House Sitting in Chatham

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Top rated Chatham house sitters

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Sitter Profile Image: Alexa T.
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Alexa T.
Star Sitter
from
$70
per night
5 out of 5.0 stars
67 reviews
12 repeat clients
20 years of experience
Brewster, MA, 02631

Alexa stayed over with our two dogs for a week. She proactively communicated with us everyday with lots of pictures and it was clear the dogs were getting a lot of TLC and exercise. When we came home our apartment was just as we left it. I would recommend Alexa for overnight dog sitting!

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Brad C.
Sitter Profile Image: Caitlin S.
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Caitlin S.
Star Sitter
from
$85
per night
5 out of 5.0 stars
441 reviews
74 repeat clients
29 years of experience
Brewster, MA, 02631

While we were away for a medical procedure, our 15 year old dog became quite ill, requiring lots of attention and complex caregiving — and house cleaning — as well as comforting. Caitlin managed all parts of this VERY difficult booking, which was much more than she bargained for, with competence and grace , and kept her safe and comfortable while we scheduled the Vet and raced home. We were so relieved to have such close and competent attention for our little girl, and grateful for Caitlin‘s grace and confidence at a precarious time. We can’t say enough good about Caitlin and we can’t thank herenough.

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Mary R.
Sitter Profile Image: Karen H.
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Karen H.
Star Sitter
from
$75
per night
5 out of 4.9 stars
100 reviews
22 repeat clients
40 years of experience
Brewster, MA, 02631

Karen communicated wonderfully, followed our requests and send photos of the babies. We were super pleased with her and will be having her back again soon next time we are away!

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Emily H.
Sitter Profile Image: Stephanie B.
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Stephanie B.
from
$30
per night
5 out of 4.8 stars
95 reviews
45 repeat clients
7 years of experience
West Yarmouth, MA, 02673

Had a great first experience with house sitting! She responded to my request quickly, sent update photos, and was respectful of our home while staying.

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Sirena K.
Sitter Profile Image: Rae G.
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Rae G.
from
$65
per night
5 out of 5.0 stars
11 reviews
3 repeat clients
8 years of experience
Brewster, MA, 02631

What an amazing and comforting experience we had with Rae while we were away for the week. She took such extra loving attentive care for our little senior dog. She kept us fully informed of his daily walks and additionally brought a stroller so he could enjoy a walk multiple times a day without tiring him out. I am so very pleased and reassured with her caring nature and love for our fur baby. ❤️ thank you so very much Rae ♥️

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Suzanne W.
Sitter Profile Image: Panayiote L.
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Panayiote L.
from
$75
per night
5 out of 5.0 stars
7 reviews
2 repeat clients
5 years of experience
South Dennis, MA, 02660

Such a caring, kind and conscientious person. I cannot recommend Panny enough. We went on a three week trip to Africa and came home to a calm dog and a spotless home. I have been hiring dog-sitters for 30 years and Panny made them all pale by comparison.

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Cheryl P.
Sitter Profile Image: Caitlin R.
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Caitlin R.
Star Sitter
from
$100
per night
5 out of 5.0 stars
30 reviews
10 repeat clients
10 years of experience
Orleans, MA, 02653

About: I’ve grown up with cats and dogs all my life. I have a cat who also likes to go on walks! I’m very reliable and can make myself available, if need be I’m currently a figure skating coach in Orleans. My coaching days are Monday-Thursday and it does not take up my entire day. Need a dog walker morning and evening? I’m your girl! For new clients I require booking request a week in advance. This is so we can set up a time for me to come meet you and your fur baby for my safety and theirs during visits. I know how to wrap bandages, if an accident ever occurred. If your pet needs to take any kind of medication, I know the best ways to feed it to them if they are reluctant!

Sitter Profile Image: Taigh L.
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Taigh L.
from
$55
per night
5 out of 4.9 stars
44 reviews
17 repeat clients
7 years of experience
Orleans, MA, 02653

Taigh was great with our dog. I appreciate his accommodating our last second request and his communication on such short notice. Highly recommend!

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Trey P.
Sitter Profile Image: Marie V.
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Marie V.
from
$70
per night
5 out of 5.0 stars
36 reviews
9 repeat clients
20 years of experience
Orleans, MA, 02653

Marie took care of our new puppy and older dog while we were gone for a day trip. Marie is a terrific communicator, sent tons of pics and updates, and took wonderful care of our dogs. We feel so lucky to have found her!

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Elizabeth O.
Sitter Profile Image: Allison V.
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Allison V.
from
$80
per night
2 years of experience
harwich, MA, 02645

About: Hi my name is Ali! I have taken care of dogs since Sumer of 2023. For people that live around me. I can walk, feed and spend the nights with them for however long you need! :). Sunday All Day Monday- Friday: Currently after 330 Summer all day Saturday All Day I am happy to schedule times according to my upcoming summer job and finishing current high school schedule. I will take them for desired time for walking, feeding, and household care if necessary. I am also willing to stay overnight when necessary for care.

Sitter Profile Image: Rowan J.
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Rowan J.
from
$70
per night
5 out of 5.0 stars
2 reviews
1 repeat client
6 years of experience
Brewster, MA, 02631

Rowan was fantastic. She kept our boy busy with swimming, walks and a lot of playtime with other dogs. He was exhausted and seemed disappointed to see us when we returned! Our house was immaculate when we got home. She sent pictures and updates all during the weekend. Thanks Rowan, we look forward to working with you again soon!

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Dave D.
Sitter Profile Image: Isabelle L.
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Isabelle L.
from
$100
per night
5 out of 5.0 stars
8 reviews
10 years of experience
Brewster, MA, 02631

About: I have had dogs my whole life, from Shih-Tzus to Golden Retrievers and I’ve never met one I didn’t love! I miss my own furry friend so I want to take great care of yours. I recently boarded my Mom’s dog for three months while she was unable to care for him, and we both had a blast. Now that he has gone home I’m ready to open up my house to new dogs to care for. I am a student and I live about a 15 minute walk from campus. I typically go to class from 9:30-12:30 in the mornings and then I am home for the rest of the day to care for your puppy. I’m home boarding is preferable; however, on weekends I can be flexible to your needs. We will walk on campus, take trips to the dog park, and go for hikes depending on your animal’s activity and socializing needs. I am available weekdays and weekends.

Sitter Profile Image: Carly B.
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Carly B.
from
$75
per night
5 out of 5.0 stars
16 reviews
6 repeat clients
5 years of experience
Dennisport, MA, 02639

Carly was wonderful! She was easy to communicate with, always on time, and took excellent care of our Doberman.

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Charles H.
Sitter Profile Image: Heather M.
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Heather M.
Star Sitter
from
$125
per night
5 out of 5.0 stars
19 reviews
3 repeat clients
25 years of experience
Orleans, MA, 02653

Heather was amazing! We used her for our wedding and she was so wonderful to have! She was super easy to get into contact with and was very reliable. My in laws were so relieved to have their pup in the best care!

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Sarah D.
Sitter Profile Image: Skyla P.
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Skyla P.
Star Sitter
from
$32
per night
5 out of 5.0 stars
15 reviews
4 repeat clients
9 years of experience
Harwich, MA, 02645

Skyla was great! She confirmed our plans and any instructions beforehand, and kept us updated with pictures and notes. She stayed at our house and everything was left in good order - including a very happy dog:)

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Karen C.
Sitter Profile Image: Sadie R.
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Sadie R.
from
$75
per night
5 out of 5.0 stars
60 reviews
1 repeat client
10 years of experience
Harwich, MA, 02645

Sadie did a wonderful job of looking after Otis this past weekend - lots of great walks with new friends and hanging out at home with Sadie and Tut! Would highly recommend!

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Betsy K.
Sitter Profile Image: Ellen B.
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Ellen B.
from
$75
per night
5 out of 5.0 stars
6 reviews
15 years of experience
Orleans, MA, 02653

Ellen is the best!!! She stayed in our home for 5 nights with our 2 year old golden retriever. She is friendly, kind, and our dog just loved her. 5+ stars!!!!

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Heather S.
Sitter Profile Image: Caroline D.
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Caroline D.
from
$75
per night
5 out of 4.8 stars
29 reviews
5 repeat clients
20 years of experience
Orleans, MA, 02653

Caroline was awesome! She was available last-minute and her actual availability matched her Rover availability, which other sitters did not. She stayed in our home with our 2 pups for 4 nights and kept our pups and our home in great shape! Would definitely recommend her!!

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Erica F.
Sitter Profile Image: Lara S.
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Lara S.
from
$75
per night
45 years of experience
South orleans, MA, 02662

About: I am a very active 49 year old mom with adult children and two small dogs. I grew up with animals my whole life, and my family even owned a chain of pet stores when I was growing up, where I worked. My family is packed with doctors and vets. I move to the Cape full time and am available to walk dogs, house sit, and board small to medium sized animals in my home in Orleans. We have a fenced in backyard and lots of space to run on the beach. I work remotely, part-time as an attorney and set my own schedule. My true love is animals! My flexibility gives me plenty of time to care for pets, in your home, in mine, or just for a walk. I take my dogs for a daily run to on the beach and am happy to take along another. I can also care for your dog alone in your home (and leave mine home with my amazing family). Finally, I am available for walking your pup, most days in your neighborhood or mine. We have an acre of land and half is fenced in for dogs. We have extra cages if desired. Ours never enjoyed their crates. We will follow your schedule and treat your pet like a member of the family. We invite interviews in advance to ensure we are the right fit for your pet.

Sitter Profile Image: Caitlin G.
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Caitlin G.
from
$60
per night
5 out of 5.0 stars
7 reviews
1 repeat client
15 years of experience
Chatham, MA, 02633

Caitlin is amazing!!! She was phenomenal with our highly energy pup. She took such amazing care of Millie and sent great pictures and updates. And Millie loves her so much. Can not recommend Caitlin enough. She is the best!

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Brooke C.
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Sitter Profile Image: Alexa T.
Verified Enhanced Background Check
Sitter Profile Image: Alexa T.
Verified Enhanced Background Check

1. Alexa T.

Star Sitter
Friendly Pet Sitters
Brewster, MA, 02631
7.0 mi. away
Boarding, House Sitting, Drop-In Visits
from
$70
per night
5 out of 5.0 stars
67 reviews
12 repeat clients
Profile image

Alexa stayed over with our two dogs for a week. She proactively communicated with us everyday with lots of pictures and it was clear the dogs were getting a lot of TLC and exercise. When we came home our apartment was just as we left it. I would recommend Alexa for overnight dog sitting!

Availability updated today
Sitter Profile Image: Caitlin S.
Verified Enhanced Background Check
Sitter Profile Image: Caitlin S.
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2. Caitlin S.

Rover 101
Star Sitter
HOME FT-FULLY INSURED-FENCED AREA❤
Brewster, MA, 02631
9.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$85
per night
5 out of 5.0 stars
441 reviews
74 repeat clients
Profile image

While we were away for a medical procedure, our 15 year old dog became quite ill, requiring lots of attention and complex caregiving — and house cleaning — as well as comforting. Caitlin managed all parts of this VERY difficult booking, which was much more than she bargained for, with competence and grace , and kept her safe and comfortable while we scheduled the Vet and raced home. We were so relieved to have such close and competent attention for our little girl, and grateful for Caitlin‘s grace and confidence at a precarious time. We can’t say enough good about Caitlin and we can’t thank herenough.

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Karen H.
Verified Enhanced Background Check
Sitter Profile Image: Karen H.
Verified Enhanced Background Check

3. Karen H.

Star Sitter
A retired INSURED dog lover
Brewster, MA, 02631
9.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
5 out of 4.9 stars
100 reviews
22 repeat clients
Profile image

Karen communicated wonderfully, followed our requests and send photos of the babies. We were super pleased with her and will be having her back again soon next time we are away!

Availability updated 2 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Stephanie B.
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Sitter Profile Image: Stephanie B.
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4. Stephanie B.

I love taking care of dogs and cats
West Yarmouth, MA, 02673
14.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 4.8 stars
95 reviews
45 repeat clients
Profile image

Had a great first experience with house sitting! She responded to my request quickly, sent update photos, and was respectful of our home while staying.

Availability updated 36 days ago
Sitter Profile Image: Rae G.
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Sitter Profile Image: Rae G.
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5. Rae G.

Reliable dog walker and sitter!
Brewster, MA, 02631
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
11 reviews
3 repeat clients
Profile image

What an amazing and comforting experience we had with Rae while we were away for the week. She took such extra loving attentive care for our little senior dog. She kept us fully informed of his daily walks and additionally brought a stroller so he could enjoy a walk multiple times a day without tiring him out. I am so very pleased and reassured with her caring nature and love for our fur baby. ❤️ thank you so very much Rae ♥️

Availability updated 4 days ago
Sitter Profile Image: Panayiote L.
Verified Enhanced Background Check
Sitter Profile Image: Panayiote L.
Verified Enhanced Background Check

6. Panayiote L.

dogs love me! conscientious and fun
South Dennis, MA, 02660
11.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Such a caring, kind and conscientious person. I cannot recommend Panny enough. We went on a three week trip to Africa and came home to a calm dog and a spotless home. I have been hiring dog-sitters for 30 years and Panny made them all pale by comparison.

Availability updated yesterday
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Caitlin R.
Verified Enhanced Background Check
Sitter Profile Image: Caitlin R.
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7. Caitlin R.

Star Sitter
Cape Cod local and animal lover!
Orleans, MA, 02653
7.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5 out of 5.0 stars
30 reviews
10 repeat clients

Caitlin is a fantastically friendly and caring woman who passes on nothing but love to the animals around her. In the 8 years I've known her, I only have positive things to say about her and her treatment of animals. From taking care of pitbulls to volunteering with wild birds, her compassion for our animal friends has been a ray of sunshine.

Availability updated 9 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Taigh L.
Verified Enhanced Background Check
Sitter Profile Image: Taigh L.
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8. Taigh L.

Attentive, flexible, and versatile
Orleans, MA, 02653
6.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 4.9 stars
44 reviews
17 repeat clients
Profile image

Taigh was great with our dog. I appreciate his accommodating our last second request and his communication on such short notice. Highly recommend!

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Marie V.
Verified Background Check
Sitter Profile Image: Marie V.
Verified Background Check

9. Marie V.

Dogs are the best!
Orleans, MA, 02653
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 5.0 stars
36 reviews
9 repeat clients
Profile image

Marie took care of our new puppy and older dog while we were gone for a day trip. Marie is a terrific communicator, sent tons of pics and updates, and took wonderful care of our dogs. We feel so lucky to have found her!

Availability updated 9 days ago
Sitter Profile Image: Allison V.
Verified Enhanced Background Check
Sitter Profile Image: Allison V.
Verified Enhanced Background Check

10. Allison V.

Excited to meet your pets!!!!
harwich, MA, 02645
4.8 mi. away
House Sitting, Dog Walking
from
$80
per night
2 years of experience

About: Hi my name is Ali! I have taken care of dogs since Sumer of 2023. For people that live around me. I can walk, feed and spend the nights with them for however long you need! :). Sunday All Day Monday- Friday: Currently after 330 Summer all day Saturday All Day I am happy to schedule times according to my upcoming summer job and finishing current high school schedule. I will take them for desired time for walking, feeding, and household care if necessary. I am also willing to stay overnight when necessary for care.

Availability updated 41 days ago
Sitter Profile Image: Rowan J.
Verified Enhanced Background Check
Sitter Profile Image: Rowan J.
Verified Enhanced Background Check

11. Rowan J.

🐾 are always in good hands with me
Brewster, MA, 02631
6.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 5.0 stars
2 reviews
1 repeat client
Profile image

Rowan was fantastic. She kept our boy busy with swimming, walks and a lot of playtime with other dogs. He was exhausted and seemed disappointed to see us when we returned! Our house was immaculate when we got home. She sent pictures and updates all during the weekend. Thanks Rowan, we look forward to working with you again soon!

Availability updated 32 days ago
Sitter Profile Image: Isabelle L.
Verified Enhanced Background Check
Sitter Profile Image: Isabelle L.
Verified Enhanced Background Check

12. Isabelle L.

Energetic and Active Sitter
Brewster, MA, 02631
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5 out of 5.0 stars
8 reviews

Isabelle is a true dog lover! I have never seen anyone give so much attention and love to an animal. Isabelle is reliable, trustworthy, friendly, and easy to work with. Most importantly she takes great care of my 100 pound English Cream Golden Retriever, taking him for long walks, brushing him, giving him medication when needed, and giving him tons of playtime.

Availability updated 9 days ago
Sitter Profile Image: Carly B.
Verified Enhanced Background Check
Sitter Profile Image: Carly B.
Verified Enhanced Background Check

13. Carly B.

Friendly, Dog lover, Nature Lover
Dennisport, MA, 02639
9.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
16 reviews
6 repeat clients
Profile image

Carly was wonderful! She was easy to communicate with, always on time, and took excellent care of our Doberman.

Availability updated 11 days ago
Sitter Profile Image: Heather M.
Verified Enhanced Background Check
Sitter Profile Image: Heather M.
Verified Enhanced Background Check

14. Heather M.

Star Sitter
Accountable worry-free pet care
Orleans, MA, 02653
6.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$125
per night
5 out of 5.0 stars
19 reviews
3 repeat clients
Profile image

Heather was amazing! We used her for our wedding and she was so wonderful to have! She was super easy to get into contact with and was very reliable. My in laws were so relieved to have their pup in the best care!

Availability updated yesterday
Sitter Profile Image: Skyla P.
Verified Enhanced Background Check
Sitter Profile Image: Skyla P.
Verified Enhanced Background Check

15. Skyla P.

Star Sitter
I have a warm heart for cold noses!
Harwich, MA, 02645
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$32
per night
5 out of 5.0 stars
15 reviews
4 repeat clients
Profile image

Skyla was great! She confirmed our plans and any instructions beforehand, and kept us updated with pictures and notes. She stayed at our house and everything was left in good order - including a very happy dog:)

Availability updated 3 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Sadie R.
Verified Background Check
Sitter Profile Image: Sadie R.
Verified Background Check

16. Sadie R.

Come join the pack!
Harwich, MA, 02645
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
60 reviews
1 repeat client
Profile image

Sadie did a wonderful job of looking after Otis this past weekend - lots of great walks with new friends and hanging out at home with Sadie and Tut! Would highly recommend!

Availability updated 4 days ago
Sitter Profile Image: Ellen B.
Verified Enhanced Background Check
Sitter Profile Image: Ellen B.
Verified Enhanced Background Check

17. Ellen B.

Dog mom in training
Orleans, MA, 02653
8.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
6 reviews
Profile image

Ellen is the best!!! She stayed in our home for 5 nights with our 2 year old golden retriever. She is friendly, kind, and our dog just loved her. 5+ stars!!!!

Availability updated 13 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Caroline D.
Verified Background Check
Sitter Profile Image: Caroline D.
Verified Background Check

18. Caroline D.

Amazing house sitter, let’s walk!
Orleans, MA, 02653
7.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 4.8 stars
29 reviews
5 repeat clients
Profile image

Caroline was awesome! She was available last-minute and her actual availability matched her Rover availability, which other sitters did not. She stayed in our home with our 2 pups for 4 nights and kept our pups and our home in great shape! Would definitely recommend her!!

Availability updated yesterday
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Lara S.
Verified Enhanced Background Check
Sitter Profile Image: Lara S.
Verified Enhanced Background Check

19. Lara S.

Loving mom to humans & pets.
South orleans, MA, 02662
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
1 review

If you're like me trusting someone to watch over your fur babies when you have to be out of town is one of the biggest challenges to having pets. In the past it has meant that I've been quick to cancel plans and have missed out on a number of special days and events of family and friends. But recently things have changed for me when it comes to my ability to travel because I now have someone I trust to watch my cats when I'll be away. Lara has been a life saver in this regard and it gives me such a sense of security to know they are under her care and that I don't have to always say sorry I can't go. You also never know when something could come up health wise with a family member and having that peace of mind that my cats are extremely well cared for is something that's hard to put into words. Lara sends me photos of the cats and keeps me updated as to how they are all doing so I don't worry about them. She absolutely adores animals and provides for them top notch care and attention so they don't feel lonely in my absence. She asks the important questions so nothing is just left up to chance and she is extremely detail oriented in her dedicated approach to pet care. I highly recommend Lara if you are looking for someone to care for your fur babies like I was.

Availability updated 24 days ago
Sitter Profile Image: Caitlin G.
Verified Enhanced Background Check
Sitter Profile Image: Caitlin G.
Verified Enhanced Background Check

20. Caitlin G.

Loves all dogs!
Chatham, MA, 02633
1.0 mi. away
House Sitting, Dog Walking
from
$60
per night
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

Caitlin is amazing!!! She was phenomenal with our highly energy pup. She took such amazing care of Millie and sent great pictures and updates. And Millie loves her so much. Can not recommend Caitlin enough. She is the best!

Availability updated 21 days ago

Over 42 pet parents in Chatham have booked house sitting

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The median cost per night for house sitting in Chatham is $75

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Sitters in Chatham average 3 repeat house sitting clients

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