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Ridgely Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Ridgely holiday rentals

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

1. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is AU$879
includes taxes & fees
27 Oct - 28 Oct
Turnbridge Manor
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is AU$229
includes taxes & fees
26 Oct - 27 Oct
First Floor Studio Apartment in Historic Chestertown
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

3. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$181
includes taxes & fees
2 Nov - 3 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is AU$407
includes taxes & fees
1 Nov - 2 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A garden path leading to a wooden building with a rustic appearance.

5. 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.
The price is AU$392
includes taxes & fees
25 Oct - 26 Oct
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is AU$491
includes taxes & fees
26 Oct - 27 Oct
Newly restored apartment in the heart of Chestertown
A bedroom with a large bed, wooden bookshelves, a tall black column, and large windows.

7. 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.
The price is AU$666
includes taxes & fees
3 Nov - 4 Nov
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.
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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
"This hotel was very well maintained and the room was very nice. The staff at the front desk were friendly, helpful, and very professional. The grounds were beautiful. Breakfast area as well stocked and maintained. The only suggestion I have is to remove the coffee maker listed on the room amenities on the website. The room does NOT have any coffee maker or supplies. There is a coffee maker available 24/7 with good coffee in the lobby. However, I prefer the coffee maker in the room. Otherwise, the hotel is perfect."
Michele 1-night trip
Posted 6 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG

Find out more about Ridgely

Everything you need to know about Ridgely holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ridgely holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Ridgely holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ridgely holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ridgely holiday rentals we have selected for you start as low as AU$229 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ridgely rentals

At Expedia, we put the best Ridgely holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Ridgely?

Yes, there are holiday rentals in Ridgely close to Adkins Arboretum, 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?

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac: This holiday home rental outside of Ridgely is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 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.