Dog Boarding Winchester

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Sitter Profile Image: Jie M.
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Jie M.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 56 reviews
10 repeat clients
10 years of experience
Swanzey, NH, 03446

“Jie and her family were amazing dog hosts. She sent us daily updates and videos and was an incredible communicator. This was the first time we’ve left our furry children with someone and could not have been happier. We were so relaxed knowing they were in great hands and will recommend her and this service to all the pet owners we know!”

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Robin H.
Sitter Profile Image: Letícia B.
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Letícia B.
from
$75
per night
5.0 out of 5 stars
• 21 reviews
4 repeat clients
10 years of experience
Brattleboro, VT, 05301

“Leticia was wonderful with our dog. After welcoming us, she showed us her fenced backyard. Lovely. She sent pictures and videos and Savannah played with new puzzles. Really appreciate the loving care.”

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Linda L.
Sitter Profile Image: Amy P.
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Amy P.
from
$38
per night
5.0 out of 5 stars
• 11 reviews
6 years of experience
Troy, NH, 03465

“Amy was amazing with Cooper! He can be very shy with new people, but she was patient and gentle with him and made him feel comfortable. It was such a relief knowing Cooper was happy and well cared for while we were away. I would definitely recommend Amy!”

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Sandra S.
Sitter Profile Image: Corin "Swift" & Brian K.
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Corin "Swift" & Brian K.
from
$43
per night
5.0 out of 5 stars
• 14 reviews
2 repeat clients
15 years of experience
Putney, VT, 05346

“Swift, Brian, family were amazing with our two dogs! They sent lots of photos throughout the weekend and responded quickly. We will definitely be using them again and highly recommend!”

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Chandler K.
Sitter Profile Image: Luiz B.
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Luiz B.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 176 reviews
34 repeat clients
40 years of experience
Gardner, MA, 01440

“Satya had a great time this past weekend with Luiz and the whole family. We got tons of pics and videos of our pup playing and having fun. We continue to be repeat customers. Satya is well cared for and we don't have to worry while we are away!”

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Sue M.
Sitter Profile Image: Christian M.
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Christian M.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 39 reviews
13 repeat clients
10 years of experience
Greenfield, MA, 01301

“Christian responded quickly to our initial request & because we had a long drive he agreed to accommodate a 2 hour drop off window (we texted updates). He was friendly at drop off, happily engaged the dogs, asked good questions about their needs & sent photos as requested. At pick-up he offered details about their stay. Both dogs were happy to see us but seemed to have enjoyed their night with Christian. Would book again”

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Ac D.
Sitter Profile Image: Hillaree H.
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Hillaree H.
from
$62
per night
5.0 out of 5 stars
• 31 reviews
10 repeat clients
40 years of experience
Conway, MA, 01341

About: My family has always had dogs, and I feel that they enhance the family unit. No discrimination against certain breeds. German Shepherd, Rottweiler, American Staffordshire, Boxer, makes no difference to me. I adore all the four-legged kids! I have my own four-legged kid, and truly appreciate the help I’ve received through Rover.com, while being at work or out of town. It’s such a relief to know that the he is taken care of, so I can continue working to provide for him. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. Dogs are family, and I would gladly treat yours as part of my pack. I would be happy to perform drop-in visits or walk your dog(s) during the day, or into the night hours, as my schedule allows. Currently, I am unavailable for midday drop-ins and walks Mondays through Thursdays. Updating you on the visit with pictures and/or videos, so you can see your four-legged kid(s) have been cared for, would be my pleasure. I happily treat your fur kids as lovingly as my own. Always checking that food and water bowls filled as needed. Utilizing the crate should they need it upon my leaving.

Sitter Profile Image: Katelyn C.
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Katelyn C.
from
$60
per night
12 years of experience
Amherst, MA, 01002

About: I have had cats and dogs my whole life growing up. I know how to care for them and love them correctly. I love being around pets. I currently work part time so I’m not too busy with work. I go to school 4 days a week but have plenty of time at night and sometimes during the day. I will always make sure to watch your pets. I have a yard for them to play in and have time to walk them. I have other teenage girls in my house who love pets just as much as I do.

Sitter Profile Image: Shelby P.
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Shelby P.
from
$50
per night
5.0 out of 5 stars
• 10 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: Vincenzo S.
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Vincenzo S.
from
$32
per night
5 years of experience
Winchendon, MA, 01475

About: I’ve always had a genuine love for animals and understand how important it is to have someone you can trust caring for your pets. I’m comfortable with dogs and cats of different sizes, personalities, and energy levels, and I always take the time to make sure each pet feels safe, comfortable, and cared for. Whether it’s walks, playtime, feeding, potty breaks, or simply providing companionship while you’re away, I’ll treat your pet with the same patience, attention, and care I would give my own. I’m dependable, responsible, and happy to follow your pet’s normal routine and any special instructions you provide. My goal is to give you peace of mind knowing your pet is in good hands. Pet care fits perfectly into my daily routine because I’m home throughout the day and able to give the dogs plenty of attention, companionship, and supervision\. Since I’m home, your dog won’t be left alone for long periods of time\. I have plenty of time for regular potty breaks, walks, playtime, feeding, and of course lots of attention and affection\. I enjoy having dogs around and love making them feel like part of the family while they’re in my care\. I can also follow your dog’s normal schedule and routine to help them feel as comfortable and at home as possible\. My home has a large open backyard with 2.12 acres, giving dogs plenty of space to run, play, explore, exercise, and enjoy the outdoors safely.

Sitter Profile Image: Heather M.
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Heather M.
from
$31
per night
5.0 out of 5 stars
• 5 reviews
3 repeat clients
10 years of experience
Ashburnham, MA, 01430

About: Before becoming a nurse, I was a vet tech for 5 years. I’ve also grown up with dogs and cats my whole life! Old or young, I'd loved to take care of your pet. Whether that's going for walks, playing vet, or just lounging around. Animals bring such joy to our lives and I'll take care of your baby like they're my own! I'm an ICU nurse with a few weeks in between contracts. Once I go back to work, I'll work 3 12s so I'll have lots of free time to spend with your babies. I usually know my scheduled a month in advance as well. I’m a very active person and if your pup is also active I can take them hiking or for a run! But if your dog is a couch potato I’m happy to just spend time with them too!

Sitter Profile Image: Sean O.
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Sean O.
from
$70
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
2 years of experience
Wilmington, VT, 05363

“Sully came home a tired and happy boy. Reliable and dependable. A+”

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Amy S.
Sitter Profile Image: Ava V.
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Ava V.
from
$60
per night
5.0 out of 5 stars
• 10 reviews
1 repeat client
5 years of experience
Amherst, MA, 01002

About: I’ve given love and care to multiple dogs and cats ranging from puppies and kittens to seniors. I feel very comfortable administering medications and will give exceptional care to animals with special needs. As an Animal Science major at UMASS, I currently study/work with farm and companion animals. I’m currently working part time, leaving optimal time to care for your pets! I am available for pet sitting or walking Sunday-Wednesday all day and Thursday-Saturday before 3pm and after 8:30pm. I am flexible to your needs! I love all pets and will provide lots of love and affection. I’m willing to give walks and/or do overnights.

Sitter Profile Image: Mike & Laura O.
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Mike & Laura O.
from
$125
per night
5.0 out of 5 stars
• 13 reviews
2 repeat clients
25 years of experience
Putney, VT, 05346

“Mike and Laura took exceptional care of our 17-year old Jack Russell. Mike was extremely communicative during the entire process and helped make our trip to Ludlow happen!”

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Peter S.
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Dog parents share their Rover experiences - Winchester

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5.0 out of 5 stars

Carter was an excellent sitter. He showed concern for my dogs health by reviewing my dogs eating habits to make sure no food would be bad for him. Oliver was in great spirits and seemed to have had a great visit full of love.

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Michael C.
Boarding
5.0 out of 5 stars

Carter was awesome!! He took such great care of our dog and also was great at communicating in advance and then whine he had the dog. Very grateful and a great recommendation for others!

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Elizabeth B.
Boarding
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How to book dog boarding

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FAQs for Dog Boarding - Winchester

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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 Winchester 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 Winchester.

<b>Tip:</b> 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 Winchester 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 NH 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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