Vacation rentals in Milton

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.

4.87 out of 5 average rating, 86 reviews

Cheerful Country Bungalow - Near Dogfish Brewery

Welcome to our cozy retreat on the outskirts of Milton, where simplicity meets comfort! Ideal for a small group of family & friends seeking a peaceful getaway. Our charming 2-bedroom, 1 sofa bed, 1-bathroom home offers a tranquil escape from the hustle + bustle of city life. Our home is located within walking and/or bicycling distance of downtown Milton attractions, including Dogfish Head Brewery, amazing restaurants, Milton Theatre, a library, and a plethora of other family-oriented activities.

4.92 out of 5 average rating, 209 reviews

A well-appointed bedroom features a full-sized bed with light bedding and decorative pillows. A bedside lamp sits next to the bed, while a dresser with multiple drawers is positioned against the wall. Warm yellow walls add a welcoming touch 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.

5 out of 5 average rating, 14 reviews

A modern kitchen space features sleek cabinetry and a stylish backsplash with a geometric design. Natural light fills the area through a large window above the sink, which overlooks a pleasant view. The kitchen island is surrounded by light-colored chairs, creating a welcoming atmosphere.

Guesthouse in Milton

Pelican's Loft Beach Retreat- (two story)

Newly built stylish private loft promises a perfect retreat for a romantic couple's escape. Access to inviting pool, enjoy refreshing dip or lounge soaking in the sun. Gather around the fire pit for a cozy and romantic atmosphere. The loft provides a comfortable queen bed with high-quality linens and kitchen. Our Airbnb includes a workout room, allowing you to maintain your fitness routine while enjoying your getaway. Experience modern coastal charm, creating memories that last a lifetime.

A circular stone fire pit is surrounded by two wooden Adirondack chairs, offering a cozy seating area. The spacious yard features grass and a custom cornhole game in the background, with trees and nearby homes providing a serene backdrop.

4.96 out of 5 average rating, 130 reviews

Near Dogfish, DE Turf Sports@Bch Linen-towels incl

Discount Rates Mon-Thurs. 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 @ Beach is 10 minutes away. This home has been renovated. Relax in the screened in porch with 2 reclining chairs & swing. Home has 3 bedrooms (1 bedroom downstairs, 2 upstairs) & queen sleeper sofa in living room. Patio has grill and fire pit. Short walk to Dogfish Head Restaurant. Easy walk/bike ride to downtown.

4.97 out of 5 average rating, 583 reviews

A silhouette of a pygmy goat is positioned atop a wooden beam, framed by bare trees and a softly illuminated sky at dusk. The fading light casts a calming atmosphere over the hobby farm.

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)

Superhost

A firepit surrounded by several adirondack chairs creates a cozy outdoor gathering space. The firepit is constructed from stone, and is situated on a grassy area, with tall bamboo trees providing privacy in the background.

4.82 out of 5 average rating, 243 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.

5 out of 5 average rating, 35 reviews

A set of wooden steps leads to a white railing, complemented by a stylish outdoor light fixture at the top. A secure mailbox is mounted next to the stairs, enhancing the welcoming entrance surrounded by greenery.

Vacation home in Milton

Serene Cozy Couples Getaway

Forget your worries in this lovely private getaway that's close to numerous attractions: The upstairs apartment is comfortable with all the amenities needed to make your stay relaxing and enjoyable. We're close to beaches, dining, shopping, and outdoor activities. The charming deck is the perfect spot to relax and enjoy reading a book, having breakfast, dinner, or a nice evening drink. Not suitable for children, pets, Not handicap accessible. No one under 20. No Smoking on premises.

4.93 out of 5 average rating, 181 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.

Apartment in Rehoboth Beach

A well-organized kitchen counter is showcased with a coffee maker and essentials. A container of Dunkin' coffee sits alongside a variety of creamers and sweeteners, all placed neatly on a textured stone surface. Nearby, a paper towel holder adds practicality to the space.

4.97 out of 5 average rating, 565 reviews

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.

4.99 out of 5 average rating, 314 reviews

Condo in Lewes

Beach Sunrise * Walk & Bike * Culinary Coast

Explore Lewes (loo-iss) from our walkable in-town spot. ✔ Walk Downtown - Restaurants, shops, parks - 2 minute walk ✔ Walk or bike to Lewes Beach - Less than a half mile ✔ Bike Trails - Plenty of options at your fingertips ✔ Cape Henlopen State Park - Less than 2 miles ✔ Easy electronic keypad entry ✔ Fast Gigabit Speed Wi-Fi (950/880 Mpbs) ✔ Roku Smart TV - includes free YouTube TV with cable channels ✔ Parking is plentiful *Bonus* Two complimentary bicycles provided

4.96 out of 5 average rating, 176 reviews

A vintage-style sign displayed on the wall features the phrase 'WELCOME TO MY COTTAGE' in large, white letters against a soft blue wooden background. The weathered frame adds a rustic touch to the overall aesthetic.

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, 181 reviews

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Milton

The interior of a barrel sauna showcases warm wooden walls and two built-in benches on opposite sides. A small table sits in the center, illuminated by soft lighting, creating a tranquil environment ideal for relaxation.

4.95 out of 5 average rating, 22 reviews

Horseshoe Haven-Roof Deck, Beach Views, Game Room

Feng-YingRating, 5 stars2 weeks ago

There are many nice features about the rental. Being by the Beach, the living spaces are on the second and third floor, so the dumbwaiter is helpful to transfer your luggage items to the top floors. With board games, bumper pool, shuffle board, arcade, 2 TV areas, large dining table and roof deck, there is plenty of entertainment in the house and plenty of nooks for everyone to occupy. All the bathrooms are inside the bedrooms except one. Roof deck has a great view of sunrise and sunset. On the ground floor, there are beach chairs, wagon, and kayaks available. We were there for Memorial weekend and horseshoe crabs were supposed to be beaching to mate at high tide, but unfortunately we didn't catch them at the right time. We still saw plenty of crabs and collected plenty of shells. The beach access is easy and feels so private. we love being away from the crowd. Rehoboth, Lewey, and Cape Henlopen state Park are only a short drive away for half day excursions. We all loved this trip!

4.95 out of 5 average rating, 99 reviews

A compact bathroom is equipped with a white vanity featuring storage underneath. A round mirror is mounted above the sink. A decorative shower curtain displays a nautical theme, adding to the coastal vibe. Soft teal rugs are placed in front of the sink and toilet.

Apartment in Ellendale

Near Beaches and outlets.

HeatherRating, 5 stars1 week ago

This place was perfect! It was clean, nice amenities, and Jose and his family were so nice, flexible and accommodating to us and our pups. We will definitely be back if planning to stay in this area again!

The spacious living area features a large blue sofa and a comfortable chair facing a wall-mounted television. A dining area with a dark wooden table and chairs is visible, along with a large kitchen that includes a center island and modern appliances.

5 out of 5 average rating, 9 reviews

Heidi’s Milton Farmhouse

MichelleRating, 5 stars1 week ago

The home is about 4 minutes away from such a cute little town. The neighborhood is quiet and the house was wonderfully stocked.

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, 5 reviews

Small wonders

WalterRating, 5 starstoday

I can’t say enough positive about Jennifer’s cottage. First off it looked & even smelled brand new. Not just the house but everything inside, from the furnishings, bedding, decorations, appliances did as well. It was immaculate. Comfortable. Convenient to so many local attractions. Jennifer also was a perfect host. Proactive and communicative. Probably the only place I’ve stayed where I didn’t need to contact the host for a question or issue after arrival. Her instructions and information were complete and clear. We are hoping that all her future guests take care of this gem so that it remains as pristine as it is now.

4.88 out of 5 average rating, 86 reviews

The spacious outdoor pool is surrounded by lounge chairs and features inflatable swans. A shaded area and decorative yard are present alongside the pool, complemented by greenery and a small play structure for children. The sky shows a hint of cloud cover.

Guest suite in Milford

Studio apt near DE turf, beaches, &hospital

JessicaRating, 5 stars4 weeks ago

We enjoyed a weekend with our 2 year old golden retriever at Jennifer’s place. We were able to take some time out at local restaurants/activities that allowed dogs as well as visiting dewy beach that was only a 30 min drive. We all were very comfortable and relaxed.

5 out of 5 average rating, 23 reviews

Home in Lewes

Luxe Lewes Carriage House: Spa Hot Tub/Estate Pool

MaryRating, 5 stars2 days ago

Let's see...if Martha Stewart had a rental cottage, it would look just like Lisa and Jay's carriage house. Everything from the splendid charcuterie board and Prosecco on ice that awaited us upon our arrival to the beautifully designed cottage and wonderful gardens helped create an amazing vacation that we will not forget anytime soon. Jay and Lisa truly paid attention to every detail right down to the perfectly placed English antiques, fresh cut flowers and towels so thick you could drown in them. Nothing was missing and their hospitality made you feel right at home. We had smiles on our face the entire time! This is now my new Happy place. The gold standard by which every rental will be judged....perfect hosts, perfect place..like I said...Martha Stewart. Thank you Lisa and Jay for making our stay a wonderful experience!! We will definitely be back to your Lewes Carriage House whenever possible!

5 out of 5 average rating, 7 reviews

A modern bathroom features a marble countertop with a circular mirror mounted above a freestanding sink. Soft lighting is provided by a sleek wall fixture. Fresh towels are neatly arranged beside the sink, and a small rug complements the contemporary design.

Apartment in Georgetown

Apartment near Rehoboth/Lewes beach, sports & shop

StephanieRating, 5 stars1 week ago

Our family spent two nights there and loved it! Plenty of space for my husband and two young kids. Everything was new and clean. The neighborhood was quiet and the host was kind and responded quickly. Would absolutely stay again. Often you find that pictures are a little deceptive and places end up smaller than you imagined from the pictures, the opposite is true this time. It was a lot bigger and roomier than I expected.