Guesthouse holiday rentals in Delaware

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Delaware

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite

Guesthouse in Lewes

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

4.95 out of 5 average rating, 141 reviews

Guest favourite

Guesthouse in Lewes

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.

4.96 out of 5 average rating, 24 reviews

Guest favourite

Guesthouse in Rehoboth Beach

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

Top Guest favourite

Guesthouse in Rehoboth Beach

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.

4.95 out of 5 average rating, 22 reviews

Top Guest favourite

Guesthouse in Newark

Idyllic carriage house private 2 car garage W/D

This is a one-of-a-kind space perched on a hill along a peaceful stretch of country-like road, surrounded by lush green space. Enjoy the convenience of your own private 2-car garage with an interior walk-up to the spacious 825 sq ft apartment above. The property also features a handicapped ramp at the front for easy access. Inside, you’ll find a washer and dryer, EV charger, dual-head walk-in shower, and a fully equipped kitchen for all your needs. Ideal for comfort and privacy.

4.99 out of 5 average rating, 67 reviews

Top Guest favourite

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.

5.0 out of 5 average rating, 46 reviews

Top Guest favourite

Guesthouse in Wilmington

Triple L Farm Cottage

Tucked on two quiet acres in Brandywine Hundred, this cozy retreat offers peaceful rural charm with excellent convenience and off-street parking. It features a king bedroom, full kitchen and bath, and a living room with two pull-out beds—ideal for couples or small families. Just 5 min to I-95 and Amtrak, 20 min to both airports, 30 min to downtown Philadelphia, and walking distance to Bellevue State Park. Perfect home base for gardens, history, hiking, and sports.

4.98 out of 5 average rating, 41 reviews

Top Guest favourite

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.

Guesthouse in Rehoboth Beach

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!!

4.88 out of 5 average rating, 379 reviews

Top Guest favourite

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!

4.97 out of 5 average rating, 233 reviews

Top Guest favourite

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.

4.96 out of 5 average rating, 70 reviews

Top Guest favourite

A comfortable sitting area features a green sofa, two blue armchairs, and a wooden rocking chair. Natural light filters through a large window draped with sheer curtains, illuminating the warm wooden paneling and area rug. A round coffee table sits in the center.

Guesthouse in Camden

The little backyard guest house

A little hideaway only a few miles away from Dover, Dover Air Force Base, Dover Speedway and Dover Downs. The beaches are only 45 mins away with great restaurants and shopping. This AirBnB is located in the historic district of Camden situated in the backyard of a private home. You have your own private building! There are stairs up to the deck as the guest house is on the second floor. Please note there is no WiFi or TV.

4.98 out of 5 average rating, 52 reviews

Guest favourite

Guesthouse in Rehoboth Beach

Relax Shack | Dog Friendly | Cozy Rehoboth Cottage

Escape to Relax Shack, a cozy cottage just minutes from Rehoboth Beach, the boardwalk, shopping, and restaurants! This peaceful retreat features 2 bedrooms, a pull-out sofa, a fully equipped kitchen, streaming TVs, WiFi, a private deck, and an enclosed porch for relaxing after a day at the beach. Enjoy the perfect blend of comfort, convenience, and coastal charm for your next Delaware beach getaway!

5.0 out of 5 average rating, 10 reviews