
Pet-friendly holiday rentals in Cumberland
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Top-rated pet-friendly home rentals in Cumberland
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

Mountain View Acres Getaway
Enjoy nature in a beautiful peaceful setting with 100 acres of privately owned property. Breathtaking panoramic views spanning 45 miles in a tranquil natural spot with hiking trails throughout. Handicap accessible. Within a short drive of 2 major ski resorts, the Flight 93 Memorial and 2 wineries. Several restaurants and a brewery also within a 15 minute drive. The property includes an outside firepit that is a favorite place for guests to relax and enjoy the breathtaking views of the mountains.

Romantic, hot tub, king bed, private, pet-friendly
Uniquely spacious escape for couple, small family, or solo traveler. 30-foot great room, wall of windows facing large deck, oak floors NEW HOT TUB in private setting. King bedroom with en suite bath; loft has twin bed. Modern with touches of mcm & vintage create a magical retreat for you in the treetops. On 2 acres. Hike to top of Cacapon Mountain from back door. Quick drive (3 mins) to private community pool/hot tub/tot pool (summer only). 10 minutes to Berkeley Springs with Roman Baths, arts s

Rooster Wrest in the Trees
Sweet 2 bedroom bungalow. Cozy, ideal for lovers, or a quiet beautiful somewhat rustic retreat environment. Rooster has 1 full bath. Living room with satellite TV, Netflix; wood burning stove fireplace, wood provided, fully equipped kitchen, dining table, linens and starter paper goods furnished. Large deck and screen porch looking out on Cacapon Mountain. Hot tub off master bedroom deck in trees, feels like a tree house. Many mornings mist rises up from river, half mile away as crow flies.

Log Cabin
The primary bedroom features a queen-size bed, while the secondary bedroom includes a full-size bed. The living area is equipped with a sleeper sofa for extra sleeping space, and the loft adds two twin mattresses for additional accommodations, ideal for kids. The cabin’s kitchen is equipped with everything you need, including an oven and refrigerator and microwave. Whether you're enjoying time indoors or exploring the outdoors, this cabin offers the perfect balance of comfort and adventure.

Grouseland's Pondside Vacation Cottage
Set about a quarter mile of the road, our pet friendly solar powered vacation cottage is a perfect getaway for anyone trying to spend some alone time with nature! Guests have complete privacy inside the cottage with a full kitchen, two TV's, Wi-Fi, and a mini split system for heating and cooling. As well as exclusive access to the hot tub, fire pit and pond outside! We also have various shared hiking trails through the woods surrounding the cottage for campers and cottage guests to enjoy!

Secluded 2 BR cabin in the forest awaits you!
Have you ever wanted to run away and live in the forest? Come and be enchanted by the sights and sounds of nature. Wake to the birds singing and deer wandering through the yard. At night, watch the stars in all of their brilliance! The cabin features a wall of windows giving you the true feeling of being in the forest! Cozy, yet spacious with 2 beds and baths, keypad entry, a front porch and large back deck, we have everything you need for a relaxing fun vacay with " Mother Nature".

Mountain Oasis Cottage
Our Cottage is located at the base of a mountain on a dead end road it is very tranquil with a lot of deer that feed in the back yard. We are 15 minutes from the city of Cumberland Maryland where the “Western Maryland Bike Trail” is located and 30 minutes from historic Bedford, PA. The Cottage has two bedrooms that each feature queen size beds, one living room with a pull out queen size sofa bed, and a sitting room with a full size pull out sofa bed. Heated and cooled w/ mini splits.

Tall Spruce Farmstead in South Central PA
A quaint old farmhouse in the hills of Southern Fulton County, PA. Only 5 miles from Hancock, MD and 12 miles from Berkeley Springs, WV. There is a small deck, ideal for watching the deer and other wildlife. Close to the C&O Canal Rail Trail where you can enjoy walking or biking. Only 30 minutes from White Tail Ski Resort, Ft. Frederick, Rocky Gap Casino, Hagerstown and Cumberland. Come and enjoy the peace and quiet of country living in the newly renovated Tall Spruce Farmstead.

The GreyLoo
Cozy, clean and friendly downstairs apartment. Stocked with all the things you need for a short stay as well as the long haul. Close to the Great Allegheny Passage, Main Street Frostburg, Frostburg State University, the Frostburg Pool, and many other locations. Located 33 mi from Wisp Resort/Deep Creek Lake and 18 mi from Rocky Gap Casino Resort. Just a few miles from I68. Enjoy this cozy place and bring your furry friends. Lots of nearby hiking, biking, and outdoor adventures.

Easygoing
Tired of the chaos and need a place to unwind and relax ? We have the perfect place for you! A quaint, quiet cabin to let you clear your mind and spirit after a day of hiking, biking or kayaking since we are only five miles from both the Paw Paw tunnel and the Potomac river. The cabin is equipped with electric, heating, stove top, microwave, large deck, hammock chairs, horseshoe pit, 2 double size futons with room to spare, indoor toilet but BEST of all is showering outside!

Cumberland Street House -GAP trail perfection!
Cyclists dream come true! The Cumberland Street House is less than a quarter mile from the Great Allegheny Passage - perfect for large groups! All of Cumberland's charm within walking distance. Downtown restaurants and shops only a half a mile away. Historic district, Cumberland Theatre & Western Maryland Scenic Railroad are just around the corner. Bikes can easily be stowed in the back room off the kitchen. Easy parking, and fenced-in yard is great for kids and pooches.

The River House
A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.
Popular amenities for Cumberland pet-friendly home rentals
Pet-friendly house rentals

Everlong ~ Pet-friendly Retreat on 2 Wooded Acres

Little Red Schoolhouse in Cross Junction

Lomalinda quiet retreat + walk to Berkeley Springs

Hot tub/Pool Table/Wi-Fi/Gym/Views/Pets/Tanning

Highland House*Dog Friendly* Garage* sleeps 7

Arden House, Inwood WV

Newly Renovated 2 Bed/2 Bath in Deep Creek

Our House on the GAP Bike Trail
Pet-friendly home rentals with a pool

Fall Special - Book 2 Nights Get a 3rd FREE

Ski-in and Ski-out Condo at Seven Springs Resort

The Mountain House

Seven Springs Sunridge year-round mountain chalet!

Seven springs * Swiss Mt. GOLF&POOL! *free shuttle

Five Oaks Cabin at The Woods Resort

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Starcatcher Chalet, The Woods Resort
Private, pet-friendly home rentals

Spacious Parkside Oasis!

Historic Eden Ranch, built 1837

The Hidden Tree

The Crick House

Activity-Packed - Pickleball - Hoops - Game Room

Mountain View Paradise

Mountain Maryland Getaway

Pond Hill Guesthouse- 2 Bedroom w/Hot Tub & WiFi!!
When is the best time to visit Cumberland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $169 AUD | $183 AUD | $174 AUD | $183 AUD | $183 AUD | $191 AUD | $198 AUD | $191 AUD | $197 AUD | $186 AUD | $191 AUD | $181 AUD |
| Avg. temp | -3°C | -2°C | 2°C | 8°C | 13°C | 16°C | 18°C | 18°C | 15°C | 9°C | 4°C | -1°C |
Quick stats about holiday rentals that are pet-friendly in Cumberland

Total holiday rentals
Explore 20 holiday rentals in Cumberland

Nightly prices starting at
Cumberland holiday rentals start at $122 AUD per night before taxes and fees

Verified guest reviews
Over 1,210 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Cumberland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Cumberland rentals

4.7 Average rating
Cumberland stays receive an average rating of 4.7 out of 5 from guests
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- Fallingwater
- Seven Springs Mountain Resort
- Wisp Resort
- Whitetail Resort
- Ohiopyle State Park
- Berkeley Springs State Park
- Cacapon Resort State Park
- Shawnee State Park
- Blue Knob All Seasons Resort
- Laurel Mountain Ski Resort
- Lodestone Golf Course
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- West Whitehill Winery