House Sitting Windham

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Windham, 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: Emilee M.
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Emilee M.
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
2 years of experience
Jamaica, VT, 05343

Emilee arrived on time and provided us with her presence that the care of our dog Elkie was in good hands. At the end of our scheduled stay we were unable to comply with the arranged end time because of a medical condition that required us to go to the ER. Easily 9.5 hours later Emilee was able to return to her home. We received regular updates, photos and reassurance that our dog was receiving quality care. I highly recommend that you consider calling her to answer to your pet’s care.

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David C.
Sitter Profile Image: Amadie C.
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Amadie C.
Star Sitter
from
$60
per night
5.0 out of 5 stars
28 reviews
7 repeat clients
2 years of experience
Swanzey, NH, 03446

I'm so lucky to have found Ami. She was caring, my puppy loves her from the start. I felt very comfortable leaving my dog in her care. She was also very punctual and sent constant updates and great pictures.

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Dan W.
Sitter Profile Image: Taryn C.
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Taryn C.
from
$75
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Jamaica, VT, 05343

Taryn was awesome during a very long day puppy sitting our 3.5month old Brittany (not an easy ask, as we all know). Our puppy loved her from the first second to the last, and we were very pleased with all aspects of the service. I would highly recommend Taryn to anyone.

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Ella B.
Sitter Profile Image: Tessa H.
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Tessa H.
from
$70
per night
5.0 out of 5 stars
8 reviews
1 repeat client
8 years of experience
Springfield, VT, 05156

Tessa is amazing!! She's very communicative and was punctual. My Fozzie took to her right away and I didn't need to worry he was alone. Thank you SO much!! We'll see you soon!

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Aimee K.
Sitter Profile Image: Brandy V.
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Brandy V.
from
$80
per night
5.0 out of 5 stars
12 reviews
3 repeat clients
18 years of experience
Newfane, VT, 05345

Brandy was fantastic! My dog is not easy due to anxiety and fear (she is a rescue). Elly didn't take that long to warm up and once she did they were able to stick to her regular schedule. Brandy was understanding and compassionate to where Elly was emotionally. She took her for great walks and played with her. Brandy sent pictures and lots of updates. Also Brandy was respectful of our house and left it as she found it. I would highly recommend her to anyone and will definitely ask her back. Thank you!

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Rachel S.
Sitter Profile Image: Daniel G.
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Daniel G.
from
$100
per night
5.0 out of 5 stars
45 reviews
11 repeat clients
25 years of experience
Winchester, NH, 03467

Danny did a great job watching our dog for a week over Christmas. She has separation anxiety so he brought her to his family’s Christmas! We were so thankful she wasn’t home alone during the holidays! Danny was also very responsible watching our house and even cleaned the sheets before he left. He kept us updated with messages and photos. We’ll definitely be using him again in the future!

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Julia K.
Sitter Profile Image: Kate B.
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Kate B.
Star Sitter
from
$160
per night
5.0 out of 5 stars
28 reviews
4 repeat clients
30 years of experience
MANCHESTR CTR, VT, 05255

Kate was super responsive and accommodating! She cared for our pup while we were skiing at Stratton, traveling to us in less-than-ideal weather. Despite the weather keeping them from big outdoor adventures, our dog seemed to have a great time hanging out with Kate and we felt she was in good hands.

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Allison P.
Sitter Profile Image: Elizabeth G.
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Elizabeth G.
from
$28
per night
4.8 out of 5 stars
12 reviews
1 repeat client
5 years of experience
Bellows Falls, VT, 05101

Lizzie was great with the dogs and everyone was happy on our return. Lizzie was on time and dependable. Everyone was loved as one of her own. I would definitely recommend.

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Amy H.
Sitter Profile Image: Erin C.
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Erin C.
from
$100
per night
5.0 out of 5 stars
5 reviews
30 years of experience
Windham, VT, 05359

About: I’ve taken care of all sorts of animals. I have no fear of animals, but of course have a respect and solid knowledge of animal behaviorism. I would do anything for the safety, care and happiness of animals. I’m a marriage and family therapist, but I have a passion for caring for animals too. My cup is filled hy working with animals. I love them so. I don’t have others’ pets in my home out of respect for my own children (three cats) but I will care for your animals the way I expect my sitters to care for my babies. Ex: I have about a 12 page document for them to follow.

Sitter Profile Image: Haddie C.
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Haddie C.
from
$80
per night
1 year of experience
Londonderry, VT, 05148

About: For all my dog sitting clients, after each sit I leave homemade dog treats, keeping allergy’s and food sensitivity’s in mind. I have gotten so much great feedback about them! Pet sitting is apart of my weekly routine, in and outside of school. I pet sit year round on top of school, and volunteering. I do pet sitting full time as my only income. I care for pets in clients home, treating the property with respect, while also making myself at home and leaving the animals comfortable and in routine.

Sitter Profile Image: Sadie M.
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Sadie M.
from
$38
per night
5.0 out of 5 stars
11 reviews
5 years of experience
Granville, NY, 12832

Highest praise and accolades to Sadie whom we recently hired to stay with our newly adopted rescue Elkie. We can’t find words to express how satisfied we are with the care and communication we experienced with Sadie. Before our booking date Sadie took it upon herself to visit with us to confirm that she would be a goof fit with our dog. On the day of our departure Sadie showed up early, well before the time we had requested. Our Elkie has a number of issues, the greatest of which is separation anxiety and having Sadie stay in our home to provide comfort and care was our number one priority. Sadie provided everything we had hoped for, and sent us regular updates that allowed us to enjoy our time away without any concern for the needs of our dog. Sadie is a caregiver whom you can trust with you pet and home for your time away. We will absolutely call on her again for future bookings when we have a need to leave our pet home. 🌟🌟🌟🌟🌟 ⭐️⭐️⭐️⭐️⭐️

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David C.
Sitter Profile Image: Kaeleen F.
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Kaeleen F.
from
$100
per night
5.0 out of 5 stars
12 reviews
8 repeat clients
26 years of experience
Lempster, NH, 03605

Kaeleen watched our dog Sadie and cat Mac for a week. She took great care of them. She provided updates and sent pictures. She was respectful to our home. I would recommend her for anyone looking for a great in-house sitter!

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Jason F.
Sitter Profile Image: anik k.
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anik k.
from
$60
per night
35 years of experience
Putney, VT, 05346

About: I’ve been caring for pets for over 35 years, and I just love it! I have to travel for work which means I can’t have my own right now, so looking after others is a true joy. I naturally treat every animal as if they were my own — and making sure they feel secure, loved, and happy while their parents are away. With every sit, I bring both reliability and heart. Over the years I’ve cared for dogs, cats, parrots, chickens, and more — each with their own unique personalities and quirks. I’ve played with energetic puppies who needed training and adventure, given gentle support and patience to sweet seniors, reassured nervous or shy animals with steady routines & space, and comforted sick or elderly pets in their final days. One of the most important lesson I learnt came from my own senior dog, who had arthritis. Beyond medication, what mattered most were the little things. I could see from her body language that her favorite time of day was simply sitting together in the sun while I gently massaged her and talked to her. Those quiet moments made her feel safe and deeply loved — and they taught me how much presence and empathy matter in pet care. I work remotely with flexible hours, which means I can spend plenty of time with your pets — for walks, play, belly rubs, or simply quiet companionship so they don’t feel alone. While I’m new to Rover, I’ve been sitting through other platforms where I’ve built excellent reviews and references. Having hosted sitters myself, I also understand the trust (and nerves!) that come with leaving your pets and home in someone else’s care. That’s why I believe clear communication is key, and I’ll always keep you updated with photos, feedback, and check-ins so you can relax knowing your pets are safe, loved, and well cared for. My work is remote so I can be anywhere as long as I have wifi. I only work part-time with flexible hours which gives me the space to adapt to your pets needs & also have the time to for plenty of walks, cuddles & play. When caring for pets in their own home, I make sure their routines stay consistent so they feel secure — from feeding and walks to playtime and rest. I pay close attention to each animal’s signals, balancing structure with the affection, stimulation, or quiet companionship they need. Safety is always a priority. I follow your instructions carefully, ensure food and medications are given correctly, and keep doors, windows, and gates secure. I maintain a calm, clean environment so pets feel relaxed, and I treat every home with the same respect as my own. I’m a naturally tidy person who cleans as I go, so you’ll return to a home that feels just as you left it. Having hosted sitters myself, I fully understand the trust (and nerves!) that come with leaving your pets and home in someone else’s care. That’s why I believe strong communication is key. I’m happy to provide updates, photos, and even video calls as often as you’d like — so you can relax knowing your pets are safe, loved, and well cared for while you’re away.

Sitter Profile Image: Mike & Laura O.
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Mike & Laura O.
from
$150
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
25 years of experience
Putney, VT, 05346

About: We are a young, active couple that recently lost our dog after over ten years together. We have experience with puppies and seniors. While we aren't professional trainers, we have plenty of experience training our own dogs. Neighbors, friends, and family have relied on us to pet-sit, walk, and train their animals. I grew up with a dog and my wife grew up with dogs and sheep. We currently have a small flock of hens as well. Our home is pet friendly, but we do not allow animals on the furniture. We don't have a fenced yard, but we live on over 30 acres, on a dirt road with minimal traffic, and in close proximity to miles of hiking trails. I work a 9a-5p job Monday - Friday, but only about 2 miles from home so I can easily run home during the day. My wife is self-employed and is more flexible with her schedule and works out of the house. Our home is pet friendly but we don't allow animals on the furniture. We have multiple large, comfortable dog beds, pillows, toys, water and food dishes, etc. We are loving and attentive. We enjoy being outdoors as much as possible, so walks, hikes, fetch, etc. is no issue. We miss having our own pup but aren't ready to adopt again, so we would love to spend some time with your animals!

Sitter Profile Image: Nadine N.
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Nadine N.
Star Sitter
from
$150
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
20 years of experience
Keene, NH, 03431

What a dear person. Nadine is a natural with knowledge and a love of animals. She showed great judgement, and was kind enough to let me know when our cat was in for the night. She was thoughtful, and clearly is great with animals. Our cat was thoroughly in love.

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Victoria F.
Sitter Profile Image: Julie H.
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Julie H.
from
$40
per night
30 years of experience
Grafton, VT, 05146

About: I have taken care of many animals, from aquatic to a variety furry friends. I am always willing to offer a hand in any kind of care or training that is needed to be kept up while their humans are away so that you can be sure the critters are getting the best care and love while you’re away. I am a paraeducator at a school that is less than a mile from my house. I come home everyday at lunch time and usually home by 3:15. Walks and playtime are a necessity for our fur babies and they love having friends to play with! I have 2 female dogs, both very friendly. We have an underground fence, though I would keep your fur baby on a leash when we go outside. We have a nice yard, about half an acre, live near a stream and love taking walks around the neighborhood.

Sitter Profile Image: Denisha L.
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Denisha L.
from
$50
per night
35 years of experience
Bellows Falls, VT, 05101

About: I have taken care of my own pets since childhood. Worked with horses for over 20 years and dogs/ cats in a daycare/ boarding setting for 4 years. I am currently working at a dog daycare, and have my own dogs that I take care of. I am available for pet sitting on weekends right now, will be looking to add more services soon. I have many years experience taking care of peoples pets in their home. I treat all pets as if they were my own, attention to details to make sure the animals are happy and healthy.

Sitter Profile Image: Chantelle M.
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Chantelle M.
from
$70
per night
5.0 out of 5 stars
4 reviews
26 years of experience
Mount Holly, VT, 05758

About: Lost my fur baby almost 2 years ago. I raised her from a puppy, I also had another dog as well along with cats. My other dog was a rescue so I’m well versed in dogs with anxiety and other social challenges. I do not shy away from dogs with all kinds of different behaviors and quirks. I love dogs (and cats!) and miss having a dog by my side. I would love to help care for other’s fur babies when they’re in need of outside support. I have a degree in Animal Science and am well versed in animal care. I can clip nails, give meds, care for wounds, support with behavioral challenges and socialization, grooming, etc. I have 11 acres where I live and can provide ample exercise through hikes in the woods, I am also open to taking them places like dog parks or vet appointments. I am available and able to handle multiple animals at a time. I have owned dogs and cats my whole life and have done pet, farm and house sitting since I was a kid off and on throughout the years. I have consistently watched a coworkers dog when she is away as well as other friends and family. I currently work full time and have availability nights and weekends. Workday evenings I’m available any time after 5pm. I’m available any time on the weekends. I am in the process of switching to part time employment. Once I am I will have more availability. I have 11 acres of land to walk and hike with dogs on or off leash. I have a cat of my own and separate housing available for dogs that aren’t cat friendly. There is an old dog on property (family member’s in separate housing) that is dog & people friendly. He stays inside in seperate housing except for potty breaks. Dog is available for play for the right fit.

Sitter Profile Image: Jessica R.
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Jessica R.
from
$88
per night
25 years of experience
Deerfield, MA, 01373

About: early years, my family were training Morgans for the Kentucky Derby. It had been an exhilarating journey, one that beautifully intertwined skill, patience, and a profound bond with these majestic horses. Each horse is unique, deserving of personalized training that not only harnesses their incredible speed and agility but also fosters a deep connection between horse and trainer. As l've grown, my focus has shifted from merely training to cherishing those heartfelt connections, as they truly enrich my life. Alongside my passion for equine training, I find immense joy in the companionship of dogs and cats, nurturing their spirits It’s all I do - besides writing. I chose to step Away from The chaos of the world to care for my own well being by taking care of animals. With respect, kindness and love as I would expect in my own home and with my own pets. Pets bring joy and peace to my life.

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

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Meet local sitters who will treat your pets like family

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Popular requests for house sitting - Windham

Select a filter and find qualifying sitters offering house sitting.

Sitters in Windham average 3
repeat house sitting clients

FAQs for House Sitting - Windham

Frequently asked questions about Rover

As of August 2026, there are 103 sitters on Rover offering House Sitting across Windham. 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 Windham 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 Windham 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 Windham 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 administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.

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