House Sitting Wooster Square

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Over 33
pet parents in Wooster Square have booked house sitting

Wooster Square, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Mads H.
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Mads H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
5 years of experience
Downtown, New Haven, CT, 06511

Mads is conscientious, dependable, friendly and the dog is always happy to see her.

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Gian-Carl C.
Sitter Profile Image: Liam H.
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Liam H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
7 years of experience
Hamden, CT, 06517

Liam had been SO GREAT with my strong, crazy dog! he's super reliable, very communicative with us, and very capable and calm with Luna. He's also done a great job staying in our home. Very grateful!!!

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Sarah M.
Sitter Profile Image: Kayla P.
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Kayla P.
from
$50
per night
8 years of experience
Wooster Square, New Haven, CT, 06511

About: I am an experienced pet sitter who has cared after both cats and dogs over the last 8 years. Through either personal favors for loved ones in my life or paid opportunities, I give all animals the time, energy and attention they thrive off of (which sometimes can be a less-is-more situation)! I will strive to make it a stress-free experience for both you and your little one! I do request that we have a Meet & Greet before finalizing bookings to ensure your I can get all relevant information and learn about the pet I'll be looking after. If I seem like a good fit we can get a booking finalized, I will be consistent with messages and updates for you, as well as enrichment and care for the furry friend! For the time being, my schedule is largely open after September 9th. Let me know what your ideal pet sitting situation looks like and I can likely accommodate. I am happy to follow the rules and routines you have set for your pets. I don't have any of my own and would prefer to keep animals at their place of residence for their comfort. If I know an animal and they are comfortable with me, I would reconsider for future sittings after an initial experience.

Sitter Profile Image: Sai D.
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Sai D.
from
$40
per night
5.0 out of 5 stars
55 reviews
8 repeat clients
4 years of experience
New Haven, CT, 06511

Sai was great with Willie. She sent us great updates and photos and made it feel so much easier to leave him. She also left the house nice and clean which is such a bonus!

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Karlee B.
Sitter Profile Image: Victoria L.
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Victoria L.
from
$60
per night
5.0 out of 5 stars
8 reviews
1 repeat client
5 years of experience
New Haven, CT, 06511

Victoria was an incredible house sitter! She kept me updated on my dog’s well-being through constant communication and sent multiple photos and videos. I highly recommend her services and would definitely book her again.

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Jireh A.
Sitter Profile Image: Karime G.
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Karime G.
from
$45
per night
5.0 out of 5 stars
5 reviews
1 repeat client
14 years of experience
New Haven, CT, 06513

Karime was amazing! She accommodated a very last minute request and took great care of my girls while they were dealing with some serious allergies. She communicated consistently and promptly and also took note of when things seemed concerning. Great and caring sitter!

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Katy M.
Sitter Profile Image: Tiera W.
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Tiera W.
from
$50
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
18 years of experience
Dixwell, New Haven, CT, 06511

Tiera was great! She came early the first time to meet my dog, played with him while I had a doctor's appointment. She clearly has a love for animals.

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Andrew S.
Sitter Profile Image: Zhiyu W.
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Zhiyu W.
from
$32
per night
5.0 out of 5 stars
4 reviews
3 repeat clients
2 years of experience
Downtown, New Haven, CT, 06510

About: I’ve grown up in a home with dogs and have always been comfortable around them. I had a Labrador before, so I’m very familiar with daily care, routines, and spending time with dogs. I graduated from UC Davis with a degree in Animal Science in 2025 and also have some experience interning at a vet clinic, which helped me better understand animal health and behavior. Since summer 2024, I’ve been helping friends with dog sitting, walking, and boarding. I’ve done three long-term stays (over a month each), so I’m comfortable caring for dogs for extended periods and helping them settle in. I’m responsible, patient, and happy to send updates and photos while you’re away! I’m currently a student, but I have good availability in the mornings before 8am and in the evenings after 5pm, so I’m able to do walks and spend quality time with your dog during those hours. I’m also flexible on weekends and can adjust based on your pet’s routine. I’m happy to follow their usual schedule to make sure they feel comfortable and well cared for. I live in an apartment right now, but I make sure pets have a clean, safe, and comfortable space. I take dogs out for regular walks and make sure they get enough exercise, attention, and care throughout the day. I pay close attention to their behavior and always follow the owner’s instructions carefully, including feeding, routines, and any special needs. I’m also happy to send regular updates and photos so you can feel at ease.

Sitter Profile Image: pauline g.
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pauline g.
from
$100
per night
5.0 out of 5 stars
119 reviews
26 repeat clients
20 years of experience
East Rock, New Haven, CT, 06511

Pauline is so phenomenal with my dogs. She sent me multiple photos and videos, which I absolutely love. She is patient and caring with them. She is also very responsive and attentive to detail. This is my second time using her for dog sitting and I hope to be able to use her again for dog sitting needs.

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Sarah F.
Sitter Profile Image: Kimberlee P.
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Kimberlee P.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
East Haven, CT, 06512

If I could give Kimberlee more than five stars, I would! From the moment we met her, it was clear she was incredibly conscientious, detail-oriented, and genuinely cared about giving Scooby the very best care. Our dog, Scooby, is anxious around other dogs and does much better staying in her own home with a trusted person. Kimberlee was absolutely perfect for her. She was accommodating, thoughtful, and went above and beyond in every way. She kept us updated with wonderful photos, and honestly, you could see in every single one how much Scooby adored her. As pet parents, that kind of peace of mind is priceless. Knowing she was not only safe but truly happy allowed us to completely relax and enjoy our time away. It takes a special person to earn the trust of an anxious dog, and Kimberlee did just that with patience, kindness, and genuine affection. We are beyond grateful that she was Scooby’s person while we were away. I cannot recommend Kimberlee highly enough, and we will absolutely be booking her again. Thank you, Kimberlee, for taking such incredible care of our girl!

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Heather B.
Sitter Profile Image: Arabelle Ilona V.
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Arabelle Ilona V.
Star Sitter
from
$65
per night
5.0 out of 5 stars
35 reviews
7 repeat clients
35 years of experience
Hamden, CT, 06517

Arabelle was a joy to work with! She was meticulous in her planning and knowing what needed to be done for Floki, plus making sure she had all emergency numbers and what to do in case of an emergency. She made sure Floki was was very well cared for while we were away and even brought him a new ball to play with! He was walked, fed on time and played with in our yard with frequent communications so that we could see all of the fun he was having. I would highly recommend Arabelle to anyone that needs overnight care or even daily check ins. She was just what we needed and expected for our fur family and will be using her again for future day trips and longer vacations!

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Krystine K.
Sitter Profile Image: Ellyana S.
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Ellyana S.
Star Sitter
from
$100
per night
5.0 out of 5 stars
67 reviews
11 repeat clients
5 years of experience
New Haven, CT, 06510

Ellyäna was a fantastic cat and house sitter! She was easy to communicate with, very respectful of our house, and clearly helped our two kitties feel comfortable while we were gone. I especially liked her voice memos with detailed updates about how everyone was doing. I would definitely recommend her services!

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Karla R.
Sitter Profile Image: Patty B.
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Patty B.
from
$78
per night
4.9 out of 5 stars
25 reviews
12 repeat clients
28 years of experience
New Haven, CT, 06511

Patty really cares about caring for animals. She was easy to schedule on short notice, made sure we met ahead of time to ensure that there was a good fit between her and Zola, and was accommodating throughout the visit. I appreciated all the photos and updates. Feels less stressful traveling when you know your four legged friend is in good hands. Thanks, Patty! Would reccomend.

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Khalil J.
Sitter Profile Image: Mai V.
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Mai V.
from
$50
per night
4.9 out of 5 stars
16 reviews
4 repeat clients
9 years of experience
Newhallville, New Haven, CT, 06511

Maverick was happy and well cared for. Mai did an excellent job caretaking for him. Maverick doesn’t warm up to new well and he liked her at first meet.

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Amber P.
Sitter Profile Image: Heather & Christopher R.
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Heather & Christopher R.
Star Sitter
from
$67
per night
5.0 out of 5 stars
84 reviews
29 repeat clients
44 years of experience
New Haven, CT, 06512

Heather is great I received pictures and updates periodically about how my pups were doing while I was away! I have a few dogs on meds and she handled those perfectly. It really gives me peace of mind to know they’re in great hands !

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Dienne H.
Sitter Profile Image: Christopher P.
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Christopher P.
from
$50
per night
5.0 out of 5 stars
10 reviews
8 repeat clients
14 years of experience
Dwight, New Haven, CT, 06511

When I had a night shift, Christopher came and took care of my dog, Honey, and did a spectacular job! He followed every direction/request without an issue, went above and beyond by offering to give Honey medication before he left, took photos promptly, and cuddled her when there was a bad thunderstorm, will book again!

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Carmen P.
Sitter Profile Image: Taresh D.
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Taresh D.
from
$34
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
6 years of experience
Edgewood, New Haven, CT, 06511

Taresh is kind and took great care of our beagle mix puppy. Would recommend and book again.

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Kristen M.
Sitter Profile Image: Sophia P.
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Sophia P.
from
$65
per night
5.0 out of 5 stars
25 reviews
7 repeat clients
16 years of experience
Prospect Hill, New Haven, CT, 06511

Sophia was great with our dogs! One of our pups had some tummy troubles while we were away and she was especially a trooper for handling that for us! Would definitely recommend!

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Madelyn K.
Sitter Profile Image: Aubrey K.
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Aubrey K.
from
$75
per night
15 years of experience
East Rock, New Haven, CT, 06511

Aubrey took excellent care of our 2 dogs, I’d recommend her to any of my friends! She sent cute pictures and kept me up to date throughout the stay

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Margot F.
Sitter Profile Image: Gabriela B.
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Gabriela B.
Star Sitter
from
$76
per night
5.0 out of 5 stars
42 reviews
15 repeat clients
6 years of experience
Dwight, New Haven, CT, 06511

Geordie is a stubborn lovable Corgi who has never been left with a sitter before. Gabriela did wonderfully with him. Primarily, she has an air of responsibility about her and I felt safe to leave. I had been worried about it for weeks. No worries. Geordie was well cared for and I’m very grateful.

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Marjorie R.
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The median cost per night for house sitting in Wooster Square is $63

Pet parents share their Rover experiences - Wooster Square

1 / 1
5.0 out of 5 stars

Aubrey took excellent care of our 2 dogs, I’d recommend her to any of my friends! She sent cute pictures and kept me up to date throughout the stay

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Margot F.
House Sitting
5.0 out of 5 stars

Geordie is a stubborn lovable Corgi who has never been left with a sitter before. Gabriela did wonderfully with him. Primarily, she has an air of responsibility about her and I felt safe to leave. I had been worried about it for weeks. No worries. Geordie was well cared for and I’m very grateful.

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Marjorie R.
House Sitting
5.0 out of 5 stars

Liam had been SO GREAT with my strong, crazy dog! he's super reliable, very communicative with us, and very capable and calm with Luna. He's also done a great job staying in our home. Very grateful!!!

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Sarah M.
House Sitting
5.0 out of 5 stars

Our girls had a great time with Heather and Chris this past weekend! They were so thoughtful to all their little quirks including not wanting to go out in the rain and being very patient with them 💗 we really could not have asked for better!

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Laura H.
House Sitting
5.0 out of 5 stars

Very communicative & proactive. Our pup doesn’t always take to new people quickly, but she seemed to be comfortable with Karime right away—Karime had great animal lover energy and took great care of our dog & managed sometimes complex care instructions well (anxious pup, allergies, etc.)

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Henry W.
House Sitting
5.0 out of 5 stars

Sai did a great job taking care of my two cats. She was super responsive and the cats were clearly well taken care of. She even vacuumed up the litter that the cats kicked around and washed the towels/sheets.

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Ava S.
House Sitting
5.0 out of 5 stars

Jocelyn was great! From the moment she met our dog and cat you could tell she loved being around animals. She was good with communication. She spent 3 nights with our animals and sent pictures. Everything seemed to work out great!

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Robin P.
House Sitting
5.0 out of 5 stars

Excellent as usual! Pauline is one of our go-to sitters. We always come home to a clean house and happy pup.

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Mel P.
House Sitting
5.0 out of 5 stars

Katherine was above and beyond my wildest expectations! I had never left my kittens with a stranger before and was super nervous. She did a meet and greet, sent me regualr updates (and the cutest pics), and made sure my girls were the number one priority. My kittens definitely fell in love with her and her daughter over the course of the week. I can't imagine a better sitter!

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Maggie Z.
House Sitting
5.0 out of 5 stars

Jassmyne took care of our cat (Tati) for a fairly long stretch (2 weeks), and she was fantastic. She was very communicative throughout, sending lots of pictures and updates, and she handled it calmly when Tati came down with a small cold. She also took great care of our house while we were away. Tati clearly liked her. I strongly recommend Jassmyne!

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Andrea C.
House Sitting
5.0 out of 5 stars

Kaitlin was wonderful! Midnight really enjoyed her time with her and she took great care of the home! She was great with updates and would definitely book again!

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Daniel C.
House Sitting
5.0 out of 5 stars

Conor spent 24 hours at our home with our elderly dog overnight. We arrived home to a happy, calm pooch and our home was just as we left it. Conor was timely, respectful, communicated well and sent photos. He even left a note for when we got home. We appreciated meeting him prior to booking and will definitely use him again in the near future. Thanks Conor!

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Lisa B.
House Sitting
5.0 out of 5 stars

Brithny was an absolute gem taking care of my dog, and I can’t recommend her highly enough. From our very first meet and greet, she put me completely at ease, she even brought her own dog sana along to help the dogs get comfortable together, which showed just how thoughtful and prepared she is. You can tell right away that she has real experience with dogs and genuinely understands them. Throughout her time with my dog, Brithny went above and beyond. She took him on fun little adventures and made sure he was active, engaged, and well cared for the whole time. She was gentle with him, responsible about his routine, and clearly poured a lot of care into how she looked after him. On top of that, she sent frequent updates and photos, which meant so much to me while I was away, since I always knew exactly how he was doing. I felt so relieved knowing my dog was in such capable, caring hands. Brithny is exactly the kind of sitter every dog owner hopes to find, and I’ll absolutely be booking with her again. I recommend her without reservation.

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Eva S.
House Sitting
5.0 out of 5 stars

We love having Daniela watch our dog, Oakley. He loves hanging with her and she takes great care of him. It’s such a treat not to have to worry about him while we are gone.

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Christina C.
House Sitting
5.0 out of 5 stars

Ashley did a wonderful job caring for my dog and my home! She was very responsive and flexible. I would definitely book with her again!

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Savannah B.
House Sitting
5.0 out of 5 stars

Lauren did a great job with our boys. She communicated well, sent pictures and left our house spotless. We were very happy with Lauren and will use her again.

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Rita C.
House Sitting
5.0 out of 5 stars

Reine did an AMAZING job sitting for our dog and cat! Our pup is prone to separation anxiety and can often be nervous around new people, but she is clearly very experienced with this and helped make him at ease right away. She even gave us behavioral suggestions for how to help him with these things in the future. She gave us frequent updates and really went beyond what I expected to make sure the animals were well taken care of. I highly recommend her!

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Megan C.
House Sitting
5.0 out of 5 stars

I can’t say enough about how great Travis is. A human gem. Great with the dogs. Went over and above in every single way. I can’t wait to have him stay with our pets again.

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Deb J.
House Sitting
5.0 out of 5 stars

Easy to communicate with, flexible, and kind. He sent daily check-in and took excellent care of my dog. Kept my home tidy, and even offered to launder the sheets that he used while there without instruction. Would definitely recommend.

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Emma O.
House Sitting
5.0 out of 5 stars

Addie was fantastic! She communicated well and sent pictures. She stayed at my house but it was like she wasn't even there, she left it just like she found it. I definitely will be asking her to dog sit again!

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Kristyn N.
House Sitting
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