Dog Boarding in Wintergreen, VA

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Top rated Wintergreen 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: Kathryn H.
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Kathryn H.
Star Sitter
from
$27
per night
5.0 out of 5 stars
23 reviews
13 repeat clients
20 years of experience
Stuarts Draft, VA, 24477

Kathryn was a WONDERFUL pet sitter for our little English bulldog, Daisy. She kept in touch with us and sent updates. We could tell Daisy really enjoyed her stay! Thank you, Kathryn!!!

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Patricia S.
Sitter Profile Image: Amy H.
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Amy H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
106 reviews
26 repeat clients
21 years of experience
Faber, VA, 22938

Amy did an amazing job taking care of our Luna! She did a great job communicating updates with plenty of pictures and videos. Luna got to go on hikes and became best friends with Amy’s sweet dog, Sylvie too! Amy had great attention to detail- Luna is a poodle so we always pack a brush in case it’s needed, but have no specific expectations with it, since it’s definitely labor of love! Amy is the first Rover sitter to actually brush her! We would highly recommend Amy to anyone looking to board their pup!

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Shannon A.
Sitter Profile Image: Sophia S.
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Sophia S.
from
$35
per night
5.0 out of 5 stars
16 reviews
2 repeat clients
20 years of experience
Stuarts Draft, VA, 24477

I cannot recommend her enough! She watched Otis for 2 nights and treated him like he was her own. From the moment I dropped him off, I felt completely at ease. She was so kind, communicative, and thoughtful throughout the entire stay. She sent me lots of updates and photos, which meant so much and made being away from my boy so much easier. You could genuinely tell how much love and attention he was getting the whole time. He came home happy, comfortable, and clearly very well cared for. If you’re looking for someone trustworthy, attentive, and truly loving with animals, she is absolutely the person to book. I would 100% use her again!

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Ashley S.
Sitter Profile Image: Hillary D.
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Hillary D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
109 reviews
26 repeat clients
5 years of experience
Crozet, VA, 22932

Hillary provided updates including photos and videos of my pup Daisy at a cadence that kept me worry free but was not excessive. Daisy came home happy and looked well cared for. Will definitely be a repeat customer.

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Daniel B.
Sitter Profile Image: Nadia G.
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Nadia G.
from
$45
per night
5.0 out of 5 stars
26 reviews
3 repeat clients
25 years of experience
Schuyler, VA, 22969

Our family was going through a really tough time and Nadia came to our rescue! She treated our puppy like her baby and provided updates and pictures multiple times a day which made us feel so safe and secure. She even made scarves and necklaces for our sweet pup and made her feel like a princess. We had an issue come up where we needed to schedule extra days and she was so kind and accommodating. Our puppy was so sad to leave her. I’d recommend Nadia to anybody and everybody and I can’t wait to be able to book with her again in the future. She’s now my puppy’s godmother😅 and she’ll always be my go-to.

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Mollie H.
Sitter Profile Image: Bertie & Lissette A.
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Bertie & Lissette A.
Star Sitter
from
$45
per night
5.0 out of 5 stars
83 reviews
33 repeat clients
16 years of experience
Charlottesville, VA, 22911

Lissette and Bernie were super communicative and sent us lots of photos of Pebbles playing, walking and relaxing on her stay! It was our first time leaving her with a sitter while we traveled, and we felt very at ease leaving her with them, especially with her being a puppy!

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Lauren M.
Sitter Profile Image: Deb K.
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Deb K.
Star Sitter
from
$30
per night
5.0 out of 5 stars
83 reviews
28 repeat clients
33 years of experience
Staunton, VA, 24401

Deb and Ralph are amazing! They welcomed my boys with open arms and spent quality time with them. This was the first time my boys were away from home while I was away and it looked like they had a great time.

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Sheryll M.
Sitter Profile Image: Basil V.
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Basil V.
from
$32
per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Shipman, VA, 22971

Basil was great with our 10 month old puppy! Very attentive and caring, and communicated with us when our dog seemed to not be doing well. Our dog returned home happy and healthy. We would definitely recommend Basil for pet sitting.

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Amanda H.
Sitter Profile Image: Casey L.
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Casey L.
Star Sitter
from
$37
per night
5.0 out of 5 stars
122 reviews
44 repeat clients
11 years of experience
Amherst, VA, 24521

Casey did a wonderful job with our 2 pups. She was thorough in her care for them and send us a couple photos and an update every evening which was so welcomed. It was our first time leaving our pups with someone we didn’t know, but Casey helped us be right at ease and we got to enjoy our vacation knowing they were in great care. Her kiddos left us some really sweet notes in their go-bag as well, which was delightful to read when we got home and unpacked.

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Clarine F.
Sitter Profile Image: Jani & Paul R.
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Jani & Paul R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
149 reviews
36 repeat clients
30 years of experience
Crozet, VA, 22932

First time Rover user and am so happy. Dogs well taken care of. hosts were lovely people who really made the difference. they sent lots of photos and could tell dogs happy and well cared for in a lovely home. highly recommend.

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Lou B.
Sitter Profile Image: Jesse & Emily H.
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Jesse & Emily H.
Star Sitter
from
$44
per night
5.0 out of 5 stars
46 reviews
17 repeat clients
20 years of experience
Charlottesville, VA, 22902

Jesse and Emily were fantastic with Kimber. Great communication with me and all the love and spoiling for Kimber. I love how they made her part of their family for the long weekend!

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Daniel B.
Sitter Profile Image: Gretchen R.
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Gretchen R.
from
$26
per night
5.0 out of 5 stars
6 reviews
1 repeat client
50 years of experience
Nellysford, VA, 22958

Gretchen was incredibly responsive, supportive, & communicative — especially for a last-minute request. If I’m in the area again and need a dog sitter, I will definitely reach out; the care from her community of neighbors was incredible! I particularly appreciated their transparency & consideration for Bugs’ needs.

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Aimee S.
Sitter Profile Image: Heather W.
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Heather W.
from
$60
per night
5.0 out of 5 stars
18 reviews
6 repeat clients
2 years of experience
Crozet, VA, 22932

Heather always takes great care of our girl!

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Tonya W.
Sitter Profile Image: Cory P.
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Cory P.
Star Sitter
from
$70
per night
5.0 out of 5 stars
108 reviews
19 repeat clients
30 years of experience
Crozet, VA, 22932

Cory saved the day by taking Gizmo in ! He was caring, attentive and went beyond the call of duty to wear Gizmo out and relax in their beautiful home in Crozet. The mountain property is Lovely and close enough to town . So grateful to Cory for helping me out last minute and with great care and generosity go Gizmo’s never ending desire to play and play some more . Kudos to Cory and his family for making Gizmo one of their family .

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Gretchen R.
Sitter Profile Image: Margaret M.
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Margaret M.
from
$39
per night
5.0 out of 5 stars
8 reviews
35 years of experience
Lyndhurst, VA, 22952

Margaret was wonderful! She took great care of my senior girl and gave her the love and attention she needed while I was away. She was easy to communicate with and provided pictures. I’d definitely book with Margaret again the next time I’m in the area!

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Abbey H.
Sitter Profile Image: Alexandra & Logan M.
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Alexandra & Logan M.
from
$60
per night
5.0 out of 5 stars
5 reviews
1 repeat client
15 years of experience
Charlottesville, VA, 22903

Alexandra and Logan were wonderful with my (sometimes overly) curious terrier, Eddie! I am always concerned about Eddie escaping to chase an animal, and they took my concerns seriously and took steps to ensure that wouldn't happen. Their fence setup was great too - the fenced-in yard wraps all the way around the house, so even if a dog slipped out of the house, they would still be in the yard. On top of that, they sent lots of pictures and were so kind to Eddie. He didn't want to leave!

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Stephanie B.
Sitter Profile Image: Svitlana F.
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Svitlana F.
Star Sitter
from
$40
per night
5.0 out of 5 stars
102 reviews
32 repeat clients
30 years of experience
Charlottesville, VA, 22901

Svitlana really knows dogs. She walked my dog and sent pics and got to know her quirks quickly. Svitlana also continued with the same house rules we use at home. I will definitely have Pi stay with her again!

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Julia M.
Sitter Profile Image: Paula C.
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Paula C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
183 reviews
49 repeat clients
25 years of experience
Charlottesville, VA, 22911

Paula is absolutely amazing! She is very responsive and provided a loving, comfortable home for my boy Archie. Her expertise and passion for dogs made me feel at ease knowing my fur baby was in a safe and caring environment. I highly recommend Paula to anyone looking for a top notch doggy sitter and will absolutely book her again.

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Britny P.
Sitter Profile Image: Tiffanie F.
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Tiffanie F.
Star Sitter
from
$45
per night
5.0 out of 5 stars
26 reviews
7 repeat clients
30 years of experience
Waynesboro, VA, 22980

This was our second time leaving the pups with Tiffanie, she is fantastic! She is great with sending photos and keeping us up to date on their activities and adventures.

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Ieva J.
Sitter Profile Image: Caitlynn M.
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Caitlynn M.
from
$40
per night
4.9 out of 5 stars
40 reviews
7 repeat clients
24 years of experience
Waynesboro, VA, 22980

Caitlynn took wonderful care of my 2 babies for 5 days. She is attentive, detailed, and gave them love and lots of exercise. I received many videos, pictures, and updates on how they were doing. Do not hesitate to choose Caitlynn as the caretaker for your furry family members.

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Erin K.
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Wintergreen dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Gretchen was incredibly responsive, supportive, & communicative — especially for a last-minute request. If I’m in the area again and need a dog sitter, I will definitely reach out; the care from her community of neighbors was incredible! I particularly appreciated their transparency & consideration for Bugs’ needs.

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Aimee S.
Boarding
5.0 out of 5 stars

Rose was great! She took great care of our dog and sent updates, giving us peace of mind while we were on a family vacation. Highly recommend Rose!

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Jacqueline R.
Boarding
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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!

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 Wintergreen 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 Wintergreen.

Rover makes it easy to find Wintergreen 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.