Holiday rentals in Dewey Beach

OCMD family vacation rental 2BR, 2BA, Pool.

Top floor end unit with large (private) wrap around balcony giving views of the ocean and bay! (54th street Bayside, 1 block from the beach). This 2 bedroom/2 bath is nicely furnished and can accommodate 8 guests. The kitchen is fully equipped with full sized fridge, microwave, dishwasher, washer/dryer, whirlpool tub, central A/C, cable and wifi. Location is perfect for walking to restaurants, miniature golf, shops and nightlife. Rental includes: pool/Hot tub, fitness center,two parking spots.

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

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

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.

Aventurra 406| Outdoor Pool| Balcony

This is an Ocean City Vacation Homes property Soak up the sun on the beautiful beaches when you stay in this bright and airy 3 bedroom condo for 8. This stylish condo is located on the fourth floor, so you can easily admire the breathtaking ocean sunrise view and the amazing bayside sunset view. Boasting 2 private parking spaces, a kitchen, and a wraparound balcony, a pool, this is the ultimate beach destination. Please not the cleaning fee includes sheets and towels.

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.

Hidden Pines in Downtown Rehoboth w/Private Yard

Everyone loves Hidden Pines, our charming cottage with a shady landscaped private yard in downtown Rehoboth Beach. Hidden Pines is just off the main street and half a mile from the beach, in a quiet, shady neighborhood. Perfect for a couple or small family, romantic retreat or solo getaway. Our yard is great for relaxing with a good book or entertaining friends. The downstairs was newly renovated Spring 2022.

Modern Escape~4 Mi from Bethany Beach

Sand, sun, and endless family fun await your crew at this newly built Ocean View vacation rental! Nestled in the quiet community with access to top-notch amenities, and a prime location just 4 miles from the shores of Bethany Beach. After long days of swimming and shopping return home to prepare a feast in the fully equipped kitchen and unwind with a family favorite on the TV.