
Ridgely Holiday Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Ridgely holiday rentals

1. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
2. Turnbridge Manor
Turnbridge Manor
3. Family Retreat at Lansdowne Manor
Family Retreat at Lansdowne Manor
4. First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
5. Guest Suite for up to 2 in a Victorian on the Chester River
Guest Suite for up to 2 in a Victorian on the Chester River
6. Cass-N-Reel Luxury Houseboat
Cass-N-Reel Luxury Houseboat
7. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places
8. Family Friendly Cozy 3 Bedroom Duplex
Family Friendly Cozy 3 Bedroom Duplex
9. Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
10. Newly restored apartment in the heart of Chestertown
Newly restored apartment in the heart of ChestertownFind holiday rentals that suit your style
Top Ridgely Hotel Reviews

St Michaels Inn
Find out more about Ridgely
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ridgely holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Ridgely. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ridgely. Seeing all the best attractions is bound to make you fall in love with Ridgely. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ridgely short-term rentals, that won’t be hard to do.






































