Pet-friendly vacation rentals in Kent County

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Kent County

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Superhost

A charming cottage is nestled among trees, featuring a gravel driveway leading to the front door. Colorful flowering shrubs enhance the exterior, while a living area is visible through large windows. White adirondack chairs are arranged on the lawn, inviting relaxation in the expansive outdoor space.

Cottage in Chestertown

4.91 out of 5 average rating, 35 reviews

Chesapeake East Shore Chestertown,Pool (May1),Dock

A bright, airy, refurnished cottage set in the grounds of an 18th century farm on the eastern shore of Chesapeake Bay, shared pool (your private use 6 hours a day) & dock. Bring your watercraft & gear. Layout is open kitchen, dining and living area. Master & bath on ground; upstairs 2 bedrm suite with bath Fiber optic & smartTVs Gas fireplace, central heat & AC Linens, kitchen utensils & Keurig coffee maker. GE washer and dryer. BBQ, deck chairs, picnic table, seating on water & dock, fire pit

Guest favorite

The waterfront home is surrounded by trees and features a spacious deck with blue chairs facing the sandy beach. A swing is visible on the deck, and kayaks are stored nearby, creating an inviting outdoor space for relaxation and activities.

Home in Middle River

4.95 out of 5 average rating, 39 reviews

Waterfront Home with Private Beach, Stunning Views

Escape to paradise at our Chesapeake Bay waterfront vacation home in Oliver Beach! Our home is the ideal place to unwind and appreciate the beauty of Chesapeake Bay. You'll love the stunning views, the private beach, the spacious upper deck and the beachside deck surrounded by trees. You'll have so much fun fishing, swimming, kayaking, paddle boarding, or just relaxing by the water! It's the perfect spot for a dreamy retreat, a romantic sojourn, or for shared fun with group of friends or family.

Guest favorite

An outdoor space features a fire pit surrounded by several adirondack chairs in varying colors. The area is landscaped with a gravel surface and is bordered by a white picket fence, with flowering shrubbery and a small building visible in the background.

Cottage in Rock Hall

4.91 out of 5 average rating, 124 reviews

Cottage with Modern Updates - Walk to Waterfront!

Historic cottage, fully renovated and located in the heart of Rock Hall. Features open living area, modern kitchen, sunny front porch, big fenced backyard, and patio with fire pit and picnic table. Enjoy everything the town has to offer - fishing, boating, festivals, dock bars, restaurants, shopping, & more. Walking distance to Main Street, marina, Harbor Shack, Waterman's Crab House, The Mainstay. A short drive to Eastern Neck National Wildlife Refuge, Washington College, historic Chestertown.

Top guest favorite

The single-story ranch home is set on a spacious lot adorned with a mix of grass and fallen leaves. Blue shutters frame the windows, and a welcoming front porch is furnished with several chairs. A two-car garage is visible to the left.

Home in Rock Hall

5 out of 5 average rating, 85 reviews

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

Guest favorite

The exterior of the home is framed by two large trees, providing a natural boundary. A brick pathway leads to the front door, bordered by well-maintained green grass and bushes. The home features a welcoming porch with white railings, creating an inviting entrance.

Home in Kennedyville

4.89 out of 5 average rating, 80 reviews

Perfect for Hunters on the Eastern Shore

Enjoy all the charms of the Eastern Shore at this spacious home in a quiet neighborhood. You'll be cooking up a storm in the well equipped kitchen. A quiet work area is available for visitors here on business. Netflix, Xumo, Amazon (must have acct), Wi-Fi provided. Games, books, cards and a ping pong table! Chestertown is only 7 miles away, so visiting is easy. See pics for room details. Home is not appropriate for children under 8. Guest assumes responsibility for injuries to child(ren).

Guest favorite

Home in Stevensville

4.95 out of 5 average rating, 87 reviews

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Top guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 234 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Top guest favorite

Home in Chestertown

5 out of 5 average rating, 191 reviews

Totally Renovated historic house near town center

Renovated 19th century home. 3 king beds, 2 queens. 55” TV in family room, 2 more. 1st floor bedroom with full bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, a 3 block walk from Wash College and the C'town waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 more bedrooms with queens. 1 loft connected to a 2nd story bedroom with 2 twins. Fenced yard and an acre of private gardens. Fire pit. New Weber grill

Guest favorite

Townhouse in Rock Hall

4.93 out of 5 average rating, 57 reviews

Walking Distance to Marinas & Main St!

Ahoy! Embark on a wonderful vacation at “Welcome Aboard!" Our adorable home is within walking distance of waterfront marinas, restaurants, and the downtown strip, with coffee shops, stores, and more! Enjoy your morning coffee while sitting on the porch in locally purchased Adirondack chairs, then head into town to enjoy everything Rock Hall has to offer! Many of the pieces of artwork you see in our home were purchased from a photographer in town and custom framed by a nearby craftsman.

Top guest favorite

A serene backyard scene features two patterned chairs and a small round table set on a wooden patio. Lush greenery and trees frame a peaceful waterfront view, while a friendly dog is seen in the grass, enjoying the tranquil environment.

Guest suite in Chestertown

4.99 out of 5 average rating, 221 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Top guest favorite

The chalet is depicted at night, showcasing its A-frame structure with large illuminated windows. The wrap-around deck features outdoor seating, while the surrounding trees provide a sense of seclusion. Soft lighting from inside highlights the inviting interior layout.

Farm stay in Chestertown

4.94 out of 5 average rating, 155 reviews

Blue Heron Farm Waterfront Chalet

Relax and unwind at the Chalet on Blue Heron Farm, a waterfront rustic retreat on the upper reaches of the Chester River. Tucked away on a 126 acre fourth-generation organic farm, the River Chalet is a peaceful and private getaway situated just 15 minutes from historic Chestertown. This recently restored 3-bedroom, 2 bath home features a giant wrap-around deck overlooking the river and floor-to-ceiling windows with serene waterfront views.

Guest favorite

A cozy living area features a mustard yellow sofa complemented by two light gray armchairs. A round coffee table with a decorative tray sits on a soft area rug. Neat window blinds provide controlled natural light, enhancing the room's inviting layout.

Home in Chestertown

5 out of 5 average rating, 38 reviews

NEW Chestertown Retreat

Enjoy this newly built (July 2023) semi-detached home with new furnishings, fully stocked with everything you need and private fenced back yard. Located less than 1/2 mile to Washington College and 1.5 miles to downtown, this home is close to everything Chestertown has to offer. Perfect for parents and families visiting students, hunting trips, weddings or anyone looking to enjoy the many eastern shore/Chestertown events and attractions.

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What guests are saying

Kent Island Waterfront Cottage

4.62 out of 5 average rating, 114 reviews1 week ago

We really enjoyed our stay at Glen’s place on Kent Island. The view was stunning. That was my favorite part, just sitting outside having coffee and enjoying that gorgeous water view in peace and tranquility. We started off with a little bit of a hiccup, but I truly appreciated their response and taking care of it quickly. Life isn’t always perfect, but it’s how you respond to those situations that make all the difference. We ultimately had a great stay and would definitely recommend this property to our friends

Guesthouse in Stevensville

What guests are saying

Owl Cottage - Cozy, Private & Walkable to Town

5 out of 5 average rating, 21 reviews1 week ago

Shari’s cottage is cute as a button! It’s a 3-4 minute walk from restaurants (some of which are dog friendly which we loved). The space is cozy and peaceful. We loved the historic charm while having all of the amenities we needed. We also traveled with our pup which is such a blessing. Shari has thought of everything; bottled water, coffee, snacks, extra toiletries. We’re sad we didn’t get to stay longer but we would absolutely book here again. Highly recommend!

Guesthouse in Chestertown

What guests are saying

1-br apt in downtown Chestertown (Unit 1)

4.9 out of 5 average rating, 78 reviews1 month ago

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

Apartment in Chestertown

What guests are saying

Traveler Guest Suite - Cinnamon By The Bay

4.97 out of 5 average rating, 30 reviews1 month ago

Deborah was a great host! Very communicative and helpful when we had questions. The contactless checkin could not have been easier. The place was super clean and had the things you need to be comfortable. We loved that it was right in town and very walkable to restaurants, grocery store, West Marine and the hardware store. It’s the perfect spot for boat cruisers who have a boat on the hard and can’t live aboard while doing the work.

Apartment in Rock Hall

What guests are saying

Oysterman Cottage Bay & Harbor views, Internet

4.81 out of 5 average rating, 36 reviews7 months ago

We had a really nice stay at the Oysterman House, James was very responsive to all our questions. In the house left on the table was a book with instructions to everything you may need in the house....working the remote, thermostat etc. The house was very charming. I'd also like to point out my favorite part was the screened in porch with ceiling fan I enjoyed sitting out there especially in the morning for my coffee it was so peaceful and rather warm so the fan to circulate the air was the perfect touch.

Cottage in Rock Hall

What guests are saying

114 High Street First Floor Unit Chestertown

5 out of 5 average rating, 10 reviews1 week ago

I have stayed at this property before and it is always a great experience. Katie is a wonderful, responsive, host. The welcome basket and handwritten note are thoughtful details. I very much look forward to my next opportunity to stay in Katie’s house again.

Apartment in Chestertown

What guests are saying

Cozy peaceful apartment

4.92 out of 5 average rating, 24 reviews2 months ago

Rebecca’s apt was exactly what I was hoping to find for the few days I was there. It was very quiet and comfortable and an easy commute to the event I was in town for. Rebecca was extremely responsive to my questions and very welcoming. The apt is very cute and very clean and comfortable. I had my little dog with me and he is elderly and he was very comfortable there as well. I’d definitely stay there again!

Apartment in Warwick