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Jessica & Toby S.

Star Sitter

Billings, MT

5.0 out of 5 stars
32 reviews
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Services

Jessica & Toby can host

0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
Spayed and neutered dogs only
No females in heat
Takes only 1 client at a time

Availability

One of us works from home and one of us is self employed. Both have flexible schedules and more than enough house and yard to share!

Available
Not available
SMTWTFS
Boarding Cancellation Policy:

About Jessica & Toby S.

Communication

11 repeat pet parents
100% response rate
Usually responds in a few minutes
100% bookings with photo updates

Skills

12 years of experience
Oral medication administration
Senior dog experience
Special needs dog experience
Can provide daily exercise

Safety, trust & environment

We have 2 chihuahuas and a Saint Bernard and they have free reign over our home. We live on an acre out towards Briarwood that is completely fenced (5ft in most areas, a slight slope of 4 ft in a small portion). Our dogs are great for socializing those that stay with us and we love having the extra company! There are a lot of deer and turkeys in our area that may trigger those "escape artists" so please take that into consideration. We want what's best for you, us, and all of the pups!

Home

Lives in a house
Has a fenced yard
Non-smoking household
Has 2 dogs
No children present
Dogs not allowed on bed
Dogs allowed on furniture
Potty breaks every 0-2 hours

Information Jessica & Toby S. would like to know about your pet

Our dogs are very friendly and that sometimes comes across as a bit invasive to other dogs at first. It's very important that our visitor pups be semi socialized for general interactions during their stay. We cannot accept aggressive breeds. Meet and greets in advance are available.

A typical day

Whether a dog would rather run around the yard, bark with the neighbors dogs through our fence, or lounge around the house, we're here for it!

Location

Billings, MT

Jessica & Toby S.'s Neighborhood

Pets

Jessica & Toby S. have Star Sitter status

The Star Sitter program highlights responsive sitters who deliver highly rated care and have a history of listing accurate availability and preferences, making it easier for pet parents to find the best care for their pets.

Dogs need vacations too!

Pet care experience

We have been fostering for local shelters for many years. The need for a safe place for adopted dogs brought us to extend our help to Rover.

Reviews

Karla H.
Boarding • Jul 19, 2026
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Harley had another great time with Toby and Jessica. Lots of play time and love.

Kelli G.
Boarding • May 23, 2026
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Thank you for the awesome care provided to Myla while we were away! She will be back to see you soon!

Karla H.
Boarding • May 07, 2026
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Harley had so much fun with Toby and Jessica. They gave him great care and affection. Shared videos and pictures daily. He had a blast which made our time away from him without worry.

Kelli G.
Boarding • Mar 11, 2026
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Thank you so much for taking great care of Myla! You are the perfect puppy sitters! See you next time!

About Jessica & Toby S.

Communication

11 repeat pet parents
100% response rate
Usually responds in a few minutes
100% bookings with photo updates

Skills

12 years of experience
Oral medication administration
Senior dog experience
Special needs dog experience
Can provide daily exercise

Safety, trust & environment

We have 2 chihuahuas and a Saint Bernard and they have free reign over our home. We live on an acre out towards Briarwood that is completely fenced (5ft in most areas, a slight slope of 4 ft in a small portion). Our dogs are great for socializing those that stay with us and we love having the extra company! There are a lot of deer and turkeys in our area that may trigger those "escape artists" so please take that into consideration. We want what's best for you, us, and all of the pups!

Home

Lives in a house
Has a fenced yard
Non-smoking household
Has 2 dogs
No children present
Dogs not allowed on bed
Dogs allowed on furniture
Potty breaks every 0-2 hours

Information Jessica & Toby S. would like to know about your pet

Our dogs are very friendly and that sometimes comes across as a bit invasive to other dogs at first. It's very important that our visitor pups be semi socialized for general interactions during their stay. We cannot accept aggressive breeds. Meet and greets in advance are available.

A typical day

Whether a dog would rather run around the yard, bark with the neighbors dogs through our fence, or lounge around the house, we're here for it!

Each sitter joining Rover needs to pass a background check. And by booking on Rover, you can get photo & message updates, 24/7 support, and reimbursement for eligible vet care.
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Verified Enhanced Background Check
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Jessica & Toby S.

Star Sitter

Billings, MT

5.0 out of 5 stars
32 reviews