Dog Boarding Oakham
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Oakham, Find top rated dog boarding
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“We had a great experience with our Rover dog sitter. Communication was excellent, our dog was well cared for, and we received regular updates while we were away. We felt comfortable knowing our dog was in good hands and would definitely book with them again. Highly recommend!”
“Erica was awesome. She took Ollie in on short notice and took excellent care of him. He had a blast while he was there and Erica provided me with updates and pictures while we were away. We will absolutely be using Erica again when we go away on vacation.”
“Once again, we couldn’t be happier that our puppy, Lucy, was able to stay with Dawn and her family while we were out of town! We love that Lucy is not only so well cared for, but also gets to socialize with Dawn’s younger kids, their friends, and other dogs throughout her stay (we love getting photos and updates!) Lucy came home happy and exhausted - thank you, Dawn!”
“Pat was a great petsitter for my little dog. She is very friendly and calm. We had a nice and thorough meet and greet at her house and went over my pup’s information. I provided some written info about my dog’s routines with feeding, meds etc that Pat was attentive to. My dog loved staying at Pat’s home, especially lying in the sunshine napping! I knew she was in good hands during the three days away, which allowed me to have a great trip. Pat’s husband was also very nice and my pup loved him too. I got a photo update each morning with a text about what Pat & my dog had been up to together. The one time my dog exhibited an unusual behavior (just instinctively trying to cover her food to save it for later!), Pat sent me a quick video to ask about it, which made me feel good about the care my dog was receiving. Overall I was totally happy with our experience having Pat petsit. We look forward to using her when I have to travel again soon and I recommend her without reservation. Thanks very much Pat!”
“Dorothy was great - she and her family made Bruno feel very welcome and secure and kept us updated while we were away. He has a special diet and daily medication and she was great with giving that to him. Definitely will book again.”
“Colette was absolutely wonderful. Winnie loved her! Her fenced in backyard is perfect for a small dog who loves to feel “free”! She sent us multiple photos and updates. We’d definitely use her again!”
“We have been bringing our dog Pepper to Tamara and her family for several years now. It is comforting to know Pepper is well cared for when we are away. Sometimes she doesn’t want to leave! 10/10, highly recommend!”
“Moe had the best time with Elizabeth and family. He was well taken care of, loved being with her dogs and was in great form when we pick him up. Moe is going back to Elizabeth and his new pooch friends and he will be delighted, as will I. Such a relief to know your pup is in good hands, safe, happy and well cared for, thank you Elizabeth!”
“Recently we lost one of our two dogs. We had a trip planned for only a couple weeks later and had to board our second dog alone for the first time. Gabe was an excellent choice and probably the most knowledgeable in training that we have had so far! He was communicative, responsible, and made us feel completely confident while we were gone! Definitely will be giving him a call again for our trips.”
“Lingwen was AMAZING! She made Nico feel super comfortable at her home and welcomed. Lingwen sent updates and pictures of Nico thought out the stay which we loved. Thank you much again for caring for Nico! If you’re looking for a sitter, do not hesitate to book her. She’s the best :)”
“Peggy was great! Communication was great - and our normally shy dog Edison was best buds with their dog Daytona right away. Hope he can visit with Peggy and her family again soon!”
“I was very nervous having to board my two pups rather emergently. Best thing to have ever happened to me was finding this angel. She sent me a frequent updates as well as pictures. Couldn’t have asked for a better family to take care of my best buds. I am 1000% grateful and will continue to use Jessica in the future.”
“Riven and Matt were great! They were able to take care of my pup, Lula Mae, while I needed to be out of town on short notice. Lu was clearly well cared for and happy with them. Really appreciate it!!”
“Tracy was amazing with our cat Pretty Girl! We were nervous as this was our first time boarding her but Tracy was very kind and helpful. She was in good hands for sure! We got updates throughout the stay and lots of pictures as well!! When we picked Pretty Girl up she was happy and healthy and well taken care of. Would definitely book with Tracy again!”
“As always, Sandra and her husband John are so attentive, caring and loving towards Lulu, they treat her as their own. She truly cares about her and provides immaculate care. Lulu requires medication as well as frequent meals and Sandra is always on top of her care!”
“Phenomenal care! Amber is a wonderful sitter, very caring, kind, empathetic and truly loves dogs. My Dante got a lot of love and attention. Amber communicated well, plenty of updates, pictures and videos. Best care for your furry kiddo! Highly recommend Amber as your sitter.”
“Larry had a great time with Nancy, she was great and took great care of Larry. She sent me updates and pictures of Larry. Highly recommend her and will definitely book with her again.”
“Kendra was absolutely amazing. From the moment I walked in I knew Scout would be well cared for and would also have a fun furry companion to play with. Kendra is very attentive to details, warm, welcoming to cuddle a sometimes shy dog and my pup enjoyed lots of exercise and play. Thank you Kendra!”
The median cost per night for dog boarding in Oakham is $60
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.
How to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog boarding - Oakham
Select a filter and find qualifying sitters offering dog boarding.Sitters in Oakham average 13 repeat dog boarding clients
FAQs for Dog Boarding - Oakham
Frequently asked questions about Rover
As of November 2026, there are 739 sitters on Rover offering Dog Boarding across Oakham. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
95% of sitters in Oakham can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Oakham home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Oakham.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
Yes, you can find sitters who have experience with handling special pet needs in Oakham. On Rover:
- 88% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% 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.
You and your Oakham sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
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.
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.
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in MA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
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