Guesthouse vacation rentals in Sussex County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Sussex County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Superhost

An overhead view captures a cozy seating area with a two-tone sofa. A ceiling fan with dark blades circulates air beneath a lofted ceiling. Natural light fills the space through large windows, while decorative shelves showcase beach-themed signs and a potted plant.

Guesthouse in Lewes

4.85 out of 5 average rating, 65 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.

Guest favorite

A tranquil bedroom features a spacious bed draped with a canopy, adorned with beach-themed decor. A desk and chair are positioned nearby, complemented by soft lighting from two lanterns. A decorative chest and a woven rug complete the cozy atmosphere.

Guesthouse in Lewes

4.95 out of 5 average rating, 111 reviews

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!

Top guest favorite

A charming two-story house with a dark shingled roof is surrounded by a well-maintained lawn and trees. A white garage with a balcony is visible adjacent to the house. Blue skies and scattered clouds provide a serene backdrop.

Guesthouse in Milford

4.98 out of 5 average rating, 57 reviews

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!!

Top guest favorite

A modern kitchen space is highlighted with wooden flooring and large windows allowing natural light. High-top bar stools surround a white island, complemented by warm pendant lighting. Appliances include a refrigerator and oven. A cozy seating area features two brown chairs, inviting relaxation.

Guesthouse in Milton

5 out of 5 average rating, 22 reviews

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 favorite

The exterior of the guesthouse is shown, featuring a charming sloped roof and a welcoming blue front door. Lush greenery surrounds the building, providing natural shade. A private driveway is visible, along with a wooden fence that enhances the sense of privacy.

Guesthouse in Selbyville

4.91 out of 5 average rating, 34 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.

Guest favorite

The exterior of a cozy cottage is showcased with a striped awning over a covered flagstone patio. Two red chairs and a small table sit on a patterned rug. Large windows framed by shutters allow natural light to fill the interior.

Guesthouse in Rehoboth Beach

4.9 out of 5 average rating, 286 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.

Top guest favorite

A comfortable seating area is presented with a dark sofa featuring cushions. A small coffee table sits on a patterned area rug, while large windows allow natural light to illuminate the space. The kitchen area is visible in the background, with modern appliances.

Guesthouse in Greenwood

5 out of 5 average rating, 21 reviews

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 favorite

A serene pool area is visible, featuring a sparkling blue pool surrounded by lush greenery. A colorful inflatable unicorn floats in the water, while sun loungers and chairs are arranged nearby. The clear sky enhances the inviting atmosphere.

Guesthouse 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

A stylish living area features a deep-seated sofa adorned with colorful cushions and an accent chair. A bright rug with bold patterns anchors the space, while cheerful artwork decorates the walls. Natural light enters through a window covered with blinds, enhancing the vibrant atmosphere.

Guesthouse in Millsboro

5 out of 5 average rating, 4 reviews

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!

Top guest favorite

The structure features a modern design with a wooden exterior and large glass windows. A spacious deck is accessible from the upper level, surrounded by lush greenery. The ground floor includes a stone facade with garage doors, creating a harmonious blend with the natural surroundings.

Guesthouse in Rehoboth Beach

4.86 out of 5 average rating, 330 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

The exterior of the cottage features a pale yellow façade and a gabled roof. Expansive windows and a glass door enhance natural light. Two planters with flowers sit by the entrance, complemented by a concrete patio area adjacent to the building.

Guesthouse in Rehoboth Beach

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.

Top guest favorite

A serene beach scene is depicted, with soft, golden sand stretching towards a calm shoreline. Gentle waves lap at the water's edge, reflecting a clear blue sky. Small shells and pebbles are scattered along the sand, enhancing the natural beauty of the environment.

Guesthouse in Milford

4.99 out of 5 average rating, 89 reviews

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!