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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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Cottage in Chestertown

4.91 out of 5 average rating, 34 reviews

Chesapeake East Shore Chestertown, Pool & 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

Home in Chestertown

4.94 out of 5 average rating, 36 reviews

Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier where you can catch your own fish or crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars and admire the wildlife. 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

Guest suite in Centreville

5 out of 5 average rating, 24 reviews

Country retreat guest suite w/ hot tub & fire pit

Welcome to the Zen Den, in Centreville, Maryland. Kick back & relax, in this cozy basement hideaway, with picture perfect sunsets & incredible stargazing opportunities. This brand new, 3 bedroom (private entrance) basement apartment, is warm & inviting, in a quiet, private setting in nature but still close to amazing bars/restaurants, shopping, and some of the countries best crabcakes. Located on Maryland's Eastern Shore, just 30 minutes to Annapolis and an hour and a half to Ocean City, MD.

Rental unit in Rock Hall

5 out of 5 average rating, 89 reviews

Inspiration Guest Suite - Cinnamon By The Bay

Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in Cinnamon By The Bay's in-town suites. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.

Cabin in Chestertown

4.98 out of 5 average rating, 231 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.

Home in Chestertown

5 out of 5 average rating, 179 reviews

Totally Renovated historic house near town center

Renovated 19th century home with modern conveniences. 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

Home in Chestertown

5 out of 5 average rating, 10 reviews

Holiday Escape to the Riverside

Relax with the whole family or a big group at peaceful river home. Huge waterfront property. Bedroom, dining and living room 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 group 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!

Home in Rock Hall

4.98 out of 5 average rating, 51 reviews

Private Chesapeake Bay Retreat w/ Bay Views!

Step into a relaxing retreat at this picturesque vacation rental on Chesapeake Bay! Complete with 2 bedrooms and 2 bathrooms, this spacious home offers a cozy fireplace and a stunning deck overlooking the water — perfect for enjoying the sunset! Explore the nearby Eastern Neck National Wildlife Refuge or take a scenic drive to the quaint shops and seafood restaurants in town. Whether you're seeking outdoor adventures or a peaceful coastal getaway, you’ll love this Rock Hall property!

Guest suite in Chestertown

4.99 out of 5 average rating, 214 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.

Home in Chestertown

4.97 out of 5 average rating, 86 reviews

River front cottage with private dock & water fun

Private cottage on the banks of the Chester River. Sleeps 8-14. Private dock with plenty of water activities. This property offers relaxation and serenity as soon as you pull in! Located right on the water with spectacular views of the Chester River, the house is renovated in a cozy, casual farmhouse style. While you will love the house you will spend your days outside enjoying life on the river thanks to your private access to the water and lots of water fun!

Home in Millington

4.96 out of 5 average rating, 26 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!

Home in Chestertown

5 out of 5 average rating, 33 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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Popular amenities for Kent County pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Chestertown

4.99 out of 5 average rating, 107 reviews

Entire River Front Home - 4 Bedrooms 4.5 Baths

Home in Stevensville

4.96 out of 5 average rating, 23 reviews

Spacious4BR home with waterviews

Home in Kennedyville

4.89 out of 5 average rating, 79 reviews

Perfect for Hunters on the Eastern Shore

Home in Rock Hall

4.94 out of 5 average rating, 52 reviews

Egret's Nest, A Waterfront Oasis near Rock Hall

Home in Rock Hall

4.88 out of 5 average rating, 34 reviews

The Blue Jimmy

Home in Middle River

5 out of 5 average rating, 34 reviews

Waterfront Home with Private Beach, Stunning Views

Home in Chestertown

4.92 out of 5 average rating, 51 reviews

Eastern Shore Hideaway Deck, Kayaks, Grill, & Pit

Home in Centreville

4.63 out of 5 average rating, 92 reviews

Peaceful Acres Guest House (A Nature's Getaway)

Pet-friendly home rentals with a pool

Home in Chestertown

New place to stay

Pet-Friendly Home on Chester River w/ Dock!

Bungalow in Rock Hall

4.89 out of 5 average rating, 37 reviews

Welcome to Mermaid Haven!

Home in Rock Hall

5 out of 5 average rating, 10 reviews

The Mariner's House

Farm stay in Chestertown

4.97 out of 5 average rating, 96 reviews

Piney Grove Farm

Home in Rock Hall

4.84 out of 5 average rating, 19 reviews

Waterfront w/pier, Hot Tub, pool, and in town

Home in Stevensville

4.98 out of 5 average rating, 86 reviews

Beautiful Kent Island Getaway with Pool

Home in Rock Hall

5 out of 5 average rating, 4 reviews

Cozy cottage with pool and beach

Home in Worton

4.97 out of 5 average rating, 30 reviews

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

Private, pet-friendly home rentals

Home in Kennedyville

New place to stay

Augustine House

Farm stay in Chestertown

4.95 out of 5 average rating, 132 reviews

Outrange at Blue Heron Farm

Rental unit in Chestertown

4.97 out of 5 average rating, 214 reviews

Romantic private cottage - center of Chestertown .

Rental unit in Rock Hall

4.95 out of 5 average rating, 22 reviews

Traveler Guest Suite - Cinnamon By The Bay

Cottage in Rock Hall

4.81 out of 5 average rating, 36 reviews

Oysterman Cottage Bay & Harbor views, Internet

Home in Chestertown

4.68 out of 5 average rating, 31 reviews

Waterfront 2bed/1.5 bath w/dock&beach close 2 town

Home in Stevensville

New place to stay

Love Point Waterfront

Destinations to explore