be well taken care of and comfortable while I was away. I can definitely recommend Candi and hope to turn to her again, many times in the future!

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Carrie S.
Sitter Profile Image: Sierra C.
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Sierra C.
from
$28
per night
1 repeat client
9 years of experience
Gardiner, ME, 04345

About: Hello, my name is Sierra. I enjoy trail walks and dogs of all ages and sizes. I have walked dogs of my own as well as neighbor’s dogs who were unable to do it themselves. I am looking for a way to meet new members in my community and help take their pets in adventures along the way. I am concluding my masters and Umaine and could use a four legged pal to explore as that chapter closes. I will provide many encouraging pats, water, treats (per your instructions) and enthusiasm. I enjoy dogs with all my heart and need something to brighten up my day during this time as well as helping those who are unable to walk their pals. I am more than happy to answer any questions and formulate a schedule if anyone is interested! I hope you be able to work with you and your companion in the near future. Thank you for your time. My availability is M-F after 5; after 6 Saturday and Sunday. I do morning walks around 5 am M-F as well for ~2 hrs for those who have pals that enjoy longer walks. To ensure your pets safety a detailed list of your pets needs and important contact information with your number and/or your vets number will be made after the initial interview with me!

Sitter Profile Image: Saber H.
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Saber H.
from
$40
per night
5.0 out of 5 stars
2 reviews
5 years of experience
Wales, ME, 04280

About: I’ve taken care of all sorts of animals since I was very young. I’ve been officially working in pet sitting for five years. Animals usually love me, and I’m willing to be as pateint as needed for the ones who are more shy and may take longer to warm up. I move at there speed. I also make sure that your house stays in the same condition you left it in. Maybe even cleaner lol. There’s no need for you to come home to a messy house after a much needed vacation. Leave the stress to me. This has become my full time job as well while I begin to build my writing career. So I am available for you whenever you may need me. I have an extremely flexible schedule and can accommodate your needs. I would love to have a meeting where we go over all your expectations and needs, every person is unique in how they care for there pet. I aim to make this process as easy as possible. I’ll bring a note pad and you tell me all the details of there regiment. I will follow them to a T and give you live updates on your little friends whenever you need!!

Sitter Profile Image: Melissa H.
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Melissa H.
from
$75
per night
5.0 out of 5 stars
33 reviews
12 repeat clients
13 years of experience
Winslow, ME, 04901

Melissa took excellent care of our pups while we were away for the weekend! She kept in touch and sent pics and videos of them frequently. Our house was immaculate when we got home and the dogs were well loved and cared for. Melissa is great with animals and made us feel good about leaving the dogs with her. She is friendly, communicative, and upbeat- a great sitter!

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Ali H.
Sitter Profile Image: Falisity H.
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Falisity H.
from
$150
per night
5.0 out of 5 stars
4 reviews
20 years of experience
Farmingdale, ME, 04344

One of my favorite Rover sitters! Communication was great! Fallowed directions. I came back after a long day to happy tired dogs. Falisity walked and played with my dogs. If you are at Shore Hills campground look for her on Rover

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Nancy B.
Sitter Profile Image: Lauren M.
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Lauren M.
from
$55
per night
5.0 out of 5 stars
8 reviews
1 repeat client
20 years of experience
Winthrop, ME, 04364

Felt very comfortable, leaving my dog with Lauren. She sent pictures of the walks and took very good care of my dog. I will use her again if she’s available

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Pamela P.
Sitter Profile Image: Ann W.
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Ann W.
from
$75
per night
5.0 out of 5 stars
10 reviews
1 repeat client
30 years of experience
Camden, ME, 04843

Thank Ann! She was everything we hoped for and more. We have a cat who can be a challenge, with his funny ways and she rolled with it - even turning him into a friend. Can’t thank her enough! Also, she left the house as near or neater than when we left! Truly grateful!!

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Rick M.
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The median cost per night for house sitting in Windsor is $65

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
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Windsor average 3
repeat house sitting clients

FAQs for House Sitting - Windsor

Frequently asked questions about Rover

As of July 2026, there are 158 sitters on Rover offering House Sitting across Windsor. 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 Windsor 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 Windsor 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 Windsor 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 Windsor. On Rover:

  • 100% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 100% 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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