House Sitting in Winchester

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Doreen R.
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Sitter Profile Image: Doreen R.
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1. Doreen R.

Dogs love me & I love them Safe fun
Keene, NH, 03431
12.1 mi. away
Boarding, House Sitting
5.0 out of 5 stars
45 reviews
19 repeat clients
from
$55
per night

Doreen and Cindy were excellent house guests and took very good care of our dogs. We have a very shy dog that took to them immediately which put us at ease for travel. Would recommend.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Stacie S.
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Sitter Profile Image: Stacie S.
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2. Stacie S.

I will love your pet like my own
Keene, NH, 03431
13.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$50
per night

Stacie took great care of our three dogs! She was also tidy while staying in our home, and was a great communicator. We wouldn’t hesitate to have her watch the pups again, and would highly recommend her services.

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Sitter Profile Image: Maggie R.
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Sitter Profile Image: Maggie R.
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3. 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
$55
per night

Maggie is a wonderful housesitter. Our very anxious grouchy dog took an immediate liking to her. We will definitely be using Maggie to house and dog sit the next time we go away.

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Sitter Profile Image: Madeline E.
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Sitter Profile Image: Madeline E.
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4. Madeline E.

Star Sitter
Bonus! Will water your plants :)
Fitzwilliam, NH, 03447
11.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
8 repeat clients
from
$75
per night

Maddy did a fantastic job sitting with our pup! She was very attentive to our needs. Rupert, our pup, absolutely adored her. I could tell from the first time they met, but more than that, he didn't look like he had lost weight when we returned. That means to me that he didn't miss us as much as usual ;) I also was happy with the updates. I knew she was enjoying him just as much as he did her. She not only took great care of Rupert but of our house and plants too! I highly recommend her. She is the best!

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Sitter Profile Image: Kiersten S.
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Sitter Profile Image: Kiersten S.
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5. 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
$32
per night

Kiersten is very easy to communicate with and took great care of my dog, Luna. She sent me lots of pictures of their time together and was very flexible when our plans changed. I would definitely hire her again.

Sitter Profile Image: Megan A.
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Sitter Profile Image: Megan A.
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6. 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
$55
per night

Megan was attentive, sent great pictures and updates, and our dog was very happy….

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Shane S.
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Sitter Profile Image: Shane S.
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7. Shane S.

Never Ending Love for Every Dogs
Greenfield, MA, 01301
15.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
6 years of experience
from
$32
per night

About: I’ve taken care of my parent’s dog, friends and relatives when they need someone to walk, feed, and watch over them. I enjoy playing with them and especially walking since I love walking 13+ miles a day, if I don’t have school! I am a full-time college student that works part-time as a letter carrier. I wanted to fit pet sitting/walking on the weekdays as I find myself having more free time after my classes. I can accommodate to the dogs needs! Unfortunately I cannot house sit at my home, but I can absolutely come to you! I would just like a heads-up on the times! I love brushing dogs and giving them baths (though more experienced with small breeds on bathing).

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Sitter Profile Image: Diane D.
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Sitter Profile Image: Diane D.
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8. Diane D.

I love dogs, and they love me.
Westmoreland, NH, 03467
12.6 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
2 reviews
from
$65
per night

Diane was fantastic, she watched our two dogs and stayed at our house while we were out of state for over a week. On the initial meet, our dogs were immediately comfortable around her (one of our dogs is a rescue and very skittish around new people). She knew how to approach her slowly, and our dog was comfortable within minutes. She provided regular updates during the stay, and communicated any concerns she had with them. The house was cleaner than when we left it, and our dogs were in great condition. We will be using her again the next time we travel and would recommend her to anyone!

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Sitter Profile Image: Amelia A.
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Sitter Profile Image: Amelia A.
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9. 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
$50
per night

Amelia took great care of Ilo, who has some behavioural quirks of his own. She sent us daily updates and we could see that he was very happy under her care. She was house sitting for several days, and the house was left in impeccable state. We really recommend her!

Sitter Profile Image: Xixi S.
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Sitter Profile Image: Xixi S.
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10. Xixi S.

Kind and Considerate Care!!
greenfield, MA, 01301
15.9 mi. away
House Sitting
5.0 out of 5 stars
3 reviews
1 repeat client
from
$45
per night

Xixi was amazing and really went above and beyond for me and my pup :) highly recommend they even helped my neighbor out ! Great job :) ? ?

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Sitter Profile Image: Margaret K.
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Sitter Profile Image: Margaret K.
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11. 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
$32
per night

Margaret was awesome to work with. I had an emergency the week before our trip and she was incredibly flexible and accommodating. I have an anxious dog who barks a lot at new people and she calmed him down quickly with her relaxed demeanor. I felt very comfortable leaving him with her. While we were away, she sent sweet updates and photos of our dog. I would hire her again in a heartbeat.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dakota C.
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Sitter Profile Image: Dakota C.
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12. 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
$45
per night

Dakota did great with my very anxious, fear-aggressive dog. He also kept the puppy on a great house training routine. Dakota responded quickly and was available on short notice.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elias V.
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Sitter Profile Image: Elias V.
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13. 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
$65
per night

Eli has spent a lot of time with my dogs. He shows them so much love, immediately getting on the floor to greet the puppy playfully, and responding to the older dog with belly rubs and affection. Eli demonstrates an understanding of dog behavior and development such as positively redirecting the teething puppy with chew toys. He is responsible and timely, showing up when he says that he will. I trust Eli with my dogs not only because of the observable interactions, but also because he genuinely loves my dogs. I highly recommend Eli as a responsible, experienced caregiver for dogs.

Sitter Profile Image: Kristen H.
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Sitter Profile Image: Kristen H.
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14. Kristen H.

Studying Animal Science & Behavior
Greenfield, MA, 01301
16.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
2 repeat clients
from
$50
per night

Kristen Was Great! Beau Immediately Took to Her. She Kept Me Up to Date & Informed About Beau’s Care Throughout the Day. She is Dedicated & Has Earned My Trust!

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Sitter Profile Image: Adrianna L.
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Sitter Profile Image: Adrianna L.
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15. 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
$40
per night

Adrianna was great! She came through on short notice and took great care of my pup and house!

Sitter Profile Image: Julia W.
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Sitter Profile Image: Julia W.
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16. 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
$62
per night

Julia Was Exceptional. She Took Such Good Care of Beau. She Listened Intently to How I Was Caring for the Boy (Who Has a Broken Leg After Getting Hit By a Car). I Was Relaxed by Her Professionalism & Dedication to Being There for Him.

Sitter Profile Image: Michelle E.
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Sitter Profile Image: Michelle E.
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17. Michelle E.

Rover 101
Animal Fun House
Orange, orange, MA, 01364
13.5 mi. away
Boarding, House Sitting, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
3 repeat clients
from
$50
per night

About: My name is Michelle and i have always had a passion for animals.I have 5 cats myself (indoor/outdoor) as well as a toddler. I am very respectful,responsible,and trustworthy. Your fur baby would be treated as if they were my own. I do my best to have a great relationship with any animal I come in contact with. My house is 100% dog and cat friendly. Plenty of space for them to roam as they wish, also a large yard with tie out leads. All animals are welcome. I am home 80% of the time. I leave home for work about 5 hours every other day. I am currently working on my degree in animal science. I have time, space, and energy to fill it with somthing i am passionate about. The level of safty is always top priority. Ensuring a safe space and plenty if toys is the key to successful play time for everyone.

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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
$40
per night

Kendra was wonderfully communicative and took great care of Cookie and Bean whole house sitting this weekend - I know they are excited for the next time she is over, thank you!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Patricia H.
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Sitter Profile Image: Patricia H.
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19. 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 night

Trish took SUCH good care of Tig, giving her lots of attention, treats, cuddles and taking her out for adventures. I came home to a very happy doggy. Trish also sent regular updates, which I love. Tig usually has a hard time when I’m gone for the day, let alone several days, but she had a great time and I knew I didn’t have to worry because she was in Trish’s capable hands :)

Sitter Profile Image: Megan G.
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Sitter Profile Image: Megan G.
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20. Megan G.

Pet Sitting Trapeze Artist
Brattleboro, VT, 05301
10.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
2 reviews
2 repeat clients
from
$40
per night

Megan did a wonderful job watching Abby! We got daily updates and pictures and came home to a happy pup and clean home! Thank you Megan!

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Never beg a friend to watch your dog again. With Rover, you can find your the perfect Winchester house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Winchester who can provide the care your dog needs, when they need it.

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