Holiday rentals in Willowstone

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Willowstone

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

%{current} / %{total}1 / 1
Top guest favourite
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, 16 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 favourite
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, 624 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.

Top guest favourite
Cottage in Charlestown
4.95 out of 5 average rating, 221 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

Guest favourite
A charming two-story red brick home features large windows with black shutters, allowing ample natural light to enter. Lush green landscaping surrounds the entrance, which includes a white front door flanked by elegant outdoor sconces. The overall impression reflects a well-maintained historic residence.
Home in North East
4.94 out of 5 average rating, 130 reviews

Historic Creekside Home - 2br 2.5ba Downtown

Built in 1875, this newly renovated two bedroom home, is centrally located in downtown North East. Modern finishes and an open concept living space compliment the original wood floors, clawfoot tub and exposed brick walls. All the amenities of Main Street are steps away, yet the home is tucked away on a quiet street with a creek in the back yard. Our home is 2.5 miles from I-95 and one block from North East Community Park, Anchor Marina and the headwaters of the Chesapeake Bay.

Guest favourite
A small dining table with two black chairs is positioned next to a low coffee table adorned with decorative vases. The warm walls complement a soft area rug, while a lamp illuminates the cozy space, creating a comfortable setting for relaxation.
Flat in Bear
4.85 out of 5 average rating, 27 reviews

Cozy Loft Above Ink Shop

Welcome to your cozy retreat above our tattoo studio! This stylish 1-bedroom apartment offers a comfortable, private space with modern touches and plenty of charm. Enjoy a comfy living area with a Smart TV, a private bedroom, and a full kitchen. Perfect for solo travelers, couples, or those visiting for tattoo appointments, this space combines comfort with convenience. Please note: the apartment is located above an active tattoo studio. Come stay, relax, and experience a vibe.

Top guest favourite
A cozy living area features a dark leather sofa with blue accent pillows, complemented by a round coffee table. Colorful wall art adorns the light blue walls, and natural light enters through the window. Two doors lead to separate areas, enhancing accessibility.
Flat in Newark
5 out of 5 average rating, 16 reviews

Cozy and private annex

Conveniently located in Newark, this cozy and private one bedroom mother in-law suite is attached to the main house. The unit is comfortable for 2 people. It has a private entrance, TV, full bathroom and a kitchenette with almost all the amenities of home. Perfect for business professional on- the- go or getaway. 15 min away from University of Delaware, Christiana Mall and many local restaurants and bars. Host lives on site full-time. ***Must be 25+ years and older to book ****

Guest favourite
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.
Guest house in Elkton
4.91 out of 5 average rating, 167 reviews

Countryside-Stable House-Open Studio-Perfect 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 favourite
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, 394 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 favourite
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 favourite
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, 89 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.

Top guest favourite
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, 103 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.

Guest favourite
A spacious room features a king bed with crisp white linens and a vibrant red accent pillow. Natural light is welcomed through a window beside a mirror. A cozy seating area with two chairs is visible, along with a kitchenette efficiency and a colorful rug on the floor.
Flat in Chesapeake City
4.98 out of 5 average rating, 45 reviews

Private entrance King Suite

Forget your worries in this spacious and serene space. Brand new private room on historic waterfront Chesapeake City Farm. You will have a private entrance to your roomy king suite, complete with luxurious bathroom, kitchenette efficiency, and coffee bar. You will have access to the Bohemia River, and a 200 acre horse farm, where wildlife abounds and the views are spectacular.

Popular amenities for Willowstone holiday rentals

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