Pet-friendly holiday rentals in Kent County

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

Traveler Guest Suite @ Cinnamon By The Bay

The Traveler offers a private bedroom and fully equipped eat-in kitchen. For those guests who prefer separation from their dining area, but don’t need a separate living space, Traveler is a perfect match. Enjoy the comfort of not being awaken when someone sneaks a midnight snack, all while being easy walking distance to Rock Hall's shopping, coffee shop, restaurants, music venue, and festivities. It is one of our pet-friendly suites with easy access to the community back deck and rear yard.

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)

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.

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.

The Colonial Farmhouse with Private Boat Rental

Escape to the beautiful Eastern Shore of Maryland and relax at the Colonial Farmhouse. This family-friendly, historic property has everything you need to enjoy a home away from home. The large gourmet kitchen and dining space allow for easy family dining while the pool, hot tub, fire pit area, and 4+ acres of land allow for fun. A short walk to the wharf allows for easy access to the Corsica River. Ask about our private boat rental options. We hope to welcome you to the Colonial Farmhouse!

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.

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

Last-Minute Retreat Center of C’town -1 night stay

Escape to a secluded studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of private gardens. Relax in front of the fire with views of gardens in the windows. Kitchenette has large toaster oven, hot plate, microwave, fridge, and Keurig/drip coffee makers. We have an under counter filtration system for pure delicious drinking water. King bed with deluxe linens and mattress, washer dryer Same property listed on Airbnb for less with 2

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!

High Tide & Hound

Welcome to your perfect getaway in the heart of historic Chestertown! This charming home is just two minutes from the iconic High Street Wharf, where you can enjoy scenic views, fishing, and waterfront strolls. We’re proudly family friendly , pet friendly, so bring your furry friends along for the adventure. Whether you’re here for the festivals, the river, or just to relax this is your ideal place. Comfortable , private, and conveniently located.

Family Retreat at Historic Lansdowne Manor

Escape to Lansdowne, a historic Federal-period manor house recognized by the Library of Congress. This private, tranquil retreat offers a unique blend of vintage charm and modern comfort for up to 8 guests. Surrounded by open fields and nature, this 4 bedroom home features a fully equipped kitchen and high-speed Wi-Fi. Perfect for families and history lovers seeking a peaceful getaway just minutes from Centreville and a state park lake and trails.