Vacation rentals in Littlestown

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Littlestown

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

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Guest favorite

A modern kitchen featuring sleek black and white cabinetry, stainless steel appliances, and a minimalist design. The space includes a gas stove, a microwave, and a refrigerator. Natural light comes in through a window, illuminating the wood-like flooring and nearby staircase.

Home in Timonium

4.92 out of 5 average rating, 190 reviews

* Lovely Gem w/ Perfect Combo of Flair & Class *

This is our 5th Airbnb in the Towson / Lutherville area. We know how important it is to feel comfortable & relaxed when you arrive back from a long day of work, sightseeing, visiting with family members, playing sports, etc. This inspiration is seen throughout this entire house and you'll find the house to be a place to recharge, relax and enjoy high end amenities to include HDTVs in living and bed rooms, fully stocked kitchen, plush bedding, luxury shower fixtures, and more. You have to see it!

Guest favorite

Cottage in Middletown

4.9 out of 5 average rating, 271 reviews

Charming "Cream of the Crop" Cape ~❤️of Middletown

Cozy cape in the ❤️ of Middletown, MD. Walking distance (1/2 mile)to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife.Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Guest favorite

A welcoming entryway features a covered porch with a classic white column structure. Potted plants are positioned symmetrically on either side of a dark front door, which is framed by a light-colored exterior and shingle accents on the upper portion.

Home in York

4.93 out of 5 average rating, 312 reviews

The Inn- Newly Renovated Designer Furnished

Newly renovated home features all of the modern amenities families enjoy. A large island for entertaining, a dining table seating 8, large living room, a bright sunroom with plenty of seating, as well as a sun porch with a bistro table & chairs, outdoor seating, & 3 spacious bedrooms upstairs each has a queen size bed. The home is a minute's walk from our popular home decor boutique, Gray Apple Market. A 10 minute drive to downtown York & other popular destinations such as the York Fairgrounds.

Guest favorite

An inviting outdoor patio area is outfitted with stylish wooden seating, complemented by plush white cushions. Lush greenery surrounds the space, offering a serene atmosphere. A wooden trellis above provides shade while allowing natural light to filter through.

Home in Bolivar

4.89 out of 5 average rating, 158 reviews

Floating tub, Movie Room, best beds Spring Flowers

Nearby "Snow Riders" snow tubing great right now!! EV enabled, cell tower, 1/4 mile from Washington St and Harpers Ferry restaurants/shopping. “Stunning design, inside and outside”, “Like walking into Architectural Digest”. (Review comments). Spa like master bath w/ floating tub, movie room, garden patio. Families or romantic couple. Fast Mesh WiFi. 85" and 65” Smart TVs, Tempur mattresses. 0.25 mile walk to Washington St. Bring mobile charger 240 plug (most EVs), or rent our charger.

Superhost

A spacious back deck features a wood railing and is surrounded by greenery. Several metal chairs are arranged around a table, providing seating for outdoor dining. Large glass doors reflect sunlight, offering views into the cabin's interior.

Cabin in Keedysville

4.89 out of 5 average rating, 136 reviews

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

MOUNTAIN MAMA VACATION HOMES Imagine soaking up the last rays of sunset with a glass of wine from the back deck of this mountaintop cabin! Or, when the weather cools off, soak in the hot tub before enjoying a roaring fire inside the great room. Blissfully secluded on 3+ acres of private woodland, this cabin will make you never want to leave once you arrive! WiFi is blazing fast at 250 Mbps, so you should have no trouble streaming or video conferencing, in case you need to work remotely.

Top guest favorite

Home in Sabillasville

4.93 out of 5 average rating, 114 reviews

Stoney Spring Overlook

This beautiful mountain farm home has breath taking scenic views of the surrounding Catoctin mountain. There are many nearby outdoor activities, including scenic hikes, mountain biking, Ski Liberty, wineries and the Catoctin zoo. While it is a peaceful get away in the mountains, it is just 30 minutes away from the Frederick, MD and historic Gettysburg, PA. Whether you want to get away from the city or explore more of Maryland, this is the perfect stay for you!

Top guest favorite

Home in New Oxford

4.98 out of 5 average rating, 107 reviews

A Place to make Memories

A premier luxury Homestay. A rustic & contemporary gem with wood ceilings & stone fireplace. Barn and outdoor area for events. Beautiful open kitchen designed like a European bistro with high-end appliances. Outdoor terrace and Firepit for entertaining or relaxing. Spacious, Mod, Cozy and Romantic all in one! Large grand room for gathering. Glamping tent available. 42 beautiful acres with woods, stream, and lots of wildlife. Perfect for dogs

Guest favorite

Guesthouse in Frederick

4.98 out of 5 average rating, 177 reviews

Romantic Getaway - Heated Spa Open Year Round

Enjoy our beautifully decorated four bedroom home, furnished with unparalleled elegance and style. This tranquil guest house is located less than an hour from Washington DC and Baltimore, MD, and a half-hour from Gettysburg and Harper's Ferry and offers luxurious rooms with unparalleled elegance and style. For the ultimate pampered experienced, guests can arrange for in-house spa services such as a full-body therapeutic massage.

Top guest favorite

A quiet garden area features a stone pathway winding through vibrant greenery and blooming plants. The pathway is bordered by large shrubs and trees, creating a serene natural setting. A blue garden sign stands prominently among the foliage, adding a touch of color.

Guesthouse in Owings Mills

4.97 out of 5 average rating, 115 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.

Top guest favorite

A charming multi-story home features a light-colored wooden exterior, complemented by stone pathways and a staircase. Flags adorn the exterior, and a spacious deck area is visible, surrounded by greenery. The building's architectural details showcase a blend of historical and modern design.

Home in Harpers Ferry

4.94 out of 5 average rating, 393 reviews

Gayte House Gay Owned, Liberal Oasis

Cozy and charming 1840's home in the heart of town. Steps from the National Park, feet from the Appalachian Trail. Relax by the fire, on the porch or on the river. We have something for every season and every age. Steve and I have lived here In HF 20 yrs., 13 of those at the Gaytehouse. We live right next door now and Love both our homes. Please, Check out the beautiful and cherished home we offer for your stay.

Guest favorite

Home in Harpers Ferry

4.86 out of 5 average rating, 28 reviews

Harpers Ferry Oasis

Escape to Harpers Ferry at an amazing quiet retreat close to EVERYTHING Harpers Ferry. Rivers, Rafting, Hiking, Touring history Lower Town and Dining. Private back yard with fire pit and patio. Hardwood floors and amazing gourmet kitchen. Fully outfitted. Check in and relax. Just up the road from the ONLY snow tubing in the area. Year round destination! Only 2 minutes from the river and river riders

Guest favorite

Farm stay in Stewartstown

4.98 out of 5 average rating, 124 reviews

Heron's Hollow- The Barn with hot tub!

Escape from the hustle to our renovated historical barn in a quiet, private valley. 3bedroom/1.5bath. There is large patio dedicated to this building, with fire pit, lights, a hot tub and a grill. Check out our two other listings (4 bedroom and 2 bedroom) with excellent ratings! Pets are welcome, for an extra fee! Please message us for rates. wifi cell reception booster we host weddings!