Photo by Marie

Ridgely Vacation 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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Ridgely Vacation Homes

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

9.8 out of 10, Exceptional, (19)
"It was a awesome great comfy house."
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

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

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (13)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"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

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

9.8 out of 10, Exceptional, (40)
"Property was perfect for our family stay. House was clean and well stocked."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (19)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (10)
"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!

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (19)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6

Waterfront Estate w Private Pier, Game Room & Bar

9.8 out of 10, Exceptional, (30)
"Overall, our stay was fantastic. The weather was absolutely magnificent the entire stay."
Waterfront Estate w Private Pier, Game Room & Bar

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Very cozy, a very quiet home"
Peaceful Queenstown Home w/ Deck & Grill!

Walk to Everything House

10.0 out of 10, Exceptional, (81)
"Clean and nice place to stay"
Walk to Everything House

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (16)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home

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

Charming Waterfront Stay close to St. Michaels

9.8 out of 10, Exceptional, (12)
"Great house, updated, amazing views "
Charming Waterfront Stay close to St. Michaels

Thorneton Point Estate

9.8 out of 10, Exceptional, (19)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate

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

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $343
CA $575 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

10.0 out of 10, Exceptional, (21)
"This was a good house for a family get together with other people staying in the area. The house was clean and well stocked. Lovely setting on the water. "
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Luxury Treehouse with Large Deck

10.0 out of 10, Exceptional, (6)
"This is a place that I we can’t wait to go back to!! Everything was so unique and done up with thought. You have to go and read the beautiful story behind the “Tree House” "
Luxury Treehouse with Large Deck

Waterfront House in Saint Michaels: Pets Welcome!

9.4 out of 10, Exceptional, (3)
"We enjoyed this lovely home on the water. The house was comfortable and beautifully decorated. The setting was very pretty with the water views. The house is on a main road and we could hear some traffic noise but only outside the home. The house was set back far enough that I was not worried about my dog being near the road. We enjoyed peaceful kayaking one evening. It was about 3 miles from St Michael’s and close enough to walk to The Chesapeake Landing Restaurant, which came in handy when we...
Waterfront House in Saint Michaels: Pets Welcome!

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (46)
"wonderful home and great views. Clean, quiet, plenty of amenities"
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
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

Top Ridgely Hotel Reviews