Vacation rentals in Secretary

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Dog friendly, Close to outlets, fire pit, Sleeps 6

Tucked away in a quiet neighborhood, this adorable cottage awaits your next peaceful vacation. With 3 beds/2 baths, there’s space to enjoy a relaxing stay for up to 6 guests with cozy blankets and beds as well as beautiful surrounding gardens. We are only 4 miles to the beaches, 1 mile to outlet shopping, and close to amazing restaurants. You may not even want to leave the cottage at all. Pet friendly (1 dog please). NEW FOR 2024: beautiful bathroom updates and NEW comfy mattress in the master!

The Villa at Bayside Resort

Introducing a stunning, professionally decorated vacation rental property nestled in the heart of the prestigious Bayside Resort. Property Features: 4 beautifully-appointed bedrooms, 3.5 baths A spacious loft A sun-soaked living area Sun room, An elegant dining room, perfect for memorable family meals A scenic patio off of a wooded lot, offering a serene outdoor retreat. Bayside Amenities: Golf course 4 pools Fitness center Tennis courts Playground Kayaking Trails Concert Venue

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Chic DT apartment with hot tub, walk everywhere

Enjoy a stylish experience at this centrally-located place. Walk to everything—beach, restaurants, shopping—and enjoy the very best of Rehoboth without ever looking for a parking spot. This newly renovated first floor private apartment of a 3-story house is spacious and loaded with every amenity, including all linens (a rarity in Rehoboth!), local coffee, a well stocked pantry, 65-inch TV with sound system, and your own private patio with dining space, grill, and hot tub.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.