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Vacation Homes in Ridgely

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

9.8 out of 10, Exceptional, (24)
"Great place to stay with a family. Very nicely decorated and clean. "
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (54)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (74)
"Great house, will stay again in the future. "
Circa 1900 Home in the Heart of Historic Downtown Chestertown

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

9.8 out of 10, Exceptional, (43)
"Wonderful home in excellent location!!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Thorneton Point Estate

9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House

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

9.6 out of 10, Exceptional, (23)
"Nice clean home, comfortable bedrooms, accommodating bathrooms and good working kitchen. Highlight is back deck leading to Chester River. You can use the kayaks at the property and fishing is very good! Overall pleasant experience and would definitely stay there again. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (19)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (40)
"We really enjoyed our stay. The house has everything needed and the sunrises are beautiful."
Stylish Home on the Choptank River (with Tidal Beach)

Charming Waterfront Stay close to St. Michaels

9.8 out of 10, Exceptional, (14)
"Great girls weekend getaway. Wonderful location and spacious accommodations. Enjoyed a relaxing stay and beautiful setting."
Charming Waterfront Stay close to St. Michaels

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.6 out of 10, Exceptional, (12)
"Nice stay, would book again. Needs new king mattress, more mirrors in the home and a water filter. Very relaxing clean, makess you want to stay in and gamg out. Close to everything cool."
The price is SAR 938
SAR 1,546 total
includes taxes & fees
2 Oct - 3 Oct
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (5)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

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

10.0 out of 10, Exceptional, (4)
"My family had a great time during our stay! The house was very clean and nice. Views were spectacular! Katie was very responsive to all of my questions. "
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"This rental is amazing and highly recommended!! Beautiful decor! Very clean! Great outside hang out area! Awesome hosts!! Thank you so much for a great stay! "
The price is SAR 739
SAR 1,642 total
includes taxes & fees
6 Oct - 7 Oct
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Downtown St. Michaels | Bikes | Kayaks | Private Pier

10.0 out of 10, Exceptional, (33)
"Lovely home in a beautiful location. Super convenient to everything and very well-appointed and comfortable. Would definitely stay here again!"
Downtown St. Michaels | Bikes | Kayaks | Private Pier

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Minutes from Downtown Easton and St. Michaels | Pool

10.0 out of 10, Exceptional, (2)
"House was perfect for 5 adults and infant. Everyone had ample space but could come together. Property was spotless. Pool and dock were wonderful. Landscaping needs attention and it would have been nice to have a fire pit for the evenings. Otherwise a great place and space!!"
Minutes from Downtown Easton and St. Michaels | Pool

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (9)
"This home exceeded our expectation. Beautiful home and property. Everything we needed."
Gorgeous Creek Side Ranch-Style Estate With Dock
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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Top Ridgely Hotel Reviews