Holiday rentals in Upperco

* Gorgeous House w/ Luxury, Charm, & Comfort *

Imagine having your entire family or friends together all under the same roof enjoying a beautifully decorated, renovated house with loads of amenities. Well, imagine no more!!!! This home has it all – 4 beds (3 king / 1 queen) with plush mattresses & high end bedding & 2 baths, 3 smart TVs, washer/dryer closet, open living space w/ 20 ft ceilings leading to farmhouse style kitchen full of functionality & style, and awesome deck w/ sectional couch, mounted TV, montrous picnic table, & 2 heaters.

Location · Family · Hospitality

Top guest favourite

Guest favourite

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!

Location · Family · Amenities

Top guest favourite

Guest favourite

Stylish Modern Basement Suite w/ Private Entrance

Experience total independence in this bright, spacious, and fully renovated walk-out suite. Whether you're visiting for a local event or need a quiet professional home base, this suite is designed for ultimate comfort while you have your own self contained apartment, please note that we live on the main floor above. You may occasionally hear the quiet "hum of the home" during the day, but we are committed to ensuring you have a five-star, peaceful experience. Queen Bed + Sofa Bed | Sleeps 3

Location · Family · Check-in

Triple F Farm. A Country Retreat

A Unique Farm Venue. 35 miles to Baltimore & 52 miles to DC. Perfect for a weekend getaway. Many nearby wineries, hiking, historic towns, local festivals, and Gettysburg . Minutes to multiple wedding venues. Explore or just relax by the pond, the barn side fire pit, and sip wine in the converted historic barn/stables. Unwind the day away in a hammock under a tree covered canopy reading your favorite book. Walk the properties farm trails to a perfect Sunset over looking the countryside

Value · Family · View

Pickleball, Blackstone & Pond: 2.5 hrs from DC

Welcome to the spacious 5BR 2.5BA farmhouse on a secluded 75-acre property near Manchester, MD, in scenic Carroll County. It promises a relaxing retreat near the state line, exciting local attractions, and natural landmarks. The unique design, beautiful surroundings, and a rich amenity list will leave you in awe. ✔ 5 Comfortable BRs ✔ Living & Sitting Rooms ✔ Full Kitchen ✔ Screened-In Porch ✔ Yard (Pickleball Court, Pond, BBQ, Fire Pit...) ✔ Smart TVs ✔ Wi-Fi ✔ Parking Learn more below!

Location · Family · Decor

Top guest favourite

Guest favourite

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.

Family · Location · Wifi

Top guest favourite

Guest favourite

A-Frame At Oak Hills: Creekside + Hot Tub + Sauna.

This one-of-a-kind A-Frame by Zook Cabins, built into the mountainside, is the perfect place to unwind. Relax in your private outdoor SAUNA or soak in the in-ground HOT TUB surrounded by forest views and the sound of the trickling creek! Enjoy peaceful mornings among the treetrops on the deck, then settle inside on the oversized plush couches! With two beautiful king bedrooms you'll have all the comforts you need for a memorable getaway. Book your stay at Oak Hills today- you deserve it!

Family · Value · Hot tub

Cozy Suite/2 Large Bedroom 1 Full Bath/5ppl/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.

Family · Location · Long stay

Cozy Farm Cottage

Come relax at our peaceful farm, nestled in the heart of horse country! We are close to Towson, Hunt Valley, the NCR trail, and 695. Our chickens, golden retriever, and cats are waiting to meet you! Come enjoy the fresh air, sunsets, and the outdoors! You can explore the farm grounds, including a pond full of bass you can fish (catch and release), streams, and woods to explore. We even have a large field we turned into an unofficial soccer field!

Family · Location · View

Cozy up in the restored 1820s Miller's House!

The Miller's House is a quaint and beautiful, newly restored two-bedroom house that sits on a small river and is also a national historic landmark. The house has been painstakingly restored recently, with modern amenities you'd expect such as all-new appliances and high speed WiFi. Proximity to the Gunpowder Falls for fishing or tubing, the NCR trail (less than .2 mile away) and endless roads to bike on make it a great escape.

Family · Location · Comfort

Top guest favourite

Guest favourite

The Master's Suite · King Suite, 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

Family · Value · Kitchen

Top guest favourite

Guest favourite

NEW spacious stylish and FUN entire home!

** New ** Welcome to the Reisterstown Retreat. A spacious, stylish, & sophisticated home with beautiful finishes and endless amenities. Plenty of space to spread out inside or outside. Fun games, plus a massive outdoor lot with serene landscape. We welcome short or long stays, couples, families and groups. We are dedicated to an amazing guest experience. Message me today about your stay.

Family · Location · Bathroom