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Compare 114 Vacation Homes in Ridgely with updated reviews, rates, and availability.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (34)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

10.0 out of 10, Exceptional, (1)
"As advertised. Great views, dock and decks. Inside is modern, functional and very clean. No complaints whatsoever."
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (85)
"Gorgeous views and surroundings"
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Walk to Everything House

10.0 out of 10, Exceptional, (78)
"Great location. Loved being near town and the Blue Crab. "
Walk to Everything House

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

9.8 out of 10, Exceptional, (9)
"Came back home from PA to visit family and this house was just perfect to do that! Had spacious bedrooms and bathrooms and comfortable furniture and SO clean!! The backyard was amazing for us all to hang out with the fire going. The hosts were amazing with communication. Definitely recommend staying and I will be back! "
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.8 out of 10, Exceptional, (12)
"I booked this house for a week as a quiet fishing trip get away. For starters Leone is awesome, always responds quick and is an amazing host.The house itself: was very clean, cozy, and had everything needed for a very comfortable stay. Other reviews said furniture was uncomfortable but I thought it was fine. Location was 3 min to foodlion, 10ish min to gas station, and about 16 min to large store for fishing gear. TV has netflix and lots of other shows to watch if thats what you want but most of...
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Serene Waterfront Minutes from St Michaels.

9.8 out of 10, Exceptional, (7)
"We truly loved our stay! The home was super comfortable and well stocked for making Thanksgiving dinner for 6. We loved just looking out at the geese, swans and blue herons ! Really lovely. We’ll be back!"
Serene Waterfront Minutes from St Michaels.

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (32)
"A beautiful and serene setting mapping the contours of nature, tranquility & relaxation. Steven is an exceptional host."
Stylish Home on the Choptank River (with Tidal Beach)

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"This house is very nice and conveniently close to Washington College. Teddi was responsive to our last minute rental. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (25)
"Owner/host was absolutely the best communicator. Spectacular views. The suite was an added bonus. Great beds in all the rooms . The kitchen provided great space to prepare family meals together. Wonderful water pressure. Stayed at the home for a special getaway for mom's 91st birthday. She kept stating "I love this little house". This home surpassed our expectations. This stay will forever have special memories. We hope to return. jold special memories "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (25)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar

Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

10.0 out of 10, Exceptional, (16)
"Our 5th year traveling to the eastern shore of Maryland. The house was great. Loved everything about Pool"
Minutes from Downtown Easton and St. Michaels | Pool | Kayaks | Private Dock

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (6)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (26)
"Excellent property ! Had everything we needed and wanted and more. Waterfront views and shorebirds beautiful ! We hope to revisit !!! "
St. Michaels Waterfront Home

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

10.0 out of 10, Exceptional, (18)
"It’s in a tranquil, bucolic setting that is relaxing to come back to after a day out enjoying activities. Lovely home all around."
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Ridgely

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (80)
"The space was very clean. Communication with the owner was a breeze. It was quiet. The neighborhood is great. It is close to downtown Chestertown. A fabulous stay! "
The price is AED 360
AED 579 total
includes taxes & fees
6 May - 7 May
First Floor Studio Apartment in Historic Chestertown

Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!

10.0 out of 10, Exceptional, (21)
"This cabin is on a farm and very, very cozy! Me and my friends were not disturbed and we greatly appreciated how clean this place was. The view from the loft is amazing! I would stay here again. "
The price is AED 569
AED 757 total
includes taxes & fees
11 Apr - 12 Apr
Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (47)
"Nice place "
Dollhouse in Central Historic St Michaels
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.