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Ridgely Vacation Rentals

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Dec 21 - Dec 22
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Dec 22 - Dec 23
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Dec 26 - Dec 28
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Our top choices for Ridgely vacation rentals

Exterior
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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Dec 31 - Jan 1, 2026
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 22 - Dec 23
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
$298 nightly
The price is $316
Dec 22 - Dec 23
Total with taxes and fees
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Fridge, microwave, dishwasher, coffee/tea maker
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
$445 nightly
The price is $472
Jan 5 - Jan 6, 2026
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Property grounds
Turnbridge Manor

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Dec 29 - Dec 30
Total with taxes and fees
Turnbridge Manor
Dining
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$389 nightly
The price is $412
Dec 22 - Dec 23
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Clean, friendly and "
Margaret 1-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina

Find out more about Ridgely

Everything you need to know about Ridgely vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ridgely vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ridgely vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ridgely vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ridgely. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ridgely in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ridgely rentals

At Expedia, we put the best Ridgely vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ridgely rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ridgely vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ridgely. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf: This vacation home rental outside of Ridgely is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Ridgely?

Explore the area and family-friendly sights such as Hazel Miner Monument, or get out into nature at a spot like Adkins Arboretum. Tuckahoe State Park and Wye Landing 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.