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Compare 89 Vacation Homes in Ridgely with updated reviews, rates, and availability.

Pet-Friendly Home on Chester River w/ Dock!
Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

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!
Backroad Getaway - Newly Built 3-bedroom retreat in Greenwood with WiFi
Exterior

Backroad Getaway - Newly Built 3-bedroom retreat in Greenwood with WiFi

10.0 out of 10, Exceptional, (1)
"We stayed at the property for a hunting weekend. The house was great, and the owners made sure you had everything you needed. If available will definitely rent again."
The price is AED 514
AED 797 total
includes taxes & fees
6 Jan - 7 January 2025
Backroad Getaway - Newly Built 3-bedroom retreat in Greenwood with WiFi
Dollhouse in Central Historic St Michaels
Front of House

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"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
Waterfront family resort Lodge with private pier, game room and bar
The Twin Ponds Lodge sits on over 7 acres of private waterfront property.

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
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront with private pier and great views

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.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

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.
Walk to Everything House
Front of House

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 Paradise on the Eastern Shore of Chesapeake Bay
Beach

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

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

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
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Master bedroom.. King-size bed and en-suite bathroom.

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (8)
"This home had to have been the most perfect VRBO we have stayed in. The home was clean, comfortable, stocked with amenities that made the stay incredibly pleasant and in a fantastic location. We particularly enjoyed the built in speakers in the dining room. I would highly recommend this home for a visit to Chestertown. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Pool

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
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Outdoor dining

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (16)
"Beautiful property with lots of thoughtful details. "
Adorable two-bedroom retreat close to Easton, Denton, Centreville
River Front, Private Single Family Home
Marina

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!
Welcome to Langford Creek Estate- a beautiful waterfront estate with an extensive amenity list!

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
Living area

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (2)
"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
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
Denton Vacation Rental | 5BR | 3.5BA | 4,496 Sq Ft | 4 Steps Required

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (3)
"This large property - inside and outside - was perfect for our family get together. We were a total of 7 adults, 3 children and an infant and there were plenty of bedrooms, bathrooms, dining room space and other areas to hang out in. The pool and fire pit were great for kids and adults, and some of the family enjoyed kayaking. The property adjoining the Choptank River was private and peaceful. The property manager - Julie - went above and beyond to provide us what we needed for a great...
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard
Living area

4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard

2.0 star property
10.0 out of 10, Exceptional, (1)
"Kyle was very responsive and a great host! This house is set up to accommodate a large group, but has space for privacy as well. Close to restaurants and shopping, but fully stocked kitchen and linens. Would recommend staying here!! Loved the chickens!!"
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

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
Pool

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
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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Other property types in Ridgely

Dollhouse in Central Historic St Michaels
Front of House

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"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.
Waterfront with private pier and great views

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.
Waterfront family resort Lodge with private pier, game room and bar
The Twin Ponds Lodge sits on over 7 acres of private waterfront property.

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
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.