
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.

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.

Southern Charm Getaway in Romney, WV - Sleeps 6
Beautiful, comfortable & clean family friendly getaway in West Virginia's first town! Located in the center of town and walking distance to restaurants, public library, boutiques, shopping, historical sites, Civil War trenches, public pool and Visitor's Center. Just a few short miles to The Potomac Eagle Scenic Excursion Train & to the South Branch of the Potomac River for fishing and canoeing. You will find many day trip activities within an hours' distance, including Skiing, hiking &biking

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.

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing
Mountain home: like in the movies, on 50 acres. Includes soaring mountain views, swimming holes, hiking trails, ATV trails, fishing creek, mini white sand beach, hot tub in a cave, huge boulder rustic fire pits, cave, lake, cabanas, all in a heavy forest exclusively for guests. Private: you cannot see another house from the front porch or back decks and it has thick woods all around. At the top of the property are soaring views with 3 miles of visibility. No need to go to the national park.

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!

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.

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.

Our House on the GAP Bike Trail
Our house in Meyersdale is a single-family house just a block from the GAP bike trail on a quiet street and walking distance to the middle of town. The house is ideal for travelers riding the GAP, skiers visiting the slopes nearby, or those looking for some quiet time in the country. Ideal for individuals or small families. (Pls note: Trains come through town and the whistles can be heard during the day or night. There is also a fire whistle to alert volunteers to emergencies.)

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.

Piney Mtn House
Become part of Mountain Maryland discovering your next cozy escape in the newly renovated modern bungalow. The Appalachian range will tuck you in the small town of Eckhart, closely boarding Frostburg, with all its unique attractions, entertainment, hiking trails, and state parks. No body does small town like local Frostburg. And there is no better way to unwind than to make the Piney Mountain House your home away from home.

Creekside Cottage
Our cottage is a private and cozy place to get away and relax. The view from the porch or fire ring area is beautiful and very peaceful. Centrally located in the Laurel Highlands close to 3 ski resorts, GAP trail, 4 State Parks, Falling Water, Flight 93 Memorial, wineries & breweries, wedding venues and more! Somerset County has so many adventures waiting for you!
Popular amenities for Cumberland house rentals
House rentals with a pool

'Little Blue Bungalow' in The Woods-pool access

NEW~Indoor Pool & Hot Tub~Game RM~Near Wisp~Dock!

4BR, 4BA, Amazing Indoor Pool, EV charger, ~10 acr

Spacious & Charming! Large deck+Game shed+Firepit

Magic Mountain Retreat - Mountain View, EV charger

The Stairway to Heaven

Mayapple

5 -Star Luxury Mountain Getaway - Grandview Lodge
Weekly house rentals

Abby's Lookout - Raised Retreat w/Hot Tub & WiFi

Lomalinda quiet retreat + walk to Berkeley Springs

Lake View Loft Lodge on Deep Creek Lake

A-Frame Mountain Retreat

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

+ the Lodge + @ Camp Potomac Peak

Hart's Overlook | HOT TUB, Mtn Views + Pond!

Arden House, Inwood WV
Private house rentals

616 Mountain Suite

Pet-Friendly Farmhouse in Laurel Hill SP & Sauna

Paloma House Retreat

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

The Farmhouse at Poverty Knob

Small, cheerful house!

Oldtown Guesthouse

Mountain Maryland Getaway
When is the best time to visit Cumberland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$25,113 GYD | G$23,020 GYD | G$25,113 GYD | G$25,113 GYD | G$25,950 GYD | G$25,741 GYD | G$27,205 GYD | G$27,205 GYD | G$26,159 GYD | G$25,531 GYD | G$26,159 GYD | G$25,113 GYD |
| 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 G$6,278 GYD 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Cumberland vacation rentals include wi-fi access

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

4.9 Average rating
Cumberland stays are highly rated by guests—averaging 4.9 out of 5!
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