Holiday rentals in Milton

4.93 out of 5 average rating, 254 reviews

A cozy bedroom features a full-sized bed covered with a nautical-themed quilt. A nightstand and a dresser with multiple drawers are situated against the walls. Decorative wall art adorns the yellow walls, while soft lighting creates a welcoming ambiance. A plush area rug adds warmth to the space.

Guest suite in Lincoln

Nicencozy, near DE Turf, Bayhealth, beaches, AFB

Stay in peace at this smoke-free, quiet abode. Within 10 mins of Milford (Bayhealth Sussex, Walmart, shopping, pharmacies, restaurants, etc.). 15 mins: DE Turf, Milton, breweries. 20-30 mins: Bowers Bch, Pickering Bch, Sports at the Bch, Dover & Georgetown, theaters & casinos. 30-45 mins: other beaches and outlets. Please review Guide Book and House Manual after booking, and call us after a last minute booking, so we can tell you how to get in. Snacks, water, etc. provided while supplies last.

Apartment in Rehoboth Beach

A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.

4.98 out of 5 average rating, 199 reviews

Renovated Condo Near Outlets, 3.5 Miles to Beach

Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

Apartment in Rehoboth Beach

A serene view of a sandy beach leading towards the ocean is depicted. A wooden fence with wire stretches along the path, bordered by patches of tall grass. The gently rolling waves and soft sky create a calming atmosphere.

4.99 out of 5 average rating, 456 reviews

High Tech Hideaway: The modern beach lifestyle

Live the beach lifestyle with every modern convenience! Roomy 2 bedroom, 2 bath condo only 10 mins from Rehoboth, Lewes and Dewey. Surrounded by craft beer, tax-free outlet shopping, and fantastic food. Cleanings exceed CDC guidelines. Three 65" 4k TVs with 221+ channels, Apps, touchscreen Amazon Echos, dimmable LED lighting, and ultra high speed wi-fi. Fully renovated with luxurious flooring, quartz countertops, and new furniture. Free washer/dryer, free coffee, free parking, and water views.

4.97 out of 5 average rating, 637 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.

Flat 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)

4.97 out of 5 average rating, 235 reviews

A spacious living area is furnished with a large sectional sofa adorned with decorative pillows. Natural light enters through multiple windows, highlighting a round dining table nearby. A decorative mirror adds a touch of charm to the room, creating an inviting atmosphere.

Apartment in Dewey Beach

Dewey Beach Condo 2BR+sleeper. Walk to the beach!

2 BR, ground floor condo on the south side of Dewey Beach! 1.5 blocks to the beach, 1 block south to beautiful bayside dining. Discounts for stays over 3 nights! The HOA maintains a relaxing, clean, family friendly atmosphere. Self check-in keypad code auto-sent upon booking. Professionally cleaned and beds made before your check in. Bed linens, shower towels/essentials, 2 Dewey Beach Street Parking Passes, and beach chairs are provided free of charge. Max occupancy of 6 at all times.

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, 264 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.

4.95 out of 5 average rating, 188 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.

4.87 out of 5 average rating, 105 reviews

Cheerful Country Bungalow - Near Dogfish Brewery

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!

4.97 out of 5 average rating, 613 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, 283 reviews

A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.

Apartment in Ocean City

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Guest house in Rehoboth Beach

The structure features a modern design with a wooden exterior and large glass windows. A spacious deck is accessible from the upper level, surrounded by lush greenery. The ground floor includes a stone facade with garage doors, creating a harmonious blend with the natural surroundings.

4.86 out of 5 average rating, 339 reviews

The Winkler

The Winkler is a comfortable fully equipped 1BR / 1 BA apartment above our detached 3 garage @ The Tree House. Nestled in lush trees and landscaping in the Rehoboth Beach Country Club. Named after Henry Winkler who played the Fonz on Happy Days, (because he lived in the apt. over the Cunningham's garage). The apartment offers privacy and separation from the main house. Giving you an opportunity to make it your home away from home at the beach. Come Enjoy!!

4.96 out of 5 average rating, 197 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

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.

4.95 out of 5 average rating, 91 reviews

Beachfront Home with Beautiful Views of the Bay

4.9 out of 5 average rating, 50 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

4.94 out of 5 average rating, 85 reviews

An inviting tiny home exterior is illuminated by soft bistro lights in the evening. A light blue front door is framed by a simple wreath, while a rocking chair is positioned on the porch. A gravel patio features two chairs and a fire pit, with expansive farmland beyond.

Tiny home in Milford

Peaceful Possibilities - Tiny Home with Farm View

5 out of 5 average rating, 52 reviews

A spacious living area features a light-colored sectional sofa and a patterned accent chair, positioned around a wooden coffee table. The adjacent kitchen includes modern appliances, a large island with bar seating, and overhead pendant lights illuminating the space.

Home in Lewes

Laid-back in Lewes

4.94 out of 5 average rating, 80 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

4.91 out of 5 average rating, 79 reviews

A comfortable living area features two navy blue sofas positioned around a round coffee table on a light-colored rug. Natural light enters through large windows, with outdoor seating visible in the screened-in balcony area. Decorative wall art adds a welcoming touch.

Flat in Rehoboth Beach

Cozy Condo at Creekwood

4.97 out of 5 average rating, 76 reviews

The studio apartment features a spacious layout with a king bed and a bunk bed. Light-colored walls complement the wooden flooring. A flat-screen TV is mounted on one wall, with a dresser and bedside table positioned nearby. Natural light illuminates the room through recessed lighting.

Flat in Frederica

The Indian Point B&B

The kitchen features modern white cabinetry and stainless steel appliances, including a refrigerator and oven. A large island with two barstools allows for casual dining. Pendant lights illuminate the space, enhancing the airy atmosphere. Countertops display minimal decor for a clean appearance.