Dog Boarding Williamsburg

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Williamsburg, 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%.

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Sitter Profile Image: Jessica C.
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Jessica C.
Star Sitter
$33
total per night
5.0 out of 5 stars
• 59 reviews
19 repeat clients
35 years of experience
Sunderland, MA, 01375

“Josie loves dogs and took great care of our Pip. The family made Pip feel good about spending the weekend with them and seemed to love her, even forgiving her for getting food off the counter. 😬 we feel fortunate to have found them.”

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Mary J.
Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
$73
total per night
5.0 out of 5 stars
• 87 reviews
23 repeat clients
25 years of experience
Greenfield, MA, 01301

“Dobby had an amazing time! She came back so happy. She spent a lot of her time in the kiddie pool, playing with other dogs, chewing bones, and being her energetic, social self. So happy to have booked Nicole again!! Highly recommend!”

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Cody S.
Sitter Profile Image: John M.
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John M.
Star Sitter
$78
total per night
5.0 out of 5 stars
• 161 reviews
62 repeat clients
15 years of experience
Turners Falls, MA, 01376

“John did a great job with our Enzo dog. He is obviously a dog person! You can tell by the way he talks with and connects with dogs. Since this was the first time our dog boarded with someone, we wondered how he would do, but he was totally comfortable with John. By the way, John sent pictures to put us at ease, but also showed that our dog was happy and comfortable.”

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Greg S.
Sitter Profile Image: Katelyn S.
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Katelyn S.
Star Sitter
$35
total per night
5.0 out of 5 stars
• 14 reviews
5 repeat clients
25 years of experience
Westfield, MA, 01085

“Posy had a great time with Katie and the dogs! She loved getting to play in the yard and get some outside time. Sue came home happy and ready for a nap!”

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Auri C.
Sitter Profile Image: Samantha & Brian S.
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Samantha & Brian S.
$56
total per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
18 years of experience
Wendell, MA, 01379

“Sam and her family took excellent care of my two dogs! Communication was top-notch, and I loved to see how happy and well cared for they were. They came home content and tired, which is the best review of all. It’s clear they had a great time in your beautiful spot in the forest. Thank you so much, Sam! 🤩”

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Margaret E.
Sitter Profile Image: Carmela A.
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Carmela A.
Star Sitter
$39
total per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
25 years of experience
Agawam, MA, 01030

“Carmela was super nice with my elder dog. My chihuahua suffered violence from a teenager and now his behavior is not the best. Carmela was so comprehensive and knew how to manage him to keep him feel safe in her home. I am so thankful that she received my baby in her home for the time I had to travel.”

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Virginia G.
Sitter Profile Image: Dorjee D.
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Dorjee D.
$67
total per night
4.9 out of 5 stars
• 53 reviews
26 repeat clients
15 years of experience
Amherst, MA, 01002

“Astrid is great! She kept us updated during the stay. Really easy to work with. Really flexible on drop off/pick up time. Mooncake had a great time!”

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Cici X.
Sitter Profile Image: Amy H.
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Amy H.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 30 reviews
10 repeat clients
25 years of experience
East Longmeadow, MA, 01028

“I have been using rover for 4 years now and Amy has been the best petson to take care of my dog "Johnny" so far. She is Highly Recommended and will be using her to take care of my Dog moving forward. The pictures she sent us we awesome and it really looked like my dog was living his best life lol. You will not be disappointed.”

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Jared P.
Sitter Profile Image: Kathleen M.
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Kathleen M.
Star Sitter
$95
total per night
5.0 out of 5 stars
• 166 reviews
46 repeat clients
12 years of experience
Becket, MA, 01223

“Kathleen took great care of our pup, sending me daily updates and photos! Her house and yard are set up perfectly with a lot of space to run around and she gave our pup lots of love and care. She gave us peace of mind while we were out of town and I highly recommend taking your dog to stay with Kathleen!”

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Charlotte M.
Sitter Profile Image: Caitlin C.
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Caitlin C.
Star Sitter
$54
total per night
5.0 out of 5 stars
• 17 reviews
9 repeat clients
20 years of experience
West Springfield, MA, 01089

“I can’t say enough wonderful things about Caitlin and the care she provided for Mocha. From the moment I dropped her off, I felt completely at ease. Caitlin and her family are genuinely kind, warm, and attentive, her children were especially sweet and gentle, which meant so much to me given that Mocha is an older dog. Throughout the stay, I received regular updates, including photos and videos, and it was clear that Mocha was not only well cared for but truly happy and loved. That level of communication and reassurance made all the difference. As someone who was initially very hesitant about using an app to find a dog sitter, I feel incredibly lucky to have found Caitlin. She followed every instruction, treated Mocha with such care and compassion, and went above and beyond in every way. I am beyond grateful and would absolutely trust her again. Highly, highly recommend.”

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Jacqueline W.
Sitter Profile Image: Irene T.
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Irene T.
Star Sitter
$73
total per night
5.0 out of 5 stars
• 24 reviews
8 repeat clients
20 years of experience
Pittsfield, MA, 01201

“Irene has been such a great find in the Berkshires! She always gives helpful communication with each stay, and Ruby seems to love her time with Irene (and her sweet dog Goldie). Thanks for all of the care that you give to Ruby - we'll see you soon!”

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Eric B.
Sitter Profile Image: Jess L.
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Jess L.
$47
total per night
5.0 out of 5 stars
• 89 reviews
22 repeat clients
5 years of experience
Pittsfield, MA, 01201

“Jess was so sweet. Our dogs were immediately interested in getting to know Jess and felt comfortable going with her into her home. Thankful for Jess’ flexibility during our pups’ stay since we had some last minute changes to our schedule. Thank you, Jess!”

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Matthew B.
Sitter Profile Image: Summer P.
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Summer P.
$56
total per night
5.0 out of 5 stars
• 16 reviews
5 repeat clients
8 years of experience
Wilbraham, MA, 01095

“Summer is the best of the best. She took such good care of our two pups and when one of our pups arthritis started to act up, she loved him and took care of him like he was her own. She was absolutely incredible and we will most certainly be rebooking and I would highly recommend Summer to watch anyone’s pups.”

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Casey Jane C.
Sitter Profile Image: Ali S.
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Ali S.
Star Sitter
$56
total per night
5.0 out of 5 stars
• 31 reviews
7 repeat clients
5 years of experience
Belchertown, MA, 01007

“Ali was very nice and was good about communicating. Minnie seemed to be in very good spirits when I picked her up. He shared photos of her daily during her stay. Minnie will be looking forward to going there again, I’m sure.”

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Brenda B.
Sitter Profile Image: Mahayla G.
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Mahayla G.
Star Sitter
$84
total per night
5.0 out of 5 stars
• 54 reviews
25 repeat clients
15 years of experience
Adams, MA, 01220

“Molly loved hanging out with Hailey. Molly went everywhere with Hailey. Molly thrives in a home setting. So glad we have Hailey to watch Molly.”

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Jean M.
Sitter Profile Image: Shelby P.
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Shelby P.
$56
total per night
5.0 out of 5 stars
• 13 reviews
4 repeat clients
15 years of experience
Amherst, MA, 01002

About: I’ve cared for dogs most of my life and truly treat them like family. I grew up in a home with four dogs, so I’m very comfortable with different personalities, sizes, and energy levels. I also adopted and lovingly cared for a difficult senior dachshund for years, which gave me valuable experience with patience, senior dog needs, routines, and extra attentiveness. Today I have a large Bernedoodle, so I’m confident handling bigger dogs as well as energetic pups who need exercise and structure. I’m active and love taking dogs on walks, runs, and outdoor time when appropriate, while also making sure they get plenty of affection, snuggles, and supervision. What sets me apart is that I’m dependable, attentive, and genuinely love dogs. I understand every dog is different, and I’ll make sure your pet feels safe, comfortable, and cared for while you’re away. I work remotely from home, which gives me a very flexible schedule and allows me to be present throughout the day for the pets in my care. Because I’m home most of the time, dogs get plenty of attention, regular potty breaks, walks, playtime, and companionship instead of being left alone for long stretches. My flexible routine also makes it easy for me to stick to your pet’s normal schedule for feeding, medications, exercise, and any special needs. I’m able to provide attentive, consistent care and make sure your pet feels comfortable, safe, and loved while you’re away. Safety and comfort are always my top priorities. I provide a calm, loving home environment where pets can feel relaxed and cared for. I have a friendly, social dog who enjoys having visitors and does well with other dogs, while always making sure introductions are done thoughtfully and safely. I have a yard for outdoor time, and while it is not fenced, I use a secure runner/tie-out system and close supervision so dogs can safely enjoy fresh air, potty breaks, and time outside. I also keep dogs leashed on walks and anytime they are outdoors for added safety. If your dog is crate-trained or more comfortable with their own space, I’m happy to accommodate crating and follow your normal home routine. I always aim to keep pets on their regular schedule for feeding, exercise, rest, and any medications or special instructions. I treat every pet like my own—with patience, attentiveness, and lots of love.

Sitter Profile Image: Kim M.
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Kim M.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 73 reviews
26 repeat clients
20 years of experience
Westfield, MA, 01085

“My dog loves Kim and her kids so much. She was so excited to see them on her last stay. I felt like the mom of a three year old being dropped off at preschool when the kid runs in and starts playing with their friends. I'm so glad our dog is so happy at Kim's place!!!”

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Michelle D.
Sitter Profile Image: Victoria S.
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Victoria S.
Star Sitter
$45
total per night
5.0 out of 5 stars
• 12 reviews
4 repeat clients
5 years of experience
Maple High-Six Corners, Springfield, MA, 01105

About: Feeding, entertaining, and walking pets. Friends and family have trusted me in caring for their pets like my own when needed. I have had pets of all kinds growing up and have a passion for caring for dogs, cats and small animals such as guinea pigs. I currently work full remote and have flexibility to add in drop ins during the work day. I also have availability during weekends if you’re taking a trip, for multiple drop ins a day as needed. I currently have two cats who are my best friends. I have grown up around dogs and have dog sat for many years for friends and family. Walking and pop ins are the best part of my day.

Sitter Profile Image: Amanda B.
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Amanda B.
$23
total per night
5.0 out of 5 stars
• 4 reviews
8 years of experience
Chicopee, MA, 01020

About: Hi! I'm a lifelong animal lover and proud pet parent to Raven (7 female dog), and Miles (8 female cat) I know how important it is to find someone you can trust to care for your pets, and I would love to provide them with the same love and attention I give my own! I work from home, so I'm able to give pets plenty of attention throughout the day and provide frequent potty breaks, playtime, and companionship. I also have a fenced yard where dogs can safely get fresh air and exercise. My home is used to being around both animals and kids. I understand that every pet has their own personality, routine, and needs. Whether your pet needs company, playtime, walks, or just a comfortable and caring place to stay, I will treat them like part of the family!

Sitter Profile Image: Ryan O.
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Ryan O.
$73
total per night
5.0 out of 5 stars
• 286 reviews
61 repeat clients
15 years of experience
Conway, MA, 01341

“Ryan is absolutely the best dog sitter we've ever worked with. Here's the easy way to explain it: we can't say Ryan in our house, because Stanley gets too excited and starts running around and wants to get in the car. Ryan truly cares about the dogs he works with. Hes treated Stanley like his own dog, like family.”

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Rachelle B.
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The median cost per night for dog boarding in Williamsburg is $50

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. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  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 boarding - Williamsburg

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Williamsburg average 11
repeat dog boarding clients

FAQs for Dog Boarding - Williamsburg

Frequently asked questions about Rover

As of November 2026, there are 318 sitters on Rover offering Dog Boarding across Williamsburg. 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.

97% of sitters in Williamsburg 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 Williamsburg 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 Williamsburg.

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 Williamsburg. On Rover:

  • 92% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 97% 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 Williamsburg 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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