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.

0 of 0 items showing

1 of 3 pages

Superhost

A quaint cottage is positioned among lush greenery, with a gravel driveway leading up to the entrance. Floral bushes are visible in front, and tall trees create a serene backdrop. Two dogs are seen exploring the expansive grassy area.

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

A wooden pier extends from the sandy shore towards a home surrounded by tall trees, with warm light glowing from large windows. The sky displays soft pink and blue hues as the day transitions to evening.

Home in Chestertown

4.93 out of 5 average rating, 43 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

Superhost

The charming exterior of a historic cottage is depicted, featuring a welcoming front porch and an American flag. Lush green landscaping with flowers adds a touch of color, while a stone pathway leads to the entrance. The house is set against a backdrop of trees.

Cottage in Rock Hall

4.88 out of 5 average rating, 128 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

A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.

Guest suite in Chestertown

4.99 out of 5 average rating, 224 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Guest favorite

The image displays a serene riverside view at dusk, featuring calm waters reflecting shades of pink and purple clouds. A wooden dock extends into the water, flanked by lush greenery and subtle seating areas, offering a tranquil atmosphere for relaxation.

Home in Chestertown

5 out of 5 average rating, 18 reviews

Holiday Escape to the Riverside

Relax with the whole family or big group at our peaceful river home. Huge waterfront property. Bedroom, dining and living room river views. River and tidal beach access. Kayak, SUP or canoe. Enjoy backyard games, outdoor dining, hammock or fire pit. Massive waterfront screened-in porch with 2 dining and 2 seating areas. 10 min walk to adorable historic downtown. Festivals, art galleries, bakeries, ice cream, shops, spa & playground. This is our happy place - we hope it becomes yours!

Top guest favorite

The exterior of a rustic carriage house is showcased, featuring a wooden façade and a gabled roof. Surrounding gardens are vibrant with blooming flowers, including red tulips. A wooden fence provides a sense of privacy, while nearby trees offer shade and greenery.

Apartment in Chestertown

4.97 out of 5 average rating, 233 reviews

Private cozy cottage - center of Chestertown .

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Guest favorite

A spacious backyard is showcased, featuring a well-maintained lawn surrounded by leafy trees. A small seating area with four colorful chairs invites relaxation. The natural setting includes various plants and shrubs, enhancing the outdoor environment.

Apartment in Chestertown

4.9 out of 5 average rating, 80 reviews

1-br apt in downtown Chestertown (Unit 1)

Note: Beginning Oct. 4, 2023, we have eliminated all booking fees and cleaning fees. The price you see is the price you get. 1-bedroom newly-renovated apartment located in a 5-unit apartment building near downtown Chestertown, MD. Unit 1 is located two blocks from High Street (think Evergrain Bakery!) and about four blocks from the Chester River. Enjoy a shared front porch with the other long-term tenants, or use the private back porch to sit and read the newspaper or enjoy the outside.

Top guest favorite

The light-filled living room features high ceilings and large windows, showcasing views of the surrounding area. A dark blue sofa and a brown leather chair complement a sizable area rug, while a wooden table and a ceiling fan add functional elements to the space.

Guesthouse in Chestertown

5 out of 5 average rating, 28 reviews

Owl Cottage - Cozy, Private & Walkable to Town

A renovated 19th century carriage house, Owl Cottage is the perfect combination of historic ambience and modern convenience, all in the center of Chestertown. It has a 1st floor bedroom with king bed, a light-filled 2nd floor living room and kitchenette, and a third story loft, with a queen size bed. There is also a bathroom with shower on the second floor. Beds furnished with luxury linens. There is a private patio with chairs and access to over 2 acres of private gardens.

Guest favorite

An expansive deck with a wooden dining table is surrounded by several chairs. Lush greenery provides a natural backdrop, and a winding path leads down toward the waterfront, offering a view of the serene Chester River.

Home in Millington

4.93 out of 5 average rating, 30 reviews

Lark's Nest on the Chester River

Escape to this stylish, private, waterfront home. Fish or kayak off a private dock on the Chester River and enjoy the views and dine alfresco on the oversized deck. Centrally located just 20 minutes from all of the events, eateries, shops and galleries in Historic Chestertown. Perfect, family and pet-friendly home for Washington College students, parents and alumni. Book today for your family reunion, wedding parties, or romantic get-away!

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, 158 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

4.98 out of 5 average rating, 43 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.

Superhost

A spacious yard features two blue Adirondack chairs positioned beside a round table, inviting relaxation. Lush green grass surrounds the seating area, and a distant view of the water is framed by trees, creating a serene outdoor setting.

Home in Betterton

5 out of 5 average rating, 3 reviews

Magnolia House by the Bay

Breath taking views of the beach with stunning sunsets over the water! Bring the whole family to relax in our traditional beach house. Betterton is known as the ‘Jewel of the Chesapeake’ and you will love the bay breezes from our deck that directly faces the water, and our screened in porch, perfect for board games or taking a nap! Inside is spacious and tastefully decorated. Outside is a gardeners treat!