
House vacation rentals in Cumberland
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Top-rated house rentals in Cumberland
Guests agree: these houses are highly rated for location, cleanliness, and more.

The Country Ranch
Nestled in the Laurel Highlands on 3 acres of private ground with surrounding farmland. Peaceful & private, this property offers a large backyard with amazing sunset views & starlit night skies. This vacation home is 3 miles from the Markleton GAP trailhead and 10 miles from Youghiogheny Lake. Other nearby attractions include Mt Davis (the highest point in PA), High Point Lake, Ohiopyle, Falling Water, Kentuck Knob, Seven Springs & Hidden Valley Ski Resorts, and Laurel Hill & Kooser State Parks.

Jacob's Cottage
Free WI-FI now available. Our place is good for couples, solo adventurers, business travelers and families (with kids). The Cottage is a quaint, Cape Cod style house built in 1950. It sits high on a hill in the heart of Maryland's Appalachian Mountains in Allegany County. It is surrounded by views of Wills Mountain and Shrivers Ridge. The Cottage sits amongst a 660 acre family managed forest. Visitors have spotted deer, turkey, rabbits, squirrels, black bear and a multitude of song birds.

Wills Mountain Ranch
Lovely, private home overlooking our beautiful valley with breathtaking views of Wills Mountain. It is the perfect setting for a family retreat/reunion. The ranch house has a red roof in the pictures. My husband & I live in the 3 story. We have a in-ground pool on property (heated from Mid-May to early September), a gas grill, and fire pit on the large scenic patio for your enjoyment. The large windows & patio offer a spectacular view of Wills Mt. The ranch house offers a quiet getaway retreat.

NEW LISTING-"Cumberland Cottage"-charming,quaint
Relax in this charming, renovated rancher in a peaceful setting. Located outside of the city limits but convenient to attractions and dining. This home is comfy with all the amenities you have in your own home. Outside area for your children to play or for you to relax on the back porch. Cumberland is in easy driving distance to PA and WV. Enjoy cooking together and dining or playing games in the dining room, then relaxing in the living area. Renovated but still keeping the charm of a rancher.

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!

Great Location, Spacious, Comfy 2 bdrm 3 bed home
This home is centrally located near all things fun and exciting to do in Cumberland. Situated in a quiet residential neighborhood in the Western Maryland mountains. Minutes from historic downtown, the Potomac River, Rocky Gap State Park, Pennsylvania, the University of Pittsburg Medical Center, the C &O canal and much more. This home features 3 queen beds, 2 bedrooms both with 55" TV's and blackout curtains, a large separate dining room, a spacious kitchen, and living room with a 65" TV.

Country Home Near Main St. & Trail
Welcome to this charming and cozy home sitting at the highest point in Frostburg. Incredible mountain and forest views from the upstairs windows, lots of old house details and including two staircases and a sleeping porch. There are hardwood floors throughout. Lots of space to relax. Two full baths, one with shower and one with tub/shower. Gas range and fully stocked kitchen. Smart TV's in two bedrooms, and in the main living room. Strong Wifi, and a washer and dryer in the basement.

Charming 1907 Home in Historic Downtown Cumberland
This charming 1907 home is located just blocks from the main pedestrian street in Historic Downtown Cumberland and a 10 minute walk from Canal Place, the C&O Canal Great Allegheny bike trails, and the Western Maryland Scenic Railroad. The remodeled interior is equipped with all the modern conveniences, including a large kitchen and bathroom with large tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

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.

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.

Queen City Quarters- cozy, historic, 1920s home
Stay in a quiet setting as you explore Cumberland, MD. Enjoy a day trip on the nearby, scenic, steam train. Bike the Gap and C&O trail, minutes away. Explore the restored historic downtown with shopping and restaurants. This space is not suitable for small children or those with mobility concerns. No large groups or parties. Bedroom doors are louvered doors. See pictures. Research city and area if you are unfamiliar with economic conditions. We have a bike rack for 3 bikes.

Allegany Connection
NOTICE: extra santizing of hand touching areas in place for your protection. This eclectic 2-story duplex, late 18th century structure has both old and new charm. Single BR & bath upstairs; LR and Kit downstairs. Only 1 block from Main St. restaurants & unique shops. All are welcomed. Please bring your own infant bed. Sorry no pets. Free reserved parking for 1 vehicle & fast Wi-Fi. Instant booking is on. ABSOLUTELY NO SMOKING, or any kind is permitted inside our home.
Popular amenities for Cumberland house rentals
House rentals with a pool

Cabin w/King Bed, Hot Tub

House

6BR Luxury Lakeside Escape w/ Indoor Pool

Spacious Lodge Perfect for Year Round Getaway

Magic Mountain Retreat - Mountain View, EV charger

Updated Baths, Wood Fireplace, Hot Tub & Fire Pit

5 -Star Luxury Mountain Getaway - Grandview Lodge

The Dacha. Rebirth sauna experience
Weekly house rentals

CJās Escape Great location & just like home

616 Mountain Suite

Spacious Parkside Oasis!

The Western Maryland Retreat

Paloma House Retreat

The Cumberland Trail House - Near GAP/C&O Canal

Oldtown Guesthouse

Mountain Maryland Getaway
Private house rentals

Riverside Cabin! Riverfront Sauna! Theater Room!

Fern Valley Chalet

Pap's Place

Berkeley Springs Jungle Lodge

Cozy Cottage

The Farmhouse at Poverty Knob

Mountain view Grand 6BR in LaVale |15min Rocky Gap

The Rivers Edge
When is the best time to visit Cumberland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $168Ā CAD | $154Ā CAD | $168Ā CAD | $168Ā CAD | $174Ā CAD | $172Ā CAD | $182Ā CAD | $185Ā CAD | $182Ā CAD | $171Ā CAD | $175Ā CAD | $168Ā CAD |
| 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 house rentals in Cumberland

Total vacation rentals
Explore 50 vacation rentals in Cumberland

Nightly prices starting at
Cumberland vacation rentals start at $42Ā CAD per night before taxes and fees

Verified guest reviews
Over 2,710 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Cumberland vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cumberland rentals

4.9 Average rating
Cumberland stays are highly rated by guestsāaveraging 4.9 out of 5!
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- Fallingwater
- Wisp Resort
- Seven Springs Mountain Resort
- Whitetail Resort
- Ohiopyle State Park
- Cacapon Resort State Park
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