Dog Boarding Windsor

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Windsor, Find top rated dog boarding

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

1 / 1
Sitter Profile Image: Michelle T.
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Michelle T.
Star Sitter
from
$40
per night
5.0 out of 5 stars
52 reviews
15 repeat clients
10 years of experience
Randolph, Richmond, VA, 23220

Michelle always does a great job sitting my dog. I had a last minute trip planned and she was able to accommodate. I even had a delayed trip back home and she was very flexible which I appreciated.

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Chelsy H.
Sitter Profile Image: Aaren & Jordon D.
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Aaren & Jordon D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
24 reviews
6 repeat clients
6 years of experience
Swansboro, Richmond, VA, 23224

Grateful to have found Aaren and Jordon. I felt comfortable trusting our boy with them the moment we met. We appreciated the great communication and the pictures/updates we received during Apollo‘s stay. Plus he got plenty of walking in so we know he loved that. Will be rebooking when that time comes. Thanks guys!

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Kila
Sitter Profile Image: Michaela Z.
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Michaela Z.
from
$45
per night
5.0 out of 5 stars
26 reviews
14 repeat clients
5 years of experience
Upper Shockoe Valley, Richmond, VA, 23223

Michaela was AMAZING! So sweet and attentive to Violet, and sent lots of updates and pictures throughout the stay, which gave us so much peace of mind. She administered Violet’s medications and special food three times a day with no issues and made everything feel effortless. Michaela was also very easy to schedule with and super responsive with communication. We’re so grateful to have found her and will definitely be booking with her again!

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Kayla E.
Sitter Profile Image: Raye J.
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Raye J.
from
$46
per night
5.0 out of 5 stars
207 reviews
89 repeat clients
7 years of experience
Oakwood, Richmond, VA, 23223

Raye is a wonderful person and was soooo caring and sweet with my shy girl. She gave her loads of snuggles and attention and sent multiple updates each day via photo and videos. So grateful to her!!!

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Sarah W.
Sitter Profile Image: Matt M.
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Matt M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
278 reviews
85 repeat clients
25 years of experience
Northern Barton Heights, Richmond, VA, 23222

Kingsley had a fantastic stay at Matt's place. Matt updated us often with photos and details of his attitude and comportment, and it was clear our dog was having fun. He seemed to get a good mix of play and rest time and we knew he was in good hands. We'll definitely be back!

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Jill W.
Sitter Profile Image: Hilary R.
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Hilary R.
Star Sitter
from
$38
per night
5.0 out of 5 stars
218 reviews
74 repeat clients
20 years of experience
Reedy Creek, RICHMOND, VA, 23225

Hilary and Wally are great. They are super easy to communicate with, and when our plans are not definite they work with us on pick up and drop off times. They have a fenced in back yard, and our dog loves it there. Hilary is also great about sending pictures during his stay.

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Emily W.
Sitter Profile Image: Ross & Ava T.
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Ross & Ava T.
from
$38
per night
5.0 out of 5 stars
79 reviews
19 repeat clients
16 years of experience
Blackwell, Richmond, VA, 23224

Alice came home from a long stay happy, relaxed, and waggy. Grateful to Ross and Ava for their thoughtful care, communication, flexibility, and laid back orientation. We (and by we, I do mean Alice…) will be back!

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Zoe & David C.
Sitter Profile Image: Miguel A.
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Miguel A.
Star Sitter
from
$40
per night
5.0 out of 5 stars
43 reviews
11 repeat clients
7 years of experience
Henrico, VA, 23231

Miguel and his wife were absolutely incredible! From the moment I connected with them, I could tell how genuinely kind, warm, and caring they are. My flight was delayed by four hours, and without hesitation they adjusted their schedule to accommodate me, which meant more than I can express. This was my very first time ever leaving my puppy alone, so I was naturally anxious and emotional, but they completely put my heart at ease. They sent frequent updates, photos, and sweet messages about how my puppy was doing, allowing me to truly relax and enjoy a peaceful, worry-free vacation. It was so comforting to see how loved, safe, and happy my pup was in their care — they truly treat the dogs as if they were their own. I am beyond grateful for the patience, flexibility, and genuine love they showed, and I trust them wholeheartedly. I will absolutely be using them again and highly, highly recommend them to anyone looking for exceptional care! 🐾💕

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Jordan H.
Sitter Profile Image: Myrna C.
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Myrna C.
Star Sitter
from
$41
per night
5.0 out of 5 stars
63 reviews
33 repeat clients
40 years of experience
Oakwood, Richmond, VA, 23223

I cant say enough good things about Myrna. She took exceptional care of my senior pup and went above and beyond to make him feel safe, comfortable, and loved during his stay. My dog has some incontinence issues and can be very attached to his people. Myrna was incredibly understanding, accomidating, and patient with his special needs. Thank you!

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yelena p.
Sitter Profile Image: Julie W.
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Julie W.
Star Sitter
from
$48
per night
5.0 out of 5 stars
76 reviews
14 repeat clients
30 years of experience
Carillon, Richmond, VA, 23221

They were fantastic! They provided loving care, daily photo updates, and fun activities that left my pup exhausted and happy. 5 stars—will book again!

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Justin H.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$28
per night
5.0 out of 5 stars
321 reviews
88 repeat clients
30 years of experience
North Chesterfield, VA, 23236

Damacia is was amazing! I found him on Rover after reading through several reviews, and I’m so glad I chose him. He was very responsive and stayed in touch throughout my entire time away, including sending pictures and videos. My dog, Jaxson, has never been around other dogs before, so I know this was a new experience for him but based on the updates I received, he did great. Damacia made me feel completely at ease, and I now have a dog sitter I truly trust to care for Jaxson while I’m away. Highly recommend 🐾✨

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M T.
Sitter Profile Image: Kendra B.
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Kendra B.
Star Sitter
from
$25
per night
5.0 out of 5 stars
44 reviews
12 repeat clients
25 years of experience
North Chesterfield, VA, 23237

Kendra is a excellent sitter. She provided great care for our fur baby. Lots of detailed updates and pictures. I could tell he really enjoyed himself.

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Shavis C.
Sitter Profile Image: Shannon O.
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Shannon O.
from
$36
per night
5.0 out of 5 stars
56 reviews
26 repeat clients
20 years of experience
Richmond, VA, 23234

Shannon is personable and professional. She followed our instructions, gave us updates with photos. And most importantly returned a happy, healthy pup when we got back from our trip. We will be back.

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Jim M.
Sitter Profile Image: Jesse D.
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Jesse D.
from
$45
per night
5.0 out of 5 stars
53 reviews
18 repeat clients
32 years of experience
Henrico, VA, 23228

Jesse was so sweet and enthusiastic about watching Ripley on short notice over the Christmas holiday. Lots of walks, attention, and hanging with other hounds…she loved being a part of his pack. 😊

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Jasmine P.
Sitter Profile Image: Elizabeth H.
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Elizabeth H.
from
$35
per night
5.0 out of 5 stars
12 reviews
20 years of experience
Westlake Hills, Richmond, VA, 23225

Libby was great! Very accommodating and communicative.

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Tyler T.
Sitter Profile Image: Tiffany B.
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Tiffany B.
Star Sitter
from
$49
per night
5.0 out of 5 stars
18 reviews
7 repeat clients
20 years of experience
Swansboro, Richmond, VA, 23225

Tiffany was awesome, she took Roxie very last minute with open arms. She sent me pictures throughout the duration & kept me updated. I felt very comfortable & will definitely be back.

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Tana J.
Sitter Profile Image: Deven & Tyreek C.
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Deven & Tyreek C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
27 reviews
14 repeat clients
15 years of experience
North Chestefield, VA, 23237

Deven and Tyreek were amazing! They took great care of my dog and kept me updated with photos. You can tell they really love animals — my dog was happy and comfortable the whole time. I’ll definitely book with them again!

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Mekira J.
Sitter Profile Image: Stacey M.
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Stacey M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
13 years of experience
Fulton, Richmond, VA, 23231

My dogs are family to me, so I'm always nervous leaving them somewhere new. No worries needed though, Stacey was great! We had a meet and greet to ensure our dogs got along, and I was able to meet her at her home in advance to see where my dogs would be staying. She asked thoughtful questions about my dogs' needs and made sure I had peace of mind while I was on my trip. She has a fully fenced in yard which was great for my younger, high energy dog to run laps around the house and get her energy out. My dogs have a somewhat significant age range - one is 1.5 years old and the other is 8.5, and she was able to cater to both of their activity levels to make sure they had a fulfilling experience. We will definitely work with Stacey again the next time we need dog care!

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Kim H.
Sitter Profile Image: Triston N.
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Triston N.
from
$30
per night
10 years of experience
Fulton, Richmond, VA, 23231

About: For the last 5 years, I've been volunteering care for a herd of goats on Gillie's Creek Park. I am also the primary farm sitter for several friends' homesteads and a frequent pet sitter for friends and acquaintances. I have a broad range of experience: handling elderly animal care, newborn feeding/monitoring, pet anxiety, unique medication/feeding schedules, and general care for most farm/domesticated animals. I have a deep love for animals and their welfare with a desire to assist you and your pet in any way possible. I'm currently working part-time with a very flexible schedule. Typically not away from home for more than 3 hours at a time during marked available hours. My schedule can be adjustable if coordinating in advance. If caring in your home, I ensure that all items are back where they were originally left and that all feeding bowls and areas accessed are cleaned and organized. My home has a fenced-in yard, plenty of plants, natural lighting, and no other pets to contend for attention or food.

Sitter Profile Image: angelica s.
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angelica s.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
16 years of experience
Brookhaven Farms, Richmond, VA, 23224

Can’t recommend Angelica enough! She took amazing care of my brand new three-month-old puppy and he definitely loved every minute. She’s super responsive and responsible and was dialed in on every detail, plus sent frequent detailed updates, which I loved. She’ll be my go-to forever!

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Damon T.
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The median cost per night for dog boarding in Windsor is $45

Dog parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

Ashley came through with a last minute request for our puppy. Really appreciate the communication before and during the stay, and pics! Our puppy had some particular needs (as all puppies do) and she took really good care of her. Thanks so much Ashley!!!

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Amzi J.
Boarding
5.0 out of 5 stars

Hilary and family were great! Nice yard/house, lots of pictures, and my dogs were well taken care of. I would book with her again.

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Sarah W.
Boarding
5.0 out of 5 stars

Morgan has taken care of my pup multiple times now, and each time she comes back very happy and healthy. Morgan is kind, responsible, trustworthy, and provides so many updates! I would 100% ask her to watch my pup in the future.

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Lindsay M.
Boarding
5.0 out of 5 stars

Noel was amazing to work with! She responded quickly after a rover cancelled. We got a quick meet in and greet in and it was perfect! Her home has a nice back yard and her and her boyfriend provided so much love and attention! Great people and a beautiful home, can’t recommend enough.

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Joshua K.
Boarding
5.0 out of 5 stars

Even though there was no meet and greet jasmine was perfect with honey. I’m happy she was able to take my request last minute and she took cute pictures of my girl :) overall great sitter and provides constant updates.

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Patricia L.
Boarding
5.0 out of 5 stars

Chris is the best!! He bought balls to throw with my dog, always takes her on walks, and is so kind to her.

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Lindsay P.
Boarding
5.0 out of 5 stars

Gaelle took wonderful care of Oakland while I was away! Oakland was feeling a bit under the weather from anxiety leading up to my trip, and Gaelle was incredibly attentive, keeping a close eye on her and sending regular updates and photos that gave me so much peace of mind. Thankfully, Oakland's stomach settled, and it was clear she was in great hands throughout her stay. I really appreciated the care, communication, and kindness Gaelle showed. I wouldn't hesitate to book with her again and would absolutely recommend her to anyone looking for a trustworthy sitter!

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Brittney R.
Boarding
5.0 out of 5 stars

I cant say enough good things about Myrna. She took exceptional care of my senior pup and went above and beyond to make him feel safe, comfortable, and loved during his stay. My dog has some incontinence issues and can be very attached to his people. Myrna was incredibly understanding, accomidating, and patient with his special needs. Thank you!

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yelena p.
Boarding
5.0 out of 5 stars

Raye took excellent care of our senior dog and sent regular photo and video updates during her stay. She is a delightful person and we highly recommend her to care for your fur babies.

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Patricia V.
Boarding
5.0 out of 5 stars

Veggie had a great time and was taken good care of by Kristine for a week when I was on vacation. Kristine was responsive and sent me pictures of Veggie when I missed her.

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Yang X.
Boarding
5.0 out of 5 stars

Emily was excellent! She sent me daily updates, pictures, and was super patient and accommodating for meeting Bennys needs! Would 100% use her services again! I felt at ease knowing she was caring for Benny like one of her own

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Abby G.
Boarding
5.0 out of 5 stars

Dani was wonderful and communicated perfectly throughout my dogs stay with her. I will definitely book with her again!

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Jimmy A.
Boarding
5.0 out of 5 stars

Booked last minute with Tiffany B. she accepted my Pup and also taught her some manners In the process lol. Overall experience was great, I will definitely be rebooking.

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Jason K.
Boarding
5.0 out of 5 stars

Ross and Ava are fabulous sitters! This was my dog’s first time staying with them and their sweet dog, George, and I was wondering if Reggie would want to come home with me after being taken care of so well! 😊 Ross & Ava were great with providing updates and also being mindful of the heat for walks. Finding a sitter can be such a stressful process but Ross & Ava were great with coordinating a meet and greet beforehand and putting my mind at ease. Your pet will be in great hands!

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Andrea M.
Boarding
5.0 out of 5 stars

Allison is the best! This is the second time we’ve used her and she’s nothing short of wonderful. She lives on our baby like they’re her own and she updated us so consistently that we felt like he was with us. I’ve used sooo many dogsitters in the past having had dogs my whole life & none compare to her level of service !

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Madison R.
Boarding
5.0 out of 5 stars

Zach was great! He made sure Hank got plenty of love and exercise! Hank’s extra needy but they seemed to have a great time. Thank you!

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Savannah L.
Boarding
5.0 out of 5 stars

Lilly took good care of Luca! She texted me with updates and photos every day. Highly recommend Lilly! !

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Deborah R.
Boarding
5.0 out of 5 stars

We are so grateful for all the love Aaren & Jordon gave to Dexter while we were out of town! They treated Dex like he was their own and we feel so lucky to have found them. 10/10 recommend!!

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Jen R.
Boarding
5.0 out of 5 stars

Kaitlyn is a great sitter! Cash loved her and felt right at home with her. She sent me lots of pictures and was responsive when I wanted to check in. I will book her again!

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Brittney H.
Boarding
5.0 out of 5 stars

Christine was Great! Franci had smiles on all of her pictures and seemed to have a lot of fun! Thanks Christine!

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Sandra F.
Boarding
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