Dog Sitting in Windham

Book a Windham dog sitter to watch your dog in your sitter’s home or yours.

End Date
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Windham dog sitters

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

1 / 1
Sitter Profile Image: Anna K.
Verified Enhanced Background Check
Anna K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
20 reviews
11 repeat clients
13 years of experience
Ocean Avenue, Portland, ME, 04103

Anna was great! She took care of our dog and reported back very thoroughly. He was such a happy camper - highly recommend using Anna to care for your fur baby.

Profile image
Abigail J.
Sitter Profile Image: Kara O.
Verified Background Check
Kara O.
from
$25
per visit
5.0 out of 5 stars
70 reviews
20 repeat clients
20 years of experience
Standish, ME, 04084

Kara was excellent…my puppies were very happy with her, as I have 3 pups with three different personalities and she had handled all three wonderfully. Punctual, attentive & caring.

Profile image
Lois S.
Sitter Profile Image: Amanda C.
Verified Enhanced Background Check
Amanda C.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
15 years of experience
Buxton, ME, 04093

Amanda understood that Walter suffers from anxiety and needs to be handled carefully. She sent me photos and described their first visit alone which I appreciated.

Profile image
Mary M.
Sitter Profile Image: Emily C.
Verified Enhanced Background Check
Emily C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
4 reviews
3 repeat clients
30 years of experience
Raymond, ME, 04071

About: Who's a good dog? All of them. My step-dog is the love of my life, and I'm the person who talks to animals more than humans at a party. I have experience with: Dogs, cats, fish, rodents, horses, chickens, other birds, reptiles, and more. As a former field biologist, I handled a wide variety of animals and completed Institutional Animal Care and Use Committee (IACUC) training. I'm open to caring for almost any critter. Send me a message so we can discuss what your critter needs. New-ish to Rover. Previously, all my clients were by word of mouth in extreme southern Maine and New Hampshire. We recently moved, and I decided it was time to join Rover. My schedule is variable, so just message me so we can discuss what your critter needs. This summer I have lots of availability. Thank you! I am currently not taking client's pets into my own home. I am open to a variety of conditions for home visits/walks/play dates/check-ins. Just send me a message so we can discuss your set up and what your critter needs.

Sitter Profile Image: Sarina D.
Verified Enhanced Background Check
Sarina D.
from
$20
per visit
13 years of experience
North Deering, Portland, ME, 04103

About: My first job was at Mainely Dog, a doggy daycare where I fed and entertained groups of dogs-all sizes and personalities. I’ve grown up with many dogs in my family. We also fostered and took in dogs with behavioral difficulties, even had up to 5 dogs at once so I’m used to handling multiple dogs at a time! My dream has always been to own my own business to help and love animals. I can’t wait to meet your pups! I currently work a part time job where I work 3-4 days a week from 4:30-10:30 so I am available the rest of those days and my days off. I am attentive and can keep your pets safe whether that’s in your home or outside in the yard. When out on walks, I am skilled at reading your dog and other dog’s ability to interact in a safe environment from my experience at the doggy daycare.

Sitter Profile Image: Lily F.
Verified Background Check
Lily F.
Star Sitter
from
$33
per visit
5.0 out of 5 stars
161 reviews
71 repeat clients
20 years of experience
Falmouth, ME, 04105

Lily has a natural way with animals. Pepper has had a rough past and doesn’t always immediately vibe with a new person. She took to Lily immediately! Lily was very communicative about her time with Pepper which I really appreciated. Can’t say enough good things!

Profile image
Justine D.
Sitter Profile Image: Bella L.
Verified Enhanced Background Check
Bella L.
from
$15
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
2 years of experience
Windham, ME, 04062

Bella took such amazing care of my Higgins like she was one of her own! She was extremely respectful of our home and all our wishes while we were away. I would have Bella back in a heartbeat in the future!!

Profile image
J D.
Sitter Profile Image: Gigi C.
Verified Background Check
Gigi C.
from
$25
per visit
5.0 out of 5 stars
14 reviews
5 repeat clients
10 years of experience
Scarborough, ME, 04074

Gigi has been absolutely fabulous with my dog Thor these past few weeks. She takes excellent care of him. Takes him for a walk around my house, fills up the water bowl and sits on the porch with him. She also gives a great detailed update on the rover card of what he did during her stay with him and sends lots of photos. I have been so happy to have her take care of Thor while we are at work and puts me at ease knowing she is there to let him out on those long days. Will definitely rebook again!!!

Profile image
Mary C.
Sitter Profile Image: Tonya O.
Verified Enhanced Background Check
Tonya O.
from
$15
per visit
5.0 out of 5 stars
1 review
38 years of experience
Far North, Standish, ME, 04084

About: Dogs have always been a huge part of my life. I’ve been caring for dogs since I was 10 years old as a pet sitter, but we got our own family dog as a toddler. Over the years, that experience has grown into a true passion, and I now have 2 dogs of my own. I’m used to all kinds of personalities, from high-energy dogs who love long walks and playtime to more relaxed companions who just want cuddles. I’m all about keeping tails wagging with lots of attention, exercise, and love. I work remotely full-time, which gives me the flexibility to provide attentive, consistent care throughout the day. Because I am not tied to an office, I’m able to let sit in your home and be present for walks, feedings, playtime, and companionship—keeping your pets routine as normal and stress-free as possible. When caring for pets in your home, my top priorities are safety, trust, and maintaining a calm, familiar environment. I follow your pets routine closely—from feeding schedules to walks and playtime—so the feel secure and comfortable while you’re away. I treat your home with the utmost respect and make sure your pet gets plenty of attention, affection, and supervision at all times.

Sitter Profile Image: Hannah S.
Verified Enhanced Background Check
Hannah S.
from
$15
per visit
1 repeat client
10 years of experience
Rosemont, Portland, ME, 04102

About: I’ve loved animals my entire life and have had three dogs and two cats over the years. I’m currently raising a golden retriever puppy with my family and absolutely love spending time with dogs. Friends have always trusted me to watch their pets while they’re out of town because they know I treat every animal like family. I’m the kind of person who stops people on the street just to ask if I can pet their dog. Caring for animals genuinely makes me happy, and I’ll make sure your pet feels safe, loved, and well cared for. I’m currently between jobs, which gives me a very flexible schedule and plenty of availability to give your pets the attention, care, walks, and love they deserve. I care for every pet like my own, always putting their safety, comfort, and happiness first. I stay alert on walks, careful around other dogs, people, traffic, and our surroundings to make sure pets feel safe and secure at all times. I also have a fenced yard for safe play and experience caring for and crate training puppies since I currently have 2 dogs.

Sitter Profile Image: Jessica F.
Verified Background Check
Jessica F.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
63 reviews
16 repeat clients
22 years of experience
East End, Portland, ME, 04101

Jess is GREAT! She very quickly gained the trust of our senior and special needs dog. He is comfortable with her and benefits from her visits every week! She is punctual, trustworthy, sends updates, flexible schedule, communicates clearly and quickly, and we feel she truly loves our dog. It is very difficult to find someone who would care for your pet as you would and we are so grateful for Jess!

Profile image
Lee M.
Sitter Profile Image: Kate S.
Verified Enhanced Background Check
Kate S.
from
$15
per visit
21 years of experience
North Deering, Portland, ME, 04103

About: I have grown up with dogs, ranging from a teacup yorkie to a bullmastiff lab. I recently adopted a mix terrier of my own who has become by best friend. I have been trusted by friends and family to care for their pets like I do my own and have been doing so much more recently! I am a recent college grad on the job hunt but in the mean time would love spending time and caring for your four legged friends! I care for you pets of course as you ask and care for them and with a lot of love. I respect the guidelines you set for your furry friends and will do my best to make them feel secure as it can be nerve racking for them to not have their people around!

Sitter Profile Image: Chelsea O.
Verified Enhanced Background Check
Chelsea O.
from
$20
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
20 years of experience
Deering Center, PORTLAND, ME, 04103

Awesome!!

Profile image
Kyle G.
Sitter Profile Image: Briana S.
Verified Enhanced Background Check
Briana S.
from
$17
per visit
4.9 out of 5 stars
11 reviews
6 repeat clients
9 years of experience
Riverton, portland, ME, 04106

Briana took excellent care of our diabetic cat! She really went above and beyond, playing with him and giving him affection, and is one of only 2 sitters who have successfully been able to administer insulin injections.

Profile image
Elizabeth S.
Sitter Profile Image: Sarah H.
Verified Enhanced Background Check
Sarah H.
from
$20
per visit
5.0 out of 5 stars
16 reviews
7 repeat clients
10 years of experience
Westbrook, ME, 04092

Sarah is incredible & takes good care of Tatertot. She ensures he has quality time, goes for walks ,feeds& waters him. Tatertot enjoys his walks and time together with Sarah.

Profile image
Crystal M.
Sitter Profile Image: Elizabeth M.
Verified Background Check
Elizabeth M.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
57 reviews
9 repeat clients
30 years of experience
Scarborough, ME, 04074

Elizabeth was literally the best sitter we have ever had. She was not only so kind to me after telling her about an awful experience with a previous sitter—but she made me feel at ease! My babies loved her, and I love that she loved my babies. I wish that she wasn’t leaving my area! I’d keep her forever!! Thank you again, Elizabeth. We were both able to fully relax knowing our kitties were in safe and reliable hands 🖤 let me know when you’re back in the area!!

Profile image
Ryann W.
Sitter Profile Image: Nishat R.
Verified Enhanced Background Check
Nishat R.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
135 reviews
61 repeat clients
3 years of experience
South Portland, ME, 04106

Nishat agreed to a multi-day, multiple visits per day, booking with less than 2 weeks notice. She stopped by to meet them in advance of our trip and took her time to get to know each of them. She was very calm, gentle, and caring. Our dog and cats took to her right away. She did a great job caring for them while we were away, even diligently providing them medication that was prescribed *after* she had agreed to the booking. We are so pleased with Nishat and grateful to have found her!

Profile image
Mia R.
Sitter Profile Image: Kelly F.
Verified Enhanced Background Check
Kelly F.
from
$30
per visit
5.0 out of 5 stars
30 reviews
12 repeat clients
40 years of experience
Falmouth, ME, 04105

We’re return customers and we couldn’t be more satisfied! Kelly will do a great job looking after your pets, and she has also helped us in a pinch.

Profile image
Jesse L.
Sitter Profile Image: Maya H.
Verified Enhanced Background Check
Maya H.
from
$20
per visit
5.0 out of 5 stars
3 reviews
6 years of experience
Portland, ME, 04103

Maya was amazing with our pups, even our problem dog warmed up super quick. She was communicative, attentive, always on time, and provided awesome photos during the visits.

Profile image
Samuel B.
Sitter Profile Image: Matthew F.
Verified Enhanced Background Check
Matthew F.
from
$30
per visit
5.0 out of 5 stars
18 reviews
4 repeat clients
40 years of experience
Falmouth, ME, 04105

Matthew did a great job with our dogs. He took them out on walks and took great pictures for us to see. He also gave them treats and was good to them. He had 3 dogs to deal with over the time and they all seemed happy with him. Great dog sitter who I would definitely use again!

Profile image
Katy H.
1 / 1
View more sitters

Over 47
pet parents in Windham have booked dog sitting

Windham dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

I was able to relax with peace of mind while Nicolette was at my house with my babies. She consistently updated me with pictures and videos and brought her son to help get some energy out with my crazy lab and I could see both of my dogs loved her and had the best time with her and her son.

Profile image
Olivia T.
Drop-In Visits
5.0 out of 5 stars

Nicolette was responsive right away when I messaged about doing drop-ins for our dog the following day. She listened to what works well for our dog, and I felt confident that our dog was in great hands! We’ll definitely continue to have Nicolette do more drop-ins for us!

Profile image
Erin B.
Drop-In Visits
5.0 out of 5 stars

Nicole was fantastic with my golden retriever, I booked her four times a week for 13 weeks and she was very reliable, had great communication and was very friendly. Highly recommend her for your pet needs around the Scarborough area!!

Profile image
Kassidy K.
Drop-In Visits
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs 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 dog sitting in Windham is $25

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Windham average 6
repeat dog sitting clients

Dog Sitting FAQs

Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Windham on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

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

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

As of Jun 2026, there are 1,013 dog sitters in Windham. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 88% of Windham dog sitters respond in under an hour.

Dog sitters in Windham have an average of 16 years of experience. Dog sitters with repeat customers have an average of 6 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Windham.

Rover makes it easy to find Windham dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

There are 1,013 dog sitters in Windham on Rover, so you’re sure to find the perfect match for your dog! In Windham, 99% of dog sitters offer daily exercise, 100% offer medication administration, and 99% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

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

Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.