Guest house holiday rentals in Sussex County

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

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.

Rehoboth's Best Kept Secret

All brand new, cool and comforting. Meticulously maintained with upscale furnishings and appointments. There is even a small sitting balcony to enjoy and evening refreshment before venturing out to discover Rehoboth's restaurants, dining and nightlife. Located right in town, there are two bedrooms and one bath with shower. One queen and one twin trundle bed converting to two twins. Full galley kitchen. Bright and airy, Wifi, expanded cable and parking for one car. Beach two blocks away.

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.

Rehoboth Cottage 1 block to Beach

With a fabulous location just footsteps to the sand, boardwalk, and Rehoboth Avenue, this renovated beach cottage features 1 bedroom and 1 bath and can comfortably sleep up to four guests. This charming haven is ideal for those who want to enjoy a variety of relaxing activities; from early morning walks on the beach to upbeat evenings on the town, the possibilities at Bradford Cottage are endless! Take pleasure in the modern amenities and spacious living area that this oasis provides.

Bishops Cottage

Private efficiency cottage. 1 queen bed- 1 queen sofa bed. All towels and sheets washed in fragrance free detergent and fabric softener. Kitchenette microwave coffee maker & small fridge. Wifi, juice, water & snacks included. Full bathroom and outside shower. Off street parking. Private deck with table chairs and sun umbrella. Near 3 beaches and all the fun. Best suited for Couples & Small Families! Members since 2016. Status Super host. There is no additional cleaning charge.

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.

Romantic Get-Away Near the Beach

5-acre country estate, away from traffic and congestion, 5-7 miles from Bethany Beach, Fenwick Island and Ocean City. Lush gardens, orchard, picnic area and grill. Cable/WiFi, fully equipped kitchen, linens and towels. We are in our 5th year of operation and have hosted more than 200 different parties at our guesthouse. Our guests are thoughtful, considerate and respectful of each other and the environment. If you appreciate nature and beauty, you will love our property.

Guest House in Dewey Beach. Walk to everything!

Comfortable guesthouse, located behind main house with a convenient location. Close to the Atlantic ocean beach, Rehoboth Bay, bars, restaurants and shopping. A great spot for: a girls weekend, couples, solo adventurers, business travelers, and families. The house is located in a peaceful residential neighborhood but also within walking distance to the vibrant Dewey Beach nightlife. Cruise the area on two complimentary bikes with maps provided to local trails.

Surf Shack with Private inground pool

*** Note*** due to damage during storms in February the Pool opens mid- June 2026 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. 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!!

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!