Guesthouse holiday rentals in Delaware

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!

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!!

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.

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.

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!!

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!

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!

Modern Guesthouse Retreat

Modern, cozy, and fully private guesthouse with its own entrance, patio, bathroom, and kitchenette. Enjoy Netflix on an oversized TV or a glass of wine from our honor bar. The bedroom includes a desk for remote work. Located in a safe, quiet neighborhood with easy access to I-95, downtown Wilmington, and shopping. Street parking for one car available. Perfect for a relaxing and convenient stay!