Holiday rentals in Sugarloaf Mountain

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Top-rated holiday rentals in Sugarloaf Mountain

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Top guest favourite
The interior of the tiny home features warm wooden walls and a skylight, providing natural light. A compact kitchenette is visible, along with a seating area that includes two metal chairs. A sliding door offers a view into the outdoor space.
Home in Harpers Ferry
4.94 out of 5 average rating, 150 reviews

Spectacular View, PET FREE, Skylight and Hot Tub

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry, quiet peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, "Mind Blowing" 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

Top guest favourite
A bright bedroom features rustic wooden walls with horizontal stripes, complemented by large windows bringing in natural light. A spacious bed with white linens is paired with decorative pillows. A dresser and bedside table are positioned nearby, along with a fan for added comfort.
Cabin in Leesburg
4.92 out of 5 average rating, 13 reviews

Cabin On Fern Ridge

Escape to our newly renovated stylish 2-bedroom cabin in DC’s Wine Country, Cabin On Fern Ridge is a Waterford Reservations Elite Property Perfect for couples, families or solo retreat, it blends modern comfort with rustic charm. Enjoy private wooded property, king size beds, and a fully equipped kitchen. Relax on the fenced stone patio with outdoor fireplace. Cabin is ideal for visiting the areas best attractions wineries, breweries, hiking and more or simply unwinding in nature's embrace.

Guest favourite
A modern kitchen and living area are showcased within an open layout. Sleek countertops and stainless-steel appliances are present in the kitchen, along with a bar seating area. A comfortable seating arrangement faces a television, while natural light streams through large windows.
Flat in Leesburg
5 out of 5 average rating, 24 reviews

Owl’s Nest at Shiloh | King Bed

Tucked away on Furnace Mountain, Owl’s Nest is your perfect escape from the everyday hustle. This charming apartment blends rustic comfort with modern amenities, offering a peaceful stay for a romantic getaway or solo retreat. Enjoy morning coffee with birdsong on the balcony, curl up with a book and some tea, or solve a mystery with a game of Clue. Located nearby well known Lucketts Antique shops, hiking, biking & river excursions. 11 miles to Leesburg, VA, and 15 miles to Frederick, MD.

Top guest favourite
The treehouse is perched among tall trees, featuring a wooden deck that wraps around its structure. A gentle staircase leads to the entrance. In the foreground, purple flowers bloom beside a rock outcropping, enhancing the natural landscape under a bright blue sky.
Treehouse in Shepherdstown
4.97 out of 5 average rating, 377 reviews

Cozy West Virginia Treehouse

Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

Top guest favourite
The exterior of a two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.
Guest suite in Smithsburg
4.98 out of 5 average rating, 317 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Top guest favourite
A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.
Home in Harpers Ferry
4.97 out of 5 average rating, 61 reviews

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

Top guest favourite
The exterior of a red brick building is shown, featuring a striking peaked roof and multiple windows. A shaded porch is visible at the entrance, adorned with potted plants. Lush greenery surrounds the property, and a gravel path leads up to the structure.
Farm stay in Leesburg
5 out of 5 average rating, 90 reviews

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

Top guest favourite
A bright living area is presented, featuring two armchairs and a sofa, arranged around a circular coffee table. Natural light floods in through four windows, accentuating the hardwood floors and a patterned rug adorned with starfish. Decorative plants add a touch of greenery to the space.
Home in Gaithersburg
4.95 out of 5 average rating, 39 reviews

Entire Modern & Cozy Private Basement w/Amenities

Relax in our private, secluded basement suite, complete with a private cozy bedroom, newly renovated full bathroom, kitchen, and private entrance. This clean, one-bedroom suite in Gaithersburg, MD, is conveniently located near - - Germantown (9 miles ) - Damascus(3 miles), - Clarksburg (6 miles), - Washington DC (33miles) -Shady Grove Metro - 16 miles It is perfect for both short stays and longer visits. You'll have full privacy while we reside in the upper two levels of the home.

Top guest favourite
Guest suite in Gaithersburg
5 out of 5 average rating, 9 reviews

Private Mini-Suite (Space NOT shared with Host)

Keeping it simple at this peaceful and centrally-located place. 1.7 miles from I-270, 4.7 miles from Germantown Soccerplex, 0.4 miles from Bowling alley, 1 mile from Kaiser Permanente, 4 miles from Shady Grove Hospital and Shady Grove Metro Station, 0.7 miles from the Gaithersburg MVA, 1.2 miles from the shopping center, 3.1 miles from Fitness centers, 3 minute walk from the RideOn bus stop (61, 74, 78), and minutes away from Tech Hub and pharmaceutical companies.

Top guest favourite
A modern kitchen is highlighted by a spacious island featuring dark cabinetry and a white countertop. Bright pendant lights hang overhead, illuminating the area. A bouquet of fresh flowers adds a touch of color, while an array of appliances is visible in the open shelving.
Farm stay in Ijamsville
4.96 out of 5 average rating, 304 reviews

Beyond Your Expectations Farm Stay

Escape to our historic farm stay, where charm meets modern comfort. Enjoy the gourmet kitchen, unwind on the magnificent patio with a huge fire pit, and indulge in the infrared sauna. Perfect for families and friends, with an adorable kid's playhouse and games. Interact with friendly animals, immerse yourself in serenity, and experience the ultimate getaway near Whiskey Creek Golf Course in Ijamsville. Contact Fingerboard Farm directly for larger gatherings.

Top guest favourite
A bright and airy bedroom features a spacious bed with a white quilt and an accent pillow. Natural light filters through two windows, illuminating the wood floor. A small dining table with chairs and a wall-mounted air conditioner add functionality to the cozy space.
Guest house in Woodbine
4.96 out of 5 average rating, 121 reviews

Garden Cottage

Located in a beautiful and peaceful part of Maryland our Garden Cottage offers a cute and cozy getaway. A perfect escape from the city, our cottage is nestled among some of Maryland's best farmers markets, breweries, wineries, and outdoor experiences while still being conveniently located near several small towns and Frederick, MD. If you’re looking for a longer stay but our calendar looks booked please reach out to us!

Top guest favourite
The living area features a spacious couch dressed in soft blankets, complemented by two armchairs and a dark coffee table. A flat-screen television rests on a media console, while large windows allow natural light to brighten the space, offering views of the surrounding landscape.
Home in Frederick
4.98 out of 5 average rating, 62 reviews

Sugarloaf Mountain Retreat- 300 Acre Estate

Welcome to Sugarloaf Retreat! This cozy one-bedroom, one-bathroom home on a 300-acre estate offers stunning views, a fully equipped chef's kitchen, and a plush king-sized bed. Relax on the patio under the stars after a day of adventure. Conveniently located near Sugarloaf Mountain trails, C&O Canal, golf clubs, roads for biking, and just a short drive from Downtown Frederick, it's the ideal luxury escape in nature.

Popular amenities for Sugarloaf Mountain holiday rentals