Dog Sitting Ashland

Book a Ashland dog sitter to watch your dog in your sitter’s home or yours.

When are you returning?
Search

Over 98
pet parents in Ashland have booked dog sitting

Ashland, Find top rated dog sitting

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

1 / 1
Sitter Profile Image: Jill M.
Verified Enhanced Background Check
Jill M.
$28
total per visit
5.0 out of 5 stars
21 reviews
3 repeat clients
30 years of experience
Medway, MA, 02053

Jill is always reliable and caring with our two cats..she also leaves great pictures and updates from every visit which gives us a peace of mind when we are away.

Profile image
Jamet P.
Sitter Profile Image: Kerry S.
Verified Enhanced Background Check
Kerry S.
$26
total per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Milford, MA, 01757

We are so happy we booked with Kerry! It was wonderful getting to meet her during our meet and greet, and we felt comfortable leaving our Labrador Retriever, Enzo, in her care. My husband and I were away for two days, and Kerry provided drop-in visits that included walks, feeding, playtime in the backyard, fresh water, and lots of great company for Enzo while we were away. She was so attentive and responsive throughout our time away and kept us updated with plenty of photos and messages, which gave us so much peace of mind. We could tell Enzo was happy and well cared for, and we truly appreciated how thoughtful and reliable Kerry was. We would absolutely book with her again and highly recommend her to anyone looking for someone who will care for their pets like their own! 🐾❤️

Profile image
Briana P.
Sitter Profile Image: Jacqueline & Derrik W.
Verified Enhanced Background Check
Jacqueline & Derrik W.
Star Sitter
$42
total per visit
5.0 out of 5 stars
321 reviews
74 repeat clients
11 years of experience
MARLBOROUGH, MA, 01752

Jacqui was great with drop in visits! Very reliable and checked in with me in the beginning to make sure she was doing all the right things for my dog Charlie. Thank you Jacqui for taking such good care of Charlie while I was away.

Profile image
Sheyla C.
Sitter Profile Image: Rebecca N.
Verified Enhanced Background Check
Rebecca N.
$34
total per visit
5.0 out of 5 stars
23 reviews
6 repeat clients
15 years of experience
Ashland, MA, 01721

About: Hey There! I'm Becky. I'm a mother, small business owner, and life-long dog lover. For my entire life I've always had dogs, but a few years my sweet dog crossed the rainbow bridge to doggy heaven. When that happened, my children started asking for a new dog, but I wasn’t quite ready. As an alternative we started helping others with theirs. It’s become an incredible journey for our family, and brings us so much joy! We’re happy to have dogs here for boarding. I only take ONE dog at a time, unless there are multiple dogs coming from the same home that already live together. I have two children (11 & 15) who both love dogs as well. However, my son is nervous around bigger dogs and certain breeds. For this reason, a trial visit is required. Dog sitting has brought an unexpected amount of happiness into our home and family. We get very excited with each new furry friend that we get to love while you’re away. ​ I have a fenced yard and a cozy home. I allowed my dog on the furniture when I had him. I don’t have a crate. Whatever rules apply in your house are what we try to do here. Dogs can run free in my fenced yard or walk on a leash around my neighborhood and in the nearby nature trails. I run a small part-time preschool enrichment program out of my basement, in a separate area where dogs would not have access. During work hours I am generally able let dogs out as needed in a separate fenced area. ​ If you are interested in having your dog stay with us, please feel free to contact me. We would love to provide a safe, happy home away from home for your beloved pet while you're away. Your pet will be treated as if they were our pet. We try our best to make our routines look like yours, creating a safe, happy home away from home. I live in a cute neighborhood abutting conservation land. It is beautiful! We use an organic pest company to keep ticks out of our yard and I keep my home tidy.

Sitter Profile Image: Chelsea V.
Verified Enhanced Background Check
Chelsea V.
Star Sitter
$32
total per visit
5.0 out of 5 stars
165 reviews
67 repeat clients
30 years of experience
Marlborough, MA, 01752

Chelsea is wonderful. Very communicative, easy to make arrangements with and my cats love her. This is the second time I’ve used her and I’ll be using her again.

Profile image
Midori H.
Sitter Profile Image: Brianna P.
Verified Enhanced Background Check
Brianna P.
Star Sitter
$28
total per visit
5.0 out of 5 stars
52 reviews
23 repeat clients
20 years of experience
Milford, MA, 01757

Brianna was an awesome cat sitter! She sent photos and updates everyday. My cats love her. Even my very shy cat, who normally hides from everyone but me, came out to say hi to her!

Profile image
Diana L.
Sitter Profile Image: Nikkita L.
Verified Enhanced Background Check
Nikkita L.
Star Sitter
$25
total per visit
5.0 out of 5 stars
28 reviews
12 repeat clients
4 years of experience
Framingham, MA, 01702

Nikkita was communicative and easy to work with! She helped out with a last minute request and was attentive, which made our dog’s first Rover visits very easy and enjoyable. Would book again!

Profile image
Audrey A.
Sitter Profile Image: Carolyn F.
Verified Background Check
Carolyn F.
Star Sitter
$56
total per visit
4.9 out of 5 stars
90 reviews
32 repeat clients
40 years of experience
Sherborn, MA, 01770

Carolyn is the most caring, respectful, and attentive sitter! Carolyn has watched our pup multiple times now and he is always so well adjusted, happy, and doesn't miss a beat after being in her care! I will always prioritize booking Carolyn and try to schedule with her availability in mind, because she is just that good! Thank you, Carolyn!

Profile image
Abby R.
Sitter Profile Image: Nicole A.
Verified Enhanced Background Check
Nicole A.
Star Sitter
$28
total per visit
5.0 out of 5 stars
20 reviews
8 repeat clients
9 years of experience
Upton, MA, 01568

Nicole takes great care of my cat Millie. She’s great at communicating and sending both pictures and updates. She’s even gets on the floor to play with Millie and give her lots of cuddles. I Highly recommend Nicole!!

Profile image
Helene B.
Sitter Profile Image: Joyce & Chao G.
Verified Background Check
Joyce & Chao G.
$45
total per visit
5.0 out of 5 stars
33 reviews
11 repeat clients
10 years of experience
Framingham, MA, 01702

Joyce and Chao did a wonderful job to take care of my cat! They are very careful and considerate, and my cat loves to play with them. Thank you so much!

Profile image
YR D.
Sitter Profile Image: Brittany S.
Verified Enhanced Background Check
Brittany S.
$45
total per visit
5.0 out of 5 stars
5 reviews
1 repeat client
5 years of experience
Framingham, MA, 01702

About: I have hands-on experience caring for geriatric, diabetic, and epileptic dogs and cats, making me comfortable with special needs pets who require extra attention. I’m skilled at administering oral medications, giving insulin injections, and monitoring pets for any changes in their health or behavior. I also have plenty of experience walking dogs of all sizes—from tiny lap pups to large, energetic breeds—always focusing on their safety, comfort, and happiness. I currently work part-time as a Veterinary Assistant, which gives me hands-on experience with animal care and handling in a clinical setting. I’m also a student enrolled in an online Veterinary Technology program, so I’m always learning and expanding my knowledge about animal health and behavior. Because of my flexible schedule, I have availability on some weekdays and weekends for pet sitting, dog walking, and drop-in visits. This allows me to combine my passion for animals with my professional training while giving pets the love and attention they deserve when their families can’t be there. Whenever I’m in a home with pets, I make it a priority to tune into their needs, read their body language, and make sure they feel safe, comfortable, and happy. Every pet has their own personality—some love long walks and playtime, while others just want cuddles and belly rubs. If your pet is the snuggly type, I’m always happy to curl up with them and give all the love, scratches, and attention they need!

Sitter Profile Image: Rachel B.
Verified Enhanced Background Check
Rachel B.
$30
total per visit
5.0 out of 5 stars
15 reviews
7 repeat clients
20 years of experience
Holliston, MA, 01746

Rachel has been an awesome find! She is flexible and super communicative. We appreciate her attentiveness to our boy Moose and look forward to continuing to have her care for him!

Profile image
Kaitlin M.
Sitter Profile Image: Gianna V.
Verified Enhanced Background Check
Gianna V.
$50
total per visit
5.0 out of 5 stars
7 reviews
1 repeat client
3 years of experience
Framingham, MA, 01702

Gianna was super communicative and attentive, she did a great job taking care of our nervous puppy and making sure he had the best experience for his first Rover visit. She was also so thoughtful about small details, like cleaning his Kong toy and bringing in packages, which goes such a long way :) will book again!

Profile image
Audrey A.
Sitter Profile Image: Lana P.
Verified Enhanced Background Check
Lana P.
$19
total per visit
5.0 out of 5 stars
7 reviews
7 repeat clients
5 years of experience
Marlboro, MA, 01752

About: I've had pets since I was a little girl and even worked at a dog grooming salon for three years, which I loved. Over the past 3 summers, I’ve been on Rover and love my experience with animals and clients. I am still recovering from surgery, and we can discuss that when booking with me. I want to create a place where owners feel like they can reach out me and trust me when needed Hello, I’m currently a college student home for the summer. Back in April, I had hip replacement surgery. Over the past few weeks, I've been able to get back on my feet and move around a little more. I was looking to help any furry friends around the area that need to be fed or let outside. Unfortunately, I can't handle large, high-energy dogs. Please reach out, and we can discuss. If anyone needs help with small dogs or cats, I'm your girl. During drop-ins, I typically follow the owners' requests, which include feeding the animals, playing with them, spending time together, letting them outside, and refilling their water, etc.

Sitter Profile Image: Lauren D.
Verified Enhanced Background Check
Lauren D.
$34
total per visit
5.0 out of 5 stars
76 reviews
30 repeat clients
12 years of experience
Holliston, MA, 01746

Couldn’t have asked for a better sitter for my precious fur baby. Communication was excellent and the photos along with videos made me so relaxed knowing she was being so well taken care of. I can’t say enough good things.

Profile image
Melissa K.
Sitter Profile Image: Stella T.
Verified Enhanced Background Check
Stella T.
$84
total per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
4 years of experience
Framingham, MA, 01702

About: I absolutely love working with animals, especially dogs! I have just about 4 solid years of experience with all types of dogs from puppies to seniors, small and large, and have even fostered before as well. I also currently have 2 mini labradoodles whom I love very much! I am a recent college grad and am living at home currently working part time, so my schedule is very flexible on any time or day for any type of sitting, drop in visit, or walk! I live in my house with my 2 other mini labradoodles and family. We have a fenced and very spacious backyard and also access to some very nice walking paths not far from the house as well!

Sitter Profile Image: Bridget M.
Verified Enhanced Background Check
Bridget M.
$23
total per visit
4.9 out of 5 stars
15 reviews
7 repeat clients
10 years of experience
Milford, MA, 01757

She’s was great it’s been a excellent experience working with her

Profile image
joseph e.
Sitter Profile Image: Carley L.
Verified Background Check
Carley L.
Star Sitter
$50
total per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
10 years of experience
Riverside, North Smithfield, RI, 02896

Carley is awesome! I would definitely have her take care of my 2 dogs again! She is reliable, professional, friendly, thoughtful and resilient. Highly recommend!

Profile image
Diana D.
Sitter Profile Image: Hailey C.
Verified Enhanced Background Check
Hailey C.
Star Sitter
$36
total per visit
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Natick, MA, 01760

Hailey was wonderful! Perfectly communicative, took great care of our kitties. 11/10 reccomend.

Profile image
Mia I.
Sitter Profile Image: Marilyn M.
Verified Enhanced Background Check
Marilyn M.
$26
total per visit
5.0 out of 5 stars
16 reviews
8 repeat clients
30 years of experience
Hopkinton, MA, 01748

Our appreciation for Marilyn is beyond words. She took care of our animals and our very sick kitty. She treated her like her own. We are forever grateful.

Profile image
Amna D.
1 / 1
View more

The median cost per visit for dog sitting in Ashland is $25

Dog parents share their Rover experiences - Ashland

1 / 1
5.0 out of 5 stars

Maanya is great! We’ve used her multiple times. Always so reliable and on time and our dog loves her!

Profile image
Caroline W.
Drop-In Visits
5.0 out of 5 stars

We couldn't have asked for a better first experience as first time dog parents! Nikkita sent tons of adorable photos and kept us completely in the loop with updates on walks, bathroom breaks, playtime, and snuggles. It gave us so much peace of mind knowing our pup was in such great hands!

Profile image
Sarah R.
Drop-In Visits
5.0 out of 5 stars

Gianna was super communicative and attentive, she did a great job taking care of our nervous puppy and making sure he had the best experience for his first Rover visit. She was also so thoughtful about small details, like cleaning his Kong toy and bringing in packages, which goes such a long way :) will book again!

Profile image
Audrey A.
Drop-In Visits
5.0 out of 5 stars

Becki is awesome with Lucy! She can be super stubborn, but Becki is so patient and knows exactly how to handle her. Lucy loved her, and we always felt totally comfortable knowing she’s in great hands. Highly recommend!

Profile image
Abbie H.
Drop-In Visits
5.0 out of 5 stars

Erin was incredibly responsive and able to help on very short notice, which I truly appreciated. She took great care of my dog and made the whole process easy and stress-free. Highly recommend!

Profile image
Angelica C.
Drop-In Visits
5.0 out of 5 stars

Trustworthy, honest, treats our crew like her own. Our pets love her! Animals are the best judge of character. We are forever clients. We hope she never leaves us.

Profile image
Amna D.
Drop-In Visits
5.0 out of 5 stars

Brittany was extremely responsive and professional ! On very short notice I made arrangements with Brittany and couldn’t have been more leased with our interaction and her care of my dog. I highly recommend her and will definitely hire her again. Thank you 🐾

Profile image
Susan R.
Drop-In Visits
5.0 out of 5 stars

So thankful for Sarah! She was able to help me out last minute when my current walker had a conflict. She was communicative and met my pup beforehand on short notice. Highly recommend!

Profile image
Samantha W.
Drop-In Visits
5.0 out of 5 stars

Paula was beyond accommodating and gave me great updates on Louie on her drop-in visit! I would highly recommend her and will happily book her again :)

Profile image
Jocelyn O.
Drop-In Visits
1 / 1
Find pet care near you

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for dog sitting - Ashland

Select a filter and find qualifying sitters offering dog sitting.

Sitters in Ashland average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Ashland

Frequently asked questions about Rover

The average cost for Dog Sitting in Ashland on Rover is $22.2 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of September 2026, there are 10,652 sitters on Rover offering Dog Sitting across Ashland. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Ashland stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Ashland choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Ashland with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Ashland. On Rover:

  • 91% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 94% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge