Dog Boarding in Winchester, NH

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Top rated Winchester dog boarders

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
79 reviews
23 repeat clients
25 years of experience
Greenfield, MA, 01301

Nicole provided excellent care for our 3 month old puppy. He had a wonderful day full of playtime and snuggles. She also provided lots of pictures throughout the day which we loved!

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

Lou had a wonderful time with Jie! Great communication all around, and extremely accommodating. I highly recommend Jie to look after anyone’s pups!

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Jessica B.
Sitter Profile Image: John M.
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John M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
146 reviews
52 repeat clients
15 years of experience
Turners Falls, MA, 01376

We highly recommend John. Our dog had a great stay! We really appreciated all the cute photos and great communication. We would definitely book with John again.

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Ellie T.
Sitter Profile Image: Rachael L.
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Rachael L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
41 reviews
17 repeat clients
25 years of experience
Dublin, NH, 03444

My two dogs enjoyed their stay with Rachael and her family. It is a very relaxed and welcoming atmosphere, and her two dogs are great! Outside time, sofa time, just perfect. We'll be back!!

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Mary T.
Sitter Profile Image: Letícia B.
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Letícia B.
Star Sitter
from
$70
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
10 years of experience
Brattleboro, VT, 05301

My dog had a great time with Leticia! She sent us pictures during the day which were much appreciated! We look forward to booking with her again soon!

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Ken B.
Sitter Profile Image: Susan B.
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Susan B.
from
$50
per night
10 years of experience
Orange, MA, 01364

About: I've been around animals my whole life and currently have two pet goats who we spoil like dogs. We have 30 acres of beautiful land surrounded by woods, which is a perfect haven for running, fetch, and all sorts of outdoor shenanigans. I work remotely from home with a flexible schedule. I typically work a few hours in the morning, and then am outside working on projects and playing with the animals all day. We have a large property (about 30 acres) surrounded by woods with lots of room for your dog to run and explore. We also live near some great hiking trails.

Sitter Profile Image: Jessica C.
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Jessica C.
from
$29
per night
5.0 out of 5 stars
54 reviews
18 repeat clients
35 years of experience
Sunderland, MA, 01375

They we're great with Ranger! I received updates and pictures each day about how Ranger was doing and any antics he was up to. Lots of walks were taken and i really appreciated the help and flexibility to work with my schedule. Ranger came home happy and tired from all his excitement!

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Kalia L.
Sitter Profile Image: Carter M.
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Carter M.
from
$45
per night
5.0 out of 5 stars
21 reviews
9 repeat clients
10 years of experience
Winchester, NH, 03470

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.
Sitter Profile Image: Holly R.
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Holly R.
from
$60
per night
4.8 out of 5 stars
4 reviews
2 repeat clients
20 years of experience
Hinsdale, NH, 03451

Holly and her family were wonderfully accommodating and helpful with our pet Sylvie. They have a wealth of experience looking after dogs, and really appreciate their individual personalities and needs.Communication was great and I would hve them watch Sylvie again, anytime.

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Laura L.
Sitter Profile Image: Samantha & Brian S.
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Samantha & Brian S.
from
$50
per night
18 years of experience
Wendell, MA, 01379

About: Ive been caring for pets for many years. I had a dog walking business over a decade ago. We taken care of our own and others elderly dogs. We like taking dogs on long off leash walks in groups if possible. Dogs are always welcome to cuddle up on the furniture. Im a stay at home-mom, homeschooling. We go to play groups and trips but we can plan our day around dog walks. We take the dogs out first thing in the morning on leash as our yard isnt fenced. We are happy to come feed kitties and water plants. We love taking dogs out on walks and caring for them in our home. We love going on long walks mid day out in nature

Sitter Profile Image: Christian M.
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Christian M.
from
$60
per night
5.0 out of 5 stars
22 reviews
11 repeat clients
10 years of experience
Greenfield, MA, 01301

Christian is great! He is patient, chill, and very good with dogs! I loved that our dog wanted to go back inside with him when we had to leave; that is a great sign!

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Gregory A.
Sitter Profile Image: Elizabeth E.
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Elizabeth E.
from
$50
per night
5.0 out of 5 stars
7 reviews
1 repeat client
33 years of experience
Mount Hermon, MA, 01354

Super grateful for Elizabeth’s help! Very communicative and took great care of Pancho!

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Malory Y.
Sitter Profile Image: Emily J.
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Emily J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
34 reviews
12 repeat clients
35 years of experience
Gardner, MA, 01440

Thank you Emily for making Sherlock feel at home!!! Sherlock was welcomed as part of their own family. Emily and all her family members made it very easy for him! He had a very comfortable stay! ❤️

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Soumya D.
Sitter Profile Image: Sandra A.
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Sandra A.
from
$60
per night
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Templeton, MA, 01468

Took awesome care of moose! Even gave him a bath! Nothing but great things!

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jeffrey g.
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
12 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: Amy P.
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Amy P.
from
$30
per night
5.0 out of 5 stars
5 reviews
6 years of experience
Troy, NH, 03465

I couldn’t have asked for a better experience. Amy was warm, kind, and incredibly attentive while caring for my dog.  It gave me real peace of mind knowing my baby was in such good hands. Communication was great, and it was clear she genuinely cared. I would absolutely trust her again and highly recommend her services!

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Julie B.
Sitter Profile Image: Karl K.
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Karl K.
Star Sitter
from
$40
per night
5.0 out of 5 stars
35 reviews
10 repeat clients
55 years of experience
West Hatfield, MA, 01088

Our energetic black lab had such a great time with Karl and his dogs! When we picked her up she was happy and relaxed. Communication with Karl was very easy: he responded quickly to any questions we had, and sent pictures every day! His place is a great set up with a fenced in yard and safe areas for dogs to move around indoors. We will definitely use Karl again in the future!

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Alexandra P.
Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$55
per night
5.0 out of 5 stars
3 reviews
15 years of experience
Troy, NH, 03465

Chief seemed properly pooped and happy when I picked him up. I got updates and pictures all throughout the stay, which always is appreciated! Thanks for doing an amazing job!

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Sean J.
Sitter Profile Image: Luiz B.
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Luiz B.
Star Sitter
from
$55
per night
5.0 out of 5 stars
171 reviews
32 repeat clients
40 years of experience
Gardner, MA, 01440

We were super comfortable leaving our dog at Luiz’s house for the week while we went on vacation! They send lots of pictures and take great care of the dogs in their care.

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Alyson H.
Sitter Profile Image: Emily M.
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Emily M.
from
$55
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
8 years of experience
Peterborough, NH, 03458

Emily was AMAZING! Our Gus had a great time! It was obvious that Emily not only took VERY good care of him but he was treated to his all-time favorite game of fetch and cooling off in the kiddie pool multiple times! He came home happy and tired. :) We highly recommend Emily, she goes above and beyond expectations, and we will definitely use her again! Thanks Emily!

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Julie M.
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Winchester dog parents share their Rover experiences

1 / 1
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
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
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How Rover works

  1. 1. Search

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  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

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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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Dog Boarding FAQs

Frequently asked questions about Rover

If you’re searching for a Winchester dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!

Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winchester.

Rover makes it easy to find Winchester dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.