Holiday houses in Westernport

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Top-rated holiday rentals in Westernport

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Top Guest favourite
A charming cabin is nestled among tall trees, illuminated by soft exterior lighting. The structure features a welcoming porch that extends around the building, while the sky transitions from twilight to dusk, creating a serene atmosphere.
Home in Rio
4.97 out of 5 average rating, 157 reviews

Mountaintop Cabin w/ Outdoor Tub

Come unwind at our mountaintop cabin! Whether it’s the (new cast iron) soaking tub on the back porch, the two hammocks, our giant firepit, or the comfy king bed in the loft, you’ll want to sit, sip, snuggle and tell tall tales as the sun sets and stars shine. Second small bedroom doubles as an office. A gas stove twinkles inside while an antique spiral staircase adds elegance. Fully-equipped kitchen, laundry, and Starlink to provide top-tier connectivity. We’re kid friendly and dog positive too!

Top Guest favourite
The treehouse is elevated among bare branches, featuring a large deck with seating. Warm lighting highlights the wooden exterior, and expansive windows provide views of the surrounding forest. Steps lead down to the ground, enhancing accessibility to the natural setting.
Treehouse in McHenry
5 out of 5 average rating, 152 reviews

Bird's Eye View

Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

Top Guest favourite
A single-story blue house is set against a backdrop of leafy trees. The front porch features a welcoming red door and two outdoor chairs. Soft landscaping surrounds the house, which has a neatly maintained lawn and a paved driveway leading to the entrance.
Home in Romney
4.99 out of 5 average rating, 145 reviews

Southern Charm Getaway in Romney, WV - Sleeps 6

Beautiful, comfortable & clean family friendly getaway in West Virginia's first town! Located in the center of town and walking distance to restaurants, public library, boutiques, shopping, historical sites, Civil War trenches, public pool and Visitor's Center. Just a few short miles to The Potomac Eagle Scenic Excursion Train & to the South Branch of the Potomac River for fishing and canoeing. You will find many day trip activities within an hours' distance, including Skiing, hiking &biking

Top Guest favourite
A well-appointed kitchen features warm wood cabinetry and a spacious granite countertop. Stainless steel appliances, including a gas range and microwave, are visible. A central island provides additional preparation space, with overhead lighting illuminating the area. Natural light enters from the adjacent room.
Guesthouse in Grantsville
4.98 out of 5 average rating, 144 reviews

Yoder School Guest House with wifi and hot tub

Built originally in the late 1800's and renovated by us in 1991, Yoder School became our home. In later years we converted part of the building into this peaceful getaway. Opportunities for outdoor activities abound. Fantastic road cycling with Strava routes start right here! Just a short drive away great mountain biking, hiking, cross country and downhill skiing, and white water rafting are yours to enjoy. Several unique and popular restaurants, and tennis and basketball courts are nearby.

Top Guest favourite
The exterior of a renovated log cabin is showcased, featuring traditional log and chink construction. A substantial stone chimney rises alongside the cabin. A spacious porch is present, equipped with a couple of white chairs, surrounded by natural greenery and autumnal foliage.
Cabin in Springfield
5 out of 5 average rating, 132 reviews

1832 Historic Washington Bottom Farm Log Cabin

Welcome to our renovated 1832 Log Cabin on the grounds of the George William Washington and Sarah Wright Washington 19th century plantation. The cabin was the first structure built. Then came barns and slaves’ quarters (no longer standing). The dairy barn is now a woodworking shop and the bank barn was recently restored. The main house, built in 1835, is Greek Revival style. Today, our 300+acre is Certified Organic. We border the South Branch of the Potomac River. It’s ALMOST HEAVEN !

Guest favourite
A spacious two-story home is set against a backdrop of greenery, showcasing a combination of stone and siding. A well-maintained lawn leads to a paved driveway, and large windows with decorative trim are visible along the facade, inviting natural light indoors.
Guest suite in Swanton
4.83 out of 5 average rating, 248 reviews

The View

Spacious, clean, modern basement efficiency apartment. Private entrance, private bath w/shower, private kitchenette with full size fridge & microwave (no stove), 1 queen size bed. Pool table, bar area and living room space with large TV equipped with satellite service. More space than a hotel room. View of Deep Creek Lake from front lawn in the distance, 11 Miles to Wisp, 6 miles to Deep Creek State Park and 1 mile to Thousand Acres Golf Course. NO Smoking, No Pets. We now have WIFI!!

Guest favourite
The living area features a modern design with a gas fireplace as the focal point. A chandelier hangs from the vaulted ceiling, illuminating comfortable seating arrangements. Large windows offer a view of the wooded landscape, while a TV is mounted on the wall, providing entertainment options.
Guest suite in Accident
4.98 out of 5 average rating, 266 reviews

New! The Butterfly Suite at Enchanted Table Meadow

Minutes from Wisp Ski Resort & Deep Creek Lake! Come as you are & take a seat at nature’s table under the canopy of stars. Embrace the wooded ambiance and meadow views from our 825 sq. ft suite as you melt your cares away in front of the fireplace. Located between I-68 and Deep Creek Lake/Wisp. Our hope is to provide a serene landscape where you can find peace and rest through nature. Our setup works well for business travelers & as a couple's romantic escape!

Top Guest favourite
A spacious living area features a large leather sectional sofa with accent pillows, paired with rustic wooden coffee tables. A sleek entertainment center holds a wall-mounted TV, while framed landscape artwork adorns the walls, adding a touch of color to the room.
Apartment in Accident
5 out of 5 average rating, 133 reviews

The Nest near Deep Creek

Kick back and relax in this calm, stylish space. Brand new, beautiful one bedroom apartment above a detached garage just 5 miles from Deep Creek Lake. Beautifully designed space with craftsman quality large kitchen, king size neo-industrial walnut bed, live-edge vanity and wall cap, articulating lamp, all made by local craftsman. Leather pull out couch with queen bed sleeps two extra guests. Relax by the fire pit and listen to the birds in the woods.

Guest favourite
The exterior of the two-story cottage features a white clapboard façade with black trim. A welcoming front porch, supported by dark columns, offers a partial view of the lush green surroundings and open space nearby.
Cabin in Grantsville
4.95 out of 5 average rating, 110 reviews

Casselman View Cottage

Casselman View Cottage is perfectly located steps from the banks of the Casselman River, next tothe Mountain Grape Tavern, Spruce Forest Artisan Village, and The Historic Casselman River Bridge. A two-story cottage, with a full kitchen, the ultimate in hospitality is provided - located in the heart of Grantsville's Arts & Entertainment District. Also onsite is Maple & Vine Market, food and wine shop, and the Garrett County Arts Council Gallery Too!

Guest favourite
An outdoor fire pit area is surrounded by gravel and features three wooden Adirondack chairs arranged around a stone fire ring. Softly glowing string lights are draped between tall trees, creating a cozy ambience amidst the forest setting.
Home in Accident
4.89 out of 5 average rating, 100 reviews

Peaceful nature retreat nestled in a forested area

Welcome to our lovely vacation House! Built in 2024, fresh, cozy and modern. Perfect for memorable family trip, romantic getaway for a couple or a fun adventure for a small group of friends. Convenient location- great combination of privacy (forest-like area) and quick access to fun places: 5-10 minutes drive from Wisp Ski Resort, Deep Creek lake, boat rentals, scenic hikes, restaurants, bars, amusement parks and grocery stores.

Top Guest favourite
The kitchen showcases white cabinets contrasted by sage green lower cabinets. Modern appliances, including a dishwasher and gas stove, are present. A farmhouse-style dining area with a small table and two chairs is nestled by a window, illuminated by natural light.
Home in Frostburg
4.99 out of 5 average rating, 112 reviews

Piney Mtn House

Become part of Mountain Maryland discovering your next cozy escape in the newly renovated modern bungalow. The Appalachian range will tuck you in the small town of Eckhart, closely boarding Frostburg, with all its unique attractions, entertainment, hiking trails, and state parks. No body does small town like local Frostburg. And there is no better way to unwind than to make the Piney Mountain House your home away from home.

Top Guest favourite
The exterior of a three-story house is showcased, featuring a light gray color and a sloped roof. Large windows allow for natural light, while a deck extends from the second level. The yard is grassy, providing open space with trees in the background.
Home in Swanton
4.97 out of 5 average rating, 272 reviews

Bev's House at Sunny Meadows

Looking for a place to stay that is quiet and relaxing, but also close to many outdoor activities? Bev's House at Sunny Meadows is just that! Located just minutes from several state parks that offer boating, fishing, kayaking, swimming, hiking and biking, there's always plenty to do. Bev's House offers a quiet place with spectacular mountain views to escape the rush and noise of everyday life.

Popular amenities for Westernport holiday rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Allegany County
  5. Westernport