Dog Boarding in Windsor

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Top rated Windsor 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: Cara S.
Verified Enhanced Background Check
Cara S.
from
$45
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
7 years of experience
Windsor, VT, 05089

Cara and her family had me completely at ease from our meet & greet through my dog’s stay. Cara shared photos every day and included notes - allowed me to remain confident in Fiona’s care. Cara is very responsive and excellent with communicating.

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Linda M.
Sitter Profile Image: Joseph & Corbin B.
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Joseph & Corbin B.
Star Sitter
from
$55
per night
4.9 out of 5 stars
225 reviews
111 repeat clients
10 years of experience
Meriden, NH, 03770

I recently had Joseph take care of my 2 dogs for a couple of days and I'm very happy with their service. They responded to my questions and sent me pictures, I felt comfortable with them taking care of my dogs. I'll use them again next time I travel.

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Matthew S.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$65
per night
4.9 out of 5 stars
51 reviews
14 repeat clients
20 years of experience
Claremont, NH, 03743

Denali had a wonderful time with Ashley and her family! She was well cared for and loved. I wondered if she would want to come home with me after such good care! Two other dogs, two boys, and someone home most of the time, what could be better!

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Ida B.
Sitter Profile Image: Hannah W.
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Hannah W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
14 reviews
4 repeat clients
25 years of experience
Claremont, NH, 03743

Hannah was great! This was our first time leaving our dog, Taco, with her, and it was for 5 days. We were of course nervous leaving him with someone new for so long, but as soon as we walked through her door, we were reassured he was going to be in great care! She kept us updated with photos throughout, and it was clear he was treated like part of the family during that time. Taco is excited to visit again!

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Hannah E.
Sitter Profile Image: Emily M.
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Emily M.
from
$55
per night
5.0 out of 5 stars
61 reviews
19 repeat clients
35 years of experience
West Lebanon, NH, 03784

Emily took great care of our two older dogs. After our initial meet and greet we felt comfortable leaving our girls in her care. We loved the daily updates and many pictures she sent and they came back to us happy and relaxed. We would definitely book Emily again in the future.

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Monika F.
Sitter Profile Image: Michele N.
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Michele N.
Star Sitter
from
$60
per night
5.0 out of 5 stars
8 reviews
6 repeat clients
25 years of experience
Grantham, NH, 03753

Michelle was terrific! Ellie stayed with her for Thanksgiving weekend and came home happy and tired! She was well-loved and Michelle kept us updated with pics and videos… and was super responsive and proactive before and during the entire experience. Thank you Michelle!

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Amy N.
Sitter Profile Image: Jessica P.
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Jessica P.
from
$70
per night
5.0 out of 5 stars
29 reviews
9 repeat clients
20 years of experience
Hartland, VT, 05048

Jessica did great with the dogs and keeping me updated! They went on multiple hikes a day and came back to me tired. She was also very understanding and flexible surrounding pick up and drop off times

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Yuki S.
Sitter Profile Image: Greta W.
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Greta W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
75 reviews
23 repeat clients
15 years of experience
Wilmot, NH, 03287

My dog was so happy, it was a perfect fit for him with the outside space and other dogs to play with. Greta was a great communicator as well and really appreciated having Manu there.

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Lawrence W.
Sitter Profile Image: Kevin & Inez W.
Kevin & Inez W.
from
$125
per night
5.0 out of 5 stars
44 reviews
14 repeat clients
40 years of experience
Woodstock, VT, 05091

Kevin was great with our highly energetic dog, Archie! He was very communicative day to day! Archie spent 4 days having the time of his life on the homestead and came home dirty, tired and happy. If we’re ever in the area again, or if we were living there, they would be our go to! Thanks again!

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Robert A.
Sitter Profile Image: Sean L.
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Sean L.
from
$50
per night
12 years of experience
Quechee, VT, 05059

About: Hi my name is Sean. I recently graduated from RIT with a BFA in illustration. I love all animals and currently have a lot of flexibility to care for your pets while I am working from home. I grew up with two labradoodles and I have also cared for friends' animals while they have been away. One of my dogs has Addison's disease, so I am familiar with giving medication to pets. Spending time with animals brings me joy and does not seem like work - I enjoy playing with your animals, going on walks and I give a great belly rub! I am extremely responsible and will love your animals like my own...you might also find some sketches of your pet when you return home. I am an artist that is currently working from home in Quechee. I am extremely flexible and am available during the week and on weekends. I make my own hours so can work around your schedule. I live with my parents and two friendly labradoodles ages 8 and 12. I could board a dog in my home if he/she gets along well with other dogs and is house-trained. I prefer to care for your animals in your own home: I can do drop-in visits, walks and daytime or overnight house-sitting.

Sitter Profile Image: Diana W.
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Diana W.
from
$40
per night
5.0 out of 5 stars
87 reviews
42 repeat clients
10 years of experience
Enfield, NH, 03748

I can’t recommend Diana highly enough! Our dog returned happy & healthy. He clearly had a great time with her (as evident in the frequent updates and his demeanor when we picked him up). Thank you, Diana <3

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Meagan S.
Sitter Profile Image: Melissa L.
Verified Enhanced Background Check
Melissa L.
from
$45
per night
5.0 out of 5 stars
8 reviews
1 repeat client
30 years of experience
springfield, VT, 05156

Mellissa was outstanding! I’m very attached to my sweet Mountain Cur, Sugar Magnolia. Mellissa accommodated me with very short notice and was very gracious and helpful and made the process very easy for me. She sent me daily reports with photographs that made me feel at ease knowing Sugar was happy and being well cared for. She was out on trails every day getting exercise and socializing with other dogs. I would not hesitate to use Mellissa services again and give her the highest recommendation.

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Gerard S.
Sitter Profile Image: Susan & John V.
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Susan & John V.
from
$50
per night
5.0 out of 5 stars
35 reviews
6 repeat clients
40 years of experience
Bradford, NH, 03221

Susan and John took excellent care of Charlotte. They sent regular photos and kept in close contact. When Charlotte ran out of food, Susan went to the pet store to buy her new food so that she would not have to switch to something that she was not used to. Amazingly they let Charlotte up on their bed. Lots of cuddling photos. Charlotte looked happy in every one of them. I was very pleased and would highly recommend them! I am so happy to now have a dog watcher that both Charlotte and I feel confident in! Thank you Sue and John!!!

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Janis S.
Sitter Profile Image: Steve & Keely L.
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Steve & Keely L.
from
$89
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
35 years of experience
Canaan, NH, 03741

Steve is awesome! He’s so nice and really knows his stuff when it comes to dogs. He sent lots of photos and kept us updated throughout the stay, which made me feel great while Mango was with him. Mango had a really good time and came home happy and tired. We’ll definitely be booking with Steve again!

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Robert C.
Sitter Profile Image: Hope R.
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Hope R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
145 reviews
34 repeat clients
30 years of experience
Peru, VT, 05152

Hope is excellent and our first experience on Rover, she exceeded our expectations and gave our dog a loving and caring experience. Our dog stayed with her overnight the week after Christmas. She was very responsive and easy to communicate with. I made a last minute request for care and Hope made the entire process simple. We were from out of town skiing at a nearby resort. Hope was generous with her time and care for our treasured Potato. We will use Hope again when we return for another ski week. I was very happy with our experience and our dog Potato had a great time playing at Hope’s house. We were lucky to find her!

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Meghan J.
Sitter Profile Image: Benjamin & Laura S.
Verified Background Check
Benjamin & Laura S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
47 reviews
13 repeat clients
15 years of experience
Canaan, NH, 03741

Our 4 year old Labradoodle started have anxiety at the kennels we brought him too. We tried Ben and Laura and it was a great experience. Goobah got along great with their beautiful dogs and loved being able to go on the furniture to get comfy. Thank you so much for providing a wonderful home for our buddy while we were away!!! We will definitely book in the future with you.

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kristen d.
Sitter Profile Image: Sarah & Ben A.
Verified Enhanced Background Check
Sarah & Ben A.
from
$60
per night
5.0 out of 5 stars
35 reviews
4 repeat clients
3 years of experience
Woodstock, VT, 05091

We cannot say enough good things about Sarah and Ben! They took amazing care of our girls and we got many updates with pictures and they looked right at home. Their dog Bean is so cute and our girls loved playing with him too! We were so happy knowing our girls were in great hands!!

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Joanna
Sitter Profile Image: Lauren C.
Verified Enhanced Background Check
Lauren C.
from
$65
per night
5.0 out of 5 stars
15 reviews
12 years of experience
Wilmot, NH, 03287

About: I’ve been providing services through Rover since 2024 and worked privately prior to that. I’ve always lived in a household with dogs of all breeds and sizes, and I’ve raised many from puppies through their adult and senior years. I understand that every dog has unique needs at each stage of life and am happy to tailor care specifically for your canine companion. Boarding Details: I have 10 acres of private land with a pond, giving dogs plenty of space to explore and enjoy. Boarding pups are welcomed as part of my pack and family during their stay—I want them to feel just as comfortable as they do at home. We also have a dedicated bedroom, with a crate available if needed, so everyone can have their own space. I can’t wait to connect with you! 🐾 I adventure daily on local trails with my own pups and love planning bigger outings on the weekends. I enjoy including daycare and boarding dogs in our activities when it fits their personality and comfort level, so every pup gets the right mix of exercise and fun. During daycare or boarding stays, dogs receive morning potty breaks and exercise, enrichment or rest during the day, and evening adventures or structured playtime. I keep feeding schedules consistent and make sure everyone has time to settle. I provide regular photo updates and am happy to accommodate special diets, crate preferences, or senior/puppy needs so your dog feels safe and comfortable throughout their stay. I’m available most evenings after 4 PM, with extra flexibility during February and April school vacations. From the end of June through the end of August, when I’m out of school, I’m much more available for weekly let-outs and boarding opportunities if needed. My goal is to keep your pet in their routine as much as possible, so they can be comfortable and things go smoothly! If boarding at our place- dogs have the accessibility to a fenced in yard, several acres of off leash trails explore, a private pond, & 2 friendly pups during their stay!

Sitter Profile Image: Meredith K.
Verified Enhanced Background Check
Meredith K.
Star Sitter
from
$95
per night
5.0 out of 5 stars
36 reviews
10 repeat clients
29 years of experience
Lebanon, NH, 03766

Our pups recently had their second overnight with Meredith. She provides very honest feedback about their stays- the fact is, our pups would rather be with us than away from us. But we know they are safe and well cared for with Meredith. She is kind and consistent with them and we know they will settle in over time. We are very happy to have Meredith care for our dogs.

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Carol S.
Sitter Profile Image: Edgar & Rene G.
Verified Enhanced Background Check
Edgar & Rene G.
from
$45
per night
5.0 out of 5 stars
8 reviews
1 repeat client
5 years of experience
South Strafford, VT, 05070

I could see that my dog was having a good time and was in good hands. Edgar and Rene have two well-trained dogs already and spend plenty of time with them out in their yard. Edgar was always available and replied instantly to messages.

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Ken Steph K.
1 / 1
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Over 41
pet parents in Windsor have booked dog boarding

Windsor dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Cara and her family had me completely at ease from our meet & greet through my dog’s stay. Cara shared photos every day and included notes - allowed me to remain confident in Fiona’s care. Cara is very responsive and excellent with communicating.

Profile image
Linda M.
Boarding
5.0 out of 5 stars

Cara was an excellent dogsitter. She communicated well, sent great photos, and made sure my older dog Cosmo was comfortable. He loved being able to sit on the couch and the bed :) We would definitely have Cosmo return to Cara's again in the future.

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Deirdre D.
Boarding
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  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

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for dog boarding in Windsor is $60

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.

Sitters in Windsor average 11
repeat dog boarding clients

Dog Boarding FAQs

Frequently asked questions about Rover

As of Jun 2026, the median cost of dog boarding in Windsor is $60 per night, including service fees. Boarding your dog for one week typically costs $420. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Windsor dog boarding rates can be found as low as $26 to as high as $77 per night.

If you’re searching for a Windsor 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.

As of Jun 2026, 44 sitters provided dog boarding in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 93% of Windsor dog boarding sitters respond in under an hour.

Dog boarding sitters with repeat customers have an average of 11 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Windsor.

Rover makes it easy to find Windsor 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

There are 44 dog boarding sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

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.