Dog Boarding South Windham

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Over 159
pet parents in South Windham have booked dog boarding

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Sitter Profile Image: Heidi A.
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Heidi A.
Star Sitter
from
$48
per night
4.9 out of 5 stars
• 480 reviews
243 repeat clients
15 years of experience
Gorham, ME, 04038

“Great communication, clearly was confident and comfortable with many dogs! Heidi sent me daily updates on my pup and it’s clear he had a blast.”

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Alida B.
Sitter Profile Image: Nicolette H.
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Nicolette H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 112 reviews
31 repeat clients
20 years of experience
Windham, ME, 04062

“Nicolette was professional, attentive and a great dog sitter taking them on sniffventures, walks, dog parks, ect. Our pet had such a great time making new friends he didn't want to leave when we came to pick him up. We'll definitely be doing business with Nicolette in the future! Thank you so much Nicolette for being exactly what we and Odin wanted/needed, you're the best:)”

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Seratto S.
Sitter Profile Image: Natalie & Timothy K.
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Natalie & Timothy K.
from
$65
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
10 years of experience
Cumberland, ME, 04021

“We are so happy that we found Natalie & Tim. They instantly made Penny feel safe and loved. We had total peace of mind. I highly recommend them for any pet care needs!”

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Theresa D.
Sitter Profile Image: Molly & Ricky W.
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Molly & Ricky W.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 79 reviews
28 repeat clients
20 years of experience
Westbrook, ME, 04092

“Never having left Roo, Matzoh and Tony with anyone, we were a bit nervous. But we were sent pictures daily with updates and upon picking them up, it was obvious that they were well taken care of and very happy!”

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Vicki V.
Sitter Profile Image: Alicia G.
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Alicia G.
from
$50
per night
5.0 out of 5 stars
• 41 reviews
14 repeat clients
3 years of experience
North Deering, Portland, ME, 04103

“Alicia and Dave were great with Cosmo. He was very comfortable there with them and their dog, and they were great at giving him his medications. Always tough to find someone to watch these dogs with some medical issues, but they didn’t miss a beat. Loved getting the picture updates.”

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Erin K.
Sitter Profile Image: Amie T.
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Amie T.
Star Sitter
from
$56
per night
5.0 out of 5 stars
• 7 reviews
4 repeat clients
40 years of experience
Westbrook, ME, 04092

“My pup Pearl had a great time with Amie and her two dogs. She came home happy, well taken care of and tired : ) I will book with her again 100%!”

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Katrina V.
Sitter Profile Image: Vicky P.
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Vicky P.
from
$75
per night
5.0 out of 5 stars
• 69 reviews
30 repeat clients
30 years of experience
Stroudwater, Portland, ME, 04102

“Vicky was a great sitter for my pup, Rhody! Rhody is super shy and can be anxious but Vicky made her comfortable right from the start. I loved all the picture updates and would definitely use Vicky again!”

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Kate L.
Sitter Profile Image: Trisha G.
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Trisha G.
from
$50
per night
5.0 out of 5 stars
• 118 reviews
47 repeat clients
34 years of experience
Scarborough, ME, 04074

“A big thank you to Trisha & Dan for taking such excellent care of Casey while we were away for 9 days, over Thanksgiving. Since Casey is older and has only stayed with family or friends for the last 13+ years, we were a little hesitant to leave him with just anyone and a kennel was not an option at his age. We found Trisha and Dan through Rover.com and the entire process was simply fantastic. Even with Casey being better than 90% deaf at this point, this was not an issue. We were able to meet Trisha before we made the reservation, to determine our and Casey’s comfort levels. In a word, we felt like they would be the right people to leave Casey with. Casey as well felt right at home during the meet and greet visit and got along great with Stout, Trisha & Dan’s dog. Drop off day came and when I brought Casey over, he “made himself right at home,” much to my dismay. Well, after that, Casey had a fantastic time. The photos we received made us feel so much better and they told the story, Casey just having a wonderful time. It even looked like he helped cook, although I am sure he was simply hoping Dan would drop his dinner. Casey slept on Stouts bed and Stout slept on Casey’s bed and both looked natural and relaxed. When we picked Casey up, he seemed sad and he did not want to leave. He slept all the next day and part if not most of the next day. Casey looked around for his new little friend Stout and he clearly misses him and the fun that they had together. We will be definitely requesting Trisha, Dan and Stout again in the future for all of Casey’s overnight stays as the comfort and confidence they provide was, in a word, incredible. Thank you again for the fantastic care and love Casey received. See you soon. ”

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Mark R.
Sitter Profile Image: Katie T.
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Katie T.
from
$50
per night
5.0 out of 5 stars
• 16 reviews
4 repeat clients
20 years of experience
Biddeford, ME, 04005

“Katie was great with drop off and pickup. She administered Clover’s meds and was quick to get back to me when I communicated with her. She was also very flexible with my late pickup when plans changed, and I really appreciate that.”

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Aimee L.
Sitter Profile Image: Laney W.
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Laney W.
from
$60
per night
5.0 out of 5 stars
• 14 reviews
3 repeat clients
26 years of experience
Saco, ME, 04072

“Laney was very accommodating of my two Huskies. I've been looking a long time to find not only a sitter, but one that would take good care of my pups and not be worried about their behavior. Although my boys are somewhat trained and are good with other dogs and kids, not everyone is willing to watch two Huskies! She also showed good care and is knowledgeable of training. I will definitely coming back!”

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Christopher A.
Sitter Profile Image: Kseniia P.
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Kseniia P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
• 98 reviews
26 repeat clients
8 years of experience
Old Orchard Beach, ME, 04064

“Kseniia was amazing with our dog. It was his first time being away from us for an extended period of time and she went above and beyond to make him feel comfortable. He was def on high alter in a new place, but she was so patient with him! I also really appreciated the daily pics and videos and her patience with us as our flights got changed and cancelled multiple times.”

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Meghan D.
Sitter Profile Image: John R.
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John R.
Star Sitter
from
$44
per night
5.0 out of 5 stars
• 21 reviews
5 repeat clients
35 years of experience
West End, Portland, ME, 04102

“John is amazing. Our little Arlo is afraid of everyone (except John) He almost didn’t want to come home with us. He took such good care of him. He will always be my go-to. One thing, your pup may be lackluster the next day from the exercise he got and missing John.”

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Lore Z.
Sitter Profile Image: Alma D.
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Alma D.
from
$70
per night
5.0 out of 5 stars
• 28 reviews
11 repeat clients
8 years of experience
Oakdale, Portland, ME, 04102

“Our dog was in great hands with Alma! She loved snoozing in the sun and sharing a couch with Alma’s dog and family. We got lots of photos and updates.”

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Emily L.
Sitter Profile Image: Michael M.
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Michael M.
from
$45
per night
5.0 out of 5 stars
• 1 review
1 repeat client
1 year of experience
Westbrook, ME, 04092

About: Hi, my name is Michael and I am a proud owner of a beautiful King Charles Cavalier Spaniel and my dog and I would both love to have your pups company. Please let me know if you have any special instructions and I promise your pup will have a comfortable stay with many fun walks. Thanks! I provide 5 walks a day for my own pup and would love for your dog to join. I work from home so your dog will have ongoing company throughout most of the day. I have one friendly dog in a quiet calm environment with no children. I will feed and walk your doggy as requested, and can provide lots of pets as well.

Sitter Profile Image: Carmen H.
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Carmen H.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 120 reviews
30 repeat clients
7 years of experience
Old Orchard Beach, ME, 04064

“Reina always enjoy her visits with Carmen and her family . Carmen sends multiple updates / pics throughout the visit . She is also very accommodating if my schedule happens to change and she treats my fur baby and I like family . Reina feels right and home as soon as she steps in the door .”

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Brandi J.
Sitter Profile Image: Celine G.
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Celine G.
Star Sitter
from
$90
per night
5.0 out of 5 stars
• 31 reviews
8 repeat clients
30 years of experience
Oakdale, Portland, ME, 04102

“Second time having my pup stay with Celine for the weekend and another wonderful experience! My dog is always so well cared for and I always receive lots of photo updates :)”

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Lex S.
Sitter Profile Image: Lucero & Ikenna P.
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Lucero & Ikenna P.
from
$60
per night
5.0 out of 5 stars
• 10 reviews
5 repeat clients
20 years of experience
Parkside, Portland, ME, 04102

“My dog Molly had such a great time spending the week with Lucy and Ike! Throughout the process they showed they cared very much for my furball by sending updates on how she was doing and I immediately felt like the pup was in safe hands when I met them.”

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Joe P.
Sitter Profile Image: Tiffany B.
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Tiffany B.
from
$30
per night
5.0 out of 5 stars
• 2 reviews
10 years of experience
East Deering, Portland, ME, 04103

About: I have cared for dogs throughout my life including my own, my family, and friends. The dogs have ranged from puppies to older adults with boarding in my home and their own. I live on the first floor of my building and there are no steps for senior dogs to have to worry about. While I do work as a teacher full time, my weekends are very open to care for dogs. I typically take a walk one to two times a day on my own through the neighborhood so adding a dog companion along would be very easy. We also have a cat who loves dogs with many dog toys of her own that she can share! I have a one bedroom apartment with no stairs so it is easily accessible for dogs of all mobility ranges and ages and I can keep an eye on them throughout the day. While we do not have a fenced in yard, we do have access to a field next door at an elementary school and neighborhoods to walk in with little car traffic.

Sitter Profile Image: Kylie K.
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Kylie K.
from
$60
per night
5.0 out of 5 stars
• 13 reviews
3 repeat clients
20 years of experience
South Portland, ME, 04106

“We needed someone for 1 night and Kylie was great and I will call her again. I would recommend her 100%. Penny loved her walkies and snacks.”

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Theresa D.
Sitter Profile Image: Alicia R.
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Alicia R.
from
$50
per night
5.0 out of 5 stars
• 59 reviews
15 repeat clients
13 years of experience
Sebago, ME, 04029

“Alicia and her family were great! She sent lots of pictures and our pup fit in very nicely with their family! We will definitely use them again in the future!”

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Kerrie-Lee L.
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The median cost per night for dog boarding in South Windham is €65

Dog parents share their Rover experiences - South Windham

1 / 1
5.0 out of 5 stars

Communication was great. Our fur baby meet new friends and I think loved her stay. Hoping Christina will have her again for future visits.

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Karyn D.
Boarding
5.0 out of 5 stars

Danielle was a life saver! She took fantastic care of my dog, and she was able to accommodate my schedule. Very professional, would highly recommend!

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Bill G.
Boarding
5.0 out of 5 stars

Christina was excellent! We booked her months in advance and planned a meet up for the month before. Communication was top notch & I felt extremely comfortable leaving my dog with her for the weekend. Our dog is massive, not great on leash, and has reactive tendencies. Christina never hesitated and made sure she had all the information she needed. Christina treated our dog as her own. I would happily book again and recommend her to anyone needing care!

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Katie M.
Boarding
5.0 out of 5 stars

Christina a wonderful and attentive dog sitter! My dog Beau injured his dew claw right before my trip, and Christina accommodated additional meds and gave lots of updates on his healing. I so appreciate her attention to Beau's needs and amazing care of my little guy.

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Catherine C.
Boarding
5.0 out of 5 stars

Danielle was able to take our dogs at the last minute and saved our plans! They were well looked after and very tired when they got home :)

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Alyssa P.
Boarding
5.0 out of 5 stars

Danielle was great! We had to book last minute, but she made sure my dog Milo was comfortable for his first time at her house and sent lots of updates and pictures. Definitely recommend!

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Jenna H.
Boarding
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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.

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  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.

Popular requests for dog boarding - South Windham

Select a filter and find qualifying sitters offering dog boarding.

Sitters in South Windham average 9
repeat dog boarding clients

FAQs for Dog Boarding - South Windham

Frequently asked questions about Rover

The average cost of Dog Boarding in South Windham is $41 per night as of November 2026. Most bookings cost between $28 and $66 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 296 sitters on Rover offering Dog Boarding across South Windham. Enter your ZIP code to see which available sitters are closest to your home.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

95% of sitters in South Windham can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their South Windham home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your South Windham.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

Yes, you can find sitters who have experience with handling special pet needs in South Windham. On Rover:

  • 92% of sitters can help with special care needs
  • 95% can help with giving oral medications or injections
  • 95% 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.

You and your South Windham sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

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.

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in ME ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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 dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog 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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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