Cottage vacation rentals in Western Maryland

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Top-rated cottage rentals in Western Maryland

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Top guest favorite
An outdoor hot tub is shown with a glass of red wine and a single rose placed beside it. A scenic view of rolling fields and trees is visible in the background, with a colorful sunset illuminating the sky.
Cottage in Winchester
4.99 out of 5 average rating, 440 reviews

Uber SXY Private Country Escape! Hot Tub & Views~

Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

Top guest favorite
A fire pit surrounded by multiple Adirondack chairs sits on a gravel surface. The backyard vegetation includes trees and shrubs, while a grey house with lit windows is visible in the background, complementing the serene outdoor setting.
Cottage in Wardensville
4.99 out of 5 average rating, 142 reviews

Cottage at Lost River Ridge

"This is a beautiful house and the perfect peaceful weekend getaway." -Guest With a hot tub, king beds, complimentary firewood, fully equipped kitchen, and 75-inch TV for movie night, this is the secluded mountain oasis you've been dreaming of for that much-needed getaway! When you're not roasting smores over the fire, or soaking in the hot tub, take a trip into town and experience local gems like a bustling farmer's market, tasty eateries, charming shops, and a wealth of outdoor activities!

Guest favorite
The exterior of the stone cottage showcases a blend of natural rock and wood. A porch extends from the cottage, providing scenic views of the rolling landscapes and greenery. Two small evergreen trees frame the view, complementing the tranquil setting.
Cottage in Bluemont
4.98 out of 5 average rating, 511 reviews

The Stone Cottage at Bluemont Vineyard

The cozy, stone, studio cottage is secluded in the vines & orchards of Bluemont Vineyard. ~ spectacular sunrise views of Virginia Wine Country ~ Stone walls built from rock found on the vineyard property ~ 5 minutes to Dirt Farm Brewing & Henway Hard Cider ~ 10 minutes to local dining & shopping ~ Over 40 other vineyards to visit within an hour's drive ~ Great Appalachian Trail hiking 10 minutes away ~ River tubing on the Shenandoah 20 minutes away at Watermelon Park

Guest favorite
A spacious deck offers unobstructed views of rolling hills and valleys, accented by vibrant autumn foliage. The sky is expansive, displaying soft clouds and blue tones. A sleek railing encircles the deck, enhancing the serenity of the natural landscape.
Cottage in Markham
4.96 out of 5 average rating, 172 reviews

Sunrise Cottage in Wine Country

The place for nature lovers and the audiophile! Newly renovated cottage with queen bed and queen sleeper sofa! Situated on five acres, at Sunrise Cottage you can see no other dwellings except those in the valley far below. Lay in bed and watch the sun rise from the East. 60 mile views with a monarch waystation off the deck. Relax in the hot tub or sit around the fire pit. Bathroom has a spa feel with rainfall showerhead. Close to Marriott Ranch for horse trail rides and surrounded by wineries!

Guest favorite
Two classic wooden Adirondack chairs are positioned near the bank of a gently flowing stream. Lush greenery surrounds the area, with trees casting dappled sunlight on the water. A clear blue sky adds a serene backdrop, enhancing the peaceful atmosphere of the outdoor space.
Cottage in Waynesboro
4.94 out of 5 average rating, 122 reviews

Antietam Toll House~an historic waterfront cabin

The Antietam Toll House (@antietamtollhouse) is a renovated historic property circa 1800. Sitting on the bank-head of the Antietam stream, this cabin has it's own private fishing hole. Secluded, yet close to amenities and attractions, this property is the perfect place for an artist retreat, respite from the city or a base from which to explore local gems of the area. Wineries, Appalachian Trail, Antietam, Gettysburg battlefields, Ski Liberty, Catoctin , Cunningham Falls and more nearby.

Top guest favorite
A spacious outdoor patio area is visible, featuring seating arranged for relaxation. Trees line the bank of the river, with open fields on the opposite side. The clear water reflects sunlight, and the mountains are visible in the background under a bright blue sky.
Cottage in Woodstock
4.99 out of 5 average rating, 107 reviews

Shenandoah Riverfront and Mountain View Cottage

The Misty River Cottage is located on one of the seven bends of the Shenandoah River and at the base of the Massanutten Mountain. It was designed, built and furnished with the goal of being one of the nicest options in the Shenandoah Valley. With views of the river and mountains from every room. Ensuite bathrooms in each of the two bedrooms. A custom built bunk bed for larger groups. Heated floors, spectacular outdoor space and direct river access all within a short drive to Woodstock.

Top guest favorite
The modern cabin is framed by lush greenery, showcasing a unique combination of wood and metal siding. A circular fire pit surrounded by black adirondack chairs is situated in a gravel area, leading to a pathway that connects to the entrance of the cabin.
Cottage in Lost City
4.98 out of 5 average rating, 104 reviews

Hidden Hideaway

Welcome to your retreat, your Hidden Hideaway. Leave the hustle and bustle of the city to relax and rejuvenate in Lost River. This luxury minimalist cabin has everything you want and need whether you are looking for a quick weekend getaway or a month-long working vacation. Immerse yourself in nature on the screened in porch, gaze into the Milky Way stars as you sit around the fire pit, or curl up with a book in the sun drenched reading nook, you will find what you need at Hidden Hideaway.

Top guest favorite
The exterior of a two-story cottage is presented, featuring a blend of dark green siding and stone accents. Large windows are illuminated, highlighting a welcoming entrance. Surrounding trees are bare, indicating the season, while a spacious yard of grass and earth is visible in the foreground.
Cottage in Shepherdstown
4.97 out of 5 average rating, 181 reviews

NEW * The Getaway Cottage at Rocky Marsh Farm

Welcome to The Getaway Cottage, a charming two-bedroom, two-bath home nestled in a peaceful country setting, located just 3.5 miles from Shepherdstown. Our location offers easy access to all the exciting activities and attractions the eastern panhandle has to offer, enjoy a short country side drive to dining, shopping, hiking trails, white water rafting and kayaking adventures. The historic town of Harpers Ferry is a short 25-minute drive away, and 15 minutes to Antietam Battlefield.

Top guest favorite
Two dogs are seated on black chairs in a grassy area, facing a charming cottage with a stone chimney. The house, featuring numerous windows, is surrounded by a spacious wooden deck. A fire pit is visible in the foreground, providing a cozy gathering spot.
Cottage in Fort Valley
4.96 out of 5 average rating, 231 reviews

Cozy Cottage/Pet Heaven

Deep breath...exhale. Looking for the perfect place to hideaway? You have found it. Enjoy big skies, picturesque landscapes, friendly farm animals and colorful sunsets. Nestled in the valley within the valley, you are surrounded by the George Washington National Forest. Offering hiking, biking, ATV trails, and so much more. Skyline Drive and Luray Caverns are just a 30 min drive. 30 minutes to shopping. Located less than 2 hours west of DC. Come see what you have been missing.

Top guest favorite
The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.
Cottage in Green Spring
4.98 out of 5 average rating, 112 reviews

The River House

A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

Guest favorite
A modern living area features a sleek brown sofa adorned with green and cream pillows. Light wood flooring complements the minimalist decor, while a round table with chairs is positioned nearby. The kitchen is visible in the background, showcasing clean lines and bright surroundings.
Cottage in Timberville
4.93 out of 5 average rating, 289 reviews

Raven Ridge Retreat: Romantic Orchard Getaway

Raven Ridge Retreat sits amidst our Granny Smith & Gala Apple Trees at Showalter's Orchard, home of Old Hill Cidery. This light-filled, recently-constructed cottage highlights extraordinary views of The Massanutten and the Blue Ridge Mountains, the Shenandoah Valley, rows and rows of apple trees, and abundant wildlife. This two-story, romantic farm stay is base for all your area adventures like hiking in Shenandoah National Park or exploring The Shenandoah Spirits Trail.

Top guest favorite
Cottage in Berkeley Springs
4.95 out of 5 average rating, 197 reviews

Cozy Cottage in the heart of Berkeley Springs WV

Welcome to Elizabeth Cottage in honor of our Queen HRH Elizabeth II. Our spacious 3 bedroom cottage will make you feel right at home in the historic town of Berkeley springs! We welcome all pets and have a fully fenced in yard and screened in porch for them to enjoy! We are walking distance from our small town shops, and restaurants! >British Cottage Style >55" TV w/ roku streambar >Xfiniti Wifi >Hot tub, Fire pit, Grill **Low Cleaning Fee**

Popular amenities for Western Maryland cottage rentals

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