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Ridgely Holiday Rentals

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Holiday Rentals in Ridgely

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 26 reviews
"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, 52 reviews
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, 14 reviews
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, 152 reviews
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Retreat Near Dover
10.0 out of 10, Exceptional, 1 review
"This house was the perfect affordable option for a coaching staff taking a team to the DE sport complex. Way more affordable than the hotels in the area and definitely cleaner. Beautiful field view in the back yard that reminded us of home. Will definitely go back!"
The price is NZ$741
per night
3 Jun - 4 Jun
Retreat Near Dover
Coastal Kent Narrows Home on Bay
10.0 out of 10, Exceptional, 4 reviews
"Very nice place to stay, right on the bay"
The price is NZ$739
per night
3 Jun - 4 Jun
Coastal Kent Narrows Home on Bay
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, 28 reviews
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, 11 reviews
"We enjoyed the property and the proximity to bars/restaurants. We enjoyed the view from the back porch and it is a nice place to relax. We would definitely recommend staying and look forward to booking another stay in the future."
The price is NZ$595
per night
5 Jun - 6 Jun
Cass-N-Reel Luxury Houseboat
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, 90 reviews
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, 1 review
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, 80 reviews
"Very much enjoyed the houseboat. Perfect location - within walking distance of all local attractions / restaurants. Sunset view on the deck is amazing! Hope to come back soon!"
The price is NZ$789
per night
16 Jun - 17 Jun
Cass-Away Luxury Houseboat
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, 127 reviews
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, 41 reviews
"This house was beautiful, clean, modern, everything we needed. Loved the huge table and living-room areas where all of us could be together. Weather wasn't great, so we didn't do anything outside, but the house alone was perfect. Host responded quickly, kitchen was fully equipped. Will definitely consider for our next stay!"
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 59 reviews
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is NZ$269
per night
11 Jun - 12 Jun
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, 3 reviews
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, 12 reviews
"We were in town for a family wedding. The house was spotless, well-stocked and centrally located for our trip. We recommend the property and would come again!"
Grasonville Home w/ Private Pool on the Water
Thorneton Point Estate
9.8 out of 10, Exceptional, 6 reviews
"We had a great time. The pool was a big hit and all the common areas in the house gave us plenty of room to spread out. The game room was super, also. A few things that would make it even greater: about half a dozen cockroaches and other bugs were found in the house; lack of instruction manuals for appliances and sauna; exterior doors very difficult to lack; comforter in bedroom 1 smelled like dogs. Matt was very helpful and responsive to questions"
Thorneton Point Estate
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
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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.

Other types of properties in Ridgely you may be interested in

St Michaels Inn
2.5 star property
8.2 out of 10, Very good, 1,001 reviews
"Toilet seat was pealing. Bathroom floor needed a scrub."
The price is NZ$181
per night
2 Jun - 3 Jun
St Michaels Inn
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, 315 reviews
"Great place "
The price is NZ$347
per night
10 Jun - 11 Jun
Hyatt Place Kent Narrows & Marina
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very good, 1,001 reviews
"Unfortunately I fell in an extremely slippery bathtub. The apparently recently recoated tub surface combined with bath products containing argon oil combined to make the surface of the tub like ice. Our stay otherwise was quite pleasant."
The price is NZ$232
per night
5 Jun - 6 Jun
Best Western Kent Narrows Inn
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.

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.

Frequently asked questions

Are there holiday rentals in Ridgely?

Yes, there are holiday rentals close to the most popular sights in Ridgely, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Ridgely has to offer?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This holiday home rental outside of Ridgely offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Ridgely?

Tuckahoe State Park and Adkins Arboretum are a couple of lovely local spots to get outside and enjoy nature. Queenstown Premium Outlets and Queenstown Harbor Golf Club are a couple of places you'll find in the wider area.

What are holiday rentals like in Ridgely?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ridgely. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for small groups.

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