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Winn C.

5.0 out of 5 stars
10 repeat clients
Profile image

Winn C.

5.0 out of 5 stars
10 repeat clients

Contact for Boarding

$98 total per night

These prices are for 1 dog, including a booking fee of 11%.

Highlights

Winn has Star Sitter status!
Enhanced background check
8 years of experience
Can administer medication
Senior dog experience
Can provide daily exercise

Pet care experience

World's Best Dog Funcle

I've been dog-adjacent for most of my life, lived with a roommate's dog for 4+ years, and have been a go-to dogsitter for various friends since moving to Boston in 2019. Your doggo would be staying with me (just me!) in a large, well-maintained 1 bedroom apartment in the middle of Coolidge Corner (within walking distance of plenty of excellent park spaces).

Qualifications

10 repeat pet parents
100% response rate
Usually responds in a few minutes
100% bookings with photo updates
8 years of experience
Oral medication administration
Senior dog experience
Can provide daily exercise

Ratings and reviews

5.0
stars
40 ratings
Nate W.
5.0 out of 5 stars
Boarding • May 25, 2026

Winn is like a professional! He's great with our dog and very flexible.

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Susan K.
5.0 out of 5 stars
Boarding • Apr 27, 2026

Winn is someone that I trusted instinctively partly because he’s so organized. He seems very knowledgeable about dogs.

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Melanie G.
5.0 out of 5 stars
Boarding • Apr 07, 2026

Winn is so great with Millie and easy to communicate with. Always know Millie is in great care!

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Brian K.
5.0 out of 5 stars
Boarding • Feb 24, 2026

Winn was great with my semi-senior dog, i highly recommend.

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Nate W.
5.0 out of 5 stars
Boarding • Jan 15, 2026

Winn did a great job boarding our dog, Frankie. He was extremely communicative and our dog didn't want leave when we came back! We will definitely be boarding with him again.

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Barry L.
5.0 out of 5 stars
Boarding • Dec 22, 2025

Winn has taken great care of Lucas while we are away!!!

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Calendar and availability

Available
Not available
SMTWTFS
Available
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SMTWTFS

Schedule

I lead a fairly predictable schedule during the week and keep my calendar updated. For any more details, please inquire within! I work full-time and in-office, however I do have flexibility to work a few days from home each week and will do so if I'm looking after your pet. Most evenings are spent at home or nearby. I have some degree of flexibility to accommodate special needs if necessary. Full honesty: my greatest differentiating feature is probably that I seldom travel on weekends when most people like to travel (holiday weekends, Thanksgiving, the December holidays).

Where your pet will stay

Home characteristics

Lives in an apartment
Does not have a yard
Non-smoking household
Has no pets
No children present
Dogs allowed on bed
Dogs allowed on furniture
Potty breaks every 2-4 hours

Safety, trust & environment

I live in a large, well-maintained and dog-safe apartment in a very safe neighborhood. Dogs will be leashed and supervised while outside. If I am taking care of your dog during a workday and unable to be at home, my next-door neighbor is an avid dog lover who will pull spot-duty if needed.

A typical day

Standard routine involves a walk first thing in the morning and again in the late afternoon (if your dog prefers to go out more, please let me know). There are a number of park spaces nearby that I frequent with the dogs I care for. I generally try to match the dog's vibe while we hang--content to play with toys around the house or simply chill/cuddle in proximity. Please let me know how your doggo enjoys spending their time and I will do my best to emulate their typical environment.

0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
Dogs over 1 year old
Spayed and neutered dogs only
No females in heat
Takes only 1 client at a time
Winn can host up to 1 pet per night
All the typical things: anxieties, likes/dislikes, health-related issues, how much they shed, other idiosyncrasies. I'm adaptable and will do my best to accommodate! Note that food, food/water bowls, treats, leashes, and toys are to be provided by owner.
Each sitter joining Rover needs to pass a background check. And by booking on Rover, you can get photo & message updates, 24/7 support, and reimbursement for eligible vet care.

These prices are for 1 dog, including a booking fee of 11%.