Pet-friendly holiday rentals in Maryland

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Ella Bella Chalet: Hot Tub, Stunning Views, Wi-Fi

Welcome to Ella Bella Chalet! Escape to our modern, yet cozy cabin boasting panoramic breathtaking views and an array of upscale amenities. Relax in the hot tub under starlit skies or gather around the fire pit for cozy evenings. Located near Wisp Ski Resort, golf courses, and endless lake activities, including boating, fishing, tubing and kayaking. Explore nearby hiking trails and attractions like Swallow Falls State Park, Adventure Sports Center International, zip lining, biking, and more.

Jewel Vinsota Artist's Guesthouse

Less than a mile from the Appalachian Trail, the dog-friendly Jewel Vinsota Artist's 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.

Red Point Lighthouse

Recently updated unique lighthouse replica on the northern tip of the Chesapeake Bay. 4 bedrooms & 2 sleeping nooks, the house can sleep up to 14 in 6 beds (3 kings, 1 queen, 2 doubles) and one queen sofa bed. 4 bathrooms - 2 ensuite. Two living rooms, fully equipped kitchen, family style dining area. Wrap around decks on multiple floors. Firepit, Adirondack seating, lawn games for enjoying 1.5 acres with water views. Community sandy beach across the street for strolling & relaxing.

Spruce Run Cottage, Farm stay on Catoctin Mountain

The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

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!

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.