Dog Boarding in Winchester

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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.

1 / 1
Sitter Profile Image: Alexsys T.
Verified Enhanced Background Check
Alexsys T.
Star Sitter
from
$45
per night
5 out of 5.0 stars
135 reviews
57 repeat clients
7 years of experience
Clear Brook, VA, 22624

Alexsys was amazing!!!! She was always so quick to respond and always sent an update each day on how my pup was doing. Sent videos and pictures of all the fun he was having and made it so easy for us to enjoy our trip without worrying about how he was doing. When my kids expressed how much they missed him she even sent extra pictures so they could see how much fun he was having. I would definitely recommend Alexsys and will definitely be using her again :)

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Alexis K.
Sitter Profile Image: Tamara G.
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Tamara G.
from
$50
per night
5 out of 5.0 stars
143 reviews
59 repeat clients
5 years of experience
Middleburg, VA, 20117

Tamara was so sweet, thoughtful, and helpful with our anxious pup. She picked him up, took fantastic care of him, sent plenty of updates during our time away, and brought him home happy and relaxed. She was super accommodating, too, when we needed to change our timing for pickup. We can’t wait to have Tamara watch our little guy again! It’s so nice to find a reliable, kind, easygoing person to watch our dog when needed. Tamara is absolutely awesome!!!

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Bess F.
Sitter Profile Image: Linda E.
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Linda E.
Star Sitter
from
$45
per night
5 out of 5.0 stars
123 reviews
51 repeat clients
40 years of experience
Inwood, WV, 25428

Henry had such a wonderful time with Linda and really enjoyed his time there. Linda was so nice to send us updates throughout the day and pictures. We are so happy to have Linda so close to where we moved and I know Henry is too!

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Rachael L.
Sitter Profile Image: Joshua & Kristen B.
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Joshua & Kristen B.
Star Sitter
from
$45
per night
5 out of 5.0 stars
26 reviews
9 repeat clients
5 years of experience
Stephens City, VA, 22655

Joshua and Kristen are always awesome. They take such good care of my dog as if she were one of theirs. I love the continual photos and updates they provide. I always feel so good/comfortable when they watch Lulu!!

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Rich R.
Sitter Profile Image: Jaclyn S.
Verified Enhanced Background Check
Jaclyn S.
Star Sitter
from
$40
per night
5 out of 5.0 stars
176 reviews
42 repeat clients
6 years of experience
Martinsburg, WV, 25401

We cannot recommend Jaclyn enough! She has always been an amazing caregiver for our pup, treating him like part of her family with love, attention, and plenty of playtime. But what truly sets her apart is her incredible kindness and flexibility. When our flight was unexpectedly canceled at the last minute, Jaclyn didn’t hesitate to extend our pup’s stay for a few extra days, giving us one less thing to stress about. It's rare to find someone so reliable, caring, and genuinely dedicated to both pets and their owners. Our pup always comes back happy, well-cared-for, and loved. If you’re looking for the best, Jaclyn is it! Thank you, Jaclyn! You’re a lifesaver! 🐶❤️

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Jay C.
Sitter Profile Image: Anahita T.
Verified Enhanced Background Check
Anahita T.
Star Sitter
from
$49
per night
5 out of 5.0 stars
62 reviews
17 repeat clients
15 years of experience
Round Hill, VA, 20141

Anahita was great. She met with me ahead of time (conveniently over video) and went over details to make sure my Bruno would be a good fit for her and her smaller dogs. She is experienced and understanding. We needed a bit of flexibility on the drop-off and pickup because of our road trip and she was very accommodating. Thanks Anahita!

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Lauren S.
Sitter Profile Image: Walter G.
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Walter G.
Star Sitter
from
$35
per night
5 out of 5.0 stars
34 reviews
12 repeat clients
20 years of experience
Winchester, VA, 22602

Walter and his family continue to take amazing care of our puppy. When leaving today, she whimpered - that’s a sign of a happy girl! We are so happy to have found this loving family. Thank you again for all that you do to make Harper feel right at home. We look forward to working with you again soon!

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Ali G.
Sitter Profile Image: Joel & Janelle E.
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Joel & Janelle E.
Star Sitter
from
$50
per night
5 out of 5.0 stars
15 reviews
3 repeat clients
28 years of experience
Kearneysville, WV, 25430

Janelle & Joel are absolutely fantastic! This was my first time using Rover, and I am so glad I chose them. They sent pics of my pup having the time of his life! Nothing better than having the peace of mind when leaving your fur baby for a weekend! Thanks you two! Will gladly be a returning client!

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Katie R.
Sitter Profile Image: Barbara D.
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Barbara D.
from
$43
per night
5 out of 5.0 stars
40 reviews
10 repeat clients
24 years of experience
Harpers ferry, VA, 20170

I absolutely made the right choice when booking her. She was great with nug and sent a picture about every day. She and her family loved and spoiled nug

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Kara D.
Sitter Profile Image: Michelle M.
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Michelle M.
Star Sitter
from
$50
per night
5 out of 5.0 stars
16 reviews
9 repeat clients
40 years of experience
Charles Towm, WV, 25414

We always feel reassured that our pup is taken care of and they’re happy to have her. Daisy is treated like the princess she is. I highly recommend their family to watch your beloved pets.

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Christian C.
Sitter Profile Image: Gabby T.
Verified Enhanced Background Check
Gabby T.
Star Sitter
from
$44
per night
5 out of 4.9 stars
45 reviews
10 repeat clients
5 years of experience
clearbrook, VA, 22624

Gabby is awesome! She took such loving care of our dog, offering updates and adorable photos throughout the stay. Came back to a happy and well-cared-for pet. Highly recommend Gabby!

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Jean S.
Sitter Profile Image: Shaghayegh H.
Verified Background Check
Shaghayegh H.
Star Sitter
from
$49
per night
5 out of 5.0 stars
181 reviews
47 repeat clients
15 years of experience
Winchester, VA, 22602

She was great with my 2 huskies. My husband and I received pictures daily. She asked questions with any concerns she had while they stayed with her. We will definitely use her again and refer her to anyone we know who needs a furry baby sitter. Absolutely loved the updates and pictures. Thank you for taking such good care of them

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Mistt R.
Sitter Profile Image: Kalley B.
Verified Enhanced Background Check
Kalley B.
Star Sitter
from
$30
per night
5 out of 5.0 stars
58 reviews
24 repeat clients
25 years of experience
Middletown, VA, 22645

Kalley is an amazing sitter. She took awesome pictures and updated me daily on how my baby was doing. Thank you so much Kalley. We’ll be booking with again soon!

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Stephanie E.
Sitter Profile Image: Katherine B.
Verified Background Check
Katherine B.
Star Sitter
from
$55
per night
5 out of 5.0 stars
117 reviews
64 repeat clients
45 years of experience
Berryville, VA, 22611

It was made apparent how experienced she is. She watched our 4 month old puppy for the weekend, and by the photos and videos she sent he was VERY happy!! Responds quickly and great communication! We definitely plan to use her again the future :)

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Jessica W.
Sitter Profile Image: Yzabella V.
Verified Enhanced Background Check
Yzabella V.
from
$30
per night
5 out of 4.6 stars
10 reviews
2 repeat clients
8 years of experience
Stephens city, VA, 22655

Bella did a phenomenal job watching Luna. We were in need of new overnight boarding arrangements and we hit the jackpot finding her. We organized a meet and greet before our pup stayed with her so Luna was very comfortable coming back to stay for the weekend. We received many videos and pictures updates during her stay.. putting our hearts and minds at ease while we enjoyed our trip our of town. I highly recommend her and we will be rebooking in the near future! Thank you for caring for Luna like your own family!

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Shannon L.
Sitter Profile Image: Jessica I.
Verified Background Check
Jessica I.
Star Sitter
from
$40
per night
5 out of 5.0 stars
29 reviews
8 repeat clients
20 years of experience
Bunker Hill, WV, 25413

We left our dog with Jessica for the weekend. She took great care of her & updated us with pics & videos . We will be booking with her again & highly recommend her !

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Patty D.
Sitter Profile Image: Haejin & Herscel L.
Verified Enhanced Background Check
Haejin & Herscel L.
from
$44
per night
5 out of 5.0 stars
9 reviews
3 repeat clients
6 years of experience
Winchester, VA, 22602

Haejin and Herscel were amazing with my elderly dog and made me feel so much more comfortable while being away from him. The provided detailed updates and you can tell they really care. Highly recommend!

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Rose & Michael B.
Sitter Profile Image: Zachary T.
Verified Enhanced Background Check
Zachary T.
Star Sitter
from
$39
per night
5 out of 5.0 stars
11 reviews
2 repeat clients
10 years of experience
Clear Brook, VA, 22624

Zachary did an amazing job watching my two dogs. He checked in with me everyday and sent photos as well. I really appreciate him taking great care of them!!

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Jaclyn S.
Sitter Profile Image: Lisette R.
Verified Enhanced Background Check
Lisette R.
from
$25
per night
5 out of 5.0 stars
67 reviews
22 repeat clients
6 years of experience
Winchester, VA, 22601

I had to leave on a business and Lisette was able to look after my cat Ogden. Communication was quick and simple, and Lisette was very accommodating . I have no problem recommending this sitter.

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kevin s.
Sitter Profile Image: Katie R.
Verified Enhanced Background Check
Katie R.
from
$55
per night
5 out of 5.0 stars
9 reviews
1 repeat client
20 years of experience
Stephenson, VA, 22656

Katie was an absolute angel for our pups during their stay with her. She stayed on top of their health and wellbeing and kept us well informed. Would 100% use again!

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Rachel R.
1 / 1
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Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

Sitter Profile Image: Alexsys T.
Verified Enhanced Background Check
Sitter Profile Image: Alexsys T.
Verified Enhanced Background Check

Alexsys T.
Star Sitter

Everything for your pet under 1woof
Clear Brook, VA, 22624
3.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
135 reviews
57 repeat clients
Profile image

Alexsys was amazing!!!! She was always so quick to respond and always sent an update each day on how my pup was doing. Sent videos and pictures of all the fun he was having and made it so easy for us to enjoy our trip without worrying about how he was doing. When my kids expressed how much they missed him she even sent extra pictures so they could see how much fun he was having. I would definitely recommend Alexsys and will definitely be using her again :)

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Tamara G.
Verified Background Check
Sitter Profile Image: Tamara G.
Verified Background Check

Tamara G.

FREE PU/DROP-overnights; S/M only
Middleburg, VA, 20117
23.8 mi. away
Boarding, Doggy Day Care
from
$50
per night
5 out of 5.0 stars
143 reviews
59 repeat clients
Profile image

Tamara was so sweet, thoughtful, and helpful with our anxious pup. She picked him up, took fantastic care of him, sent plenty of updates during our time away, and brought him home happy and relaxed. She was super accommodating, too, when we needed to change our timing for pickup. We can’t wait to have Tamara watch our little guy again! It’s so nice to find a reliable, kind, easygoing person to watch our dog when needed. Tamara is absolutely awesome!!!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Linda E.
Verified Enhanced Background Check
Sitter Profile Image: Linda E.
Verified Enhanced Background Check

Linda E.
Rover 101
Star Sitter

I'll love your fur baby for you!!
Inwood, WV, 25428
13.6 mi. away
Boarding, Doggy Day Care
from
$45
per night
5 out of 5.0 stars
123 reviews
51 repeat clients
Profile image

Henry had such a wonderful time with Linda and really enjoyed his time there. Linda was so nice to send us updates throughout the day and pictures. We are so happy to have Linda so close to where we moved and I know Henry is too!

Availability updated 9 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Joshua & Kristen B.
Verified Enhanced Background Check
Sitter Profile Image: Joshua & Kristen B.
Verified Enhanced Background Check

Joshua & Kristen B.
Star Sitter

Dog lovers who want to help out.
Stephens City, VA, 22655
8.2 mi. away
Boarding, Doggy Day Care
from
$45
per night
5 out of 5.0 stars
26 reviews
9 repeat clients
Profile image

Joshua and Kristen are always awesome. They take such good care of my dog as if she were one of theirs. I love the continual photos and updates they provide. I always feel so good/comfortable when they watch Lulu!!

Availability updated today
Sitter Profile Image: Jaclyn S.
Verified Enhanced Background Check
Sitter Profile Image: Jaclyn S.
Verified Enhanced Background Check

Jaclyn S.
Rover 101
Star Sitter

Magickal Paws, loving pet care
Martinsburg, WV, 25401
21.2 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
176 reviews
42 repeat clients
Profile image

We cannot recommend Jaclyn enough! She has always been an amazing caregiver for our pup, treating him like part of her family with love, attention, and plenty of playtime. But what truly sets her apart is her incredible kindness and flexibility. When our flight was unexpectedly canceled at the last minute, Jaclyn didn’t hesitate to extend our pup’s stay for a few extra days, giving us one less thing to stress about. It's rare to find someone so reliable, caring, and genuinely dedicated to both pets and their owners. Our pup always comes back happy, well-cared-for, and loved. If you’re looking for the best, Jaclyn is it! Thank you, Jaclyn! You’re a lifesaver! 🐶❤️

Availability updated today
Sitter Profile Image: Anahita T.
Verified Enhanced Background Check
Sitter Profile Image: Anahita T.
Verified Enhanced Background Check

Anahita T.
Star Sitter

U’r Pet’s BFF. Experts with Heart!
Round Hill, VA, 20141
22.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$49
per night
5 out of 5.0 stars
62 reviews
17 repeat clients
Profile image

Anahita was great. She met with me ahead of time (conveniently over video) and went over details to make sure my Bruno would be a good fit for her and her smaller dogs. She is experienced and understanding. We needed a bit of flexibility on the drop-off and pickup because of our road trip and she was very accommodating. Thanks Anahita!

Availability updated today
Sitter Profile Image: Walter G.
Verified Background Check
Sitter Profile Image: Walter G.
Verified Background Check

Walter G.
Rover 101
Star Sitter

Lots of love, attention and play...
Winchester, VA, 22602
3.5 mi. away
Boarding, Doggy Day Care
from
$35
per night
5 out of 5.0 stars
34 reviews
12 repeat clients
Profile image

Walter and his family continue to take amazing care of our puppy. When leaving today, she whimpered - that’s a sign of a happy girl! We are so happy to have found this loving family. Thank you again for all that you do to make Harper feel right at home. We look forward to working with you again soon!

Availability updated 22 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Joel & Janelle E.
Verified Enhanced Background Check
Sitter Profile Image: Joel & Janelle E.
Verified Enhanced Background Check

Joel & Janelle E.
Star Sitter

WE CAN'T WAIT TO MEET YOUR FURRY BF
Kearneysville, WV, 25430
18.5 mi. away
Boarding
from
$50
per night
5 out of 5.0 stars
15 reviews
3 repeat clients
Profile image

Janelle & Joel are absolutely fantastic! This was my first time using Rover, and I am so glad I chose them. They sent pics of my pup having the time of his life! Nothing better than having the peace of mind when leaving your fur baby for a weekend! Thanks you two! Will gladly be a returning client!

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Barbara D.
Verified Enhanced Background Check
Sitter Profile Image: Barbara D.
Verified Enhanced Background Check

Barbara D.
Rover 101

Animal lover with vast experience
Harpers ferry, VA, 20170
19.7 mi. away
Boarding, Doggy Day Care
from
$43
per night
5 out of 5.0 stars
40 reviews
10 repeat clients
Profile image

I absolutely made the right choice when booking her. She was great with nug and sent a picture about every day. She and her family loved and spoiled nug

Availability updated 9 days ago
Sitter Profile Image: Michelle M.
Verified Enhanced Background Check
Sitter Profile Image: Michelle M.
Verified Enhanced Background Check

Michelle M.
Star Sitter

Cat and Dog friendly house for boar
Charles Towm, WV, 25414
15.4 mi. away
Boarding
from
$50
per night
5 out of 5.0 stars
16 reviews
9 repeat clients
Profile image

We always feel reassured that our pup is taken care of and they’re happy to have her. Daisy is treated like the princess she is. I highly recommend their family to watch your beloved pets.

Availability updated 8 days ago
Sitter Profile Image: Gabby T.
Verified Enhanced Background Check
Sitter Profile Image: Gabby T.
Verified Enhanced Background Check

Gabby T.
Star Sitter

where the tails never stop wagging!
clearbrook, VA, 22624
6.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$44
per night
5 out of 4.9 stars
45 reviews
10 repeat clients
Profile image

Gabby is awesome! She took such loving care of our dog, offering updates and adorable photos throughout the stay. Came back to a happy and well-cared-for pet. Highly recommend Gabby!

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Shaghayegh H.
Verified Background Check
Sitter Profile Image: Shaghayegh H.
Verified Background Check

Shaghayegh H.
Rover 101
Star Sitter

Your bestie will have lots of FUN
Winchester, VA, 22602
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$49
per night
5 out of 5.0 stars
181 reviews
47 repeat clients
Profile image

She was great with my 2 huskies. My husband and I received pictures daily. She asked questions with any concerns she had while they stayed with her. We will definitely use her again and refer her to anyone we know who needs a furry baby sitter. Absolutely loved the updates and pictures. Thank you for taking such good care of them

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kalley B.
Verified Enhanced Background Check
Sitter Profile Image: Kalley B.
Verified Enhanced Background Check

Kalley B.
Star Sitter

They'll never know you were gone!
Middletown, VA, 22645
11.9 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
58 reviews
24 repeat clients
Profile image

Kalley is an amazing sitter. She took awesome pictures and updated me daily on how my baby was doing. Thank you so much Kalley. We’ll be booking with again soon!

Availability updated today
Sitter Profile Image: Katherine B.
Verified Background Check
Sitter Profile Image: Katherine B.
Verified Background Check

Katherine B.
Star Sitter

Secure outdoor play to puppy pile!
Berryville, VA, 22611
11.8 mi. away
Boarding, Doggy Day Care
from
$55
per night
5 out of 5.0 stars
117 reviews
64 repeat clients
Profile image

It was made apparent how experienced she is. She watched our 4 month old puppy for the weekend, and by the photos and videos she sent he was VERY happy!! Responds quickly and great communication! We definitely plan to use her again the future :)

Availability updated 15 days ago
Sitter Profile Image: Yzabella V.
Verified Enhanced Background Check
Sitter Profile Image: Yzabella V.
Verified Enhanced Background Check

Yzabella V.

Eat, Play, BellyRub, Sleep, REPEAT
Stephens city, VA, 22655
6.4 mi. away
Boarding, Doggy Day Care
from
$30
per night
5 out of 4.6 stars
10 reviews
2 repeat clients
Profile image

Bella did a phenomenal job watching Luna. We were in need of new overnight boarding arrangements and we hit the jackpot finding her. We organized a meet and greet before our pup stayed with her so Luna was very comfortable coming back to stay for the weekend. We received many videos and pictures updates during her stay.. putting our hearts and minds at ease while we enjoyed our trip our of town. I highly recommend her and we will be rebooking in the near future! Thank you for caring for Luna like your own family!

Availability updated 53 days ago
Sitter Profile Image: Jessica I.
Verified Background Check
Sitter Profile Image: Jessica I.
Verified Background Check

Jessica I.
Star Sitter

Home full time - large fenced yard
Bunker Hill, WV, 25413
10.9 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
29 reviews
8 repeat clients
Profile image

We left our dog with Jessica for the weekend. She took great care of her & updated us with pics & videos . We will be booking with her again & highly recommend her !

Availability updated today
Sitter Profile Image: Haejin & Herscel L.
Verified Enhanced Background Check
Sitter Profile Image: Haejin & Herscel L.
Verified Enhanced Background Check

Haejin & Herscel L.

The Hooman Hotel 🐕🐈
Winchester, VA, 22602
3.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$44
per night
5 out of 5.0 stars
9 reviews
3 repeat clients
Profile image

Haejin and Herscel were amazing with my elderly dog and made me feel so much more comfortable while being away from him. The provided detailed updates and you can tell they really care. Highly recommend!

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Zachary T.
Verified Enhanced Background Check
Sitter Profile Image: Zachary T.
Verified Enhanced Background Check

Zachary T.
Star Sitter

Let your companion have a vacation!
Clear Brook, VA, 22624
6.4 mi. away
Boarding, Doggy Day Care
from
$39
per night
5 out of 5.0 stars
11 reviews
2 repeat clients
Profile image

Zachary did an amazing job watching my two dogs. He checked in with me everyday and sent photos as well. I really appreciate him taking great care of them!!

Availability updated yesterday
Sitter Profile Image: Lisette R.
Verified Enhanced Background Check
Sitter Profile Image: Lisette R.
Verified Enhanced Background Check

Lisette R.

💓🐶💓
Winchester, VA, 22601
1.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per night
5 out of 5.0 stars
67 reviews
22 repeat clients
Profile image

I had to leave on a business and Lisette was able to look after my cat Ogden. Communication was quick and simple, and Lisette was very accommodating . I have no problem recommending this sitter.

Availability updated 3 days ago
Sitter Profile Image: Katie R.
Verified Enhanced Background Check
Sitter Profile Image: Katie R.
Verified Enhanced Background Check

Katie R.

Caring, attentive and experienced
Stephenson, VA, 22656
3.3 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
9 reviews
1 repeat client
Profile image

Katie was an absolute angel for our pups during their stay with her. She stayed on top of their health and wellbeing and kept us well informed. Would 100% use again!

Availability updated 3 days ago
Confirmed availability for Labor Day Weekend

Over 940 pet parents in Winchester have booked dog boarding

Winchester dog parents share their Rover experiences

1 / 1
5 out of 5.0 stars

I was so nervous to leave our little fur baby with someone other than family but Nyla immediately bonded with Allison and her beautiful family! I could tell she would feel comfortable being there and that was most important. During our time away, Allison sent pictures and she was very communicative in person and afterward. This was Nyla’s first time being around kids and Allison said she was great around them. We would definitely book her again or even drop Nyla off for doggy daycare so she can become more comfortable with Allison and her family for future drop offs. When we picked her up she seemed just as happy than when she did her meet and greet!

Profile image
Bianca G.
Dog Boarding
1 / 1
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  1. 1. Search

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  2. 2. Meet & Greet

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  3. 3. Book & Pay

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The median cost per night for dog boarding in Winchester is $45

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    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.

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

Sitters in Winchester average 14 repeat dog boarding clients

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