Dog Boarding Cummington

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Over 33
pet parents in Cummington have booked dog boarding

Cummington, 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: Brooke B.
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Brooke B.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 139 reviews
36 repeat clients
25 years of experience
Pittsfield, MA, 01201

“Once again we are so please with Brooke and grateful we found a happy safe second home for our pups. We needed to leave out of town rather quickly and she was able to fit us in on short notice. We love the pictures and updates she sends of the pups. Thank you!!”

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Teena G.
Sitter Profile Image: Jess L.
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Jess L.
$47
total per night
5.0 out of 5 stars
• 89 reviews
21 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: Karl K.
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Karl K.
Star Sitter
$62
total per night
5.0 out of 5 stars
• 55 reviews
16 repeat clients
55 years of experience
West Hatfield, MA, 01088

“Karl took great care of our two dogs. He knew I was nervous since it was the first time leaving them with someone and he kept me posted with updates and photos. They had a great time!”

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Jessica W.
Sitter Profile Image: Krystal N.
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Krystal N.
$40
total per night
1 repeat client
7 years of experience
Williamstown, MA, 01267

About: I have a sweet 4 yr old toy poodle girl and 3 yr old Siamese boy cat who love new friends! I’m attentive, patient, and treat every pet like family.🐾 Pet care is something I genuinely enjoy making part of my routine. I love starting the day with a walk and making time for play, cuddles, and companionship throughout the day. Since I work from home, I’m able to give pets plenty of attention without leaving them alone for long periods. I’m happy to follow each pet’s usual routine so they feel comfortable and at home! I love getting to know each pet and making sure they feel happy, safe, and right at home! I have a large, open yard where pets can enjoy some fresh air and playtime while I’m outside supervising (weather permitting). My sweet toy poodle also loves making new friends and would be happy to keep your pup company! I’ll follow their usual routine, including meals, walks, playtime, cuddles, and any special instructions you provide. My goal is for every pet to feel comfortable, loved, and part of the family while they’re with me!

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 is the best! She is very responsive and caring with our slightly neurotic dog. 🐶 He always comes home happy and calm. Irene has a great setup for playtime (fenced yard, screened porch).”

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rochelle d.
Sitter Profile Image: Francy & William S.
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Francy & William S.
$28
total per night
1 year of experience
Pittsfield, MA, 01201

About: We have one year of experience caring for small dogs. We are responsible, attentive, and ensure a safe, loving and confrable environment at all times We work from home, so we have plenty of time to take care of pets. Provide constant attention follow daily routines. And we are also available on weekends when needed. We have a fenced yard where pets can play safetly. And we can take them for once or two daily walks ensuring exercise, attention, and a conformable environment

Sitter Profile Image: Carmela A.
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Carmela A.
$39
total per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
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: Jessiana V.
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Jessiana V.
$34
total per night
5.0 out of 5 stars
• 47 reviews
19 repeat clients
10 years of experience
Indian Orchard, Indian Orchard, MA, 01151

“Varg's stay with Jessiana was great and she is a fantastic sitter. Took great care of him and couldn't have asked for more. Highly recommended!”

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Vincent R.
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: Heather R.
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Heather R.
Star Sitter
$47
total per night
5.0 out of 5 stars
• 47 reviews
26 repeat clients
22 years of experience
Feeding Hills, MA, 01030

“Riley and Hudson had an amazing stay with Heather. I received photo and videos of the dogs playing and doing tricks. The dogs even came home smelling better than they did when I dropped them off. She did such a good job I booked her for more weekends over the summer.”

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Matthew G.
Sitter Profile Image: Wendy A.
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Wendy A.
$39
total per night
4.9 out of 5 stars
• 8 reviews
3 repeat clients
30 years of experience
Westfield, MA, 01085

“Wendy was great! I needed a dog sitter at the last minute and came across her profile. I loved that she was so close to my home, and she made the entire experience stress-free. During my dog's stay, I received nightly text updates along with photos and videos, which I really appreciated. This was the first time I'd traveled over 13 hours away from my sweet girl, so I was super nervous. After the first day went so well, all my worries disappeared, and I was able to fully enjoy my trip knowing she was in great hands. I will definitely book with Wendy again and maybe next time she'll even get to meet my kitty too!”

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Sarah H.
Sitter Profile Image: Western B.
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Western B.
$84
total per night
5.0 out of 5 stars
• 4 reviews
20 years of experience
Dalton, MA, 01226

About: Dogs and I understand each other. I've always gotten them and they've always gotten me. Maybe because I grew up with three mammoth Samoyeds and Malamutes, and shared my life with Max, my sweet Cavalier, until he passed. Beyond love and care, I'm good at training and socializing, and dogs respond to my calm, confident leadership. I once cared for a reactive dog who barked at everyone who came near her, and I was the only one who could get her to settle and listen. After a month with a young Portuguese Water Dog, her owners told me she moped after I left. But mostly I think dogs feel good around me because they sense I genuinely care about them. I believe dogs are here to teach us to love and I want every dog to experience great care. For me, good dog care starts with getting to know the dog and the people who love them. I think dogs feel safest when their sitter truly knows them. Before any stay, I like to meet you and your dog, take a short walk together, and learn the little things that make your dog feel at home. That's why every stay begins with a meet and greet. What I offer that's different: - Pick-up and drop-off for longer stays: For stays of a week or more, I'll pick up and drop off your dog anywhere within a 30 minute drive of Dalton, including Lenox, Stockbridge, and Great Barrington. One less thing to manage before your trip. My home is calm and quiet, with a large, fully fenced backyard on a peaceful street in Dalton. I work from home, so your dog has company through the day, plus walks, play, and plenty of affection. I follow your instructions to the letter so your dog's routine stays as close to home as possible, and you'll get photos and a quick update every day so you can relax and enjoy your trip. Also happy to reinforce any training your dog is working on like leash manners. How I work: Every new client starts with a meet and greet, about 30 minutes with a short walk together, so your dog and I can meet before the stay. It helps make sure we're a great match, and your dog arrives already knowing a friendly face. Boarding in my home is a great fit if your dog: Settles comfortably for stretches after the initial sniffing and cuddles to get used to a new space. Is house-trained and walks well on a leash Is not a heavy shedder or super vocal Services Boarding: 2-night minimum House sitting: 2- night minimum, 2 night maximum for first sit I'd love to hear about your dog! I work from home so your dog will have plenty of companionship and attention from morning to evening. I usually walk dogs according to the schedule they are used to. In between, they can hang with me. IFeeding times will also coincide with your instructions. I'm an early riser so you are welcome to drop your dog off (with notice) as early as 7:30 am. I have a large three bedroom home with an huge fenced back yard on a quiet street near trails. It's single floor so no stairs for older dogs to contend with.

Sitter Profile Image: Mindi S.
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Mindi S.
Star Sitter
$50
total per night
5.0 out of 5 stars
• 7 reviews
4 repeat clients
15 years of experience
LUDLOW, MA, 01056

“Hailey loved staying with Mindi and her family and is looking forward to her next sleepover.”

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Jr G.
Sitter Profile Image: Taylor A.
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Taylor A.
Star Sitter
$47
total per night
5.0 out of 5 stars
• 22 reviews
8 repeat clients
10 years of experience
Ludlow, MA, 01056

“Taylor and his wife did a great job watching Rex. This is our second time using them to watch our dog. Their house is open and clean. They sent updates and pictures daily and were great at coordinating drop off and pick up times with us. Rex absolutely loves them!”

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Eddie & Julie K.
Sitter Profile Image: Saktah K.
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Saktah K.
$45
total per night
5.0 out of 5 stars
• 11 reviews
5 repeat clients
30 years of experience
Upper Hill, Springfield, MA, 01109

“Saktah did a great job taking care of my elderly and rather unfriendly kitty, Koshka, for two weeks while I was vacationing. She was very professional, organized, and caring, kept me updated on how my kitty was adjusting, and showed genuine affection and concern for her. She's driven to get things right and wants your pet to be as comfortable as they can be while you're gone. So if you (like me) have a pet that needs extra love and care, and you'd like to relax during your vacation knowing they're in good hands, go with Saktah. She's got you covered.”

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Blink B.
Sitter Profile Image: Aishea A.
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Aishea A.
$56
total per night
5.0 out of 5 stars
• 59 reviews
24 repeat clients
25 years of experience
Liberty Heights, Springfield, MA, 01104

“Aishea was nice and welcoming to Charlie. He felt comfortable immediately with her. Charlie was very well taken care of. Kept me updated of how he was and sent picture and videos. Will definitely recommend. Thank you Aishea!”

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Luz R.
Sitter Profile Image: Shelby P.
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Shelby P.
$56
total per night
5.0 out of 5 stars
• 11 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

“Kim was so responsive and was a great sitter for our ten month old puppy with medical issues. She had no problem giving him his medication and taking him for a walk in his stroller. Jett made doggie friends, and when I picked him up, he greeted me with his usual vigor and then lay down at her feet. A sign that he trusts her and had fun! She sent updates and photos. I’ve already booked Kim for our next trip!”

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Sera R.
Sitter Profile Image: Yasmin Jamal A.
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Yasmin Jamal A.
$89
total per night
5.0 out of 5 stars
• 2 reviews
20 years of experience
Pittsfield, MA, 01201

“She was great.. very caring and responsible. I will use her again. Thank you Yasmin.”

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Vina P.
Sitter Profile Image: Jennifer F.
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Jennifer F.
$62
total per night
5.0 out of 5 stars
• 7 reviews
40 years of experience
West Springfield, MA, 01089

“Our dog had a wonderful stay with Jenny. Super easy. Everyone had fun. Definitely recommend.”

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Katie B.
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The median cost per night for dog boarding in Cummington is $55

Dog parents share their Rover experiences - Cummington

1 / 1
5.0 out of 5 stars

Emily is great! SO easy to work with and communication was excellent; Maui was well taken care of and came home happy and tired :D

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Kate B.
Boarding
5.0 out of 5 stars

Emily and family did a great job watching Tronti for the weekend - consistent updates and pictures, feedback on pickup. Definitely recommend!

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Caitlin J.
Boarding
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How to book dog boarding

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Sitters in Cummington average 9
repeat dog boarding clients

FAQs for Dog Boarding - Cummington

Frequently asked questions about Rover

The average cost of Dog Boarding in Cummington is $39 per night as of October 2026. Most bookings cost between $30 and $67 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 198 sitters on Rover offering Dog Boarding across Cummington. Enter your ZIP code to see which available sitters are closest to your home.

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.

98% of sitters in Cummington 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 Cummington home-away-from-home, 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 Cummington.

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.

You and your Cummington 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 , 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 .

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.

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