Holiday rentals with a fireplace in Dover

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Bowers Beach: A Slice of Paradise

Please note: We require guests to book the total amount of persons staying as we charge per-guest. We do not have a TV and our home is not suitable for unsupervised young children. Between Whitwell’s Delight and Bowers Beach Road, across from the old Tuthill Brothers Farm, we have a quiet space that is perfect for up to eight people to feel at home; great for couples or a tight-knit group of friends or family. We also have records, board games and puzzles to enhance the feeling of a cozy stay.

Secluded and romantic getaway in Chestertown

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. We also host ‘Wren Retweet”, a 5 bedroom house by the carriage house.

Baybreeze Bungalow Luxury Couple’s Retreat

Baybreeze bungalow by the bay, is just blocks from the beautiful Cape May sunsets and the Cape May-Lewes Ferry. The entire bungalow is your home during your stay. It is a short walking distance to the beach and a close drive or bike-ride to the center of Cape May. This lux bungalow sleeps 2 comfortably and is great for adult getaways. All amenities for a great, worry-free, and relaxed stay are provided for you. We do not allow dogs/pets in the bungalow. There will be a $100 penalty.

THE SORA with Disco, Hot Tub & Pool

Immerse yourself in the timeless beauty of this 12 acre riverfront property. Experience the peaceful beauty of 800+ feet of direct river frontage on the deep Cohansey River. This river leads to the Delaware Bay/ Atlantic Ocean. Situated on the site of the Prestigious Sora Gun Club, this historic 4 Bedroom, 2 1/2 Baths light-filled home with magnificent great room has classical details and distinctive appointments. One of the 4 bedrooms and the 1/2 bath is in the 2 story guest house.

Hot Tub Backyard Oasis, Private Beach, Local Pool

Start your morning soaking in the hot tub, or sipping coffee in rocking chairs on the front porch. Just 1 block away, have the beach all to yourself in this truly secluded beach neighborhood. Enjoy one of the local waterfront eateries or the neighborhood pool. Spot a school of dolphins under a red-sky sunset before returning home to enjoy the night sea breeze and a movie in front of a wood burning fire in the outdoor gazebo. Click our icon to check out our other Cape May homes!

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.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

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.

The Hepburn-Hot Tub & Fire Pit

The Hepburn is a beautifully renovated and decorated by home by Harlow Grey Homes. This meticulously restored glass cabin is located on over an acre of private grounds on a serene 75 acre lake. Firewood included! The separate seven-person hot tub is OPEN for the season. The private pool + built-in spa is closed and is set to reopen mid May 2025