Pet Boarding in Headingley

Find a loving Headingley pet sitter to watch your cat or dog overnight at your sitter’s home.

End Date
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Headingley pet boarders

Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

1 / 1
Sitter Profile Image: Birch S.
Verified Background Check
Birch S.
$50
total per night
5.0 out of 5 stars
5 reviews
1 repeat client
18 years of experience
Stonewall, MB, R0C

It was a fantastic stay, with walks and photos. She also very thoughtfully made Sophie a bandana. Our dog would definitely enjoy staying again!

Profile image
Lindsay N.
Sitter Profile Image: Ranchelle O.
Verified Background Check
Ranchelle O.
$50
total per night
4.9 out of 5 stars
70 reviews
26 repeat clients
29 years of experience
Winnipeg, MB, R2R

Our corgi seemed to have had a great time. Ranchelle was a great communicator, was accommodating to our schedule and appreciated all the videos and pics sent.

Profile image
Julie H.
Sitter Profile Image: Oleksandr & Liudmila T.
Verified Enhanced Background Check
Oleksandr & Liudmila T.
$56
total per night
5.0 out of 5 stars
19 reviews
4 repeat clients
15 years of experience
Winnipeg, MB, R3R

Thanks for being such an amazing dog-sitter! I'm sure my pup had a tail-wagging good time with you, and I appreciate your dedication to his well-being. Cj says 5 paws for being his best friend for the week!

Profile image
Jessica C.
Sitter Profile Image: Jaspreet & Carlos K.
Verified Enhanced Background Check
Jaspreet & Carlos K.
$45
total per night
4.4 out of 5 stars
7 reviews
3 repeat clients
3 years of experience
Winnipeg, MB, R3C

Very good with Communication, always quick updates and responses!

Profile image
Justice A.
Sitter Profile Image: Vladliena M.
Verified Background Check
Vladliena M.
$45
total per night
5.0 out of 5 stars
1 review
1 repeat client
12 years of experience
Winnipeg, MB, R3R

Jojo Spent 2 nights with Vlad, she took such great care of my Jojo, made him feel welcome and gave him so much love while I was away. Will definitely board Jojo with Vlad again

Profile image
Mercedes H.
Sitter Profile Image: Pamela H.
Verified Background Check
Pamela H.
Star Sitter
$45
total per night
4.9 out of 5 stars
46 reviews
14 repeat clients
14 years of experience
Winnipeg, MB, R2H

Thanks so much again Pam for taking care of Lambros during our vacay. Even buying him boots so you could walk him and also using your baby boy's diaper when Lambros diaper was all consumed. Thank you for all the love for Lambros! We really appreciate it!

Profile image
Annabelle R.
Sitter Profile Image: Ariana R.
Verified Background Check
Ariana R.
Star Sitter
$45
total per night
5.0 out of 5 stars
36 reviews
11 repeat clients
5 years of experience
Winnipeg, MB, R3T

She was fantastic with our dog Milo. He stayed a week with her and was very easy going for drop off and pick up. She was gentle with him let him sleep with her and her own dog. Milo also seemed to get along with her dog. I would recommend her to anyone who is looking for a dog sitter.

Profile image
Weena P.
Sitter Profile Image: Sunisha M.
Verified Background Check
Sunisha M.
$56
total per night
5.0 out of 5 stars
19 reviews
3 repeat clients
10 years of experience
Winnipeg, MB, R3Y

Sunisha took great care of my puppy! He is very energetic and can be nervous around new people but she handled him perfectly. She gave regular updates and had great communication.

Profile image
Alexandria W.
Sitter Profile Image: Polina B.
Verified Enhanced Background Check
Polina B.
Star Sitter
$50
total per night
5.0 out of 5 stars
49 reviews
18 repeat clients
12 years of experience
Winnipeg, MB, R3C

Polina was wonderful! Gary really enjoyed his time with her, and I loved the pics and texts she sent every day. He was obviously very well taken care of in our absence. We will definitely be using her again in the future.

Profile image
Jackie C.
Sitter Profile Image: Paul S.
Verified Background Check
Paul S.
$56
total per night
5.0 out of 5 stars
10 reviews
1 repeat client
20 years of experience
Winnipeg, MB, R2M

Zeus had a great time with Paul. I received updates throughout each day. Zeus can be pretty shy and unsure at first, but seemed like he got comfortable right away. Will definitely be rebooking.

Profile image
Carina H.
Sitter Profile Image: Karen R.
Verified Background Check
Karen R.
Star Sitter
$23
total per night
5.0 out of 5 stars
45 reviews
14 repeat clients
8 years of experience
Winnipeg, MB, R3J

We couldn’t be happier with Shirley’s stay at Karen’s! From the start, Karen showed genuine care for our cat. She provided regular updates and photos, which reassured us that Shirley was having a great time. Karen was attentive to Shirley’s needs and when we picked her up, she was relaxed and content. We highly recommend Karen as a sitter and will definitely be using her services again.

Profile image
Jhunell d.
Sitter Profile Image: Amanda H.
Verified Background Check
Amanda H.
$45
total per night
5.0 out of 5 stars
6 reviews
10 years of experience
Winnipeg, MB, R3T

About: Providing a loving place to stay for your pup while you’re away. Experienced pet loving family happy to provide a fun and cozy home away from home. My name is Amanda, I work from home full time and a mom of two animal loving daughters. Our pup Duke is a 2 year old Cavapoo, very submissive and loves to cuddle and play. We love to play fetch and chase in our fully fenced in backyard, go for walks to the park and hang out at home. A great environment for dogs like Duke who do not like being alone! Positive reinforcement, exercise and play have been key for us as pet parents to train and raise our pups. We provide a fully fenced in and secure back yard, strictly on leash in the front and for walks, and a clean homey environment inside. Our dogs have always been treated as family and that includes those we care for while their families are away.

Sitter Profile Image: Anghelly A.
Verified Background Check
Anghelly A.
Star Sitter
$39
total per night
5.0 out of 5 stars
9 reviews
4 repeat clients
25 years of experience
Winnipeg, MB, R3T

Aspen and Ember had a great stay! Anghelly kept me updated with pictures, throughout! I can tell her and her daughter gave them lots and love and cuddles during their visit!

Profile image
Kerstie K.
Sitter Profile Image: Taina D.
Verified Background Check
Taina D.
$28
total per night
5.0 out of 5 stars
3 reviews
2 years of experience
Winnipeg, MB, R2Y

This was our first time using a pet sitter and the experience was awesome. Taina was great! Loved the check ins and picture updates. Will definitely be a repeat customer.

Profile image
T R.
Sitter Profile Image: Erin L.
Erin L.
Star Sitter
$76
total per night
5.0 out of 5 stars
10 reviews
4 repeat clients
25 years of experience
Winnipeg, MB, R3T

Erin was amazing. She provided lots of updates and made sure to communicate with me or ask questions if needed. She provided lots of exercise and mental stimulation as well. Was super accommodating, polite and just overall a pleasure. My pup had a great time and I would 100% book her again.

Profile image
Jennifer E.
Sitter Profile Image: Tanya G.
Verified Background Check
Tanya G.
$47
total per night
5.0 out of 5 stars
2 reviews
15 years of experience
Winnipeg, MB, R3N

Tanya communicated very promptly both pre-booking and during. She sent photos and updates throughout the week which were much appreciated. Would recommend!

Profile image
Karen C.
Sitter Profile Image: Titiksha T.
Verified Enhanced Background Check
Titiksha T.
Star Sitter
$28
total per night
5.0 out of 5 stars
72 reviews
22 repeat clients
10 years of experience
Winnipeg, MB, R3C

Awesome sitter! I had to drop off my kitten a little earlier than the drop off time and she was incredibly accommodating. Communication was great and I’ll definitely be using her again

Profile image
Gabby-Lisa
Sitter Profile Image: Omar R.
Verified Background Check
Omar R.
$45
total per night
5.0 out of 5 stars
6 reviews
11 years of experience
La Salle, MB, R0G

Omar was amazing! Took great care of Choco and sent pictures and videos of him enjoying his time with Omar. Thank you vert much Omar for everything!

Profile image
Perla G.
Sitter Profile Image: Lin L.
Verified Background Check
Lin L.
$45
total per night
5.0 out of 5 stars
12 reviews
1 repeat client
17 years of experience
St.Germain South, MB, R5A

Lin was very nice and patient, gave us updates about Luka with photos and videos everyday. She lives in a farm, which is a very nice place for pets to play. I strongly recommend Lin if you need a reliable sitter.

Profile image
Echo Y.
Sitter Profile Image: Karina & Lucas E.
Verified Enhanced Background Check
Karina & Lucas E.
Star Sitter
$54
total per night
4.9 out of 5 stars
162 reviews
61 repeat clients
15 years of experience
Winnipeg, MB, R2N

Karina & Lucas were amazing!!! They accepted Leo last minute and truly treated him like their own. I got frequent updates with photos, which really helped me feel at ease while I was away. Leo looked happy, relaxed, and comfortable the entire time. He also got plenty of walks and attention, which he loves. I was able to enjoy my trip with complete peace of mind, and I will definitely be coming back again!!!

Profile image
Linoy K.
1 / 1
View more sitters

Over 108
pet parents in Headingley have booked pet boarding

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your 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!

The median cost per night for pet boarding in Headingley is $45

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 pet boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.

  • World-class support

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

Sitters in Headingley average 6
repeat pet boarding clients

Pet Boarding FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for pet boarding in Headingley on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

As of Jun 2026, 209 sitters provided pet boarding in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, pet boarding sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 97% of Headingley pet boarding sitters respond in under an hour.

Pet boarding sitters with repeat customers have an average of 6 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Headingley.

Rover makes it easy to find Headingley pet boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet boarding is great for:

  • Dogs and cats of all ages and abilities, including puppies and kittens
  • Pet parents looking for a safe, loving alternative to a kennel or hotel
  • Pets who’d love to socialize with their sitter’s pets

There are 209 pet boarding sitters in Headingley on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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.