Guest house holiday rentals in Sussex County

4.9 out of 5 average rating, 49 reviews

Casa Cottage | Classic Cottage, 1 block to beach!

Welcome to Casa Delaware! Our Casa Cottage is located in the heart of Rehoboth Beach with 2 onsite parking spots and 2 additional parking permits. One short block from the beach and around the corner from the best restaurants/shops, you are literally just steps from the best Rehoboth has to offer and the best part is that you will never need to move your car! Note: May 15 - Sept 15 we primarily rent weekly from Friday to Friday, but please contact us to see if we can accommodate a shorter stay

Superhost

Guest house in Lewes

4.85 out of 5 average rating, 66 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, 111 reviews

Guest house in Lewes

Crow's nest! Guest house-bike trail-3.7mi 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!

4.98 out of 5 average rating, 57 reviews

Guest house in Milford

Freddy's B & B

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!!

5 out of 5 average rating, 22 reviews

Guest house in Milton

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.

Guest house in Selbyville

4.92 out of 5 average rating, 36 reviews

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.

4.9 out of 5 average rating, 288 reviews

Private In-Town Garden Cottage

Cozy private cottage in one of Rehoboth's best in-town neighborhoods. Away from the crowds; easy walk to the beach, restaurants, and shops. Dedicated free parking for 1 car. Note: Loft with double bed. Bathroom on 1st floor. Sorry, no pets. Owner oversees cleaning. Freshly laundered bed and bath linens are provided for each reservation -- bedspread, mattress pad, pillow coverings, pillow cases, sheets, towels, bathroom rugs, kitchen rugs and towels. TV. Wifi modem updated 2020.

5 out of 5 average rating, 21 reviews

Guest house 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.

Guest house in Ocean View

4.93 out of 5 average rating, 135 reviews

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

4.86 out of 5 average rating, 331 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!!

Superhost

5 out of 5 average rating, 10 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.