Holiday houses in Milton

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, 210 reviews

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.

4.98 out of 5 average rating, 181 reviews

Condo in Rehoboth Beach

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.

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, 586 reviews

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)

4.98 out of 5 average rating, 208 reviews

Condo in Dewey Beach

DeweyBeach 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.

4.82 out of 5 average rating, 244 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.

4.85 out of 5 average rating, 80 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.

4.95 out of 5 average rating, 162 reviews

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, 276 reviews

Condo in Ocean City

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Apartment in Rehoboth Beach

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.

4.96 out of 5 average rating, 177 reviews

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.

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Other great holiday rentals in Milton

4.97 out of 5 average rating, 38 reviews

Pets Friendly Waterfront Large backyard with grill

MatthewRating, 5 stars3 weeks ago

We enjoyed our stay. Considering how close it was to the beach, the house was a great deal. Probably the best value for an AirBNB I've ever stayed.

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.

5 out of 5 average rating, 32 reviews

Milton Hide Away

HannahRating, 5 stars11 months ago

Lisa's house was clean and comfortable, the kitchen was well-equipped, and the location was fantastic - a very short drive to multiple beaches. We had a wonderful getaway in Milton, in no small part because of Lisa's cosy and convenient accommodations.

5 out of 5 average rating, 5 reviews

Small wonders

WalterRating, 5 stars6 days ago

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.

Townhouse in Milton

4.73 out of 5 average rating, 15 reviews

Milton Townhouse ~ 9 Mi to Delaware Bay!

NicoleRating, 5 stars7 months ago

Thank you so much for your home. We had a great weekend in Milton. The house was private and quiet. Thank you again

4.98 out of 5 average rating, 50 reviews

Condo in Lewes

Water Views * Balcony * Pool * Fast Wi-Fi

ChrisRating, 5 stars2 weeks ago

The best place anyone could stay! Amazing views, clean, comfortable and great location. Quiet, yet close by needed amenities. Well stocked kitchen allowed us to cook and enjoy the time with family. Teen boys and dad LOVED the boat dock and ability to go out with our paddle boards. Loved biking and running the open areas around getting ready for an Ironman. While the rest enjoyed coffee on the deck in the morning. Super flexible when we needed another day added to our stay as well. Thank you for the amazing stay! We’ll be returning now that our son has moved to the Delaware.

4.84 out of 5 average rating, 19 reviews

Quaint Beachfront Cottage

ElliRating, 5 stars1 week ago

We were three college friends celebrating our 50th birthdays. The house was lovely and very close to the beach. We enjoyed our stay!