Vacation rentals with a fireplace in Kent County

4.95 out of 5 average rating, 148 reviews

The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.

Farm stay in Chestertown

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Superhost

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.

4.9 out of 5 average rating, 51 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

4.96 out of 5 average rating, 106 reviews

The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.

Home in Stevensville

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.

4.99 out of 5 average rating, 112 reviews

A charming yellow cottage is viewed from the front, featuring a prominent porch with large windows. Lush greenery surrounds the property, complemented by well-maintained landscaping and a brick chimney. The inviting home is bathed in warm sunlight, surrounded by tall trees.

Cottage in Rock Hall

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

4.96 out of 5 average rating, 248 reviews

A spacious studio interior features a king bed positioned near a sloped ceiling. A seating area includes a gray sofa and a recliner, complemented by a coffee table. A wooden dining table is set for two, and large windows provide ample natural light.

Apartment in Chestertown

Chestertown Private cottage with NFL Sun Ticket

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.

The front of a colonial-style house features a yellow facade with dark green shutters, framed by lush trees and vibrant garden plants. A white picket fence lines the yard, leading to the entrance with a red front door and stone steps surrounded by flowers.

5 out of 5 average rating, 46 reviews

Magnolia House: walk to shops, restaurants, river

Historic details abound in this 1750s colonial gem surrounded by inviting gardens and located in the heart of historic Chestertown. 2 blocks from the scenic Chester River, and just steps away from High Street's (aka Chestertown's "Main Street") Saturday Farmer's Market, bakery, historic soda fountain, shopping, art galleries, dining, and downtown community events. As described by the New York Times: "This house is one of the contributing buildings in the town's historic district..."

4.94 out of 5 average rating, 102 reviews

A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.

Cabin in Worton

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.

4.93 out of 5 average rating, 15 reviews

Large windows offer unobstructed views of Chesapeake Bay, allowing natural light to fill the space. A spacious seating area with a light-colored sofa is visible, alongside a dining table that accommodates multiple chairs. The outdoor deck can be seen through the doors, extending towards the water.

Home in Rock Hall

Chesapeake Bay Retreat W/Breathtaking Views

Escape to serenity on the shores of Chesapeake Bay! This luxurious, multimillion-dollar waterfront retreat offers sweeping water views, upscale furnishings, and timeless historic charm. Minutes from vibrant Rock Hall and Chestertown. Relax on the deck with morning coffee, stroll or bike the scenic waterfront paths, enjoy sun dips at Ferry Park beach, catch live performances at The Mainstay, or explore birdwatching trails at Eastern Neck Wildlife Refuge.

An open-concept living area is featured, incorporating a kitchen with a large marble island and dark-stained seating. A wooden dining table is positioned nearby, while a comfortable seating area is arranged around a stone fireplace, illuminated by natural light from surrounding windows.

5 out of 5 average rating, 19 reviews

Relaxing Waterfront - Golf Course & Sunset Views

Our home away from home in Chestertown is truly an extraordinary property. Water and golf course views from every room. And wildlife! Some of the birds and animals we've seen: - blue herons - bald eagles - ospreys - ducks - turtles - otters Inside, there's room enough for 8, with 3 bedrooms and 3 full bathrooms, including one of each on the main level. Just one mile from downtown Chestertown, and a short walk to Chester River Yacht & Country Club

Adirondack chairs are arranged around a fire pit on a grassy riverside. A vibrant sunset casts pink and orange hues across the sky and reflects on the calm water, creating a serene outdoor atmosphere. A tree stands nearby, adding to the peaceful setting.

5 out of 5 average rating, 46 reviews

Down by the River

Relax while taking in the beautiful river views in this bright and welcoming home. Walk to town to enjoy all the delights of charming historic Chestertown. Kayak on the river, unwind on the dock, cook a gourmet meal in the huge open kitchen, relax by the fire-pit. This fully updated, light, and open home is a calming oasis and welcoming gathering place for family and friends. Fully accessible as well.

Two flags, one American and one Maryland state flag, are raised on a dock overlooking the calm waters of the creek. Adironack chairs are positioned along the edge, facing the serene landscape of trees lining the shore.

5 out of 5 average rating, 68 reviews

Waterfront house with private dock & kayaks!

Escape to tranquility at Mill Creek House, a contemporary waterfront sanctuary just 15 mins from Chestertown. Enjoy sunset views from the private dock, watch wildlife, and explore the creek with kayaks. Modern amenities like central AC, WiFi, and a gas grill ensure a comfortable stay. With 2 bedrooms and water views from nearly every room, it's the perfect retreat for relaxation and exploration.