Vacation rentals in Ridgely

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Top-rated vacation rentals in Ridgely

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

AkiimaRating, 5 stars2 months ago

Perfect Stay in Deale, MD I had a fantastic stay at this beautiful waterfront home on Carr’s Creek. The hosts were incredibly attentive and made sure I was comfortable the entire time. We had snow during my stay, and they had the driveway and sidewalks cleared almost immediately after it stopped—such a thoughtful touch! The views here are stunning—pictures don’t do this place justice. It’s peaceful, quiet, and in a friendly neighborhood where I felt completely safe. It’s also super convenient, close to great food and anything else you might need. The house felt like home—spacious, welcoming, and fully stocked, especially the fantastic kitchen. Whether cooking, bird watching, soaking in the hot tub, or taking in the view, it was the perfect getaway. If you’re looking for a peaceful escape with family or loved ones, I can’t recommend this place enough!

Top guest favourite

Cottage in Frankford

4.99 out of 5 average rating, 151 reviews

19th Century Coastal Cottage with Modern Amenities

KennethRating, 5 stars1 week ago

Walking into Hobbs and Rose was like entering a welcoming haven…the peace embraced us as we crossed the threshold into the rustic luxury of the cottage. Our favorite snacks and drinks were waiting for us, along with fresh eggs laid by the hens in the quaint chicken house visible from the sunny meditation room. We enjoyed our morning coffee, a special blend ground fresh by the hosts Lisa and Larry, in that same meditation room or sitting in the hammock chairs just feet from the door, an audience to the sometimes animated and sometimes sleeping ducks. We indulged in the offered enhancements of a dinner prepared by Larry, an executive chef and a luxury picnic that lasted us more than two days. The linens were richly comfortable, everything in the cottage was top-of-the-line, and the decor was all lovingly chosen by Lisa. We’re already searching for dates to return to Hobbs and Rose and even though we don’t yet know when we’ll be going back, we can’t wait.

Guest favourite

Cottage in Pasadena

4.97 out of 5 average rating, 172 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars5 months ago

The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !

Superhost

Home in Georgetown

4.82 out of 5 average rating, 160 reviews

Maplewood - Simply Comfortable, Dog Friendly

LeahRating, 5 stars2 weeks ago

We love coming to Georgetown and love staying at Rick's place. It's perfect for us, and we can relax there. The house is beautiful with great amenities. My mom appreciates the walk-in shower. The kitchen is fantastic for cooking. The beds are comfortable, as is the furniture in living and dining rooms. Rick is a fantastic host. I highly recommend this home!

Top guest favourite

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

AcaciaRating, 5 stars1 week ago

Cheryl’s stay was so peaceful, comfortable and fun — even before pool season started. We could not believe how large the yard was and how quiet it was. Amazing wildlife. We saw bald eagles, heron, geese and lots of ducks! The house was squeaky clean and had everything we needed. We watched the stars at night and slept soundly. Downtown St. Michael’s is only about 10 minutes away and full of fun things to do. We’re so happy to be acquainted with the area after staying at Cheryl’s!

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Other great vacation rentals in Ridgely

Guest favourite

Home in Edgewater

4.92 out of 5 average rating, 143 reviews

House in Edgewater Maryland

NancyRating, 5 stars2 weeks ago

Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.

Superhost

Home in Wye Mills

4.91 out of 5 average rating, 11 reviews

⇚Family Getaway⇛| Lakeside + A Nature View |

LisaRating, 5 stars11 months ago

Kevin is a great host to us year after year! we love staying at his place!

Guest favourite

Home in Deale

4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

CourtneyRating, 5 stars4 weeks ago

This air b&b is in a beautiful setting with plenty to do (kayaking, hot tub, fire pits, bird watching, etc). It's also very centrally located so we could easily get to more populated areas in no time. The most stunning part of the house is the master suite in my opinion which is on the upper level (the upper level is shared with another apartment, but you don't really hear the air b&b tenants of this suite and it's completely separate with a separate entrance). Stunning views from both the master bedroom and the bath tub in the master suite! The downstairs is also quite lovely with two regular bedrooms, one small bedroom, and a sun room that has a pull out couch (we didn't use it). It's a lovely house to entertain in. It has personal photographs to the owner downstairs that speak to the family's history. The owner is communicative. The overall experience was quite lovely. We'd be happy to return.

Superhost

Home in Pasadena

4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

EvaRating, 5 stars1 month ago

This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.

Guest favourite

Apartment in Canton

4.97 out of 5 average rating, 31 reviews

Patterson Park Apt; Walk to Hopkins, Bars, Cafes

RachelRating, 5 stars1 week ago

Jenny’s place was exactly what we needed for our long weekend trip. I loved that it was spacious, clean and had excellent natural light. We spent lots of time walking through the park across the street and appreciated how quiet the street/block was at night. 10/10 would recommend!

Guest favourite

Home in Stevensville

4.97 out of 5 average rating, 32 reviews

Carolina Cottage - 2 story, pet-free home

AmberRating, 5 stars2 months ago

This little cottage had my family feel right at home. Very cozy and close to the bay with a beautiful view. Also the neighbors are very friendly!

Guest favourite

Apartment in Annapolis

4.94 out of 5 average rating, 17 reviews

Crow’s Nest Cottage - Down Under: Chesapeake Bay

RickRating, 5 stars1 month ago

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

Superhost