Photo by Marie

Search Vacation Homes in Ridgely

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 92 Vacation Homes in Ridgely with updated reviews, rates, and availability.

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (47)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Walk to Everything House

10.0 out of 10, Exceptional, (74)
"House was centrally located in town. We parked the car and walked! Beds were very comfortable it was wonderful to have seperate beds for everyone. Well stocked kitchen. Washer & dryer a plus. We will be back. "
Walk to Everything House

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (23)
"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."
Waterfront family resort Lodge with private pier, game room and bar

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

9.6 out of 10, Exceptional, (4)
"My family and I cannot say enough great things about the home or hosts! The home was everything pictured plus so much more. Perhaps "thoughtful" in all regards is the one word to describe everything about both the home and hosts! The home location is rural and peaceful while only 30 minutes from the heart of Rehoboth Beach. We'll never forget the memories of our amazing stay - and plan to become regulars:-)! In fact, we're getting ready to book again:-)!"
The price is SAR 447
SAR 737 total
includes taxes & fees
12 Jan - 13 Jan
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

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

9.8 out of 10, Exceptional, (33)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

10.0 out of 10, Exceptional, (1)
"This property is a phenomenal place to spend time with family and enjoy beautiful St. Michael’s. The house is well stocked and convenient to town. We’d love to come back. "
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (30)
"We enjoyed the beautiful views, nature and clean comfortable house with all amenities. Will definitely book again on our next trip to Eastern shore."
Stylish Home on the Choptank River (with Tidal Beach)

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (5)
"The house and property were wonderful. Right on the river with all you need. Fantastic stay, great communication, would love to return again!"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (10)
"Beautiful and it was located close to my daughter and her family. It is close to shopping both food and outlets. The morning view of the water was so relaxing and beautiful while having a cup of coffee. There was plenty of room for 4 adults and two kids. I will definitely stay here again. "
River Front, Private Single Family Home

Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

9.2 out of 10, Wonderful, (5)
"The owners were very flexible with us and understanding when it came to a booking mistake on my end. The house is lovely and the property is absolutely gorgeous. The deck was picture perfect. Highly recommend for a getaway on the eastern shore!"
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (3)
"This property was in a great location for attending the Waterfowl festival. The host thought about each detail and our stay was more than comfortable. "
Cozy 2BR Home near Idlewild Park

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

10.0 out of 10, Exceptional, (2)
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

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

10.0 out of 10, Exceptional, (129)
"Wonderful home for our girl's weekend getaway. Beautiful property on the water and close to Easton and St Michael's"
Modern St. Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks & More

St. Michaels Waterfront Home

9.6 out of 10, Exceptional, (25)
"Excellent property ! Had everything we needed and wanted and more. Waterfront views and shorebirds beautiful ! We hope to revisit !!! "
St. Michaels Waterfront Home
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.
Don't see what you're looking for?
See all available properties in Ridgely
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Ridgely

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

9.8 out of 10, Exceptional, (50)
" We ( a group of 16 women) enjoyed having our annual retreat at Nauti or Knot. We stayed for a weekend and the accommodations could not have been better! The bedrooms and bathrooms were wonderful. The living room was able to sit 16 comfortably and the dining room table was big enough for all of us to have dinner together. This is an excellent house!! Our only complaint and it’s minor is that the freezer door was really hard to open."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (47)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels
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.