Pet-friendly holiday rentals in Hagerstown

Historic Scrabble, Shepherdstown

The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Mountain Church Cottage

Mountain Church Cottage offers a great stay in the hills of Middletown, Maryland. Activities nearby include access to the Appalachian Trail. The roads are a perfect challenge for the serious cyclist and runner, but it’s just a 15 minute drive to the flat terrain of the C&O Canal bike path. For kayakers, Potomac River access is in Harpers Ferry, West Virginia. It's just a short drive to Antietam National Battlefield. And for those who enjoy a glass, there are a number of wineries in the region.

The 1780 Cabin on Main

A charming cabin built circa 1780 situated right on Main Street, just steps from Pubs and Restaurants and easy walking distance to historic Mercersburg Academy. There is a separate sleeping area upstairs with a queen-size memory foam bed. The lower level features a foldout couch and air mattress for additional guests, as well as a 55" TV and a wet bar and bathroom. Visitors have universally enjoyed the cabin's cozy feel. While there is no yard available, the town is great for walking dogs.

Pond Hill Guesthouse- 2 Bedroom w/Hot Tub & WiFi!!

Reserve two get the third (Sun-Thur) night free! Set among the rolling hills near Berkeley Springs, WV, Pond Hill Guesthouse has everything you'll need. Perfect for stargazing! This guesthouse has a private drive and plenty of privacy. Relax in the hot tub or by a fire and enjoy the stars. Lots of room for couples or small families. WiFi provided. This beautiful guesthouse is owned, and hosted a by local superhost, Doug. Pond Hill is great place to enjoy a piece of West Virginia Heaven!

Antietam Toll House~an historic waterfront cabin

The Antietam Toll House (@antietamtollhouse) is a renovated historic property circa 1800. Sitting on the bank-head of the Antietam stream, this cabin has it's own private fishing hole. Secluded, yet close to amenities and attractions, this property is the perfect place for an artist retreat, respite from the city or a base from which to explore local gems of the area. Wineries, Appalachian Trail, Antietam, Gettysburg battlefields, Ski Liberty, Catoctin , Cunningham Falls and more nearby.

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Darling Duplex

*NO cleaning fees in 2025!* Hands down BEST Value in Hagerstown and Surrounding areas Perks include: •Pet friendly •Baby friendly •Entire private home •Central HVAC (dual units) •Walk-in shower •Fenced-in backyard •Full size washer and dryer (with essentials!) •Dishwasher/Garbage disposal •Piano •2 bathrooms and 6 beds • and so much more! Comfy 100 year old duplex minutes away from downtown. Remodeled kitchen and posh upstairs bath. A short walk to the beautiful Hagerstown city park.

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!

Hummingbirds Hideaway Treehouse

Come experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun our little slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please Please Please message us prior to booking

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.

Steps to Winery and Battlefield – 1 Acre Retreat

Unwind at this breathtaking 1-acre hilltop retreat overlooking Antietam Battlefield and lush vineyards. Perfect for a romantic escape or family getaway, our newly remodeled home offers stunning views from the deck, cozy interiors, and easy access to Antietam Creek Vineyards—just a short walk away. Explore nearby trails, relax by the outdoor fire pit under the stars, and enjoy the peaceful setting while experiencing all the comforts of home.

Waterfront Cabin on the Potomac River w/ Hot tub

Our Cabin is located right on the Potomac River. Walk right down and sit right in it. Sleeps 5 people. It has2 bedrooms & 2 balconies facing the water & brings such peace and serenity. Read a book? Take a nap? Go Fishing? At this location, it's the perfect depth to swim, float, kayak, wade fish & more. Also facing the River is a private Hot tub Outdoor Pavillion w/ Gas Grill, Fridge, Sink, Seating, Fire pit, & more.