
Places to stay near Black Ankle Vineyards
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Top-rated holiday rentals near Black Ankle Vineyards
Guests agree: these stays are highly rated for location, cleanliness and more.

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

Sleepy Hollow Log Cabin
Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

Downtown Frederick Modern Studio
Modern 1-bedroom studio apartment located on North Market Street (NOMA) in charming downtown Frederick. Walking distance to great restaurants, shops, breweries and nightlife. Studio includes a full kitchen and luxurious bathroom providing everything you need to enjoy your time in downtown Frederick. Conveniently located behind laundromat (Noma Laundry) which is open from 5AM-11PM. 5 minute walk to the heart of Frederick and minutes away from Gravel & Grind coffee cafe and Olde Mother brewery.

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.

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.

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**

Free Parking, Dogs • Walk to Breweries & Coffee
This charming downtown Frederick flat is made for foodies, coffee lovers, and city explorers. Just steps from Frederick’s top breweries and cafés, it’s the perfect home base for a weekend getaway with your pup. With pet amenities, local recs, parking, and fast Wi-Fi, it’s both fun and functional. Free parking in a dedicated spot on a gravel lot behind the home, which is a 2 minute walk to the front door.
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

Downtown 1 BR Condo Steps to Everything

Lovely, Country Apartment, Just Minutes From Town.

BRIGHT 1 BD w/ LARGE BALCONY in PRIME BETHESDA LOC

Your Hideaway awaits/1-bedroom downtown pad.

Cozy Private Condo in Mt. Vernon w/ Rooftop

New, Sunny, 2BR - Parking, Patio, Firepit

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

Peaceful Deck, Game Room Near DC, Gettysburg

Farmhouse Getaway | Close to Wineries & Breweries

Private Suite • 10 mins to BWI, Fort Meade & Mall

Comfort • 1BR w/ Fast Wi-Fi

Bright and Spacious Walkout unit

Saadallah Casita Farm & Garden

Studio Apt full of amenities, cozy and quaint

Sunset View Country House
Apartment rentals with air conditioning

Mother-in-law suite with yard

Downtown Frederick Getaway

The Barn at Belgrove

2 Bedroom Apartment in Quiet Area

Carroll Creek Private Apt./Luxury King Bed

Your own "Tiny House"

Heart of Sykesville! 2 Bedroom Suite! Walk to town

Barn Apt on Tranquil Historic Farm--Amazing Views
Other great holiday rentals near Black Ankle Vineyards

The Glowing Logs Cabin

Copper Flat Cottage

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

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Cozy Farm Stay – Retreat with Goats, Pony & More

Luxury Mountain Getaway: Sunsets, Wines & Views.

Casa Blanca Upscale Retreat: Indoor Pool, Fire Pit

The Caretaker's Cottage-Historic Roundabout Hills
Destinations to explore
- Nationals Park
- Georgetown University
- National Mall
- M&T Bank Stadium
- The White House
- District Wharf
- Smithsonian National Museum of Natural History
- Oriole Park at Camden Yards
- Hampden
- National Museum of African American History and Culture
- Stone Tower Winery
- Arlington National Cemetery
- Liberty Mountain Resort
- National Harbor
- Georgetown Waterfront Park
- Washington Monument
- Patterson Park
- Whitetail Resort
- Cunningham Falls State Park
- Caves Valley Golf Club
- Great Falls Park
- Six Flags America
- Codorus State Park
- The Pentagon




