Holiday rentals in Milton

4.89 out of 5 average rating, 123 reviews

A charming porch features intricate latticework and decorative trim, surrounded by vibrant flower boxes. The open entry leads into the living space, revealing a staircase and dining area in the background, enhancing the welcoming atmosphere.

Apartment in Cape May

World Famous Stockton Row Cottages John Wesley Inn

The Carriage House building is located 1/2 block to the beach and two blocks to the center of the historic downtown. It offers two individual apartments, each with two floors of living space. Apartment "B" has 1 bedroom, 1 bath. Apartment "A" has 2 bedrooms, 2 1/2 baths. Both have a porch and a bedroom balcony. Pricing is for double occupancy. Each can accommodate a maximum of 4 people (children welcome). Conveniences include a full kitchen and complement of electronics. Central air and heat.

The exterior of a historic blue home is captured in this image. The house features two levels, with a gable roof and a welcoming front door. Brick accents are visible near the foundation, complemented by a neatly maintained yard and surrounding greenery.

4.83 out of 5 average rating, 266 reviews

Glennie's Place Quiet Historic Street/Town

A small historic home in the city of Milton, De. Milton offers small USA hometown charm that is close the world famous Delaware beaches. This home was lovingly upgraded, renovated by Glennie's grandson. Enjoy the sunshine off of the back deck while preparing your BBQ. Take a short walk to Milton's city park which is a few minutes from the house off of the Broadkill River. Check out some of the gift shops, eateries, The Milton Theatre, or a tour of the world renown Dogfish Head Brewery.

4.98 out of 5 average rating, 114 reviews

A bright living area features a light-colored sofa and armchair with coastal patterns. A wooden coffee table sits on a textured rug, while a mounted television is visible on the wall opposite. The open layout allows for glimpses of a dining area with a table set for six.

Apartment in Lewes

First Floor Comfort and Convenience

This first floor condo is conveniently located in a family-friendly community with all you need within walking distance, including several restaurants and a grocery store. A short and easy 3-mile drive to Lewes Beach and the charming town of Lewes makes this an ideal location. Amenities include access to two pools, tennis courts, pickle ball courts and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

Apartment in Rehoboth Beach

A modern kitchen area features wooden cabinets, stainless steel appliances, and a stone accent wall. A circular glass dining table is surrounded by wicker chairs, providing a cozy space for meals. The overall layout is bright and inviting, with natural light highlighting the contemporary decor.

4.94 out of 5 average rating, 122 reviews

Cozy Condo on Silver Lake - Walk to the beach!

Located in the middle of a nature preserve on Silver Lake, and walking distance to the beach this end unit condo boasts stunning views and cozy modern decor. Enjoy the pool just steps from your lakeside patio or take a short walk to the beach or town crossing the footbridge (known by locals as turtle bridge.) Lovely boutiques and fine dining in town plus numerous family friendly restaurants. 5 minute drive to Tanger Outlets. Rehoboth Beach parking pass provided with each rental.

A two-story yellow house is featured, with a spacious front porch framed by wooden railings. Stairs lead up to the entrance, where a screened-in porch is visible. Surrounding greenery adds to the peaceful ambiance of the exterior.

4.93 out of 5 average rating, 203 reviews

Broadkill Beach, seafood, fishing, beach, birds

If you have never been to Broadkill, this is a must. If you are looking for a quiet place to relax, read your favorite book on an empty beach, fish or crab, visit the famous Rehoboth Boardwalk or shop at the outlets, this is the place for you. Located only 1 1/2 block from the beach. Bird watchers paradise. Home on dead end street with very little to zero traffic. Located next to Prime hook National Wildlife Refuge. The extra person charge is for adults only exceeding 4 guest.

4.95 out of 5 average rating, 193 reviews

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.

An outdoor seating area features a sectional sofa with navy blue cushions and white striped accents. A light-colored table is positioned in the center, surrounded by natural wood decking. A large navy umbrella provides shade, and greenery is visible in the background.

4.88 out of 5 average rating, 112 reviews

Cheerful Bungalow- Near Dogfish + Milton Theatre

Welcome to our charming retreat on the outskirts of Milton, where comfort meets simplicity! Perfect for families and friends, our home features two inviting bedrooms, a cozy sofa bed, and a bathroom for a peaceful escape from city life. Just a short walk or bike ride away, you’ll find downtown Milton's attractions, including Dogfish Head Brewery, great dining options, and the historic Milton Theatre. Enjoy a delightful blend of relaxation and adventure in this inviting haven!

A wooden deck features two light green Adirondack chairs and a small round table, offering a view of the ocean through trees. The horizon showcases a bright blue sky with scattered clouds, enhancing the serene atmosphere.

4.99 out of 5 average rating, 105 reviews

BeachHaven: STEPS TO SAND, Pet-Friendly, +Linens

Peaceful, secluded, tranquil, yet close to attractions. Our home is located at the more private (i.e. no crowds) southern end of Broadkill. The boardwalk in front of our home leads to the beach path access across the street. You will enjoy views from both the front and back decks: including the beach & Prime Hook Wildlife Refuge. If this property is booked or you need multiple homes for a group, we host several nearby beach homes. Click on my host profile to see them.

4.91 out of 5 average rating, 225 reviews

The cozy cottage showcases a welcoming exterior with wooden shingles and a front porch. An American flag is displayed, and two small shrubs frame the entrance. A clear pathway leads to the door, surrounded by a grassy area and trees in the background.

Tiny home in Ocean View

Tiny Cottage at Good Earth, near Bethany Beach

Welcome to the "Tiny Thyme Cottage" at Good Earth. The cottage is super cozy, perfect for a couple, with 1 queen bed, a kitchen & bathroom, and a small living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include 2 on-site restaurants, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, and 2 cottages on the property. Staying at Good Earth is more than just a beach trip!

4.99 out of 5 average rating, 145 reviews

A serene view of the sunset over the water, with golden light reflecting on the surface. Grassy banks extend along the shoreline, and the distant horizon showcases gentle landforms. The scene exudes calm, complemented by soft clouds in a pastel sky.

Cottage in Milford

"Mary's Place" Sunsets, walks on the beach , bird watching & more

Welcome to Mary's Place! Wait until you see the amazing views from the roof deck, which overlooks the Prime Hook Wildlife Refuge. The Sunsets are spectacular, and it's a bird watchers dream! Mary's Place has a large screened porch and a large outdoor shower. Enjoy walks on the beach along the Delaware Bay, which is directly across the street. Bikes are available for your enjoyment. Dogfish Brewery and several restaurants are less than 10 miles away in the town of Milton.

4.97 out of 5 average rating, 631 reviews

A spacious bedroom features a large bed with dark bedding, complemented by wooden nightstands and lamps on either side. A world map accent wall adds visual interest, while natural light from a window with sheer curtains brightens the room. An adjoining bathroom is visible in the background.

Flat in Rehoboth Beach

Cozy condo / 3,5 miles from the beach.

Cozy condo in a perfect location, close to Rehoboth and Lewes. This is a spacious and bright ground level condo 2bedrooms/2 full bathrooms in Sandpiper Village. Is a perfect spot for having a great time with family, friends or couples. Sandpiper Village its located between Rehoboth Beach (3.5miles) and Lewes (4 miles). Our condo unit includes free parking, full kitchen, living room, dining room, washer/dryer, dishwasher, Youtube TV /wi-fi. We supply sheets and towels.

4.96 out of 5 average rating, 199 reviews

A blue decorative anchor rests on a white surface, featuring a rustic rope detail. The soft lighting highlights the anchor's design, creating a nautical theme. A blurred background suggests a bright and airy space, complementing the apartment's beach-inspired decor.

Flat in Milton

Beachin' Inn Milton

Welcome to Beachin' Inn Milton! This cozy apartment located in the quaint, historical town of Milton, DE is the perfect getaway. Our apartment is light and airy with a beach theme. Enjoy the entire apartment to yourself with a keyless private entrance, full bath, washer/dryer, free Wifi and stocked assorted coffee pods. There is no stove/oven, however, we offer a microwave, toaster oven, Air Fryer and induction burner.There is private parking right out front

Popular amenities for Milton holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Milton

5 out of 5 average rating, 12 reviews

Guest house in Lewes

Pool, dog friendly, fenced yard in Lewes

The kitchen features modern cabinetry and sleek stainless steel appliances. A spacious countertop provides ample workspace, accompanied by a beverage bar. Natural light enters through a window above the sink, highlighting the warm wood flooring and inviting atmosphere.

4.96 out of 5 average rating, 49 reviews

The Retreat at Broadkill Beach

An aerial view of a two-story beach house showcases a spacious roof deck equipped with a high-top table and seating. The surrounding area includes paths leading to the beach, grassy spaces, and neighboring homes, with the ocean visible in the background under a clear sky.

4.97 out of 5 average rating, 31 reviews

Horseshoe Haven-Roof Deck, Beach Views, Game Room

5 out of 5 average rating, 53 reviews

A modern dining space is depicted with a round table set for four, featuring light blue plates and glasses. Contemporary bar stools line the kitchen counter, which showcases stainless-steel appliances. Adjustable lighting illuminates the area, enhancing the welcoming atmosphere.

Flat in Rehoboth Beach

Velo Condo-2 BR, 2 BA, Pool view

The large kitchen features modern appliances, including a stainless steel refrigerator and a built-in microwave. A center island provides additional seating with two bar stools. A dining table with six chairs is set for meals, and abundant natural light fills the space through multiple windows.

5 out of 5 average rating, 36 reviews

Heidi’s Milton Farmhouse

5 out of 5 average rating, 54 reviews

A spacious kitchen features a large island with seating for four, white cabinetry, and stainless steel appliances. Natural light streams in through nearby windows, illuminating the quartz countertop. A cozy living area is visible in the background, enhancing the open-concept design.

Townhouse in Lewes

Luxe Lewes Townhouse: Pool, Roof Deck & Bike Trail

Superhost

Home in Rehoboth Beach

4.76 out of 5 average rating, 214 reviews

Delightful Cottage•Pet Friendly•Fenced Yard

A cozy living room features two large couches arranged around a central coffee table. A large window allows natural light to fill the space, with a decorative rug underfoot. A small entertainment unit and potted plant are visible against a neutral-toned wall.