Vacation rentals in Willowstone

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Top-rated vacation rentals in Willowstone

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Top guest favorite
A welcoming living area features exposed wooden beams and hardwood flooring. A gray sofa and patterned armchair provide comfortable seating options. Light streams through large windows, illuminating a circular area rug. A coastal-themed artwork and a leafy plant add character to the space.
Home in Chesapeake City
5 out of 5 average rating, 14 reviews

Modish Cottage w/Bar Shed Charm!

Welcome to your perfect getaway in the heart of historic Chesapeake City! Just steps away from local restaurants, nightlife, boutique shops and scenic canal views, you'll love exploring all this waterfront town has to offer. Inside, a stylish retreat for relaxing. But the real gem...the back yard. Kick back with a drink at the bar shed, grill a meal, and gather around the fire pit to relax under the stars. Don't forget your bike (for the bike trail) or kayak for the more adventurous at heart!

Top guest favorite
A spacious living area is shown, featuring a well-equipped kitchen, dining space for four, and a cozy seating area. Light green chairs provide a pop of color, while a large mirror reflects the room's dimensions. Soft natural light filters in from the window.
Guest suite in Newark
4.97 out of 5 average rating, 166 reviews

Charming Fully Equipped Private Guest Suite Studio

Relax in a stylish guest suite studio in a quiet, safe neighborhood. Its private entrance and parking for 2 vehicles makes the cozy space all the better. Enjoy the full kitchen, work space, high speed internet (1200mbps), 50” TV, full bathroom, and more. Perfect for the business professional on-the-go, or getaway. Take a stroll through White Clay Creek Park with your furry friend. Just a short 5 minute drive from Main St.'s restaurants, local bars, and UD. Only 10 minutes from Christiana Mall.

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
4.98 out of 5 average rating, 613 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
Cottage in Charlestown
4.95 out of 5 average rating, 216 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

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, 147 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.

Superhost
An open layout showcases a dining area with a light-colored table set for six, adjacent to a cozy living space featuring a neutral-toned sofa and armchairs. A horse-themed artwork is displayed on the wall, while soft curtains frame the windows allowing natural light in.
Guesthouse in Elkton
4.91 out of 5 average rating, 162 reviews

Countryside-Stable House-Open Studio-Quiet for 2

Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

Top 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, 390 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.

Top guest favorite
Aerial view of the waterfront property reveals expansive green lawns surrounded by lush trees, with the C&D Canal visible nearby. The water reflects the clear blue sky, and a boat is seen traversing the canal, highlighting the active water traffic and serene natural surroundings.
Home in Elkton
4.9 out of 5 average rating, 100 reviews

Waterfront Retreat for Weekends and More!

Nature at its finest: Find peace and tranquility in this waterfront home with breathtaking water views from all freshly decorated rooms. Enjoy the water traffic on the C&D Canal along with the multitude of wildlife living in the area. Launch your kayak, canoe or row boat from the boat ramp. Relax here in the evenings while spending the day visiting the University of Delaware or other local Cecil County venues.

Guest favorite
A stunning sunset over the Elk River is displayed, featuring vibrant hues of orange, pink, and purple reflecting on the water's surface. The tranquil scene is framed by silhouettes of trees along the shoreline, creating a serene atmosphere.
Cottage in Elkton
4.92 out of 5 average rating, 86 reviews

Sunset River Shack -amazing waterfront view

Sunset River Shack is both Nauti and Nice!This awesome Nauti -Boho styled waterfront cottage has fantastic water views overlooking the Elk River on the Upper Chesapeake Bay. Sunsets all year long. The cottage is newly renovated and perfect for a romantic getaway, family vacay, boating trip, girls getaway, or no occasion at all. You'll never want to leave! Enjoy Chesapeake Bay life at Sunset River Shack.

Guest favorite
A bright and serene bedroom features a spacious bed with a light-colored quilt and decorative pillows. Two large windows offer natural light and views of lush greenery outside. A vintage dresser sits beside the bed, complemented by a nearby radiator.
Townhouse in Port Deposit
4.95 out of 5 average rating, 232 reviews

Quarry Landing • River Views in Historic Town

Enjoy easy access to everything from this perfectly located home. Quarry Landing is a turn-of-the-century Duplex filled with charm and beauty. Located on High Street in the quaint small town of Historic Port Deposit, (Maryland), perfect for couples or families. Great location in a safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more.

Top guest favorite
A welcoming porch features white adirondack chairs and a small blue table. A lantern and a decorative container are placed nearby, with the house's yellow exterior and orange shutters providing a cheerful backdrop. The view includes trees and street activity.
Cottage in Chesapeake City
5 out of 5 average rating, 100 reviews

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

Top guest favorite
A serene river view features vibrant orange and pink hues reflected in the calm water at sunset. Silhouetted dock posts and boats create a tranquil atmosphere against the expansive sky, enhancing the peaceful setting of the Elk River.
Home in Elkton
5 out of 5 average rating, 17 reviews

The River House - waterfront

Relax with the whole family at this peaceful home on the Elk River. Enjoy breathtaking sunsets in the backyard overlooking the river. The kids will love running and splashing around in the yard. Outside patio features sectional sofa, Adirondack chairs and a fire pit to enjoy nights on the river. Plenty of restaurants and things to do in the area. Come enjoy the beauty of life on the Chesapeake!

Popular amenities for Willowstone vacation rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Cecil County
  5. Willowstone