Vacation rentals in Henderson

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Top-rated vacation rentals in Henderson

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

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Guest favorite

Home in Deale

4.96 out of 5 average rating, 26 reviews

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.

Guest favorite

Home in Georgetown

4.76 out of 5 average rating, 17 reviews

Salty Roots Ranch_Yard & Game Room_Mins to Milton

Country Vibes at the Delaware Beaches. Expertly designed for large group vacations. 5 bedrooms, 2 living spaces, immense backyard, games, activities, & more. Traveling for sports? Only 5 minutes to Sports at the Beach. De Turf and Sandhill fields also close proximity. Tourism at your fingertips with Historic Downtown Milton & World Famous Dogfish Head within 5 minutes travel. Broadkill, Lewes, Rehoboth beaches all under 20 minutes. Cape Henlopen State Park, Fort Miles Museum, & more to explore!

Guest favorite

Cottage in Rehoboth Beach

4.9 out of 5 average rating, 109 reviews

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!

Superhost

Townhouse in Bethany Beach

4.93 out of 5 average rating, 109 reviews

Lakefront slps 6; beach, pools, tennis, gym, view!

Lake front in Sea Colony Resort! Walk to beach, pools, tennis/pickleball, putting green, bocce, shuffleboard, fishing ponds, fitness center & more! 24/7 security. Completely renovated. Well equipped kitchen opens to bright, charming living/dining rooms with seating for six. AC, charcoal grill, washer/dryer, wifi, 3 flat screen TV's & 3 queen beds. Beach tram & pool across street. Large deck with great view of lake and fireplace in living room! Professionally cleaned between guests.

Superhost

Cottage in Pasadena

4.88 out of 5 average rating, 121 reviews

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!

Superhost

Cottage in Pasadena

4.82 out of 5 average rating, 17 reviews

Sunset Lagoon Home

Have fun with the whole family at this stylish place! Our cozy cottage sits at the edge of a beautiful creek. Peaceful and tranquil, yet close to shops and restaurants, this waterfront property is perfect for serene getaways and family gatherings! Everyone will enjoy a unique and private space to relax. From peaceful mornings lounging on the balconies, to afternoons filled with fishing to magical sunsets on the 110-foot pier, this setting will quickly become a family favorite!

Guest favorite

Cottage in Easton

5 out of 5 average rating, 100 reviews

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

Superhost

Home in Rehoboth Beach

4.84 out of 5 average rating, 62 reviews

As Seen In Dwell-Stunning Modern Coastal Getaway

Newly renovated beach getaway! Modern design with coastal charm redefines vacation rentals! screened in porch with swing bed, deck with outdoor shower. Gourmet kitchen, an open living/dining area, sectional, fireplace, TV. 3 bedrooms each have their own personality. Enjoy a queen sized bunk bed, a bohemian guest room, and master suite with king bed, private bathroom. The neighborhood has views of Rehoboth Bay, is 2 miles from the beach.

Guest favorite

Condo in Rehoboth Beach

4.93 out of 5 average rating, 102 reviews

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.

Superhost

Cottage in Rehoboth Beach

4.73 out of 5 average rating, 44 reviews

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.

Superhost

Home in Ocean View

4.88 out of 5 average rating, 8 reviews

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.

Guest favorite

Apartment in Betterton

5 out of 5 average rating, 15 reviews

Bayside Bungalow

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.