House Sitting Windsor Road
Find a loving house sitter to watch over your pets and your home.

Over 246 pet parents in Windsor Road have booked house sitting
Windsor Road, 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.
“Delilah was amazing with my doggie boi!!! Definitely hope to hire Delilah again next time I travel! Totally went the extra mile picking up my dog’s medication when I accidentally packed it in my luggage.”

“Kiersten was absolutely wonderful with our pup Isabelle! She was punctual, communicative, and went above and beyond to make me feel comfortable, especially since it was our first time working together. It was so reassuring knowing Isabelle was in such caring hands, and our girl clearly had the best time with her! We’re so happy to have found such an amazing sitter and will definitely be having Kiersten care for Isabelle again. Highly recommend! 🐾💜”

“Melondy was great! We booked this trip over a month ago and it unfortunately landed during the weekend of the winter storm and she was still very understanding. Our two gremlins were super happy when we returned and had a great time.”

“We had a great experience with Debbie! She was very communicative and kept us updated the entire time we were away, sending frequent pictures and thoughtful notes. What meant the most was that I truly felt like she cared, not just about their basic needs, but about their entertainment, comfort, and overall health. We came home to happy, well-loved pets and total peace of mind. I would absolutely book with her again 🤍”

“Thomas was great with my pups! He filled a longer, relatively last minute sit, for which I’m appreciative of. He followed instructions perfectly and I’m happy to have had the peace of mind that their medications and needs were being met while I was away. My younger dog is very particular and she took to him right away. Thanks, Thomas!”

“Nic was just great. I have one pretty large dog and a medium German shepherd and he handled them very well. Everyone was happy when I got home. He also took care of my two cats, which was amazing. He also gave me some great tips and advice on handling my dogs and gave me great suggestions on new gear for them. I will definitely be using Nic again.”

“My husband and I needed a sitter for a quick trip we had. Anne responded quickly, met the dogs before hand and took amazing care of our fur babies while we were away! We will definitely be rebooking :)”

“Diana was very good with our pack. From the pictures it seemed they spent time outside together and they must have been calm as they did not get into anything they shouldn’t. Diana left the house tidy. We would book her again.”
“Havana is an exceptional dog sitter—trustworthy, communicative, and truly wonderful with dogs! My pup, Buckley, absolutely adores her and is always happy and well cared for after their time together. I have complete peace of mind knowing he’s in such great hands. Highly recommend her services—10/10!”

“Zoe was great with my pup! I’ve been hesitant to leave him home alone and Zoe allowed me to enjoy a night out without worry! Highly highly recommend them for your pet sitting needs!”

“This was my first time using Rover, and it was very last minute. I didn’t really know what to expect, but Emily did such a great job at explaining the process and making me feel at ease! She took such great care of my babies and was very respectful of my home! I am so happy I chose to go with Emily, she will definitely be my go to girl moving forward!”

“Emma is so kind and caring! She took great care of our two medium energy dogs and our house. Would definitely book again. She was great at communicating and sending us pictures!”
“Paige was an amazing dog sitter!! She took such wonderful care of Piper, and was amazing about sending pictures and updates throughout the day. I will absolutely reach out to Paige again for any future dog sitting or walking!”

“Danika took such good care of our girl, Bella! We adopted Bella a few months ago so we wanted to leave her with someone great and Danika met us ahead of time so Bella would be comfortable. She sent updates and cute photos too - Great overall everything!”

“Grace was amazing as always! She’s very communicative and genuinely cares about animals. She gave me peace of mind while I was away by sending continuous updates and pictures! She took great care of my home, and I’ve already booked with her for my next outing ♥️”

About: I’ve done a lot of dog sitting in Boston and for friends and family over the years, and I genuinely love it. I didn't have pets of my own as a kid, but always loved being around dogs. I’m comfortable with all kinds of dogs — big, small, high-energy, or total couch potatoes. I stick to their usual routines, make sure they get plenty of walks, playtime, and attention, and just try to keep things as normal and stress-free as possible while their owners are away. Lots of updates, lots of love, and happy pups are always the goal. Expect many photos and selfies. I work in a nursing home, and love bring pets along with me to visit the residents if approved by the owner! I work a typical Monday-Friday 8-5pm and have about an hour commute. I am available for evenings or early morning walks, as well as weekend/overnight boarding or house sitting. I live in an apartment in Charlestown with a fenced in back yard. Pets are allowed. I live with two family members with a lot of pet experience who also support boarding pets. I am happy to stay in someone's home if needed.
The median cost per night for house sitting in Windsor Road is $50
Pet parents share their Rover experiences - Windsor Road
Thanks Iva for taking care of Poe and keeping us informed! The house was clean and Poe was very happy on our return. You always are responsible and easy to communicate with while we are out of town and we appreciate you. We will definitely use you again for our travels
Kiersten was exceptional! She took excellent care of my senior dog, Lennon, while housesitting. Her communication was great and I received multiple updates and pictures throughout her stay. Lennon got exercise, stimulation, and lots of attention. I came home to a happy pup and it was clear he had been well cared for. I’d definitely recommend Kiersten and hire her again!

I cannot recommend this sitter enough! I travel frequently for work and have hired many sitters over the years, and she is easily one of the absolute best I have ever had. From our initial meet and greet, Emma was incredibly warm and affectionate with my dog. Her communication throughout the entire stay was fantastic. When my travel plans shifted and I had to change my flight time, she was extremely flexible and accommodating with adjusting the schedule. She went above and beyond in ways I never expected. My flight ended up getting in at midnight, and coming home to find that she had washed my bedding was such a thoughtful and wonderful treat after a long journey. She is compassionate, empathetic, down to earth, and a complete delight to work with. I would jump at the chance to book her again!

Noa watched our 11-week-old Ridgeback puppy for a full overnight and was honestly amazing! Puppies are a lot, and she handled it all like a pro. We came home to a happy, chill puppy and two cats who didn't seem bothered at all, which is a win in our house. Super easy to communicate with, and it was such a relief to leave him with someone we trusted. Any pup would be lucky to have her!!

Krista was amazing! She housesat our 1yo puppy Peach for almost two weeks and took incredible care of our girl and home. She sent photos and updates letting us know Peach was happy. Our house was spotless and she did the laundry. It was so reassuring having Krista stay with Peach and we highly recommend her!

Will came to the rescue when a friend backed out from watching my dog, River. He was very responsive, and I could tell River liked him immediately at the meet and greet. Will sent lots of pictures throughout his overnight stay, and River looked so happy. We’ll definitely book with him again in the future!

Rachna has been an amazing from the very first walkthrough. She is trustworthy, sweet, and a dog lover at heart. She truly just wants to love on your pups and make sure they are taken care of while you are away and I feel like the luckiest human to have found her. She has given me the peace and permission to travel and do things in a way I have not previously done due to not being able to find proper care for our fur babies. Thank you Rachna. Bonus information; she left our house spotless and that’s definitely something hard to find and appreciated.

Yuliia provided wonderful care to our rescue dog Hank and complete peace of mind to us while on a 2+ week trip overseas. We returned to a happy dog and a beautifully maintained home. Yuliia communicates so well and sends wonderful photos. We have used her multiple times. Highly recommend! Thank you Yuliia!

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?
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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How to book house sitting

1. Search
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