Vacation rentals in Ridgely

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Top-rated vacation rentals in Ridgely

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A stately historic home is depicted from the front, showcasing a charming design with white siding and a blue front door. The property features a peaked roof and is surrounded by lush greenery, including several trees and well-maintained shrubs.

Place to stay in Denton

4.95 out of 5 average rating, 103 reviews

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

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Top guest favorite

A comfortable living room features plush seating arrangements, including reclining chairs and a spacious sofa. A coffee table sits in the center, complemented by a large television mounted above a brick fireplace. Bookshelves filled with titles line the walls, adding a cozy touch.

Home in Easton

4.97 out of 5 average rating, 102 reviews

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre

Bring the whole family to my spacious house. 3 bathrooms for everyone to get ready. 2 king beds and 2 queen beds across 4 bedrooms. Huge living room, kitchen, and dinning room. Enjoy a sun room and fenced in back yard. Fresh eggs from backyard chickens. Merry Maids regularly cleans the bathrooms and kitchen. The basement, garage, and shed are for storage, and are not part of the rental. While quiet just outside of the city, there maybe some highway noise or farm animal noise. Large driveway

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Guest favorite

A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.

Home in Preston

4.93 out of 5 average rating, 127 reviews

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.

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Guest favorite

A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.

Home in Grasonville

4.95 out of 5 average rating, 313 reviews

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.

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Top guest favorite

A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.

Home in Stevensville

4.99 out of 5 average rating, 150 reviews

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

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Top guest favorite

A cozy living area features two brown leather sofas, a patterned rug, and a soft ottoman. A reading nook is created with a gray chair draped in a yellow blanket. Natural light streams in through a large window, with plants and bookshelves enhancing the space.

Home in Chestertown

4.98 out of 5 average rating, 196 reviews

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

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Top guest favorite

The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.

Apartment in Greenwood

4.97 out of 5 average rating, 700 reviews

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)

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Top guest favorite

Farm stay in Greensboro

5.0 out of 5 average rating, 13 reviews

Frosty Acres Choptank River Farm

Bring your family for a memorable stay on our family waterfront farm, "Frosty Acres." Located on Maryland's Eastern Shore between Greensboro and Ridgely, this 3 bedroom/2 bath Victorian house on 60 waterfront acres surrounded by barns, fields, woods & farmland, once occupied by Choptank River Native Indians! Walk the trails and dirt roads that will take you through the farm to the campground area where you can launch your own boat, BBQ, kayak, fish, swim, have a campfire and tent camp.

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Top guest favorite

A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.

Home in Greensboro

4.97 out of 5 average rating, 145 reviews

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.

LocationFamilyWalkability

Top guest favorite

A living area is featured, highlighted by a red sectional sofa and two brown armchairs. A small round table sits between the chairs, complemented by large windows adorned with orange curtains. A cozy black rug covers the floor, adding warmth to the space.

Home in Denton

5.0 out of 5 average rating, 13 reviews

Welcome to Harmony House!

Welcome to our cute, tiny but mighty home that offers a convenient location with just the perfect amount of space to relax and recharge. Each of the three bedrooms comes with a Nectar mattress and plenty of comfortable options for sleeping, along with storage for your items and luggage. The walk-in shower and complete kitchen will allow you to bring comforts from home and the lightning fast wi-fi signal keeps you connected during your stay. Convenient access to Highway 404.

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Guest favorite

A cozy outdoor seating area is set up on a grassy lawn, facing the water. Adirondack chairs and a low sofa surround a fire pit, creating a welcoming space for relaxation. A private dock extends into the Chester River, offering scenic views of the water.

Home in Chestertown

4.96 out of 5 average rating, 105 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!

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Top guest favorite

Home in Centreville

5.0 out of 5 average rating, 63 reviews

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.

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