Dog Boarding Woolford

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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.

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Sitter Profile Image: Johanna T.
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Johanna T.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 18 reviews
3 repeat clients
15 years of experience
Cambridge, MD, 21613

“Great dog sitter and took wonderful care of my pups Moe and Bear. She worked so hard and even went above and beyond writing down the medication schedule for our pups!!! Thank you so much Johanna!!”

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Lauren B.
Sitter Profile Image: Lori W.
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Lori W.
from
$45
per night
5.0 out of 5 stars
• 79 reviews
31 repeat clients
20 years of experience
Chesapeake Beach, MD, 20732

“Lori is always amazing! We love having our dog stay with her when we can’t take him with us. We always know he will be well loved and taken care of!”

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Emily D.
Sitter Profile Image: Vy L.
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Vy L.
Star Sitter
from
$65
per night
5.0 out of 5 stars
• 24 reviews
10 repeat clients
15 years of experience
Easton, MD, 21601

“V was very easy to work with and accommodating with watching my dog on such short notice, sent me daily photo updates. Took great care of my dog”

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Jason S.
Sitter Profile Image: Kerri L.
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Kerri L.
from
$50
per night
5.0 out of 5 stars
• 13 reviews
6 repeat clients
20 years of experience
Lusby, MD, 20657

“Kerry and her family took amazing care of my dog Briggs while I was out of town. I got loads of adorable pictures, and he was returned groomed and fluffy with a new bandana. I highly recommend them and will be reaching out again when I travel.”

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Angela K.
Sitter Profile Image: Linda W.
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Linda W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 127 reviews
47 repeat clients
20 years of experience
Lexington-Park, MD, 20653

“She’s the best ! I had a last minute family situation and she was able to accommodate getting my dog later in the evening and kept her longer than expected! Thank you !”

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Lacey W.
Sitter Profile Image: Melissa B.
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Melissa B.
from
$50
per night
5.0 out of 5 stars
• 41 reviews
18 repeat clients
10 years of experience
Lexington Park, MD, 20653

“Thank you Melissa! Max and Ringo had a great stay with you. They loved your fenced and shaded backyard and appreciated splashing in the doggie pool. It was the perfect environment!”

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Andrew And Ann D.
Sitter Profile Image: Christianna & Mary & Miriam-Ellen B.
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Christianna & Mary & Miriam-Ellen B.
Star Sitter
from
$38
per night
5.0 out of 5 stars
• 107 reviews
38 repeat clients
25 years of experience
Lexington Park, MD, 20653

“Christianna is absolutely wonderful and has been an incredible dog sitter for us over the years. She’s extremely flexible, easy to work with, and clearly cares deeply about the dogs she watches. Our dogs are always so well taken care of with her, and she even celebrated their birthdays while they were staying with her, which meant so much to us. I also accidentally had the wrong dates for our booking, and she went out of her way to accommodate us and take them earlier than planned. We feel very lucky to have found her and trust her completely with our dogs. We would highly recommend! 🐾”

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Heidi C.
Sitter Profile Image: Faith M.
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Faith M.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 22 reviews
8 repeat clients
2 years of experience
Chesapeake Beach, MD, 20732

“Faith is very prompt at responding to requests and questions. She provides photos and my dog runs right into Faith's house when we drop her off. I think Faith spoils our pup, which is great because our doggie is a senior :)”

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Meghann O.
Sitter Profile Image: Amber M.
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Amber M.
from
$50
per night
4.4 out of 5 stars
• 9 reviews
10 years of experience
Mechanicsville, MD, 20659

“Hermione had a great experience with Amber. She loved playing with her children. Hermione’s first boarding experience was great. Looking forward to getting Amber again!”

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Freddie H.
Sitter Profile Image: Bianca T.
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Bianca T.
Star Sitter
from
$37
per night
4.9 out of 5 stars
• 146 reviews
85 repeat clients
15 years of experience
Sunderland, MD, 20689

“Bianca was attentive and skilled with our beloved Ali who can be a handful with his rambunctiousness. We had a family function to attend in another city and unexpectedly needed a sitter. Bianca was quick and reliable upon request. In addition, Bianca kept us updated on Ali’s stay which he appeared not to miss us with all the love and affection doted on him during his stay. If I ever in the future need a sitter or even just a walker for any event, I would trust Bianca more than my family for the care Ali. I wholeheartedly recommend her fully for the care and wellbeing of your pet.”

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William L.
Sitter Profile Image: Lacy M.
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Lacy M.
Star Sitter
from
$28
per night
5.0 out of 5 stars
• 33 reviews
17 repeat clients
20 years of experience
Laurel, DE, 19956

“Lacy and her daughter were great! They frequently sent me pictures of koda to insure me that he was ok and happy while I was away. Definitely recommend ☺️”

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Sarah P.
Sitter Profile Image: Tanya L.
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Tanya L.
from
$30
per night
4.9 out of 5 stars
• 57 reviews
29 repeat clients
5 years of experience
Cambridge, MD, 21613

“We were blessed to find Tanya on such short notice and on a holiday weekend. Our dog has a lot of energy and she did great with him. We will definitely be using her again in the future.”

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Lisa S.
Sitter Profile Image: Alicia S.
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Alicia S.
from
$45
per night
5.0 out of 5 stars
• 20 reviews
5 repeat clients
10 years of experience
Chance, MD, 21821

“Thank you Galicia for always taking great care of our pups! You are awesome and accommodating during our recent emergency. I would recommend you to everyone 🩷”

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Melissa B.
Sitter Profile Image: Shawn L.
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Shawn L.
from
$48
per night
5.0 out of 5 stars
• 4 reviews
13 years of experience
Lexington Park, MD, 20653

“Shawn was amazing! My dog Buddy didn’t want to come home! Regular updates with pictures! Could not have asked for anything more. Thanks!”

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James H.
Sitter Profile Image: Rose R.
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Rose R.
from
$65
per night
5.0 out of 5 stars
• 93 reviews
31 repeat clients
18 years of experience
Saint Inigoes, MD, 20684

“Rose took great care of our dog. We received updates throughout the weekend, and he seemed very happy and relaxed when we came to pick him up. Our pup is good with other dogs, so it was great that he had some good play time with them as well. I would definitely book with her again!”

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Allison S.
Sitter Profile Image: Dylan C.
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Dylan C.
from
$31
per night
20 years of experience
Cambridge, MD, 21613

About: I have been around dogs my whole life. I combine real-world experience, behavioral training, and problem-solving approach focused on building confident, reliable dogs and owners. I currently have a full-time job but I am very flexible with scheduling. we can chat about scheduling. I am usually off at least 4 days a week. I have a fenced in back yard that sits on 2 acers of land. I have different rooms in my house to crate or keep your dog if it needs to be away from my dogs.

Sitter Profile Image: Anika C.
Verified Enhanced Background Check
Anika C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 47 reviews
13 repeat clients
45 years of experience
Mechanicsville, MD, 20659

“Mocha is ALWAYS in great hands with Anika. I am never worried about her care and wellbeing. Does my heart good to leave my baby in the hands of someone who cares for her like I do.”

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Nija H.
Sitter Profile Image: Aleah J.
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Aleah J.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 16 reviews
5 repeat clients
10 years of experience
Chesapeake Beach, MD, 20732

“Aleah is absolutely amazing. I expressed how nervous i was leaving my fur baby and she instantly eased my nerves. I can really tell she cared for my pet. She sent me pictures keeping me updated during his whole stay. I will 100% be booking with her again & i recommend anyone looking for a sitter to chose her!”

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ms l.
Sitter Profile Image: Julie W.
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Julie W.
from
$46
per night
4.9 out of 5 stars
• 31 reviews
8 repeat clients
20 years of experience
Seaford, DE, 19973

“Julie and her family were so welcoming!!! Duke loved spending time with them and getting all the attention!! We will definitely be having Julie watch Duke again!!”

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Andrea T.
Sitter Profile Image: Kristi M.
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Kristi M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
• 19 reviews
6 repeat clients
20 years of experience
North Beach, MD, 20714

“If you're looking for someone to care for your fur baby like their very own, look no further than Kristi — she is absolutely wonderful! I entrusted Kristi with my dog Maize, and I couldn't have made a better decision. Kristi didn't just watch Maize — she completely spoiled her! Maize had what I can only describe as a little mini vacation, and I think she may have enjoyed herself more than we did on our trip! What truly sets Kristi apart is how thoughtful and communicative she is. She kept us well informed throughout the entire stay, sending the most adorable pictures that gave us total peace of mind. There's nothing better than seeing your pup happy, comfortable, and clearly being showered with love while you're away. I highly recommend Kristi to anyone who wants their pet to be in the most caring, attentive hands possible. You'll leave knowing your fur baby is safe, loved, and maybe a little spoiled — and you'll actually be able to relax and enjoy your time away. We are so grateful for Kristi and will absolutely be booking with her again! 🐾”

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Julie A.
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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog boarding - Woolford

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FAQs for Dog Boarding - Woolford

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Woolford home-away-from-home, packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Woolford.

<b>Tip:</b> You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

You and your Woolford sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to 25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit .

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in MD ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

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