Family-friendly holiday rentals in Sussex County

Ranch Stay- Farm Animals, Jacuzzi, Arcade, Beaches

Welcome to the Swedish Cowboy, your ultimate escape! This unique BARNDOMINIUM home is designed to offer a memorable retreat for up to four (4) guests, with the flexibility to accommodate two (2) additional guests for a small fee. Enjoy the charming backyard where you can meet a variety of fuzzy and feathered friends or head inside and play on the arcade or relax in the jacuzzi. Perfectly situated near popular beaches and bustling boardwalks, you'll have plenty of options for fun and relaxation.

Dewey Beach 1 BR+sleeper sofa. Walk to the beach!

Enjoy all of Dewey Beach at this delightful 1 BR, ground floor, apartment on the north side of town. 1.5 blocks to the beach, and 3 blocks to the start of restaurants and music venues. Quiet, relaxing location on a side street. Perfect for a small family or group of 4 friends! Custom self check-in keypad code for Private Entry sent upon booking. Professionally cleaned + bed made before your stay. 4 beach chairs, 1 on-property parking spot + 1 free Street Parking Passes provided at no charge!

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)

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.

First Floor Comfort and Convenience

This first floor condo is conveniently located in a family-friendly community with all you need within walking distance, including several restaurants and a grocery store. A short and easy 3-mile drive to Lewes Beach and the charming town of Lewes makes this an ideal location. Amenities include access to two pools, tennis courts, pickle ball courts and kids play area. The Georgetown Lewes Biking/Walking Trail, that connects to the town of Lewes, is literally steps from our front door.

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

Beach Sunrise: Walk to Downtown & Lewes Beach

Skip the traffic and parking stress — stay where everything is steps away. Experience the best of Lewes (pronounced loo-iss) from this perfectly located, walkable condo. Step outside and you’re minutes from the beach, downtown dining, scenic parks, and bike trails. With ultra-fast 2-Gig Wi-Fi, free bikes, coffee bar, easy parking, and thoughtful amenities, this is the ideal home base for couples or small families seeking comfort, convenience, and an authentic local stay.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

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.

Maplewood - Simply Comfortable, Dog Friendly

Have fun with the whole family at this stylish place in the center of it all. Near the beach, away from the crowds. Local attractions: Sandhill Fields - .5 miles Sports at the Beach - 1 mile Dogfish Head Brewery - 5 miles Lewes Beach -8 Cape May Lewes Ferry Terminal Cape Henlopen State Park Tanger Outlets - 12.4 miles - 13.9 miles And lots of other tax free shopping. Rehoboth Beach Boardwalk - 17.5 miles Dover Downs - 39.1 miles Many other attractions nearby.

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!

*Radcliffe Retreat* Studio, Pool & RB Parking Pass

Spacious pet friendly guest suite with Rehoboth parking permit provided. The suite is near outlets, beaches, dining, & Rehoboth boardwalk. Large community pool next door. Charming neighborhood that is a great base to explore all the nearby attractions! Rehoboth boardwalk & beach- 4 mi Outlets- 1 mi Lewes downtown- 4 mi Cape Henlopen State Park- 6 mi 1 dog is allowed with permission.