Vacation rentals in Milton

4.96 out of 5 average rating, 138 reviews

Chestnut-Near Dogfish&DE Turf Monthly/Wkly Rates

Monthly/Weekly Discounts Chestnut Retreat is a historic farm style home located in historic town of Milton, DE (12 miles from local beaches). DE Turf is 25 minutes away & Sports @ Bch is 10 minutes. This home has been renovated. Relax in the screened in porch with 2 reclining chairs & swing. Home has 3 bedrooms (1 bedroom down, 2 up) & queen sleeper sofa in living room. Patio has grill and fire pit. Short walk to Dogfish Restaurant. Easy walk/bike ride to downtown. Golf Courses minutes away.

4.93 out of 5 average rating, 236 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.

Guest suite in Rehoboth Beach

A welcoming outdoor terrace features a round table surrounded by two wicker chairs with blue cushions. Hanging planters filled with greenery create a vibrant atmosphere, while a decorative pot adds a pop of color. Sunlight filters through lush trees, enhancing the serene environment.

4.99 out of 5 average rating, 200 reviews

Treetops beach getaway walkable to beach/boardwalk

East of Route 1, equidistant to both Rehoboth & Dewey beaches, about 1/2 mile easy bike/walk. Brand new for 2021, this fully equipped guest suite offers a private entrance, bedroom with a king bed on an adjustable frame, full bath, laundry, and a kitchenette. There is NO STOVE in this unit but we have provided a microwave and toaster convection oven/air fryer for easy beach meal prep. There is also a gas grill for barbecuing. Please note that this unit is strictly limited to 2 mature adults.

4.86 out of 5 average rating, 318 reviews

The exterior of a custom-built tiny house is displayed, featuring a combination of horizontal siding and large windows. Two yellow chairs with a small table sit on the porch, framed by surrounding greenery, creating a connection to the natural environment.

Tiny home in Lincoln

Tiny house w/ Pool on water near Beaches / turf

Enjoy a peaceful waterfront stay in our custom-built tiny house, located on Cedar Creek just off Route 1. Conveniently situated only 10 minutes from Delaware Turf and 15 minutes from the beach. The home comfortably sleeps four and includes hot tub access. We live on-site and are happy to assist throughout your stay. Ideal for families, pets (please review rules under “The Space” section), contractors, and long-term renters. Perfect for travel nurses & remote workers – Monthly stays welcome!

4.97 out of 5 average rating, 105 reviews

The image captures a sandy beach scene with gentle dunes and a wooden fence leading to the ocean. The sun casts a warm glow over the water, illuminating the horizon where the sea meets the sky. Grasses sway softly in the foreground.

Home in Milford

Pet Friendly Home In A Private Beach Community!

Forget your worries in this spacious and serene space. Single-floor home with a very short walk to quiet Bay Beach. Spectacular 4 season Sunroom facing west over Primehook's 10,000-acre National Wildlife Refuge. Stunning sunsets and birding while dining or just relaxing after a day at the beach make this room a favorite. The home offers views of Delaware Bay. There is an outdoor shower for rinsing away the day's salt and sand. The fully fenced backyard includes a grill and space for your dog!

4.97 out of 5 average rating, 617 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)

4.99 out of 5 average rating, 181 reviews

A charming cottage facade is framed by white columns and features a gabled roof. Two black rocking chairs, adorned with pillows, sit on a brick porch surrounded by colorful potted flowers. Lush greenery enhances the inviting atmosphere.

Cottage in Frankford

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

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.

4.82 out of 5 average rating, 257 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.

Superhost

An in-ground pool glistens under clear blue skies, surrounded by a wooden deck. Lounge chairs are positioned near the water, while an air-conditioned pool house offers shaded seating with umbrellas. Lush trees provide a natural backdrop, creating a private outdoor space.

4.86 out of 5 average rating, 93 reviews

Teeny's Place: A Historic Milton Home.

Family friendly get-away filled with fun. All the amenities of a single family home, plus a backyard made for life at the beach. Proudly offering an in-ground pool, air-conditioned pool house with changing room, 3 season entertainment space, fire pit and deck spaces. The Pool is opened May 1st-October 1st. Walking distance to Downtown Milton's shops, restaurants, and -of course- Dogfish Head Brewery. Just a short drive to the Delaware Beaches. Newly renovated Pool House in 2024.

4.96 out of 5 average rating, 180 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.

4.96 out of 5 average rating, 189 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.

4.97 out of 5 average rating, 201 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!

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Popular amenities for Milton vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Milton

A charming single-story home is framed by a large flowering tree, showcasing vibrant pink blooms. The well-maintained lawn adds to the inviting exterior, while the driveway accommodates a parked vehicle. Surrounding greenery contributes to a peaceful environment in the front yard.

4.86 out of 5 average rating, 29 reviews

Lilly Pad: Fenced in yard, close to beaches & more

A two-story beach house is featured, nestled among greenery. A wraparound deck with wooden railing provides access to an upper entry, while a staircase leads to the ground level. Vibrant flowers and shrubs are visible in the foreground, enhancing the inviting appearance of the home.

5 out of 5 average rating, 9 reviews

Broadkill Beach Getaway

5 out of 5 average rating, 48 reviews

A charming guesthouse is pictured, featuring a green roof and light-colored exterior. Windows are arranged in a welcoming manner, surrounded by well-maintained landscaping, including grass and decorative plants. The inviting porch is accessible, enhancing the outdoor appeal.

Cottage in Lewes

Unique Creative Private Cottage Gated Acreage

5 out of 5 average rating, 32 reviews

A charming studio cabin, nestled among tall trees, features a brown exterior with white trim. Large windows allow natural light to fill the interior. A stone pathway leads to a main entrance, framed by a serene woodland setting.

Guesthouse in Lewes

Studio Bedroom in the Woods

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.

4.94 out of 5 average rating, 89 reviews

Beachfront Home with Beautiful Views of the Bay

The exterior of a newly renovated cottage displays a modern A-frame design. Classically styled white siding contrasts with warm wood accents on the upper portion. Two lantern-style lights flank the entrance, where double doors with large glass panels provide a welcoming entryway.

5 out of 5 average rating, 13 reviews

Small wonders

4.98 out of 5 average rating, 58 reviews

A charming midcentury white house is framed by a wooden fence, with a welcoming path leading to the entrance. Large windows allow for natural light, while tall trees are visible in the background, creating a serene atmosphere. The setting is brightened by sunlight filtering through the foliage.

Bungalow in Milton

The Milton Bungalow - Midcentury Style Experience