Guesthouse holiday rentals in Sussex County

4.95 out of 5 average rating, 138 reviews

Crow’s Nest • 1 BR Lewes Guest Apt – Bike to Beach

Lovely 1 bed/1 bath detached upstairs guest apartment right off the bike trail. The space provides privacy & convenience to Lewes activities with tropical landscaping. It boasts beachy decor with locally sourced touches, a fully stocked kitchen, and a beautiful bedroom complete with a desk and a canopy bed to provide guests with the perfect escape. Enjoy al fresco dining under a pergola & lawn games. Just 3.7 mi to Lewes beach: bike to Old World Bread Bakery, Vino Del Mar & Lewes Brewing Company

An overhead view captures a cozy seating area with a two-tone sofa. A ceiling fan with dark blades circulates air beneath a lofted ceiling. Natural light fills the space through large windows, while decorative shelves showcase beach-themed signs and a potted plant.

4.87 out of 5 average rating, 79 reviews

Life is better at the beach!

Enjoy a stylish experience at this centrally-located tiny house. 2 miles from the beach! Has everything you need for a relaxing beach getaway. Private fenced in yard. Sleeps up to 4 but is most ideal for 2 adults. It is also kid friendly for small families. Some of the best restaurants in Delaware are within 2 miles. Under 4 miles to Cape Henlopen State Park. Private parking for 2 vehicles. Bus stop 50 yards away which offers a $4 all day pass. Bed sheets, pillow cases and towels not provided.

4.95 out of 5 average rating, 20 reviews

Apothecary Garden Cottage

Peaceful homestead on 3 quiet acres. Close to local restaurants, shops, wineries, breweries, meaderies, beaches, trails, farmers markets, & charming small town goodness!! The bright, airy cottage was formerly a functioning herbal apothecary — medicinal & culinary herbs grow here! Enjoy lazing in shaded hammocks under mature trees or play yard games in the sun. The cottage has a charcoal grill & its own patio for watching sunsets & stars. The Lewes-Georgetown bike Trail is across the street.

Superhost

4.92 out of 5 average rating, 12 reviews

Waterfront Escape, Everything You Need, Unit B

Relax in this cozy waterfront retreat, a perfect tranquil getaway. Conveniently located just 3 miles from both Rehoboth Beach and Dewey Beach, you'll enjoy easy access to dining, shopping, and entertainment while returning to a peaceful canalfront setting. Clean, comfortable, and unforgettable. Unit B features a comfortable king bed, full bathroom, and kitchenette. Fully stocked with essentials for a relaxing stay. Wake up to stunning water views and abundant nature right outside your door.

4.95 out of 5 average rating, 19 reviews

Casa Sol y Cielo – Airy Scandi-Boho Retreat

*Please note - minimum age requirement to book is 25 years. Welcome to Casa Sol y Cielo, a place where you can relax & enjoy the surrounding nature. The space was just completed in early 2026 and is located just 15 minutes from Rehoboth Beach, you'll also enjoy access to many fantastic amenities. Our guesthouse is located on the ground level of our 3 story townhome within a gated community and offers the perfect getaway for couples, solo travelers, or friends looking to unwind.

5.0 out of 5 average rating, 42 reviews

A comfortable seating area is presented with a dark sofa featuring cushions. A small coffee table sits on a patterned area rug, while large windows allow natural light to illuminate the space. The kitchen area is visible in the background, with modern appliances.

Guesthouse in Greenwood

Guest Suite, Private Entrance

One bedroom guest suite w/ private coded entrance. The space is complete with full kitchen stocked with the essentials, including microwave and Keurig coffee maker. Queen size bed in bedroom w/ extra pillows and blankets. Sofa queen size pull out bed complete w/linens. 12 miles to DE Turf, 7 miles to First State BMX, 26 miles to Lewes, 29 miles to Rehoboth, 27 miles to Dover Downs, 16 miles to Dogfish Brewery. Our home is attached and we are happy to answer any questions.

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.

4.88 out of 5 average rating, 370 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!!

4.93 out of 5 average rating, 14 reviews

Cozy cottage 1.5 blocks to Beach.

This cozy 3 bedroom beach retreat is located within walking distance from the beach, restaurants, and city nightlife. With a private backyard, beautiful landscaping, and ocean breezes, Laurel Cottage is a perfect vacation spot for families and friends. Prepare meals in our classic cottage kitchen and enjoy dining in the adjacent entertainment room. The living areas provide a wonderful atmosphere for lounging around during quiet evenings and watching movies.

4.97 out of 5 average rating, 228 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!

4.95 out of 5 average rating, 65 reviews

The exterior of the guesthouse is shown, featuring a charming sloped roof and a welcoming blue front door. Lush greenery surrounds the building, providing natural shade. A private driveway is visible, along with a wooden fence that enhances the sense of privacy.

Guesthouse in Selbyville

Drifted Pines - Loft Suite

Keep it simple at this peaceful, private, and centrally-located place. Enjoy the entire upstairs guest house on an old tree farm with many amazing varieties of trees, just 5 miles from the Atlantic Ocean! You will be a quick 10 minute drive from the best of the Delaware and Maryland Beaches. Relax in the shade by day and star gaze with extremely low light pollution at night. We have room for your bikes, kayaks, and trailer.

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.

4.86 out of 5 average rating, 78 reviews

Studio Bedroom in the Woods

Enjoy a peaceful getaway in our cozy studio with a comfortable queen bed, TV, microwave, K-Cup coffee maker, and hot water kettle. Free parking includes 1 designated space plus 1 overflow space. Your private bathroom is detached, about 40 feet away via a short outdoor walkway, with your own passcode. Enjoy shared amenities including the seasonal pool, 7-person hot tub, and fire pit, shared with guests of the other Airbnb.