Guest house holiday rentals in Delaware

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

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, take a nature walk on the trails around the property, and star gaze at night with extremely low light pollution. We have room for your bikes, kayaks, and trailer.

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.

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.

Surf Shack with Private inground pool

*** Note*** Pool opens June 2025 New "surf shack" private beach cottage. Part of a restored 1940's cottage. Best sunset views around & just steps from your door! Close to Bethany Beach (6-10 minute ride) away from the noise of traffic & beach crowds. Within easy walking/biking distance of James Farm ecological park & beach. Community bay access is steps from the house. Beach chairs, towels, surfboards, boogie boards are available. 2 adults and 2 children max capacity

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!!

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.

Country Guest House

Relax with the whole family at this peaceful place to stay on the farm. You will see horses, cows, goats, chickens & ducks. Family friendly. Animals roam the property & are safe to pet. You will hear many farm noises such as roosters crowing, cows mooing & more. This home is located in the country & a min of 5 miles from stores and shopping. Full kitchen, 1 full bathroom & 1 queen bed included. Upon request Queen Air Mattress or Twin Bed can be provided.

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!

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.

Studio Bedroom in the Woods

We have noticed some Airbnb guest haven’t put exact amount of people that are staying please make sure you put the correct amount of people staying because of insurance purposes. Quiet time is at 10pm !! NO USE of the Hot Tub after 10pm !! Take it easy at this unique and tranquil getaway. Important information : Bathroom is located at end of walkway by where you park by the Hot Tub! Visitors must not stay overnight!

Country Cottage, private and cozy,

You’ll love my place for its outdoor space and peaceful country setting. The cottage is best suited for couples. Up to two dogs are welcome and should be groomed prior to arrival. Conveniently located: Cape Henlopen State Park (9.9 miles), Rehoboth Beach (10 miles), Dewey Beach (11 miles), and Tanger Outlets (7.8 miles). Please note that while distances are accurate, travel times may be longer due to seasonal traffic.