House Sitting in Chatham

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
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Calendar Recently Updated
Sitter Profile Image: Alexa T.
Verified Enhanced Background Check
Sitter Profile Image: Alexa T.
Verified Enhanced Background Check

1. Alexa T.

Friendly Pet Sitters
Brewster, MA, 02631
7.0 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
48 reviews
9 repeat clients
from
$50
per night

Alexa stayed in our home with our 3 month old Puppy and was amazing! Gave her lots of love and took great care of her while we were away for 4 nights. She sent us daily pictures of her and even taught her how to sit during this time! Thank you for taking such great care of her! She left our home as if she was never here and was very respectful and professional.

Calendar Recently Updated
Sitter Profile Image: Margaret W.
Verified Enhanced Background Check
Sitter Profile Image: Margaret W.
Verified Enhanced Background Check

2. Margaret W.

Rover 101
Loving care when you’re not there!
Orleans, MA, 02653
8.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
7 repeat clients
from
$75
per night

Maggie was absolutely wonderful!! I had never booked anyone to come in and do overnights so was somewhat nervous since my dog has separation anxiety. Maggie sent pictures of Theo laid out on the floor with his pillow and was completely relaxed… even through the night!! She provided regular updates which was so appreciated! Elizabeth

Calendar Recently Updated
Sitter Profile Image: Brooke C.
Verified Enhanced Background Check
Sitter Profile Image: Brooke C.
Verified Enhanced Background Check

3. Brooke C.

Avid animal admirer and lover
Orleans, MA, 02653
8.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$60
per night

Very caring and gentle. Responsible. Stayed at our place to watch my senior dog, left the place clean and followed all instructions. She is my new go to person.

Calendar Recently Updated
Sitter Profile Image: Haley P.
Verified Enhanced Background Check
Sitter Profile Image: Haley P.
Verified Enhanced Background Check

4. Haley P.

Pawsitively Perfect Pet Services!
Chatham, MA, 02650
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5 reviews
from
$75
per night

Our lives have gotten instrumentally better since Haley started walking our two pups. One is a little 9yo bulldog (on the heftier side) and our other is the sweetest 2yo pittie mix, and whether it be taking them for walks, bring them to the dog park, coming over to feed them, or staying at our place for a night or two while we go visit the kids at college, Haley has our backs. She clearly grew up taking care of animals and it shows. You can't go wrong having Haley take care of your fur babies!

Sitter Profile Image: Jessi C.
Verified Enhanced Background Check
Sitter Profile Image: Jessi C.
Verified Enhanced Background Check

5. Jessi C.

Active Aussie Mom
Harwich, MA, 02646
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$50
per night

Jessi is a an animal lover at her core. She shows the same care for your pet and she does her own. Her dog Luana has accompanied Jessi to work, hiking trails, weekend getaways and moved across the country with her. You can trust that Jessi will ensure your dog is fed on time, exercised as needed and snuggled with!

Calendar Recently Updated
Sitter Profile Image: Morgan D.
Verified Enhanced Background Check
Sitter Profile Image: Morgan D.
Verified Enhanced Background Check

6. Morgan D.

Pawsitively Perfect Pet Sitting
Eastham, MA, 02642
12.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$90
per night

Morgan is amazing! She wrote down all the important details and made sure my pups were happy!! Definitely will book again!

Calendar Recently Updated
Sitter Profile Image: Paige N.
Verified Enhanced Background Check
Sitter Profile Image: Paige N.
Verified Enhanced Background Check

7. Paige N.

pet lover dedicated to helping
Yarmouth, MA, 02673
14.0 mi. away
House Sitting
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$55
per night

Paige was fantastic! We have a Jack Russell mix who has a lot of energy and needs to go out and walk and play a lot! Also, because of a health condition, requires a bit more care and has to be very regimented. Paige took care of everything! I was able to enjoy my vacation without any worry or hesitation that my girl would be cared for like she was Paige’s own! Bonus — She sent me pics everyday! Paige will be my go to and I would recommend her to any and everyone!

Calendar Recently Updated
Sitter Profile Image: Dakota L.
Verified Background Check
Sitter Profile Image: Dakota L.
Verified Background Check

8. Dakota L.

Experienced Animal Professional
West Harwich, MA, 02671
8.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
15 reviews
6 repeat clients
from
$70
per night

Dakota was awesome! Extremely responsive and sent lots of photos and videos. It was my first time using Rover and she made it stress free. Will definitely book with her again. Thank you!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Liberty R.
Verified Enhanced Background Check
Sitter Profile Image: Liberty R.
Verified Enhanced Background Check

9. Liberty R.

Passionate about all animals!!!
Harwich, MA, 02645
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$50
per night

Liberty was great with my high maintenance dachshund! Juniper has separation anxiety and is a bit of a grouch but they were best friends by the end of the visit.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth L.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth L.
Verified Enhanced Background Check

10. Elizabeth L.

Everything You Need Under One Woof.
Harwich, MA, 02645
8.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
127 reviews
30 repeat clients
from
$100
per night

Elizabeth was wonderful with our shy pup Oliver! She spent 4 hours house sitting with him including running around our fenced yard with him as a way to get him to feel comfortable with her. We would definitely have her stay with Oliver again.

Calendar Recently Updated
Sitter Profile Image: Anna J.
Verified Enhanced Background Check
Sitter Profile Image: Anna J.
Verified Enhanced Background Check

11. Anna J.

Local who loves animals!
Orleans, MA, 02653
5.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$130
per night

Anna was wonderful with our sweet labradoodle. She stayed at our home and took great care of our pup, going for long walks and sending us photos to keep us up to date. Anna is a warm and caring person and we will definitely will call her again! Thanks Anna!

Sitter Profile Image: Erin L.
Verified Background Check
Sitter Profile Image: Erin L.
Verified Background Check

12. Erin L.

Loving sitter, w/animal experience!
Dennis, MA, 02660
10.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
from
$120
per night

Erin was perfect for our situation

Sitter Profile Image: Jessen S.
Verified Enhanced Background Check
Sitter Profile Image: Jessen S.
Verified Enhanced Background Check

13. Jessen S.

Certified Veterinary Technician
West Harwich, MA, 02671
7.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
from
$85
per night

I would definitely book with Jessen again!! She left the house in great shape and took such great care of my dogs. She is very responsible and respectful and a true animal lover! My dogs were very happy with Jessen when she stayed with them for a few days. Thanks Jessen!

Sitter Profile Image: Aidan K.
Verified Enhanced Background Check
Sitter Profile Image: Aidan K.
Verified Enhanced Background Check

14. Aidan K.

Taken care of dogs for 18 years!
West Harwich, MA, 02671
8.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$100
per night

Everything went great! We were able to enjoy our vacation knowing our pets were cared for.

Calendar Recently Updated
Sitter Profile Image: Sadie R.
Verified Background Check
Sitter Profile Image: Sadie R.
Verified Background Check

15. Sadie R.

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

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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Laine K.
Verified Background Check
Sitter Profile Image: Laine K.
Verified Background Check

16. Laine K.

Your furry friend & me = ❤️
WEST HARWICH, MA, 02671
8.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
from
$80
per night

Laine was amazing…gentle, calm, patient, reliable, caring. She stayed with my elderly, timid dog in my home for 5 days. She sent me updates and pictures daily and left the house and kitchen pristine. I would highly recommend.

Sitter Profile Image: Sophia G.
Verified Enhanced Background Check
Sitter Profile Image: Sophia G.
Verified Enhanced Background Check

17. Sophia G.

Here to give a good scratch & play!
Chatham, MA, 02659
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$150
per night

Sophia is a trustworthy and reliable person. Her love and respect for dogs is evident, and I would fully trust her with my dog any time. Her dog, Hudson, is well-behaved and trained and it’s clear that Sophia takes a dogs needs and well-being very seriously.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Colleen F.
Verified Enhanced Background Check
Sitter Profile Image: Colleen F.
Verified Enhanced Background Check

18. Colleen F.

Leaving is ruff… Here to help!
Orleans, MA, 02653
5.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$150
per night

Colleen took care of our Amazon parrot and Maine Coon cat while we were out of the country. Our original sitters had a last minute emergency. Colleen graciously accepted the position. She was a wonderful communicator and took the utmost responsibility and care of our pets. She took care of them like they were her own with personal attention and consideration. She was sensitive to our concerns for their well being....so much so that she picked us up at the airport so we could not waste a moment getting back to them. Colleen will take great care of your furry friends.

Sitter Profile Image: Mary S.
Verified Enhanced Background Check
Sitter Profile Image: Mary S.
Verified Enhanced Background Check

19. Mary S.

Walk and Wag
Chatham, MA, 02631
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
17 reviews
5 repeat clients
from
$40
per night

Mary was wonderful with our senior Aussie/Doodle. She was easy to coordinate and communicate with during Bogart’s 3 week stay. We will definitely use Mary again. And again. Thank you so much!

Sitter Profile Image: Courtney D.
Verified Enhanced Background Check
Sitter Profile Image: Courtney D.
Verified Enhanced Background Check

20. Courtney D.

Active, loving, and reliable!
Chatham, MA, 02659
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
from
$65
per night

About: Hi! I’m Courtney and an ultimate dog lover. I’ve had my own pup Taco for 7 years, and several family dogs since before I can remember. Taco and I are always at the beach or taking long walks in the woods and we love having our friends dogs over for sleepovers when their parents go away! I work at a local elementary school, so I’d be able to walk your pup before school and again when I’m home at 2 ish. I’m available for boarding on weekends, and weekdays after 2! I have a fenced in back yard and as mentioned, Taco, to keep your dog company while I’m working. Otherwise, they’ll always be with me! I have experience with dogs of all ages- I’ve fostered puppies while they wait for their forever homes and I’ve loved elder dogs as well! I’m happy to follow any routine your pup is used to and can set up a crate if need be. Otherwise your dog can have free range of the house, couches and beds included!

Search Map

Chatham House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Chatham are rated on average 4.9 out of 5 stars based on 30 reviews.

Rover also offers House Sitting in:

Rover also offers other services in Chatham:


Rover.com is the simple, savvy way to find and book Chatham house sitting. It's easy to find the perfect house sitter — many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Chatham on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Chatham house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

House Sitting