Vacation rentals in Upperco

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Top-rated vacation rentals in Upperco

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Guest favorite

Apartment in Sykesville

4.96 out of 5 average rating, 129 reviews

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

Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

Jul 18 – 25

G$19,767 GYD per night

Guest favorite

Apartment in Monkton

4.94 out of 5 average rating, 137 reviews

Apartment in the 1858 Monkton Hotel!

Love the outdoors? Love to fish, hike, bike, kayak? All of the above? The Monkton Hotel is a registered landmark that sits on the NCR trail, which runs along the Gunpowder River, home for some of the best trout fly fishing in the country. This fully renovated apartment, themed the "Fisherman's Lodge", is on the second floor and has the latest amenities. Nothing in the area matches the charm, convenience and history. A yoga studio, bike and tube rental and great cafe are all in the same building.

Dec 3 – 10

G$31,513 GYD per night

Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 251 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across 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. Amazing place to unwind, de-stress & get away. 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.

Sep 4 – 11

G$23,691 GYD per night

Guest favorite

Guesthouse in Westminster

4.86 out of 5 average rating, 274 reviews

The Pig Shed Writer’s Retreat at Barter Lady Farm

Newly renovated with all new bathroom! The Pig Shed is an idyllic setting, close to Gettysburg and McDaniel College. Dogs under 50lbs welcome for Additional Fee, see House Manual for rules/fees for dogs. A unique retreat, fantastic for exploring local sites and nature watching. The studio features a queen sized bed, a full size futon, 3/4 bath, microwave, air fryer, hot plate, gas grill, incredible views and lots of quiet, access to a pond, hiking trails, a fire pit, and can visit the chickens.

May 6 – 13

G$21,433 GYD per night

Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 110 reviews

Scenic, private 2 room-guest suite, near Bel Air

Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.

Feb 13 – 20

G$21,368 GYD per night

Guest favorite

Guesthouse in Owings Mills

4.97 out of 5 average rating, 116 reviews

Shamrock cabin with hot tub, large yard

Please no cats! We are allergic. Backyard tiny house/guest house fits 2 adults comfortably. Equipped with small kitchenette, queen bed, and private bathroom. Kitchenette equipped with mini fridge, toaster oven, microwave, Keurig coffee machine, and silverware/dishware. Snacks/breakfast items and assorted k-cups provided. Dog friendly with spacious enclosed back yard containing private hot tub, small above ground pool, propane grill, fire pit, and badminton net. Includes Wi-Fi & TV with roku.

May 26 – Jun 2

G$19,143 GYD per night

Guest favorite

Home in Railroad

5.0 out of 5 average rating, 181 reviews

The Creek House - A Restored Historic Cottage

A hidden gem, right in the heart of Historic Railroad, Pennsylvania. Newly restored from ground up, The Creek House is situated on the Northern Central Railway Trail - perfect for hiking or cycling. With the occasional passing of the Northern Central Railway tourist train, guests have the opportunity to wave to riders and experience life of a different era and pace. A perfect getaway for family and friends with two bedrooms, one bathroom, a cozy living room and a kitchen with creek views.

Sep 11 – 18

G$60,673 GYD per night

Guest favorite

Cottage in Manchester

4.94 out of 5 average rating, 143 reviews

Magnificent Acres farm, a jewel of ecotourism

Magnificent Acres is a unique jewel of ecotourism segment! Whether you want to spend an unforgettable weekend with your family, have a romantic trip with your significant other or have a great time with your friends, birthday party, wedding you have come to the right place! The unique location allows you to enjoy not only the amenities we offer our guests, but also great number of attractions in the immediate surroundings, which you can reach on foot, by bike, by car and even on horseback!

Jul 22 – 29

G$21,031 GYD per night

Guest favorite

Guest suite in Monkton

4.96 out of 5 average rating, 137 reviews

Private Garden Apartment in Historic District

Our 1919 charming home, surrounded by 50 acres of preserved land, is in an historic district and a stone's throw from the NCR hike/bike trail. We have tubes to float down the Gunpowder River which winds around our property and is accessible by foot. The bike path is lovely! Inverness Brewery is located 5 minutes away, Starbright farm is a glorious lavender farm 15 minutes north, Boordy Vineyards, a family run winery, is 20 minutes east, and Ladew Toipiary Gardens is another gem to behold!

Aug 16 – 23

G$19,099 GYD per night

Guest favorite

Cabin in New Oxford

4.9 out of 5 average rating, 598 reviews

Conewago Cabin - Near Gettysburg!

Rustic, cozy one-room apartment down a long lane on the Conewago river. The apartment is attached to the house but has its own entrance without going through the main house. Private bathroom and shower included. PLEASE NOTE: There are several steps in the cabin going down into the kitchen, up into the living room, and down into the bedroom nook. The floor of the bathroom is not completely even. This cabin may not be suitable for senior citizens or those who have problems with mobility.

Jan 23 – 30

G$14,335 GYD per night

Guest favorite

Guesthouse in Smithsburg

4.97 out of 5 average rating, 641 reviews

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota guesthouse is the perfect get away to explore nature or your artistic leanings. The house is full of original artwork, hand-crafted details, and books on art and architecture. Wander the grounds and find sculpture, ponds, and trails through the woods. Want to hike the entire 40-mile length of Maryland on the Appalachian Trail? Start and end at the Jewel Vinsota and we can drop you off and pick you up.

Jan 17 – 24

G$19,311 GYD per night

Guest favorite

Apartment in Sykesville

4.97 out of 5 average rating, 278 reviews

In the Heart of Sykesville! 2 Bedroom Suite

Located in the heart of Sykesville, Linden, a two bedroom basement suite, welcomes you to relax and rewind! We have designed our space to feel like your home away from home.The kitchenette includes a full refrigerator and numerous utensils for meal prep. Enjoy a bonfire, walk down to the Splashpark to cool off, watch deer graze from the private deck, or stroll down to Main St. to dine, shop, and explore our very cool town! Your can literally give your car a rest!

Aug 27 – Sep 3

G$19,250 GYD per night