
Places to stay near Black Ankle Vineyards
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Top-rated holiday rentals near Black Ankle Vineyards
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Cabin on Middle Creek - Myersville MD - Middletown
Park the car & walk across the creek on the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Great place to unwind & de-stress. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting

Enchanting PET FREE W/Amazing ViewHot Tub Overlook
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 away from the train in old town Large patio, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

The Caretaker's Cottage-Historic Roundabout Hills
The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

Carroll Creek Private Apt./Luxury King Bed
Within footsteps to Carroll Creek Promenade offering easy access to posh restaurants, fun Breweries, local shops and festivals galore! Modern remodel and furniture including a posh memory foam king bed. Enjoy your own apartment w/ wide open spaces & high ceilings that bring in fantastic light. Historic bldg. (circa 1840) with all the modern appointments to make your stay super comfortable and fun! Owners provide advice on their favorite places and restaurants! Easy self checkin. Free parking.

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.

The Crooked Cottage: a Cozy, Curated Escape
You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

Poole House at Friendship Farm
Welcome to Poole House at Friendship Farm! Escape to the country at this historic stone house built in the 1700s. With accommodations for eight guests it is perfect for a getaway with friends and family, wedding parties and work retreats. The house received a meticulous restoration that includes all mechanical systems and a modern addition with a gourmet kitchen and master bedroom. The property also includes a three car garage as well as a restored smoke house and log cabin.

Historic Peace and Plenty Farm: Pool House
Peace and Plenty Farm is a 40+ acre, stunning rural escape located in Frederick County, two miles from Historic New Market, 45 minutes from Gettysburg, and an hour from Baltimore or Washington D.C. Feel free to explore our farm’s trails and hidden gems, play yard games with the family, or swim in our lap pool (open from June through October). Our generous space is suitable for a couple's getaway, a weekend with friends, a family vacation, a working vacation, or a quiet retreat.

Colonial Era Spring House
A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.

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!

Luxury Downtown Loft
The only luxury loft available in Westminster! Looking for a clean and convenient place to lay your head while exploring Westminster, this is your spot! Brand new apartment with luxury amenities at your finger tips. Within walking distance to downtown Westminster and a short drive to some of Westminster's hidden gems! **Please be advised that the sleeping area has a low ceiling! If you are taller than 6ft be advised**

Cozy Pine Tree Nest
This is a private, upstairs efficiency apartment over garage with stunning space features luxury laminate plank flooring, split unit a/c and heat, cherry wood beams harvested from the property, a full bathroom with tile/stone shower, pine ceilings, recessed lighting and a large deck to watch the amazing sun rises. Within minutes from Gambrill State Park, the Appalachian trail, restaurants, shopping, and downtown!
Popular amenities for holiday rentals near Black Ankle Vineyards
Other top sights near Black Ankle Vineyards
Apartment rentals with wifi

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Bijou Space in Downtown Bethesda

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable

Stunning Remodeled 1 BR Condo Steps to Everything.

The Grand Delphey: Downtown Artist Retreat

Lovely, Country Apartment, Just Minutes From Town.

Your Hideaway awaits/1-bedroom downtown pad.

One-bedroom apartment with separate entrance.
Family-friendly house rentals

Entire Modern & Cozy Private Basement w/Amenities

Farmhouse Getaway | Close to Wineries & Breweries

Peaceful Farmette, Red Bedroom

Rabbit Hill

Cozy room for solo travelers (No cleaning fee)

Bright and Spacious Walkout unit

Luxury 5BR Getaway |Hot Tub, Game Room & Fire Pit

Room Near BWI & Baltimore NO Cleaning Fee!
Apartment rentals with air conditioning

Downtown Frederick Getaway

2 Bedroom Apartment in Quiet Area

Escape to a Sunny Apartment in a Quiet D.C. Suburb

Heart of Sykesville! 2 Bedroom Suite! Walk to town

Barn Apt on Tranquil Historic Farm--Amazing Views

Charming 1 Bedroom Apt- Best Location in Downtown

Private Studio right on the Monocacy River!

Rebel Hollow
Other great holiday rentals near Black Ankle Vineyards

Renovated 1973 Aframe with Hot Tub

A quiet, restful retreat.

Brent House | Downtown Frederick

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Sleepy Hollow Log Cabin

Sunsets from a Haven on a Hill

Cozy Farm Stay – Retreat with Goats, Pony & More

Beyond Your Expectations Farm Stay
Destinations to explore
- Nationals Park
- Georgetown University
- The White House
- National Mall
- M&T Bank Stadium
- District Wharf
- Oriole Park at Camden Yards
- Smithsonian National Museum of Natural History
- National Museum of African American History and Culture
- Hampden
- Stone Tower Winery
- Arlington National Cemetery
- Georgetown Waterfront Park
- National Harbor
- Cunningham Falls State Park
- Caves Valley Golf Club
- Washington Monument
- Great Falls Park
- Liberty Mountain Resort
- Six Flags America
- Caledonia State Park
- The Pentagon
- Codorus State Park
- Patterson Park