A forest with tall trees and a sunset in the background.

Ridgely Vacation Rentals

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Ridgely vacation rentals

Property grounds

1. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Sep 22 - Sep 23
Total with taxes and fees
Turnbridge Manor
Exterior

2. 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
9.8 out of 10, Exceptional, (28 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Sep 22 - Sep 23
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$144 nightly
The price is $159
Sep 29 - Sep 30
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Interior

4. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (107 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
$271 nightly
The price is $299
Sep 28 - Sep 29
Total with taxes and fees
Cass-Away Luxury Houseboat
Smart TV

5. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
$254 nightly
The price is $280
Oct 8 - Oct 9
Total with taxes and fees
Cass-N-Reel Luxury Houseboat
Dining

6. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
$419 nightly
The price is $463
Sep 23 - Sep 24
Total with taxes and fees
Family Retreat at Lansdowne Manor
Dining

7. 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, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
$479 nightly
The price is $508
Sep 22 - Sep 23
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
TV, fireplace

8. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$264 nightly
The price is $274
Sep 23 - Sep 24
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Smart TV

9. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
$293 nightly
The price is $311
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Property grounds

10. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
$463 nightly
The price is $481
Sep 29 - Sep 30
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ridgely Hotel Reviews

The Tidewater Inn

The Tidewater Inn

10/10 Excellent
"For an older hotel, this venue was very nicely maintained. The staff was wonderful, with the only drawback being the parking situation on the weekends. While normally adequate, there was a large wedding at the hotel while we were there, and all of the parking spaces were taken. Fortunately however, there was adequate parking on the street, so we made do. Once again, it was the professionalism and the courtesy of the staff that stood out in our minds as the best part of this stay at The Tidewater Inn."
Thomas 1-night trip
Posted 2 hours ago
The Tidewater Inn

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 $280 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?

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac: This vacation home rental outside of Ridgely is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 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.