Vacation rentals in Ridgely

Turnbridge Manor - Waterfront Historic House

A waterfront property located in the heart of downtown Denton, on Maryland's Eastern Shore, the stately historic home built in the 1860’s offers modern amenities and luxurious accommodations. Guests can take in the charm of Denton from our sunny front porch or sit in the many outdoor oases to relax and enjoy the beautiful terraced grounds overlooking the tranquil Choptank River. Located less than 60 minutes to the beach, 35 minutes to historic St. Michaels and minutes to the Harriet Tubman Byway

Nicencozy, near DE Turf, Bayhealth, beaches, AFB

Stay in peace at this smoke-free, quiet abode. Within 10 mins of Milford (Bayhealth Sussex, Walmart, shopping, pharmacies, restaurants, etc.). 15 mins: DE Turf, Milton, breweries. 20-30 mins: Bowers Bch, Pickering Bch, Sports at the Bch, Dover & Georgetown, theaters & casinos. 30-45 mins: other beaches and outlets. Please review Guide Book and House Manual after booking, and call us after a last minute booking, so we can tell you how to get in. Snacks, water, etc. provided while supplies last.

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

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.

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Captain’s Quarters - Unique home on Corsica River!

The Captains Quarters was built in 1880 by local waterman, Captain John H. Osman. The Captain built 4 identical houses for the Captains of his fleet to enjoy. The Captains Quarters is registered with the Maryland National Historical Trust. This unique and cozy home takes you back in time, all while enjoying all of the modern amenities. Our guests can expect to enjoy coffee on the patio overlooking the Corsica River, games and a bar in the brick floor basement and tons of relaxation!

Mast Cabin

Enjoy a peaceful stay in our cabin set in the edge of the woods. The cabin is 100 feet from our house, and has its own gravel driveway along the woods. We are located in a rural area on 8 acres . You are welcome to explore and enjoy our property. We are located 30 miles from Delaware beaches. When requesting to book, please include a brief message telling us who is coming (max 2 guests) and the purpose for your travel plans. Requests without this basic info won’t be approved.

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

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 state park trails. An amazing and well-cared-for property.

Private bungalow with fire pit near Easton, Denton

- High-speed Internet - Premium Samsung washer and dryer - Fire Pit - Level 2 EV Charger - Two (2) cruiser bicycles - Memory foam mattresses - Full kitchen - Smart TV - Quiet, secluded space with easy access - 5 minutes to Denton - 15 minutes to Easton - 15 minutes to Centreville - 30 minutes to St. Michaels Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure.

Cozy apartment in a quiet Amish country setting

Relax in our fully furnished 1 bedroom (and a spare room with a futon for extra bedding ) 1 bath, living room, and kitchenette apartment, with a private ground level entrance, in a peaceful Amish country setting. The unit is 5 miles away from the Dover city limits. While here, be sure to enjoy shopping at Byler’s Store, a local destination stop featuring a deli, bakery, grocery and gift shop.