House Sitting In Westchester Gardens

Find a loving house sitter to watch over your pets and your home.

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Top rated Westchester Gardens house sitters

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

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Sitter Profile Image: Emma R.
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Emma R.
from
$30
per night
5.0 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Sun Prairie, WI, 53590

Emma was communicative, kind, and took great care of our dogs while we were away!

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Valerie W.
Sitter Profile Image: Renee L.
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Renee L.
from
$40
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Sun Prairie, WI, 53590

Renee was ABSOLUTELY AMAZING! So accommodating, GREAT communication and just a really great person to work with. You know your dog is getting 100% attention and love when you come home and they're completely worn out. At an energetic year old, Asha NEVER gets worn out from playing...that is until she met her match in Renee! This was out first time using Rover and it was last minute and I had my concerns just because we had to trust this person in our home for the first time without ever meeting her. Every concern was gone as soon as I met Renee! I can't recommend her highly enough! She's amazing!!!

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Theresa F.
Sitter Profile Image: Cassandra B.
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Cassandra B.
Star Sitter
from
$35
per night
5.0 out of 5 stars
38 reviews
11 repeat clients
15 years of experience
Madison, WI, 53704

Cassie was wonderful! We had no worries, as we were gone for 11 days. She stayed at our home, so it didn’t stress out our dog, Zoe. Cassie was very proactive with asking detailed questions about her and just genuinely concerned about all her needs. She even suggested coming over for some visits prior to our vacation, so Zoe could get use to her. Highly recommend!!?

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Tammy B.
Sitter Profile Image: Karina M.
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Karina M.
from
$45
per night
5.0 out of 5 stars
26 reviews
6 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

Karina always shows such care for my pets. My dog and cat both have health issues that require multiple medicines and supplements. She always follows their routine closely, asks questions to make sure she’s providing good care, takes my dog on daily walks, and sends daily pictures. I also come home to a clean house. I will not hesitate to request pet/house sitting from Karina again and I highly recommend her!

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Hailey L.
Sitter Profile Image: Isaac T.
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Isaac T.
Star Sitter
from
$45
per night
4.9 out of 5 stars
19 reviews
7 repeat clients
5 years of experience
Cottage Grove, WI, 53527

Isaac was amazing with our pups, they really enjoyed having him take care of them! He’s been great at communicating and very polite and thoughtful.

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Lucas M.
Sitter Profile Image: Mary M.
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Mary M.
from
$45
per night
5.0 out of 5 stars
62 reviews
13 repeat clients
6 years of experience
Madison, WI, 53718

Mary is a very responsible sitter. She had great communication and left me very detailed notes of Gracie’s schedule while I was away to let me know that Gracie was very well taken care of. I would highly recommend Mary.

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Isaac W.
Sitter Profile Image: Sylvia L.
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Sylvia L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
9 years of experience
Ridgewood, Madison, WI, 53704

Sylvia did an amazing job! Everything went smoothly and she was flexible with care given the extremely cold weather. We highly recommend and will definitely be a repeat customer.

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Jill M.
Sitter Profile Image: Tina B.
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Tina B.
Star Sitter
from
$35
per night
4.9 out of 5 stars
76 reviews
22 repeat clients
38 years of experience
Windsor, WI, 53598

This was my first time using Rover, and I appreciated Tina walking me through the process. I appreciated her daily updates, clear communication, and my house was as I'd left it.

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Heather E.
Sitter Profile Image: Tatyana K.
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Tatyana K.
Star Sitter
from
$55
per night
4.9 out of 5 stars
72 reviews
23 repeat clients
4 years of experience
Fitchburg, WI, 53713

Tatyana did a great job with our three dogs who range in size from a 90 lb German shepherd down to a 25 lb mutt. She sent pictures and videos, and with it being the first time she watched our dogs, it made me feel 100x more comfortable. We also had one dog who needed to take medication that she ensured was administered.

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Paige S.
Sitter Profile Image: Jennifer H.
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Jennifer H.
from
$35
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
11 years of experience
Sun Prairie, WI, 53590

Our little dog was sooo happy with Jennifer. I would give 10 stars if I could. She maintain great communication, was flexible, and tended to our little fur guy like it was her own pet. She was truthworthy to stay in our home for 2.5 days and very reliable. We will always try to book again with Jennifer!

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Linda A.
Sitter Profile Image: Maureen H.
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Maureen H.
Star Sitter
from
$65
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
20 years of experience
Madison, WI, 53705

Maureen did a fantastic job taking care of our dog. She was reliable, friendly, clean, and responsive to all our messages. She even sent us photo updates reassuring us that all was going well. We will definitely ask for her help in the future!

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Nicole H.
Sitter Profile Image: Jesse T.
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Jesse T.
Star Sitter
from
$28
per night
5.0 out of 5 stars
19 reviews
10 repeat clients
1 year of experience
Madison, WI, 53719

Once again, Jesse is incredible with our pets. She cares for them just like we would, and I couldn’t leave them with anything less than that level of love and care. Thank you Jesse for being awesome!

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Seb A.
Sitter Profile Image: Ruby K.
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Ruby K.
from
$60
per night
4.9 out of 5 stars
18 reviews
3 repeat clients
6 years of experience
Madison, WI, 53704

Ruby was great! We got back a tired, happy pup and a house as clean as we left it. We’ll definitely hire her again when we need a house sitter.

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Scott K.
Sitter Profile Image: Nicole W.
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Nicole W.
from
$35
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
5 years of experience
Madison, WI, 53705

We (and our dogs) loved having Nicole sit for us. She is an excellent communicator and took care of our pups like they were her own. I’d absolutely have her stay with our dogs again—and based on their lukewarm reaction to us coming home, I think they’d like to see her again too. 🤣

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Kim B.
Sitter Profile Image: Ashley H.
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Ashley H.
Star Sitter
from
$60
per night
4.9 out of 5 stars
18 reviews
3 repeat clients
7 years of experience
Madison, WI, 53716

Ashley was wonderful - came all the way to us for a meet and greet and gave good vibes right away. Before our event, she came on time and provided updates and we felt very reassured. Our pup also loved her right away. Would recommend!

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Rachel M.
Sitter Profile Image: Julia M.
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Julia M.
from
$50
per night
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
University Apartments, Madison, WI, 53705

Julia was so pleasant and professional! She asked great questions to prepare for her time with Princeton, and you could tell she really cared - Princeton warmed up to her immediately :) I highly recommend Julia and would definitely hire her again!

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Aisha B.
Sitter Profile Image: Robert L.
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Robert L.
Star Sitter
from
$44
per night
5.0 out of 5 stars
269 reviews
52 repeat clients
40 years of experience
Capitol, Madison, WI, 53703

Robert housesat with our 2 dogs and was fantastic with the pups and as a houseguest. He worked so well with our pups and their personalities. Robert's communication is very helpful and reassuring. I was "at peace" during our entire trip away because he sent regular updates and stayed in touch during our travel days. Robert is very professional, communicative, and so good with animals. You can tell he really does this for the joy he gets taking care of your pets. You will not be sorry if you book Robert!

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Kathryn (Kate) H.
Sitter Profile Image: Ayomi O.
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Ayomi O.
from
$40
per night
2 years of experience
Madison, WI, 53704

About: Hi! I’m Ayomi, and caring for animals has always been a natural part of who I am. I’ve had the joy of working with dogs of all ages and personalities from energetic puppies still learning the world to older dogs who move a little slower and need some extra love. I approach pet care the same way I would care for my own patient, present, and with a whole lot of heart. I take the time to learn each dog’s unique needs and routines because I know how important it is for pets to feel safe and comfortable while their people are away. Whether your dog needs long walks, gentle play, quiet companionship, or help with medication or anxiety, I’m here to meet them where they are and give them the attention they deserve. I truly love building trust with both pets and their humans. You can expect regular updates, happy photos, and the reassurance that your pup is in loving, capable hands. Every visit is a chance to create a little joy and comfort for your furry friendcand that’s a responsibility I take seriously and gratefully. Pet care fits naturally into my routine because I often work from home in my downtown Madison apartment. I love taking long walks around town or heading to Picnic Point for a quiet hike, so having a pup along for the journey just makes it that much better. I usually walk about a mile or two a day, but I’m happy to adjust based on your furry friend’s energy level and needs. My schedule is flexible, and with at least a week's notice, I can make sure I’m fully available to give your dog the time and attention they deserve. I’ve always loved traveling, so pet sitting is a fun and fulfilling way for me to enjoy the company of dogs while I’m still settling down. Whether it’s a weekend stay or daily walks, I’m excited to share my time! Creating a safe and comforting environment is my top priority, whether I’m caring for your pet in my home or yours. I treat every dog like family—with patience, attentiveness, and a whole lot of love. In my downtown apartment, pets are kept in a clean, calm space free of hazards, with plenty of room to stretch, nap, or play. I don’t have any other pets, so your dog will get my full attention and care without distractions. When I’m in your home, I’m always respectful of your space and routines, making sure your dog stays comfortable in their familiar surroundings. I follow all care instructions closely and provide regular updates so you know exactly how your pup is doing. I believe trust is built through consistency, communication, and genuine care and that’s what I bring to every visit. Whether it’s daily walks, overnight stays, or just keeping your pup company, I’m committed to making sure your dog feels safe, loved, and right at home.

Sitter Profile Image: Christina K.
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Christina K.
from
$22
per night
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Marquette, Madison, WI, 53704

About: Experienced house and pet sitter with eight 5-star references out of 9 sits I booked through Trusted Housesitters in 2025-26 (link below). I have had cats my whole adult life and fell in love with dogs while spending time with my siblings' dogs. I am now a fully converted dog lover who hopes to get my face licked by every passing puppy. Down-to-earth Midwest woman with lots of common sense. I was a homeowner for almost 25 years. I am not one of those people who looks at my phone constantly so your pet will get my attention, not just my presence. On long walks I may listen to a book on tape or podcast with only one ear bud so I am always situationally aware. No substance use or bad habits other than knitting and chocolate. I am in the process of getting direct testimonials but below are reviews copied from THS website (copy and paste link to view these live on the site.) ........?promo=RAF908909&utm_campaign=house-and-pet-sitters&utm_medium=house-and-pet-sitters&utm_source=copy Carol, Wheat Ridge, CO · 18 Jan - 02 Feb 2026 Christina was wonderful with Zappa. She sent daily photos and texts. She tried everything to get him to play, moved his “step” to her bed so he could sleep with her and spent most of her time with him. She left the house spotless and even lef5 a pot of homemade soup for us. Would highly recommend. Melanie, Verona, WI · 07 Jan - 16 Jan 2026 Christina was truly wonderful!! She gave so much love to each of my four babies, and they absolutely adored her company. She took my doggos for walks and sent me videos, they were so happy and excited! My two cats were super in love with her too and slept and cuddled with her. She was very organized, communicative, self-sufficient, and left my house in impeccable shape. She has a great sense of humor too! :) Thanks a million again Christina for your super precious help and for all the love you gave to my dearest precious fur babies. Hope we meet soon again! Melanie Verona, WI · 31 Dec 2025 - 01 Jan 2026 Christina is an amazing pet sitter! She is very thoughtful about pet care and clearly LOVES animals. She took super great care of my cats who immediately felt at ease with her and slept with her, even if one of my two cats is pretty shy. She was attentionate, loving with them and left my house in a great shape! She also sent me pictures which I greatly appreciated. Thanks a million again Christina for you super precious help! Melanie Annabel, Denver, CO · 26 Nov - 03 Dec 2025 Christina was great- Nelly was obviously very content when I got home and basically ignored me for the first day- always a good sign! She was very self sufficient and I didn’t worry at all while I was gone. I would definitely recommend her for future sitters! Emily Boulder, CO · 20 Nov - 26 Nov 202 We are so grateful for the care Christina provided to our dog, cat, and home. She went out of her way to meet with us in person before the sit which gave us peace of mind. Our shy cat warmed up instantly to her (thanks to the gifts Christina brought her) and we appreciated the pictures and videos she sent us. The dog got lots of walks and was well cared for. She was thoughtful and careful with our home and was willing to adjust her schedule at the last minute during the final day of her sit. She was communicative throughout. We’d welcome Christina back any time. Elaine, Dallas, TX · 30 Aug - 08 Oct 2025 It was a pleasure to have Christina at my house in Dallas for 5 weeks. She was organized before and during the sit and responded promptly to communication. The true sign of a good sitter is when my cat ignores me when I get home, and Duffy was pretty indifferent to my return! I know that he got lots of attention from Christina. She sent photos of him, and even bought him some new toys, which was very thoughtful. She also watered my 9tiny) yard, which i appreciated during an unusually hot September-october. Suzanne, Evergreen, CO · 12 Aug - 19 Aug 2025 Christina was wonderful. She checked in and was very responsible with the dogs. She was also very flexible!! James, Madison, WI · 18 Jun - 14 Jul 2025 Christina was amazing from the initial contact, right the way through to the visit. Christina was fantastic in both her communication, cleanliness respectfulness of the house, and (most importantly) looking after our 3 cats. In speaking with her prior to the visit and her care during the housesit, as well as all the pictures and videos we received while we were away, Christina was the perfect person to take care of our fur babies. I am available for day-time visits, or overnight care. Digital nomad so I am around a lot during the day, with a flexible schedule so I can meet your pet's needs first. I will keep tabs on them, put reminders for scheduled events on my phone, and check in with them frequently outside of scheduled care, and will contact the pet owner with any and all questions. I'm good at reading their cues, love to snuggle and play, I'm happy to have them sleep with me if they prefer. I'm strict about following owner's rules and instructions. I prefer to learn a little bit about your pet's personality, quirks, likes and dislikes to provide better care--and so I can tell quickly if something is a bit off. I will communicate with you as much or little as you like, happy to send pictures. I like to be able to ask questions to make sure that I understand your pet and its needs as well as your house and its needs.

Sitter Profile Image: Della H.
Verified Enhanced Background Check
Della H.
from
$40
per night
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
Windsor, WI, 53598

Della was wonderful with our dog Lacy.

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Steve M.
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Westchester Gardens pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Ayomi was a wonderful sitter! Received updates on my puppy every day. Ayomi was also incredibly flexible when flight plans went awry. Would book with Ayomi again!

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Isabel V.
House Sitting
5.0 out of 5 stars

Baylee was amazing with our pets. She was very communicative with us when we were out of town and our pets loved her!

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Alyssa G.
House Sitting
5.0 out of 5 stars

Alicia stayed with our dog Hazel for a long weekend and we will definitely book her again! Hazel sometimes struggles to warm up to new people but she loved Alicia immediately during our meet & greet. Alicia asked lots of good questions to make sure she was prepared to care for Hazel, and she sent us photos every day.

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Elise & Kyle
House Sitting
5.0 out of 5 stars

Nia and Lauren were so wonderful to our pups!!! It was great to have such peace of mind during our trip knowing these two were caring for our dogs. We’ll definitely be rebooking in the future!

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Chantal M.
House Sitting
5.0 out of 5 stars

Sylvia was great. Our dog is people shy & Sylvia earned her trust quickly, she communicated with us daily which helped us have peace of mind while we were away. She respected our space. We are glad we found her.

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Hex H.
House Sitting
5.0 out of 5 stars

Josh really went above and beyond for our 2 dogs while house sitting. We felt relaxed and comfortable knowing they were well taken care of. Will definitely request his services again.

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Molly M.
House Sitting
5.0 out of 5 stars

Lizzie was a great in-home option for us while we were away for a few nights. I wasn’t concerned about our dogs while we were away and appreciated coming home to happy dogs! Thanks, Lizzie!

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Ellyssa E.
House Sitting
5.0 out of 5 stars

Sabrina is amazing! Contacted her on pretty short notice (ahead of a holiday weekend nonetheless!) and she was quick to respond and be available. Additionally, she came for a meet and greet and hung out long enough to really get to know Eddie. She was so so flexible, kind and caring and left my place looking perfect.

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Haley M.
House Sitting
5.0 out of 5 stars

We love it when Cassie stays with Leo. She’s great with him and it’s always reassuring that he’s in good hands while we’re gone.

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Matthew B.
House Sitting
5.0 out of 5 stars

Maricel was great with Oreo and kept me uptodate with walks and activities. She took great care of Oreo and he was a happy dog when I got home!!!

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John T.
House Sitting
5.0 out of 5 stars

I booked Jen to sit my senior dog who is very sweet but particular, and she did a fantastic job. Super clearly asking about his needs and his schedule so I could go on a family trip with no worries about my boy. Super timely and clear updates with fantastic pictures that made me feel immediately comforted. I’m looking forward to booking with Jen again when Peanut needs some extra care.

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Marian A.
House Sitting
5.0 out of 5 stars

Kristina was fantastic! Great communication leading up to and during the booking. We always appreciate knowing our pets are going to be truly CARED for, not just "watched" and Kristina did a great job. Will definitely book again if they're available!

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Joce G.
House Sitting
5.0 out of 5 stars

Anna is very communicative about how each visit went leaving detailed notes and sending great photos. My pups love her to bits! Planning on hiring her again in the future!

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Emily P.
House Sitting
5.0 out of 5 stars

Adeline watched our dog Ruby during an overnight visit in our house. She went above and beyond in communication by sending text and picture updates and we felt confident Ruby was very safe in her hands. We will definitely book Adeline again!

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Kayla A.
House Sitting
5.0 out of 5 stars

We couldn’t have asked for a better pet sitter! Kirsten watched our cat for 11 days, providing both drop-in visits and overnight care, and went truly above and beyond. She spent lots of time with him, played with him often, and kept us updated with frequent messages, pictures, and videos — which gave us so much peace of mind while we were away. Our cat looked completely comfortable and happy in her care, which says a lot! She was always quick to respond and so easy to communicate with. We would absolutely recommend her to anyone looking for a reliable and attentive pet sitter.

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Bliss G.
House Sitting
5.0 out of 5 stars

Katie was wonderful! She kept me updated and all of my pets were well taken care of. I appreciated it so much especially since it was a last minute booking. I will definitely be booking Katie again.

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April W.
House Sitting
5.0 out of 5 stars

Oliver did an excellent job taking care of our dog! Great communication while we were away and sent lots of cute pictures.

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Keelin M.
House Sitting
5.0 out of 5 stars

Scott really helped us out with a week of drop-in visits for our two dogs, one of which is rather unpleasant with strangers. He also agreed to oversee our coop of chickens which was very helpful. Scott was accomodating and generally a good communicator, and the pups seemed to like him. I think he did a fine job. We would definitely work with Scott again.

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Jessy P.
House Sitting
5.0 out of 5 stars

I couldn’t have asked for a better dog watcher! Jess was extremely responsive and communicative from the start, which gave me so much peace of mind while I was away. When I came home, not only were my dogs happy and well cared for, but my house was also clean and tidy—such a thoughtful touch. What really stood out was how much effort she put into getting to know my dogs. It was clear she genuinely cared about their personalities, routines, and comfort. She truly went above and beyond in every way. I would absolutely trust her again and highly recommend her to anyone looking for reliable, attentive pet care.

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Shana W.
House Sitting
5.0 out of 5 stars

I appreciated that Lora was communicative. Best sign of a good sitter ㅡmy kitties were happy when I returned.

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Michelle R.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

House Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Westchester Gardens house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Westchester Gardens.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Westchester Gardens house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.