Photo by Marie

Ridgely Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
10 Jul - 11 Jul
Tomorrow
11 Jul - 12 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Ridgely

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Relax by the serene pool surrounded by lush greenery and a comfortable bench.

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relax in a serene park setting surrounded by lush greenery and a central gazebo.

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Guests can enjoy a serene waterfront view from this tranquil pier.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"We really enjoyed this property. It had everything we would want and plenty of space. It was very clean and quiet. The water, fire-pit, porch and living spaces were wonderful for a nice long-weekend get-away!"
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
First Floor Studio Apartment in Historic Chestertown
Relax by the pool surrounded by a tranquil golf course view.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (90)
"Very pretty location. Few minutes drive to town center."
The price is HK$777
HK$1,247 total
includes taxes & fees
17 Jul - 18 Jul
First Floor Studio Apartment in Historic Chestertown
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Escape to a serene cabin surrounded by lush greenery and natural beauty.

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (4)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Waterfront Sunset Bayview: sleeps 6
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is HK$3,917
HK$6,607 total
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6
St. Michaels Waterfront Home
Relax by the serene lake with a dock and a small boat, surrounded by lush greenery and comfortable Adirondack chairs.

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (29)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Cass-N-Reel Luxury Houseboat
Enjoy waterfront views from the dock, surrounded by boats and a marina.

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (30)
"We really enjoyed our stay. Looking forward to staying again!"
The price is HK$848
HK$2,172 total
includes taxes & fees
24 Jul - 25 Jul
Cass-N-Reel Luxury Houseboat
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Relax in this serene living space with a glass-top dining table and comfortable armchair.

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (12)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
RELAX- Eastern Shore Creek Home
Cozy up by the fireplace in this inviting living room with a stunning view of the outdoors.

RELAX- Eastern Shore Creek Home

10.0 out of 10, Exceptional, (2)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Relax in this inviting living space with a comfortable sofa, a cozy bed, and a peaceful atmosphere.

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Relax in a serene hot tub under a covered pergola with a breathtaking view of the surrounding landscape.

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

10.0 out of 10, Exceptional, (5)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is HK$1,547
HK$3,462 total
includes taxes & fees
23 Jul - 24 Jul
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Kitchen area with a stove, dishwasher, refrigerator, sink, and countertop with a kettle.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (101)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Historic Downtown Garden Oasis with Private Patio
Stroll through the serene garden, surrounded by lush plants and a majestic tree.

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Grasonville Home w/ Private Pool on the Water
Relax by the serene pool overlooking the lake, surrounded by a lawn and shaded by a large tree.

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and microwave, and dine at the wooden table.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Stylish single-story home with a symmetrical facade, featuring evenly spaced windows and a central entrance.

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

9.6 out of 10, Exceptional, (10)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is HK$1,962
HK$3,328 total
includes taxes & fees
14 Jul - 15 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Gorgeous Creek Side Ranch-Style Estate With Dock
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and wine cooler.

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock
Guest Suite for up to 2 in a Victorian on the Chester River
Stunning two-story home with a gabled roof and inviting front porch.

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (14)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is HK$480
HK$925 total
includes taxes & fees
15 Jul - 16 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
Stunning hallway with a chandelier, large mirror, and bookshelf.

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (9)
"The property is a great place to get away and enjoy some time with family. We enjoyed swimming in the pool. Fishing was fun as well catfish for days. Nice sunsets by the fire and just overall a great time with the family. "
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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?

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks: This holiday home rental outside of Ridgely is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 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 patio, 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 Martinak State Park 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.