Dog Boarding Woolford

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Woolford, 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.

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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
• 81 reviews
32 repeat clients
20 years of experience
Chesapeake Beach, MD, 20732

“ALL THE STARS!! 100% This is the 2nd time Lori has watched our rescue dog, Luna Lovegood (LuLu), only this time it was 12 days, not 4. Luna has always been timid and didn’t know how to play. Lori has a very gentle and kind dog CoCo (or was pet sitting CoCo also), and by the end of the trip they were playing everyday — Lori sent videos and I couldn’t believe my eyes!!! I may have teared up a bit!! Lori sent out countless photos and videos. She also never put Luna in her room (kennel) and Luna was allowed to sleep on her bed, CoCo’s bed, the couch, etc. Please believe this is a VERY pet friendly home, absolutely wonderful with great energy. Luna hesitated to go in on this 2nd time, but the second she saw/realized it was Lori, she was wagging her tail and VERY happy — she didn’t even say goodbye to us!! That says so much to me!! Again, Lori sent to many videos showing my Luna coming out of her shell and reassuring us that she was okay, which I always need and love!! To know your pet is okay while you’re so far away is a blessing and makes vacation SO MUCH MORE RELAXING! I didn’t have to worry about LuLu, but in the end, I worried she wouldn’t want us back!! Hahahaha!! This is so much better than putting your dog in a kennel. I 100% recommend Lori, she works with your needs, your pets needs, she is 100% involved in communication and updates. She is very easygoing and goes with the flow, if you need something, she will do it! I will NEVER schedule another vacation, until I know Lori is free to watch our beloved Luna. I 100% recommend. SO SO SO much better than any Kennel or doggy daycare. Lori provides love and kindness and understanding and all our doggies need that. Thank you Lori and Rover!!!!”

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Holly K.
Sitter Profile Image: Tina R.
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Tina R.
from
$45
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
40 years of experience
California, MD, 20619

“Tina was a fantastic sitter for our 10-year old pup! She is clearly a “dog person” at heart and set us at ease right away. Snowball settled in right away and acted confident and comfortable with Tina. She took him for walks and played with toys and sent us cute photos each day! It was evident Tina took excellent care of him! Tina was also quick to respond and communicated well throughout our booking. Will definitely book with Tina again!”

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

“Linda was great with our dog! She was very responsive and sent pictures. We could tell he had a blast with her dogs, as he napped the entire evening when we brought him home.”

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Christin R.
Sitter Profile Image: Denise R.
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Denise R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 151 reviews
59 repeat clients
5 years of experience
hollywood, MD, 20636

“My dogs had a great stay! Denise even got my picky dog to eat from a dish. I have a very hard time with. Her eating. The pictures of my dogs relaxing with the family gave me peace of mind so that I could enjoy my vacation. I would highly recommend Denise.”

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Mary A.
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
• 111 reviews
38 repeat clients
25 years of experience
Lexington Park, MD, 20653

“Absolutely amazing! Loved Christianna! She kept me updated throughout the day with texts, pictures, and videos. She went above and beyond to ensure my pup was well cared for and happy. I trust her implicitly and will use her again the next time I leave town.”

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Kathryn J.
Sitter Profile Image: Elizabeth G.
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Elizabeth G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 55 reviews
13 repeat clients
30 years of experience
HUNTINGTOWN, MD, 20639

“Liz always takes wonderful care of our dog. She provides plenty of updates and is confident in providing the care our dog needs. I’ve never worried about how our dog is when she’s with Liz.”

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Jolene N.
Sitter Profile Image: Emily H.
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Emily H.
from
$30
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
4 years of experience
Hollywood, MD, 20636

“Emily was GREAT! As soon as we met her for a meet & greet prior to her dog sitting we knew she was perfect for our dog Pablo! Emily made me feel at ease by sending updates on Pablo and providing us pictures of Pablo as well. Definitely will rebook with her again!”

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Vanessa D.
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: Amelia P.
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Amelia P.
from
$45
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
8 years of experience
Chesapeake Beach, MD, 20732

“Amelia is very kind and communicative. She was able to send me updates and photos throughout the duration of my dog’s stay with her. Highly recommended and would use her services again!”

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Damon G.
Sitter Profile Image: Laura L.
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Laura L.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 21 reviews
8 repeat clients
10 years of experience
Chesapeake Beach, MD, 20732

“Laura was awesome! Chacco had a blast during his weekend sleepover and loved hanging out with the other pups. She took great care of him, and I felt totally at ease knowing he was in good hands. He came home happy and tired—always a good sign! Definitely booking with her again.”

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Chellie Pearl P.
Sitter Profile Image: Mya P.
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Mya P.
from
$65
per night
5.0 out of 5 stars
• 6 reviews
3 repeat clients
25 years of experience
Chesapeake Beach, MD, 20732

“Mya cared for our dog (Harley) like she was her own! Harley has anxiety when we leave her but she was clean, calm and relaxed when we picked her back up. Mya sent us photos and communicated with us consistently while we were away so we felt at ease that our girl was well cared for in our absence. We will be booking with Mya again soon!”

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Christina C.
Sitter Profile Image: Tyler G.
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Tyler G.
from
$30
per night
4.8 out of 5 stars
• 6 reviews
2 repeat clients
1 year of experience
Shady Side, MD, 20764

“Lovely couple with a baby and a toddler. Buffy had to warm up to Parker, their German Shepherd but I hear it went well. Tyler and wife watched Buffy on a holiday, July 4th. They were very gracious when I requested an itinerary change. I felt like they were really attuned to Buff-dog. Will definitely ask again for their assistance.Highly recommend.”

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Penny B.
Sitter Profile Image: Sharon R.
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Sharon R.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
30 years of experience
CHURCHTON, MD, 20733

“Sharon is an excellent communicator and very accommodating to my many changes (the weather wasn’t my friend). We had a great meet and greet. She sent sweet pics and took awesome care of my pup. Thank you!”

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Renee R.
Sitter Profile Image: Sarah F.
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Sarah F.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 58 reviews
12 repeat clients
30 years of experience
Leonardtown, MD, 20650

“Sarah and her family were great!! She made my dog feel so comfortable at home. Sarah was very communicative during Ari’s stay sending photos and updates. I felt so comfortable with Ari in her care.”

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

“Once again we had Anika watch our Max and once again we had one happy puppy both when we dropped him off and when we picked him up! We are so happy we found her and Max loves his time spent with Anika and Chip.”

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Ty J.
Sitter Profile Image: Brooke H.
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Brooke H.
from
$35
per night
5.0 out of 5 stars
• 43 reviews
17 repeat clients
26 years of experience
Leonardtown, MD, 20650

“Brooke is excellent with Jasper her reports are very detailed and she is proactive in trying to help Jasper with his training accomplishments. Also a very good individual for boarding.”

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Mike R.
Sitter Profile Image: Kendall T.
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Kendall T.
from
$40
per night
5.0 out of 5 stars
• 3 reviews
20 years of experience
Chesapeake Beach, MD, 20732

“Kendall was great! Very responsive, and kept me updated while caring for my dog. Would absolutely recommend her.”

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anthony g.
Sitter Profile Image: Rose R.
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Rose R.
from
$65
per night
5.0 out of 5 stars
• 94 reviews
32 repeat clients
18 years of experience
Saint Inigoes, MD, 20684

“Our dog squid had a fantastic time with Rose and her dogs while we went away for a 4 day trip. Rose was very easy to work with and sent pictures and updates all throughout squids stay with her. We are super grateful and will absolutely be reaching out to her next time we need a reliable dog sitter.”

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Andrew H & Emma S.
Sitter Profile Image: Rozlynn & Alexander H.
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Rozlynn & Alexander H.
from
$35
per night
5 years of experience
Shady Side, MD, 20764

About: I grew up with a small dog and have been a pet sitter for friends and family for just under 5 years. My husband grew up with 4 French bulldogs, although we do not have any special skills to train dogs we enjoy spending time with them. Pet care fits into our schedules on most weekends and some holidays. Our jobs limit us from having our own pets so we enjoy watching others during our time off. I will often be pet sitting with my husband as we live together. We care for pets by doing what’s instructed of us from their owners to keep their routine as close as possible in our home as it would be at theirs.

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

Book with peace of mind

  • 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

    Book and pay through Rover’s secured platform—no cash or checks required.

  • 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

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Woolford average 9
repeat dog boarding clients

FAQs for Dog Boarding - Woolford

Frequently asked questions about Rover

As of November 2026, there are 199 sitters on Rover offering Dog Boarding across Woolford. Enter your ZIP code to see which available sitters are closest to your home.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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.

94% of sitters in Woolford can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this 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, we recommend 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.

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

Yes, you can find sitters who have experience with handling special pet needs in Woolford. On Rover:

  • 89% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 94% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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 Rover Guarantee, 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 Rover's Trust & Safety page.

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.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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