Family-friendly holiday rentals in Milton

A calm waterway is highlighted, with a boat launch area leading to the water. Trees provide shade along the banks, and accessibility signage is visible. A small dock can be seen, while nearby parking and grassy areas are present, offering space for leisure activities.

4.98 out of 5 average rating, 113 reviews

Wkly/Mthly Rates- Near Dogfish, Sport@Bch&DE Turf

Weekly Discount (7 days) & Monthly Discounts (30+ days) Close to Lewes Beach(12 miles), Rehoboth(16 miles), Dewey Beach, Broadkill Beach (7 miles). Sports at the Beach (14 minutes), Sandhill Fields (15 minutes) and DE Turf (20 minutes). Near Dogfish Head Restaurant. Close to Hospitals - Beebe (11 miles) & Bayhealth (11 miles). Short drive to Tanger Outlet for Tax-Free shopping. Easy Walk to Kings Ice Cream, Restaurants & Park. Near Rookery, Southern DE Golf & More. TOWELS & LINENS INCLUDED

KitchenFamilyBiking

A sleeping area is furnished with a spacious bed dressed in soft, muted linens. A wooden headboard features vertical slats, while a bedside table holds an antique-style clock. Warm lighting is provided by wall-mounted fixtures on either side of the bed.

4.79 out of 5 average rating, 102 reviews

Milton bnb near the Sea close to Dogfish Brewery

Spacious & Stylish Home - just 1 Mile to Dogfish Brewery! 🏠 3 Bed, 2 bath single family home w/ yard 🍻 Brewery tours & tastings, available 6 days a week! 🎣Even closer is Wagamons Pond, a prime spot for bass fishing. 🌳Close to Historic Milton, dining, & kid & pet-friendly parks 🏖️ Lewes, & Cape Henlopen beaches just 20 mins away! ️‍🔥Unwind in our fenced backyard & firepit ⚾ For sports enthusiasts, 'Sports at the Beach' is a mere 15-minute drive. Thanks for looking, enjoy your stay!

KitchenFamilyLayout

4.97 out of 5 average rating, 701 reviews

The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.

Apartment in Greenwood

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

FamilyIndoor spacesWi-Fi

4.93 out of 5 average rating, 100 reviews

A spacious living area features a large sectional sofa, a coffee table, and a flat-screen television mounted on the wall. The open layout connects to a fully equipped kitchen and dining space, with sliding glass doors leading to the outdoor area. Decorative plants add a touch of greenery.

Home in Lincoln

Discovery Rancher

This stylish new family ranch-style home, designed for comfort and privacy, was just completed in 2023. 3 bedrooms, 2 bathrooms, an outdoor grilling area, and a fully equipped kitchen make it the perfect spot for your group's beach vacation. Nearby - 4 miles to Food Lion grocery, 10 miles to Prime Hook National Wildlife Refuge & Rookery Golf Course, 15 miles to Lewes and Cape Henlopen State Park Beaches, 20 miles to Rehoboth Beach. 15 Minutes drive to Sports on the Beach in Georgetown, DE

FamilyKitchenBarbecue

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, 285 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.

Indoor spacesFamilyHeating

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.

4.91 out of 5 average rating, 222 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.

KitchenFamilyAccess

4.94 out of 5 average rating, 240 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.

KitchenFamilyDecor

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.

4.89 out of 5 average rating, 127 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!

FamilyKitchenValue

4.97 out of 5 average rating, 232 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.

Apartment 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.

FamilyIndoor spacesComfort

Superhost

The exterior of a rustic beachfront home is depicted, featuring weathered wood siding and multiple large windows. The structure is two stories, with a sloped roofline and steps leading to the entrance. A sandy path and grassy area are visible, creating a natural coastal setting.

4.91 out of 5 average rating, 106 reviews

Beachfront Home with Unobstructed Water Views

Beachfront/Bayfront home with 4 bedrooms and 3 full bathrooms located in the quiet and relaxing community of Broadkill Beach. The property is just steps from the beach and features stunning, unobstructed water views from almost every room. The home has a coastal design with natural light, soft-tones and a clean aesthetic so that it feels like summer all year-round. We hope that you'll book your vacation with us and enjoy all that Broadkill Beach has to offer!

Indoor spacesFamilyHospitality

4.9 out of 5 average rating, 119 reviews

A quaint tiny house with a charming exterior features a combination of blue siding and brown shingles. The covered porch includes a wooden railing and two colorful chairs. Lush greenery from surrounding trees creates a serene setting, while a few decorative elements enhance the welcoming appearance.

Tiny home in Lincoln

The Little house W/ Pool & Spa

Nestled in the woods and just steps from cedar creek, The little house is a charming, pet-friendly tiny house that offers a magical escape from the everyday. Thoughtfully designed and comfortably sleeping up to 6 guests, this unique hideaway is perfect for couples, families, or friends looking to unwind and relax. 10 Minutes from DE turf, 20 minutes from the beach, directly beside yogi bear. Perfect for travel nurses & remote workers – Monthly stays welcome!

KitchenIndoor spacesCleanliness

4.97 out of 5 average rating, 230 reviews

A spacious common area features tall ceilings and large windows, allowing natural light to fill the room. Bookshelves line the walls, filled with a diverse collection of books. A comfortable white sofa and glass coffee table create a cozy seating area, with a TV positioned nearby.

Guesthouse in Milton

The Book Nook - A Private Downtown Retreat

In the heart of downtown Milton, you will find a newly renovated guest cottage less than 10 miles to the beach! If you plan on staying local, simply park your car at the designated off-street parking space and travel by foot to the many shops, restaurants, and attractions offered in historic Milton. Whether you're walking the few short blocks to Dogfish Head Brewery or spending an evening at the theater, The Book Nook will serve as the perfect location!

Indoor spacesKitchenParking

Popular amenities for Milton family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 109 reviews

A private hot tub is set on a paved patio beneath a shaded gazebo. Wooden decking surrounds the area, enhancing the serene outdoor setting. Lush greenery provides privacy, while outdoor lighting can be seen strung above, creating a welcoming space for relaxation.

Home in Rehoboth Beach

Perfect Rehoboth Beach Getaway with Hot Tub

FamilyKitchenTV

4.94 out of 5 average rating, 187 reviews

A spacious kitchen is highlighted by an 11 ft island with four round bar stools. Pendant lighting above creates a warm ambiance. Modern appliances and a stylish backsplash are featured, enhancing the functionality of the space. Neutral tones and open shelving provide a clean, inviting atmosphere.

Home in Rehoboth Beach

Hot tub, Pool, Shop & Dine, Sleeps 8

Indoor spacesFamilyDecor

4.98 out of 5 average rating, 320 reviews

A welcoming space is featured, showcasing a luxurious jacuzzi with a wooden tray holding candles and decor. Nearby, a cozy living area with a modern couch is highlighted against an artistic forest mural. An adorable Highland cow stands nearby, adding a touch of rustic charm.

Farm in Selbyville

Sleep in a One-of-a-Kind Barn near Ocean City Mary

Indoor spacesKitchenView

Cottage in Rehoboth Beach

A cozy sleeping area features a soft blue quilt covering the spacious bed, adorned with colorful dog-themed pillows. A neatly folded stack of white towels rests on the bed, while a bedside lamp provides gentle lighting, enhancing the room's warm ambiance.

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

Indoor spacesFamilyComfort

4.96 out of 5 average rating, 224 reviews

4.91 out of 5 average rating, 107 reviews

The open living space features light wooden paneling and natural light streaming through multiple windows. A blue sofa faces a flat-screen TV, while a small dining table with stools is positioned nearby. The kitchen area is equipped with modern appliances for convenience.

Cottage in Dewey Beach

Uncle Buck's Cottage

Indoor spacesKitchenLocation

4.9 out of 5 average rating, 146 reviews

The spacious living area features a large sectional couch, designed for relaxation. A central coffee table sits in front of it, surrounded by natural light from multiple windows. A stylish dining area is visible in the background, complete with a wooden table and chairs.

Apartment in Lewes

HUGE bright 5BR, steps from the beach & downtown!

KitchenIndoor spacesLocation

4.96 out of 5 average rating, 114 reviews

A spacious outdoor pool area features a large swimming pool with a vibrant blue interior and a jacuzzi nearby. Lounge chairs are arranged around the pool for relaxation. Fountains are visible at one end, adding a calming water feature to the setting.

Condo in Rehoboth Beach

Bright condo-On bike trail & 1 mile to boardwalk

FamilyIndoor spacesGetting around

Tiny home in Lower Township

Hot Tub | Mini Golf | Arcade | Gym — Coastal Quad

Indoor spacesKitchenHeating

5.0 out of 5 average rating, 325 reviews

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 327 reviews

Modern & Cozy Retreat | Pool | Close to Beaches

Indoor spacesKitchenDecor

4.94 out of 5 average rating, 108 reviews

The exterior of a multi-level home is displayed, featuring a large front porch with white railings and a peaked roof. The house is set amidst a natural landscape with a gravel driveway and sparse tree growth, showcasing a peaceful and secluded environment.

Home in Milford

Beautiful New Beach House-1 minute drive to beach!

KitchenIndoor spacesDecor

4.83 out of 5 average rating, 103 reviews

Cottage in Milton

Bayshore Cottage, Steps to the beach!!

Indoor spacesFamilyWi-Fi

4.99 out of 5 average rating, 238 reviews

A wrap-around deck overlooks a tranquil waterfront view, featuring lush greenery and calm waters. A seating arrangement includes four chairs with cushioned backs, positioned for relaxation. The scene is punctuated by nearby trees, contributing to a serene atmosphere.

Home in Lewes

Beautiful Waterfront Home-Private, Clean, Relaxing

KitchenFamilyHeating

4.81 out of 5 average rating, 219 reviews

Home in Georgetown

The 1934 Farmhouse (close to the beaches)

FamilyIndoor spacesNearby

Superhost

The exterior of the beach house is seen from an angle that highlights large windows and a welcoming entryway. A staircase leads to the elevated porch, which features a railing, while a colorful flag adds a touch of character.

4.81 out of 5 average rating, 116 reviews

Delaware Beach Bliss, steps from the sand & surf!

Indoor spacesFamilyLayout

4.95 out of 5 average rating, 150 reviews

The kitchen features modern appliances and a spacious island with seating for three. Natural light enters through a skylight and glass door, illuminating the light-colored cabinetry and countertops. A hallway leading to other areas of the house is visible in the background.

Home in Lewes

Woodsey Beach House - Beach, Lake, Woods!

KitchenIndoor spacesBeach

4.9 out of 5 average rating, 140 reviews

A wooden sign featuring the name 'Sandy Paws Cottage' is displayed prominently. The artwork depicts the cottage with a landscape background and silhouettes of dogs, showcasing a rustic charm with subtle earthy tones.

Cottage in Milford

SandyPaws Cottage at Big Stone Beach on the DE bay

KitchenFamilyLocation

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 239 reviews

A round wooden dining table surrounded by eight woven chairs is positioned in a well-lit dining area. Soft natural light enters through large windows adorned with white blinds. A coastal-themed wall art piece enhances the serene ambiance, and a smaller table can be seen in the background.

Home in Rehoboth Beach

Beautiful Beach House in Rehoboth

KitchenFamilyNearby

4.98 out of 5 average rating, 106 reviews

A light-filled living room features a cozy seating arrangement with two patterned chairs and a soft sofa. A coffee table with a checkerboard design sits atop a textured area rug, with a flat-screen TV positioned nearby. Soft blue walls complement the space.

Townhouse in Lewes

Spacious, Conveniently Located Townhouse

Indoor spacesFamilyComfort

A balcony view captures a wide expanse of lush green fields and dense trees, framed by a soft gray sky. The natural landscape offers a serene backdrop, highlighting a peaceful atmosphere. A railing can be seen in the foreground, providing a sense of depth.

4.98 out of 5 average rating, 222 reviews

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

KitchenIndoor spacesRiver

4.95 out of 5 average rating, 123 reviews

A spacious living area is presented, featuring a comfortable green sofa and a matching armchair. A large television is positioned on a low cabinet. Natural light streams through sliding glass doors, leading to a screened-in porch, enhancing the atmosphere with a view of greenery.

Condo in Rehoboth Beach

2BR Coastal Escape with Pool Near Rehoboth Beach

FamilyKitchenCheck-in

Two spacious beds with white bedding are positioned against a clean, white wall. A lamp and a small plant rest on a bedside table situated between the beds. Framed botanical artwork is displayed above each bed, adding a touch of nature to the serene space.

4.97 out of 5 average rating, 244 reviews

Villa Del Sol, Beautiful stay near beaches/outlets

KitchenFamilyTV

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.

4.91 out of 5 average rating, 101 reviews

Beautiful Updated Condo Waterfront, Pool, Sunsets

Indoor spacesFamilyBathroom

Apartment in Rehoboth Beach

An open-concept living area features a light-colored sectional sofa adorned with textured pillows. A round coffee table sits on a soft area rug. The dining area, equipped with a sizable wooden table and stylish woven chairs, is visible in the background alongside modern kitchen appliances.

Cozy Rehoboth Beach Condo w/ 2 bedrooms

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 181 reviews