Holiday rentals in Cape Henlopen

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Top-rated holiday rentals in Cape Henlopen

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Top guest favourite

Apartment in Lewes

2BR Coastal Retreat Walk to Beach & Downtown Lewes

Welcome to Lewes DE, home of exquisite dining, tax free shopping, and a laid-back atmosphere. This ground floor, single-story condo is (in our humble opinion) in THE BEST location on the Delaware shore. ⭐️ Walkable to both the beach and downtown. ⭐️ Minutes away from Cape Henlopen State park. ⭐️ 3 Roku TVs to keep the family busy during down time ⭐️ Wi-Fi provided ⭐️ Free Disney+ ⭐️ Keurig with k-cups ⭐️ paper products ⭐️ bath towels ⭐️ Fenced in outdoor area for chilling and drying off 😎

4.95 out of 5 average rating, 177 reviews

Guest favourite

Flat in Lewes

Charming Apartment in Downtown, Historic Lewes

Unwind in this bright, freshly updated 1-bedroom apartment perfectly situated in the center of charming downtown Lewes. Overlooking the peaceful Mary Vessels Park, this second-floor retreat offers a full kitchen w/coffee bar, spacious layout, and unbeatable walkability. Just steps from local shops, restaurants, historic landmarks, and the scenic Canalfront Park, it's the ideal home base for your coastal getaway. Whether you're here to relax, dine, or discover, you'll love our welcoming hideaway!

4.86 out of 5 average rating, 331 reviews

Top guest favourite

A blue multi-story beach house features a wraparound porch, large windows, and a screened upper porch. Lush green trees and shrubs surround the front, providing a sense of privacy. The inviting architecture reflects a coastal aesthetic, suitable for family gatherings.

Home in Lewes

Lewes Delaware Beach House

4 BR/2 BA beach house in Lewes DE. Fully furnished and equipped. Sleeps EIGHT MAX. INCLUDING KIDS. THIS IS NOT A PARTY HOUSE. No MAGAs. No WEDDINGS. Available for rent Off-Season (Sept 15 to May 15): weekly, weekend, or mini weeks, two-night minimum. Great location: 1 short block to Lewes Beach on Delaware Bay, 3 blocks to downtown Lewes shops/restaurants/harbor, 1/2 mile to Cape May NJ ferry, 1 mile to Cape Henlopen State Park. 2 hours 15 mins from Baltimore, Washington DC and Philadelphia.

4.93 out of 5 average rating, 158 reviews

Top guest favourite

Apartment in Lewes

A bit of Paradise

Charming end unit secluded in the heart of Lewes. Shady sitting area for viewing the waterfowl & enjoying the peace & quiet. Lewes marina is across the street so is Quest where can rent Kayaks etc. Over the bridge you will enjoy the historic district, town shops, eateries, food market; kiddy park, canal front park; trolley into Rehoboth Beach Henlopen State Park 1 mile; surfing, fishing & nature trails; Bay Beach 1/4 mile w Walk to everything We offer a %15 discount for 7 days or more

4.87 out of 5 average rating, 346 reviews

Top guest favourite

A two-story condo is presented with light-colored siding and large windows adorned with sheer curtains. A coral front door welcomes guests, complemented by a small staircase leading to the upper level. A private balcony with white railings is visible above the entrance.

Apartment in Lewes

Lewes Beach Vibes

This sweet Lewes Beach condo is steps to the beach access & walking distance to town! The main level features a well equipped kitchen, a comfy living area and a powder room. Upstairs are 2 spacious bedrooms & a full bath. Linens & towels are included! You'll also find cozy outdoor living spaces - a balcony off of the primary bedroom & a rear deck complete with an outdoor shower for rinsing off after a day on the beach. 215 Cedar Street at the Rose Garden #4 is your perfect beach get away!

4.98 out of 5 average rating, 109 reviews

Top guest favourite

A modern open-concept living area is presented, featuring comfortable seating arrangements and large windows that provide ample natural light. The space includes a dining area with barstools and a kitchen counter. Views of the waterfront are visible through the sliding glass doors.

Apartment in Lewes

Beautiful Updated Condo Waterfront, Pool, Sunsets

WATER FRONT VIEWS AT LEWES HARBOUR! This newly renovated condo is a unique gem as it sits right between town and the beach on the canal in the heart of Lewes. Waterfront views welcome you into a large, modern kitchen; the sitting room has an electric fireplace and the condo includes its own washer/dryer. After a hot day at the beach cool off in the pool, walk into town for dinner or shopping. Or stay home and enjoy happy hour on the waterfront decks; the sunsets are unbeatable.

4.91 out of 5 average rating, 101 reviews

Top guest favourite

A cozy sleeping area features a spacious bed with a quilted grey coverlet. Two decorative yellow pillows are positioned at the head of the bed. A small bedside table holds a lamp and books, while a colorful area rug adds warmth to the space.

Tiny home in Lewes

Cozy Woodland Cottage

Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

4.94 out of 5 average rating, 241 reviews

Top guest favourite

An open living space features a comfortable gray sectional sofa and a light coffee table, creating a cozy seating area. A dining table set for six is visible near large windows, while modern kitchen appliances are seen in the background, contributing to a bright atmosphere.

Flat in Lewes

Bright 2BR, steps from the beach & downtown Lewes!

Relax and escape to this beautiful space, mere steps to the beach! This open, bright two-bedroom features brand-new construction and furnishings, and has everything you need for a fantastic getaway. ✔ One block from the beach! ✔ 10-15 minute walk to the charming restaurants, bars, shops and parks in downtown Lewes ✔ Lots of bike trails nearby, including through gorgeous Cape Henlopen State Park ✔ A quick drive to the neighboring DE beaches: Rehoboth, Dewey and Bethany.

4.92 out of 5 average rating, 179 reviews

Top guest favourite

An outdoor deck is featured with comfortable seating and a fire table, inviting relaxation with a clear view of the bay. A grill is positioned nearby, while an umbrella provides shade over the seating area. The surrounding beach landscape is visible in the background.

Home in Milton

"Sandy Feet" Broadkill Beachfront Home

Beachfront home w/ unobstructed bay views. Your group will enjoy front-row seats to breathtaking sunrises & water views from the elevated LR and wrap-around deck. The expansive deck with grill & fire table is a great place to sip your morning coffee or gather for dinner & enjoy the unobstructed sights & sounds of the bay. Stay and discover what makes Broadkill Beach so special! Linens are not provided but can be rented from local linen companies.

4.93 out of 5 average rating, 144 reviews

Top guest favourite

A modern living room features a large, L-shaped blue sectional sofa accented with bright throw pillows. A round coffee table sits at the center, adorned with a decorative tray. Soft lighting from a nearby lamp complements the colorful wall art and greenery from a potted plant.

Apartment in Lewes

Beach Sunset: Walk to Dining, Shopping & Beaches

Your coastal Delaware adventure starts right at the front door. From canal-side sunsets to the pristine dunes of Cape Henlopen, everything that makes Lewes famous is within walking or biking distance. We’ve stocked this beach retreat with everything you need: Beach chairs, two cruiser bikes, and a local coffee bar to fuel your morning. It’s more than a stay; it’s your key to the best of Delaware’s historic beach charm.

4.99 out of 5 average rating, 207 reviews

Top guest favourite

Home in Lewes

Blue Haven Cottage - Cozy Beach Escape in Lewes

Blue Haven Cottage offers coastal comfort in the heart of historic Lewes. Centrally located on the Georgetown- Lewes Bike Trail, it’s less than a mile to Lewes Beach, one mile to the Cape May–Lewes Ferry, and only three miles to Cape Henlopen State Park. Enjoy easy access to shops, dining, and trails, then unwind in a cozy, light-filled cottage with beachy charm—your perfect home base for a relaxing coastal getaway.

5.0 out of 5 average rating, 17 reviews

Top guest favourite

A tranquil garden path leads to the cottage entrance, flanked by lush greenery and vibrant flowers. A small fountain gently flows, surrounded by well-manicured grass and white gravel. The serene ambience is highlighted by the dappled sunlight filtering through the leaves.

Cottage in Lewes

Charming, Historic Lewes Cottage

This charming cottage is a great romantic getaway. It is cozy and an easy walk into the historic town of Lewes ~ many great restaurants are nearby. It is not good for tall people because the doors of the Cottage have low head jams and the stairs are compact. There is some noise from the nearby road ~ a white noise machine is provided. The cottage is compact, the refrigerator for the Cottage is a small one.

4.97 out of 5 average rating, 313 reviews