Vacation rentals in Secretary

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Popular amenities for Secretary vacation rentals

Other great vacation rentals in Secretary

Top guest favorite
A private in-ground pool is surrounded by a spacious patio, featuring lounge chairs with blue striped cushions. A small cottage is visible in the background, framed by trees and greenery, offering a peaceful outdoor retreat.
Guesthouse in Cambridge
5 out of 5 average rating, 15 reviews

The Place in Cambridge-Summer is in the Air!

PhilRating, 5 stars2 weeks ago
Catherine’s place was perfect location for Ironman eagleman. We were able to walk everywhere we needed to go. The place was clean, quiet, and comfortable. Being able to cool off in the pool was great. They were very friendly and I would stay again.
Top guest favorite
A long wooden pier extends into the calm water, leading towards lush green trees and an open space in the background. The clear blue sky provides a serene backdrop, enhancing the tranquil waterfront setting.
Home in Piney Point
5 out of 5 average rating, 20 reviews

Waterfront Studio | Bikes & Kayaks | Beach Access

LEVENARating, 5 stars3 days ago
The place was amazing. I could not imagine seeing a sunset like this within an hour from my home. The amenities offered her are like a resort. Heck... we felt like I was at a resort from the moment we checked in. We had everything we needed at our finger tips. The attention to detail was superb. The hosts was responsive and available yet it was still private. This is a Luxe rental.
Guest favorite
Condo in Cambridge
5 out of 5 average rating, 13 reviews

The Drinking Gourd: Stunning Cambridge Penthouse

MelanieRating, 5 stars1 month ago
We had a great stay at Jen's place! It was very spacious and comfortable, and walkable to downtown Cambridge which had plenty of restaurants and bars to explore. The beds were comfortable and the amenities were as described. Jen was a very responsive host and helped out with all our questions. She also offered lots of local recommendations in Cambridge and the surrounding area. I'd definitely recommend Jen's place if you find yourself in Cambridge, MD :)
Guest favorite
A sign for Oystershell Outfitters in Eastern Shore, MD is positioned prominently in the foreground. The backdrop features a serene landscape with a body of water and a colorful sunset. Nearby, two farming tools are placed on the grass, complementing the natural setting.
Place to stay in East New Market
4.94 out of 5 average rating, 18 reviews

Beautiful Waterfront Getaway on the Choptank River

AmyRating, 5 stars1 week ago
We had a wonderful two-night getaway at this beautiful home! It was perfect for our little family—super clean and incredibly comfortable. Our toddler loved having space to explore, especially with the beach and water just a walk away on the property. There's also so much to do locally that's close to this listing as well (all within 10-20 min drive). Lee and his wife were so friendly and welcoming. We’d come back in a heartbeat! Highly recommend for anyone traveling with kids.
Top guest favorite
The outdoor pavilion area features a mix of comfortable seating options, including chairs and a spacious sofa with vibrant cushions. A central glass table is surrounded by the seating, all set on a coated floor that enhances the outdoor experience.
Apartment in East New Market
5 out of 5 average rating, 5 reviews

Cozy apartment in Dorchester County

NoahRating, 5 stars2 weeks ago
Jennifer was a great host and the location was beautiful, the street was very quite and wooded, the place had many amenities beds and sofa were very comfortable. They were very friendly and helpful with local tips, information and things to see. Really appreciated it
Top guest favorite
A cozy living space is highlighted by a brick fireplace, adding warmth to the room. Two comfortable armchairs are positioned nearby, inviting relaxation. The open layout features wooden flooring and a bar-style seating area with a granite countertop, fostering a welcoming atmosphere for gathering.
Private room in Seaford
5 out of 5 average rating, 134 reviews

Off Shore - 1 or 2 private rooms/private bath.

StephanieRating, 5 stars2 days ago
Edna is a wonderful hostess! She is kind and attentive making sure I had everything I needed for a pleasant stay!
Top guest favorite
An inviting living area is showcased, featuring a round glass table set on a patterned rug. Two chairs provide comfortable seating, while large windows frame a stunning view of the water, allowing plenty of natural light to brighten the space.
Home in Cambridge
5 out of 5 average rating, 9 reviews

Magical Waterfront Home Dock, Firepit, Family Fun!

JoyceRating, 5 stars1 week ago
This was our second stay at Heron’s Rest with our extended family—siblings, partners, and one teen—and we’re already planning our return. It truly feels like our home away from home. Claire and Dominique could not be lovelier. From the moment we booked, everything felt seamless and welcoming. Their thoughtfulness shows in every detail—from the beautiful kitchen and quality linens to the heartfelt notes and local recommendations. The house and outside space is designed for comfort and peace, with stunning views of the Choptank River and soothing bird melodies. We love to cook, and Heron’s Rest is a dream—fully stocked, complete with cookbooks and even an ice cream maker. Their crab chowder recipe is now a favorite at home. And the art! Each room features something special—sophisticated yet cozy. Dominique’s eye is truly inspiring. Heron’s Rest is more than a rental—it’s a space to unwind, reconnect, and savor. We can’t wait to come back. We all already miss Heron's Rest!
Top guest favorite
A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.
Cottage in Princess Anne
5 out of 5 average rating, 11 reviews

Waterfront Cottage in Mt. Vernon

KylieRating, 5 stars3 days ago
Can’t beat the views. It’s a quick drive into town. There is a great take out seafood restaurant!

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  4. Dorchester County
  5. Secretary