Pet Sitting in Winchester

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Sitter Profile Image: Maggie R.
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Sitter Profile Image: Maggie R.
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1. Maggie R.

Dogs are actually my best friends!
Gill, MA, 01354
12.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
7 repeat clients
from
$18
per visit

Maggie is a great pet sitter. She always knows what she’s doing when it comes to taking care of animals whether it’s house pets or farm animals. I’d say she has great experience and I would definitely trust Maggie to watch my dog or cat. She’s done pet sitting for me and she is 5 stars for sure.

Sitter Profile Image: Devon P.
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Sitter Profile Image: Devon P.
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2. Devon P.

Would love to care for your pets!
Winchendon, MA, 01475
18.2 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
38 reviews
16 repeat clients
from
$25
per visit

Devon is kind and patient, and very reliable. It feels great to know my dog is being well taken care of while we are at work. I would recommend her!

Sitter Profile Image: Heather C.
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Sitter Profile Image: Heather C.
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3. Heather C.

Home full-time - Ready to play
greenfield, MA, 01301
13.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
53 reviews
18 repeat clients
from
$25
per visit

Heather took great care of my animals. Love the pics and the detailed notes.

Sitter Profile Image: Adrianna L.
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Sitter Profile Image: Adrianna L.
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4. Adrianna L.

No dog too big or small!
Winchendon, MA, 01475
16.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$20
per visit

I highly recommend Adrianna! I have 2 dogs 1-3year old long hair german shepherd (90lbs) and 1-8year old shepherd mix (50lbs). Adrianna often watches them for long weekends in her home and is always on top of checking in with me and letting me know how they are. She takes them on trail walks and makes sure they get plenty of exercise daily. She's also great about sending picture updates. I don't trust anyone else with my dogs!

Sitter Profile Image: Elias V.
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Sitter Profile Image: Elias V.
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5. Elias V.

Part time pet walker/sitter
Putney, VT, 05346
15.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$25
per visit

Wonderful, kind and reliable.

Sitter Profile Image: Kiersten S.
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Sitter Profile Image: Kiersten S.
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6. Kiersten S.

Responsible, smart animal lover!
Orange, MA, 01364
13.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
17 reviews
3 repeat clients
from
$20
per visit

Kiersten came to my rescue when I needed last minute help with my dog.

Sitter Profile Image: Amelia A.
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Sitter Profile Image: Amelia A.
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7. Amelia A.

I am Kind, Clean, and Respectful :)
Hinsdale, NH, 03451
7.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$15
per visit

Amelia did a drop-in visit to walk Ilo. We had a get-together the evening before when she took time to get to know Ilo, me, and my place. She is very kind and respectful, honest, and funny. She sent the picture as promised and was generally very responsive. It is also very clear that she loves animals very much and knows what is good for them (that includes respect of their personal space, which I liked very much). Cheers!

Sitter Profile Image: Megan A.
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Sitter Profile Image: Megan A.
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8. Megan A.

Excellent Care for Any Pet
Troy, NH, 03465
10.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
3 repeat clients
from
$25
per visit

Megan is fantastic! Great communication - timely & easy. Personable & flexible. My pets seemed to really enjoy her & I know she took care of them.

Sitter Profile Image: Aley M.
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Sitter Profile Image: Aley M.
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9. Aley M.

Here for you and your fur baby!
Keene, NH, 03435
11.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
3 repeat clients
from
$22
per visit

Thanks Aley! Great job

Sitter Profile Image: Margaret K.
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Sitter Profile Image: Margaret K.
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10. Margaret K.

"Go Ask Alice" To sit for you!
Richmond, NH, 03470
6.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
from
$15
per visit

It is my pleasure to let you know about Margaret's love for animals. She has cared for and nutured my pets over the years. Minnie , my current dog is sweet and also very active. It is assuring to know that my pet caregiver has the energy to keep up with her. Margaret is also very intuitive. My pup is not very verbal when it comes to her needs. Minnie speaks with her eyes. Margaret has learned what each expression means. I have watched her with her pets and other along the way. I can say she is a kindred spirit.

Sitter Profile Image: Patricia H.
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Sitter Profile Image: Patricia H.
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11. Patricia H.

Dogruns, Horsewhispers, catcuddles!
Montague, MA, 01376
14.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
6 repeat clients
from
$15
per visit

Did a great job caring for our kitty!

Sitter Profile Image: Eleana L.
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Sitter Profile Image: Eleana L.
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12. Eleana L.

Love cats and dogs of all sizes
keene, NH, 03431
12.2 mi. away
Drop-In Visits, Dog Walking
4 years of experience
from
$17
per visit

About: i currently work at a doggy daycare and have experience with many breeds of dogs and i’ve been an owner of multiple cats over the years. Friends and family have trusted me to watch their pets while they’ve been away as well. I’m currently working full time but i get out earlier some days and have others off. When i’m not at work my schedule is very flexible. I can understand how to take care of your fur babies every need and make sure they’re comfortable and happy until you come back! I can take them for walks, follow eating schedules, and make sure their routine stays as normal as possible.

Sitter Profile Image: Jillian C.
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Sitter Profile Image: Jillian C.
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13. Jillian C.

Friendly Neighborhood Pet Lover
Brattleboro, VT, 05301
13.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
5 repeat clients
from
$25
per visit

We feel fortunate to have Jillian care for our cat when we are out of town. Her communication has been excellent and she seems to truly enjoy the time she spends with him.

Sitter Profile Image: Christopher B.
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Sitter Profile Image: Christopher B.
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14. Christopher B.

I'm here for your furkids!
Keene, NH, 03431
12.2 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$22
per visit

Chris is great. Very playful and attentive. My dog loves him!

Sitter Profile Image: Julia W.
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Sitter Profile Image: Julia W.
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15. Julia W.

A human friend for your furry one!
Keene, NH, 03431
13.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$25
per visit

Julia did a great job taking care of my cat while I was gone. Everything was clean and Misty was alive and well. Thanks Julia!

Sitter Profile Image: Amber D.
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Sitter Profile Image: Amber D.
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16. Amber D.

Pawsomely the best!
Hinsdale, NH, 03451
5.8 mi. away
Drop-In Visits
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$17
per visit

We’ve had Amber drop in on a few separate occasions now and have had a great experience each time. She’s been attentive to both dogs behaviors and makes sure to check in with questions or concerns. I have a peace of mind when Amber visits if I’ll be away from home for an extended time during the day. Based on the photos, the dogs definitely have a great time with her too!

Sitter Profile Image: Hannah H.
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Sitter Profile Image: Hannah H.
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17. Hannah H.

Enthusiastic dog walker!
Keene, NH, 03431
12.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$18
per visit

Hannah did a great job with my cat! He requires a lot of extra attention cuz he has daily medication but she did a great job. Would definitely book her again.

Sitter Profile Image: Kendra K.
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Sitter Profile Image: Kendra K.
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18. Kendra K.

Woman Chasing Her #SteveIrwinLife
Vernon, VT, 05354
6.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
8 repeat clients
from
$25
per visit

Kendra was willing to go above and beyond what we expected from her time taking care of our cat, Velvet, and was very patient while we worked out a miscommunication with our landlord. We hope to have Kendra take care of Velvet again in the future!

Sitter Profile Image: Deb L.
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Sitter Profile Image: Deb L.
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19. Deb L.

Rover 101
Personalized pet care!
Chesterfield, NH, 03466
11.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
from
$20
per visit

Deb stepped in when we were out of town and our dog sitter got sick and couldn't care for our dogs. She left us wonderful updates after each visit filled with information and photos. I felt our dogs were well taken care of the whole time. We arrived home to a wonderful note and dog treats for our pups.

Sitter Profile Image: Dakota C.
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Sitter Profile Image: Dakota C.
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20. Dakota C.

I'll walk your dog
Fitzwilliam, NH, 03447
10.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$30
per visit

She's great with my pets when she walks them. I have no problems with Dakota. She's very professional and very nice! Rate 10 out of 10

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Winchester Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Winchester are rated on average 5 out of 5 stars based on 3 reviews.

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Rover.com is the simple, savvy way to find and book Winchester drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Winchester. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

Drop-In Visits