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Ridgely Vacation Rentals

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Vacation Rentals in Ridgely

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (121)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (34)
"We really enjoyed our stay. Looking forward to staying again!"
The price is CA $206
CA $446 total
includes taxes & fees
Sep 7 - Sep 8
Cass-N-Reel Luxury Houseboat

Studio in Downtown – Walk to Everything!

10.0 out of 10, Exceptional, (22)
"This was the perfect spot for a long weekend. Excellent location and the unit itself was more than we expected. "
Studio in Downtown – Walk to Everything!

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

9.8 out of 10, Exceptional, (19)
"It was a awesome great comfy house."
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (184)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

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

9.8 out of 10, Exceptional, (40)
"Property was perfect for our family stay. House was clean and well stocked."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

9.6 out of 10, Exceptional, (19)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (10)
"The property is a great place to get away and enjoy some time with family. We enjoyed swimming in the pool. Fishing was fun as well catfish for days. Nice sunsets by the fire and just overall a great time with the family. "
Riverfront Denton Estate on 7 Acres w/ Fire Pit!

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home

Walk to Everything House

10.0 out of 10, Exceptional, (81)
"Clean and nice place to stay"
Walk to Everything House

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (9)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (93)
"Very pretty location. Few minutes drive to town center."
The price is CA $136
CA $219 total
includes taxes & fees
Aug 13 - Aug 14
First Floor Studio Apartment in Historic Chestertown

Waterfront House in Saint Michaels: Pets Welcome!

9.4 out of 10, Exceptional, (3)
"We enjoyed this lovely home on the water. The house was comfortable and beautifully decorated. The setting was very pretty with the water views. The house is on a main road and we could hear some traffic noise but only outside the home. The house was set back far enough that I was not worried about my dog being near the road. We enjoyed peaceful kayaking one evening. It was about 3 miles from St Michael’s and close enough to walk to The Chesapeake Landing Restaurant, which came in handy when we...
Waterfront House in Saint Michaels: Pets Welcome!

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (46)
"wonderful home and great views. Clean, quiet, plenty of amenities"
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (2)
"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

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (45)
"Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!"
The heart of St Michaels awaits.

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (16)
"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
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

Frequently asked questions

Are there vacation rentals in Ridgely?

Yes, we have vacation rentals in Ridgely close to Adkins Arboretum, or you can choose a secluded option if you'd like a relaxing place to stay. Ridgely is known for its shopping and restaurants. Make sure you have time to check out the parks while you're in the area.

What's the top vacation rental that Ridgely has to offer?

St. Michaels Waterfront Home: This vacation home rental outside of Ridgely is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of books.

What can I see and do in Ridgely?

Explore the area and family-friendly sights such as Delaware State Fairgrounds, or get out into nature at a spot like Adkins Arboretum. Tuckahoe State Park and Martinak State Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Ridgely?

Vacation rentals are privately owned properties you can book for a short or long stay in Ridgely. Vacation rentals feature extras such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.