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Ridgely Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Ridgely

Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (46)
"Super nice for me an my wife for her birthday weekend. Very clean and close to nice restaurants. "
United States
Zack L.
Cass-N-Reel Luxury Houseboat
Property grounds
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Vacation Home in Greenwood

9.8 out of 10, Exceptional, (30)
"Great place to stay with a family. Very nicely decorated and clean. "
United States
Meg E.
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Apartment in Saint Michaels

Downtown St. Michaels | Porch + Pet-Friendly
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Nov 25 - Nov 26
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Vacation Home in St. Michaels

9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Cottage in St Michaels

9.6 out of 10, Exceptional, (146)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Apartment in Saint Michaels

10.0 out of 10, Exceptional, (54)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Private kitchen
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Vacation Home in Chestertown

10.0 out of 10, Exceptional, (2)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cottage in Saint Michaels

9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Dining
Cass-Away Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (104)
"What a unique experience to stay on a houseboat. Such a fun locale & comfortable accommodations. "
United States
Robin L.
Cass-Away Luxury Houseboat
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Cottage in St Michaels

9.6 out of 10, Exceptional, (125)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Outdoor dining
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (73)
"This trip was a girls get away & we thoroughly enjoyed ourselves .. the house was by far the best I’ve ever rented .. clean, well appointed, & decor was gorgeous … the owner was so attentive & acted on anything we needed right away .. I highly recommend this property & we will definitely be returning …"
United States
Denise O.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Property grounds
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Vacation Home in Grasonville

10.0 out of 10, Exceptional, (23)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Property grounds
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Vacation Home in Chestertown

10.0 out of 10, Exceptional, (76)
"Great house, will stay again in the future. "
United States
Gary N.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Marina
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Vacation Home in Easton

10.0 out of 10, Exceptional, (95)
"A beautiful location and a lovely home. Our children absolutely enjoyed having the pool table, ping pong table, basketball net and all the equipment for water fun. And of course the pool was delightful. "
United States
Janet R.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Exterior detail
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Vacation Home in Grasonville

10.0 out of 10, Exceptional, (6)
"Located in a quiet area. Beautiful place. Wish we could have stayed longer. An information sheet/welcome booklet could have been helpful in learning how to start the fireplace and the wifi info."
United States
M
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
Fridge, microwave, oven, stovetop
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Cottage in Centreville

10.0 out of 10, Exceptional, (105)
"Great vacation. Relaxing and views are incredible. The host is amazing!!! "
United States
Melissa S.
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Property grounds
St. Michaels Waterfront Home

Vacation Home in New comb

9.8 out of 10, Exceptional, (31)
"Immaculate, very responsive and proactive host, and a fabulous location!"
United States
Morgan Z.
St. Michaels Waterfront Home
Smart TV, fireplace
RELAX- Eastern Shore Creek Home - 6 Guests

Vacation Home in Grasonville

10.0 out of 10, Exceptional, (5)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
United States
Sherry N.
RELAX- Eastern Shore Creek Home - 6 Guests
Fridge, microwave, dishwasher, coffee/tea maker
Serene Waterfront Cottage with dock and gorgeous views.

Vacation Home in Rock Hall

9.6 out of 10, Exceptional, (38)
"Easy check in and check out. Beautiful water veiw. We really enjoyed having access to the kayaks. The house was just as the listing said it would be. Definitely would rent again. "
United States
Tim S.
Serene Waterfront Cottage with dock and gorgeous views.
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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great staff at check in desk!"
Joseph 1-night trip
Posted 21 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This vacation home rental outside of Ridgely offers a garden, a barbecue grill, 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 you can cook with friends or family.

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 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.