Holiday rentals in Upperco

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Top-rated holiday rentals in Upperco

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

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Top guest favourite

The historic brick building features a classic architectural style, with several evenly spaced windows and two prominent blue doors at the entrance. A pathway leads to the doorway, with a flag displayed on the left side. Lush greenery surrounds the property, creating a serene outdoor setting.

Flat in Monkton

4.95 out of 5 average rating, 185 reviews

The Fisherman's Lodge at 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. An electric bike store, tube rental and great cafe are all in the same building.

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Top guest favourite

A charming cabin is set beside a serene pond, featuring a colorful fountain that lights up the water. Soft string lights illuminate the outdoor space, creating a cozy atmosphere amidst the surrounding trees.

Cabin in Wrightsville

4.98 out of 5 average rating, 239 reviews

The Roundtop Chalet (romantic couples retreat)

Indulge in a getaway to our charming cabin, the perfect retreat for all your special celebrations - be it anniversaries, birthdays, or simply a much-needed escape from routine. Perfectly designed for romantic getaways, this cabin seamlessly blends rustic charm with modern comforts. Savour the warmth of a cozy fireplace, unwinding in a hot tub,and indulge with unlimited lattes, crafted by our Breville Touch Espresso Machine. Embrace serenity at its finest and make memories that will last forever

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Top guest favourite

A warm living room is highlighted by wooden beams overhead and natural light streaming through French doors. A cozy sofa is positioned beside a rustic coffee table adorned with decorative items. Soft greenery is placed on surfaces, enhancing a serene environment.

Cabin in Railroad

5 out of 5 average rating, 118 reviews

The Creek House: Waterfront with Hot Tub & E-bikes

Featured on Magnolia Network’s “In with the Old” Season 1, Ep. 2 (HBO Max), The Creek House is a hidden gem in the heart of Railroad, PA. Nestled between the NCR Rail Trail and two flowing creeks, this location offers both adventure and relaxation at its finest. Explore the over 40 mile bike trail via E-bike, soak in the hot tub while you enjoy sounds of the creek, or ride the train right through the front yard! This idyllic cabin features professionally designed spaces that are sure to please!

LocationFamilyTV

Top guest favourite

Place to stay in Shippensburg

5 out of 5 average rating, 467 reviews

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ

Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures. *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

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Guest favourite

The exterior of the cottage is framed by lush greenery and features a welcoming white facade with green trim. Soft outdoor lighting illuminates the entrance, while flower bushes add a touch of nature to the charming setting.

Cottage in Reisterstown

4.92 out of 5 average rating, 100 reviews

Unique Tiny House Getaway on An Historic Farm

The Hen House Cottage is a tiny house located on an historic farm in central Maryland. It is surrounded by six acres of beautiful pasture and gardens. The Cottage has great light throughout the day, a well-equipped kitchen (microwave, oven, coffee grinder, coffee maker, large fridge, etc.), a full bathroom (with shower), a sleeping area with a comfortable queen-sized bed, dedicated (free) wi-fi, a smart TV, blue tooth sound system, and an eclectic library. Linens and towels are provided.

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Top guest favourite

A wooden gate adorned with longhorn decorations frames a vast green field, leading towards rolling hills in the distance. The sky above is clear with a few fluffy clouds, enhancing the serene rural landscape.

Farm stay in New Park

4.96 out of 5 average rating, 163 reviews

Dusty Roads Ranch

Relax, rejuvenate and enjoy the scenery. This is a impeccably maintained private property in southern York county, Pennsylvania. Located in a convenient location from York, Lancaster, and Baltimore. Close by to county parks, breweries/wineries, and farms. Enjoy your sunset fireside on our lush horse farm or take a walk through our trailed woods. Massage therapy available upon request. We recommed 4-wheel drive for winter bookings. There is a camera that faces the driveway as you pull in.

LocationFamilyDecor

Top guest favourite

The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.

Home in Myersville

4.98 out of 5 average rating, 302 reviews

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!

LocationFamilyWalkability

Top guest favourite

The exterior view of the log cabin is set amidst a lush, wooded landscape. A stone path leads to the cabin, which features a spacious outdoor deck adorned with plants and seating. The serene ambiance of the surrounding nature invites relaxation.

Place to stay in Airville

4.98 out of 5 average rating, 268 reviews

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

ValueFamilyWifi

Superhost

An inviting swimming pool is surrounded by a white picket fence, with clear blue water reflecting the sky. Leafless trees are visible in the background, providing a serene natural setting. The pool area is spacious, perfect for relaxation and enjoyment.

Guest suite in Finksburg

4.9 out of 5 average rating, 10 reviews

Cozy Suite/2 Large Bedroom 1 Full Bath/4ppl/pets

Welcome to your private getaway in Finksburg, MD just minutes from Baltimore! This serene 2-bedroom, 1 full bath suite features a private pool, firepit, and river access for peaceful mornings and scenic walks. Enjoy a fully stocked kitchen, comfortable living areas, and a dedicated workspace—perfect for remote work. Home is Pet-friendly! Whether you're looking to relax, explore nature, or work in a quiet setting, this home offers the perfect balance of comfort and tranquility.

LocationFamilyQuiet

Guest favourite

A polycarbonate dome is nestled among trees, illuminated in soft green light. The spacious deck includes a seating area and a small table. A colorful sunset is visible in the background, casting a warm glow over the Appalachian landscape.

Dome in Shippensburg

4.91 out of 5 average rating, 161 reviews

Spectacular views, intimate dome

Come experience a truly one of a kind polycarbonate dome tucked away in the Appalachian mountains! Situated on the mountainside overlooking the scenic Cumberland valley. Complete privacy, stunning sunsets, and amazing amenities! The dome is climate controlled. The spacious deck is equipped with a meticulously maintained hot tub, and a blackstone griddle. This offers the unique opportunity to be immersed in nature, yet enjoy numerous amenities and comfort.

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Top guest favourite

A bright living area is presented, featuring a grey sofa adjacent to a rich brown ottoman. A small kitchenette is visible with a stove and refrigerator, complemented by open shelving. Natural light enters through a skylight and windows adorned with blinds. A doorway leads to a bathroom.

Guest house in Owings Mills

4.96 out of 5 average rating, 141 reviews

The Garden Studio

Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

LocationFamilyAmenities

Top guest favourite

A spacious master suite features a king-size bed with a decorative canopy, flanked by nightstands. Two armchairs provide seating, and a woven area rug adds warmth. A mural depicting nature adorns the wall, while large windows allow natural light. An accessible doorway leads to the bathroom.

Farm stay in Cockeysville

4.95 out of 5 average rating, 131 reviews

Master's Suite · 1920s Tudor Estate, Hunt Valley

A king-size suite in the gatehouse of a 1920s English Tudor estate, deep in Maryland’s horse country — peaceful and private, but an easy drive from the city. • King bed, vaulted ceilings, hand-painted mural • Carrara marble bath with a clawfoot soaking tub • Private sun porch over open farmland • Pool, tennis & miles of farmland to wander • Hunt Valley 10 min · Towson 15 · Baltimore 25 · Ellicott City/Columbia ~35

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