Vacation rentals in New Windsor

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Top-rated vacation rentals in New Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

A stunning sunset is displayed over a rural landscape, with warm orange and yellow hues spreading across the sky. Silhouettes of trees and rolling hills create a serene backdrop, while the softly illuminated horizon adds to the tranquil atmosphere.

Farm stay in Union Bridge

UB Paradise - Rustic, Relaxing, Amazing View

A unique rustic atmosphere, relaxing location with amazing view. Private entry, open floor plan basement is 1,300 square feet; 4 double beds, wrap around window seat, bar with kitchenette, bath/shower, and game area. We welcome those who are looking for a unique place to stay. We are close to Taneytown (Antrim 1844), Gettysburg, Frederick, Ski Liberty, Catoctin Mountain, Carroll County Wine Trail, Flood Zone. We do live upstairs, you are renting a walkin basement, and have use of outdoor spaces.

ValueLocationNearby

4.92 out of 5 average rating, 213 reviews

Top guest favorite

Guesthouse in Frederick

The Landing in the Woods | Near Downtown Frederick

Escape to a beautiful one-bedroom retreat. The guesthouse has a queen bed, kitchenette, luxurious bathroom with two shower heads, including a rain head, and a queen pull-out sofa bed. Nestled in the woods with a covered porch for morning coffee, yet a short drive to downtown Frederick, Civil War sites, Frederick Watershed with hiking and cycling trails, Mount St. Mary’s University, Cunningham Falls, and Catoctin. Free WiFi, and Smart Roku TV’s. Parking for 2 cars is included. Dogs are welcome.

LocationFamilyCleanliness

4.96 out of 5 average rating, 109 reviews

Guest favorite

The farmhouse exterior is showcased, featuring a white façade with brown shutters. A wide path leads to the front entrance, framed by landscaped gardens and a spacious lawn. The metal roof and symmetrical design contribute to the country charm against a backdrop of blue sky and fluffy clouds.

Farm stay in Thurmont

Private Farmhouse Escape w/ Mountain Views

Welcome to The Farmhouse at Magnolia Meadow Farms! This thoughtfully updated, 5 bedroom, 3.5 bathroom ranch-style home lives on 22 acres of total seclusion. Need a place to stay for a wedding or event, or just need to breathe some fresh air? This stunning home is the perfect, private getaway for you and the whole family while still being conveniently located. You are near: Catoctin Mountain Park Cunningham Falls State Park Downtown Frederick, MD Liberty Mountain Resort Gettysburg, PA & more!

LocationFamilyBathroom

4.96 out of 5 average rating, 169 reviews

Superhost

Home in New Windsor

New Windsor Tranquil Family Getaway

Treat your family to the peace & tranquility of the New Windsor countryside. Our 4 bedroom home is located at the end of a long driveway and offers you the rare experience of getting away from the hubbub of everyday life. At the same time, we're just a 14 min. drive from the quaint town of Westminster where you'll find some great restaurants, McDaniel College, and the Carroll Co. Farm Museum. We're 40 min. from Gettysburg Nat. Park & Catoctin Mountain Park, and just 30 min. from Frederick MD.

ValueLocationHospitality

5.0 out of 5 average rating, 4 reviews

Guest favorite

The living area features a navy blue sofa and a cushioned light-colored loveseat, accented by decorative pillows. A glass coffee table sits atop a patterned area rug. A television is positioned against a wall, with natural light filtering through the window.

Apartment in Westminster

Spacious 1 Bedroom Apt, Main St. Westminster, MD

This spacious 1 bedroom, 1 bath apartment was completely renovated in Dec., 21. Apt easily accommodates 4 guests with the queen bed in the Master & the queen sleeper sofa in the living room. Great Main St. location makes it easy to enjoy shopping, restaurants, Westminster’s Farmers Market, theater, art galleries, and many other specialty boutiques! We are conveniently located and are approximately 35 miles from Baltimore, MD, 35 miles from York, PA & are mere minutes from McDaniel College.

LocationFamilyKitchen

4.86 out of 5 average rating, 71 reviews

Top guest favorite

A comfortable seating area is highlighted by a green sofa and armchair, complemented by a modern floor lamp. A glass coffee table sits atop a light area rug, while a dining table with four chairs is positioned nearby, offering a cozy space for meals.

Apartment in Westminster

The Ivy Loft in Westminster

The Ivy Loft is a beautiful, serene one bedroom loft with private garage entrance. This modern suite is nestled within Westminster, a town rich in history. It is minutes from shopping, historic landmarks, Baugher's PYO farm and orchards and just miles from America's 9th ranked winery. Amenities include a full kitchen, smart tv, WiFi and in-unit laundry. Perfect for R&R, we have included life's little pleasures such as a Nespresso machine, towel warmer and mini library to enhance your stay.

FamilyLocationView

4.99 out of 5 average rating, 102 reviews

Top guest favorite

A stone rancher is shown with a neatly manicured lawn and landscaping. The covered front porch displays decorative railings and a light fixture. Windows allow natural light into the home. A macadam driveway leads to a two-car garage on the right side.

Home in Keymar

Keymar Cottage

Stay in this stone rancher in beautiful rural Frederick County half an hour from historic Gettysburg and Frederick. The property is surrounded by fields on three sides with a great view of the mountains (unless the corn is too tall). Watch the sunrise from the front porch and sit on the back patio to watch the sunset. There is a two-car garage and a macadam driveway for parking. The six-tenths acre property includes a nice grassy lawn, trees and shrubbery and a picnic table on the patio.

ValueFamilyAccess

4.96 out of 5 average rating, 69 reviews

Guest favorite

Farm stay in Woodsboro

Farm Retreat- Sauna, Hot Tub, Cold Plunge, Trails

Welcome to our 210 acre farm retreat, featuring a beautifully renovated farmhouse from the 1800s. With 4 spacious bedrooms and 2 baths, it's perfect for family gatherings and wellness retreats. Enjoy a 4-person hot tub, sauna, and cold plunge for relaxation. Explore scenic trails ideal for hiking and biking amidst stunning landscapes. Experience farm education and immerse yourself in nature’s tranquility. This is the perfect setting for unforgettable memories. Book your escape today!

LocationFamilyGetting around

5.0 out of 5 average rating, 7 reviews

Guest favorite

The historic stone house features a large front porch with a railing and several steps leading to the entrance. Its facade includes multiple windows framed by red shutters, with a modern addition visible on one side. Lush green grass surrounds the house, adding to the rural setting.

Farm stay in Mount Airy

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.

FamilyLocationIndoor spaces

4.98 out of 5 average rating, 123 reviews

Top guest favorite

A charming white farmhouse is set against a backdrop of rolling hills, with a vibrant row of sunflowers blooming in the foreground. The open pasture offers a serene landscape, enhanced by the warm light of the setting sun casting a gentle glow.

Farm stay in Mount Airy

Sunsets from a Haven on a Hill

Come rest & relax in the high hill country of Mount Airy, MD. Find an oasis of beautiful views, rolling hills, open skies, and pastureland. This three-story farmhouse sits on one of the highest points in Mount Airy, MD with views of both the sunrise and the sunset. With an open kitchen plan, large family room, and beds to sleep 9, it’s a perfect place to gather family together for the holidays. Unwind, unplug, and connect with your loved ones in this beautiful farm setting.

FamilyLocationAccuracy

4.98 out of 5 average rating, 110 reviews

Top guest favorite

A cozy living area features a yellow sectional sofa adorned with blue and patterned pillows. A glass coffee table with a dark wooden base sits in front. Two framed bird prints hang on the wall above the sofa, while a floor lamp and a decorative mirror enhance the space.

Apartment in Union Bridge

Luxury, Charm and Privacy in Spacious Apartment

This light and airy, basement walkout apartment is located off the beaten path on a beautiful country acre. This airy space is filled with character and charm and is fully equipped. The apartment is perfect for couples, solo adventurers, and business travelers. Located 7 miles from McDaniel College and Westminster, 20 miles from Gettysburg, and 23 miles from Frederick, it's a great location for dining, exploring, shopping and enjoying all the college has to offer.

ValueFamilyBreakfast

5.0 out of 5 average rating, 227 reviews

Guest favorite

Home in Westminster

Charlie's Country Cottage at Destiny Farm

Relax with the whole family at this peaceful place to stay. Family Reunions, Wedding guests, Friend Reunion are Welcome. Handicapped Accessible!!! Located on our family homestead of 40 acres. Enjoy the relaxing surroundings of the farm .The farm is home Rescue Horses, Miniature Goats, Chickens and Ducks and even The Three Amigo's (aka Peacocks) With a fire pit, grill and outdoor space.

FamilyLocationGetting around

4.95 out of 5 average rating, 83 reviews