Vacation rentals in Sassafras River

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Top-rated vacation rentals in Sassafras River

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Guest favorite

A private swimming pool is surrounded by lounge chairs and landscaped greenery. The clear blue water reflects sunlight, and a white fence offers privacy. The pool area includes a concrete deck, creating an inviting space for relaxation and enjoyment.

Home in Chesapeake City

4.91 out of 5 average rating, 106 reviews

The Mint Cottage in Chesapeake City

The Mint Cottage is new to the air bnb market. It is a 3 bedroom Cape Cod on .5 acre lot in Charming Chesapeake City! The 1st floor features a master bedroom suite with updated amenities, large living room and kitchen, PLUS a full hair and makeup station (great for bridal parties). The 2nd floor has two bedrooms- a queen and 2 twin beds. The house features 3 full baths.The back yard has a private swimming pool, fire pit and patio. Terrific location to walk to waterfront, shops, and restaurants!

Top guest favorite

The exterior of the houseboat is shown with a modern design and a spacious rooftop deck adorned with vibrant umbrellas. A wooden walkway leads to the structure, which is positioned on calm waters, accompanied by a small boat moored nearby.

Houseboat in Grasonville

4.99 out of 5 average rating, 190 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Top guest favorite

A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.

Cottage in North East

4.97 out of 5 average rating, 599 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested the day of your arrival.

Guest favorite

The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.

Apartment in Greenwood

4.97 out of 5 average rating, 617 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Top guest favorite

An open studio space showcases natural light flowing through large windows. A cozy seating area includes a sofa, pull-out couch, and a coffee table. A kitchenette with appliances is visible alongside a small dining area, all framed by wooden accents and warm flooring.

Guest suite in Newark

4.99 out of 5 average rating, 224 reviews

Spacious, light filled studio 2 blocks from UDel

DISCOUNT FOR 30+ DAYS. Our quiet, private studio is located in the historic Old Newark neighborhood, next to the Univ of Delaware, a few minutes' walk to downtown. Newark is a college town with restaurants, history museum, library and small stores. The studio is in a quiet, residential, friendly and walk-able neighborhood. If you are looking for privacy and serenity in this charming town, this is the place! Guests describe our studio as immaculately clean, private and calming.

Top guest favorite

A private deck is presented with woven seating arrangements, including a unique hanging chair and a sofa. A round table is placed at the center, surrounded by natural greenery. The wooden flooring and patterned rug enhance the outdoor relaxation space.

Guesthouse in Elk Mills

4.98 out of 5 average rating, 141 reviews

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

Top guest favorite

A cozy living area features a green sofa adorned with colorful cushions. A wooden coffee table holds a bouquet of flowers. The kitchenette is equipped with modern appliances, including a refrigerator and stove, surrounded by light-colored cabinets and decorative accents.

Guest suite in Newark

4.99 out of 5 average rating, 102 reviews

Inviting, comfortable & private suite near Univ.

Enjoy this comfortable, relaxing guest suite with a kitchenette in a desirable and quiet neighborhood in Newark. Close to Downtown and Main St, this is a great base to explore the area and the University. We are less than 3 miles from the University and Main Street. The suite is tastefully furnished in a neighborhood with mature trees. It is totally private, with a separate entrance and a keypad for self check in. Parking is available in the driveway. Truly a serene getaway!

Top guest favorite

The front entrance of the home features a well-maintained pathway bordered by lush greenery and flowering plants. An elegant lamp post stands beside the path, illuminating the approach to the entrance where double doors and a decorative American flag are positioned.

Apartment in Chadds Ford

5 out of 5 average rating, 210 reviews

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Guest favorite

The cottage exterior features a white vinyl facade, framed by black shutters on the windows. A welcoming front porch with steps leads to a glass door, complemented by flowering plants in front, with a well-maintained lawn and clear evening lighting enhancing the inviting ambiance.

Cottage in North East

4.94 out of 5 average rating, 382 reviews

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

Guest favorite

A comfortable living area features two dark brown sofas positioned around a glass-top coffee table. Natural light filters through sheer curtains, illuminating the space. A potted plant and decorative wall art enhance the ambiance, while a wall clock adds a functional element.

Apartment in Dover

4.89 out of 5 average rating, 155 reviews

Cozy apartment in a quiet Amish country setting

Relax in our fully furnished 1 bedroom (and a spare room with a futon for extra bedding ) 1 bath, living room, and kitchenette apartment, with a private ground level entrance, in a peaceful Amish country setting. The unit is 5 miles away from the Dover city limits. While here, be sure to enjoy shopping at Byler’s Store, a local destination stop featuring a deli, bakery, grocery and gift shop.

Top guest favorite

Two mini donkeys graze peacefully in a grassy field, surrounded by trees with green foliage. A blue sky with a few scattered clouds provides a bright backdrop, and wooden fences outline the pasture, enhancing the farm-like setting.

Farm stay in Frenchtown

4.95 out of 5 average rating, 567 reviews

DREAM BIG! Rustic Tiny Home on Hidden Farmlet

Ready to kick back and relax from your busy life? Have you ever dreamed of waking up on a farm? Then our charming 170 sq ft tiny home is perfect for you! Situated on 10 picturesque acres, and home to one horse, two mini donkeys, two goats, a pig, twenty-two chickens, five ducks, a goose and, of course, a barn cat. This is the place to disconnect and get back to nature!

Top guest favorite

An airy living area features a large curved sectional sofa on a textured rug, complemented by two elegant lamps. Floor-to-ceiling windows provide ample natural light, and a tall stone fireplace is accentuated by wood detailing. The open layout includes a glimpse of the kitchen in the background.

Cabin in Greenwich

4.92 out of 5 average rating, 236 reviews

The Hepburn-Hot Tub & Fire Pit

The Hepburn is a beautifully renovated and decorated by home by Harlow Grey Homes. This meticulously restored glass cabin is located on over an acre of private grounds on a serene 75 acre lake. Firewood included! The separate seven-person hot tub is OPEN for the season. The private pool + built-in spa is closed and is set to reopen mid May 2025