Guest house holiday rentals in Sussex County

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.

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

Lovely 1 bed/1 bath detached upstairs guest apartment. The space provides privacy & convenience to Lewes activities with serene garden 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: walk or bike to Old World Bread Bakery, Beach Time Distilling & Lewes Brewing Company!

Freddy's B & B We will be closing Nov 30th 2025

Freddy’s B and B Welcomes you! . We are in a quiet tree lined neighborhood where you can relax after a day at the beach. 6 miles from the Delaware Turf right off route 1. Close to all amenities. Freddy is our 20 month old Border Collie. He’s hilarious and lovable. We have a garage parking spot for your vehicle with private entrance access to Freddy’s. We have very competitive rates. We strive to make your stay the best! When you are at Freddy’s B and B you are family. 🐾 Please no hook ups!!

Pelican's Loft Beach Retreat- (two story)

Newly built stylish private loft promises a perfect retreat for a romantic couple's escape. Access to inviting pool, enjoy refreshing dip or lounge soaking in the sun. Gather around the fire pit for a cozy and romantic atmosphere. The loft provides a comfortable queen bed with high-quality linens and kitchen. Our Airbnb includes a workout room, allowing you to maintain your fitness routine while enjoying your getaway. Experience modern coastal charm, creating memories that last a lifetime.

Drifted Pines

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.

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

New adventures

This special place has a retro flair, deep seated sofa that sleeps 3 comfortably, futon velvet couch with fun bright colors! Rear doors to the yard that over looks a gorgeous golf course, watch golfers swing all day! Resort has access to 2 pools and gyms. 2 wristbands and 1 key fob will be available for access to these amenities. Full bathroom complete with towels and toiletries, also a fun bright kitchenette, coffee maker, microwave, dishes etc. you will love this new home!

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.

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!!

Beachfront Bliss-Quiet Bay Condo

This cozy beachfront cottage offers a perfect blend of comfort and entertainment with stunning views of the Delaware Bay. Enjoy a tranquil beach, breathtaking sunrises/sunsets, and various indoor/outdoor activities. Features a Roku Theater Sound TV, High-Speed Wi-Fi, game room with air hockey, foosball, and Ping-Pong, plus kayak, fishing poles, and beach toys. Easy access walkway to a quiet beach. Great way to enjoy the bay and National Wildlife Refuge!