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Cumberland vacation rentals

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Top-rated vacation rentals in Cumberland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Home in Cumberland

4.94 out of 5 average rating, 234 reviews

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.

Home in Springfield

4.98 out of 5 average rating, 126 reviews

Riverside Oasis w/ private estuary & Pup friendly

Otters Way is nestled on 4 sprawling aces; this idyllic retreat boasts a natural estuary pond of the S.B.P. River, providing a serene backdrop for your stay. Our home offers ample space for you to unwind and create lasting memories! Immerse yourself in nature as you gather around the firepit or our expansive back deck, perfect for cozy evenings under a starlit sky. Just 1/4 mile walk to the river! A quiet getaway or adventurous escape, Otters Way is the ideal vacay! Cleaning discount <3 bdrms

Guesthouse in Cumberland

4.96 out of 5 average rating, 127 reviews

No cleaning fees - The Dove’s Nest

The Dove's Nest features a fully equipped chefs kitchen , dishwasher, washer and dryer, plenty of parking and a large private patio with bike parking. Easily accessible from I-68 and ideally located in a comfortable part of town. Less than 1 mile from the University of Pittsburgh Medical Center (UPMC), Allegany College of MD and the Constitution Park. A quick 2 miles to historic downtown Cumberland where the C & O Canal meets the Great Allegheny Passage. Perfect location for hiking and biking.

Bungalow in Great Cacapon

4.9 out of 5 average rating, 512 reviews

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.

Rental unit in Cumberland

4.99 out of 5 average rating, 406 reviews

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

Cottage in Cumberland

4.99 out of 5 average rating, 177 reviews

The Cottage on the Hill

Nestled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in one of your reserved spaces and step down to a unique retreat high above the city to enjoy a vintage cottage with modern amenities. Walk to Historic Cumberland, enjoy local and regional attractions, or stay in and grill, build a fire, or play pool, poker, board or yard games. Well appointed, fully equipped, and with a beautiful view, come relax and enjoy this one of a kind location.

Rental unit in Frostburg

4.89 out of 5 average rating, 154 reviews

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.

Home in Cumberland

4.9 out of 5 average rating, 520 reviews

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.

Cabin in Fort Ashby

4.85 out of 5 average rating, 119 reviews

Hilltop Cabin Retreat - Secluded & cozy - Wi-Fi!

The Sonny Side Hilltop 10-acre Cabin is the perfect secluded getaway to unwind and enjoy nature. Spend quality time with friends/family, explore the outdoors, ATV trails, or hunt with appropriate tags - contact for more details. My father (Sonny) built this cabin in 2004 with his own two hands. It was his primary residence until passing from cancer at my sister's home in Maryland in 2019. We would like to share this lovely cabin with guests to help offset costs. Please Enjoy!

Home in Frostburg

4.85 out of 5 average rating, 278 reviews

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.

Farm stay in Romney

4.98 out of 5 average rating, 334 reviews

Potomac Hills B&B on 15 Acre Farm with a View

Escape to where beauty and serenity abound in a brand NEW guest house on a 15 acre farm in the Potomac Highlands. Just 2 hours from DC, this accessible, yet peaceful escape provides options for relaxation and outdoor adventure. Located 10 minutes from Romney, WV, this spot is convenient to hiking, river activities, hunting/fishing, and skiing. Explore or simply relax and enjoy life on the farm.

Rental unit in Cumberland

4.96 out of 5 average rating, 198 reviews

Braddock Suite in Corner Tavern Residences

Nestled above Corner Tavern & Cafe in historic downtown, this modern apartment supplies you with all the comforts of home. Our location provides all the benefits of a night out of town, located in historic downtown, above a tavern & cafe, you'll find food, drink & maybe even music in a few short steps from your apartment.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Cumberland vacation rentals

Laptop-friendly workspace

Stay near Cumberland's top sights

Western Maryland Scenic Railroad19 locals recommend

Ristorante Ottaviani15 locals recommend

Queen City Creamery, Cafe & Deli13 locals recommend

Cafe Mark11 locals recommend

Canal Place10 locals recommend

Puccini Restaurant8 locals recommend

Other great vacation rentals in Cumberland

Farm stay in Ellerslie

5 out of 5 average rating, 41 reviews

Historic Eden Ranch, built 1837

Rental unit in Oldtown

5 out of 5 average rating, 43 reviews

Sierra Farmstead - Guest House

Home in Cumberland

5 out of 5 average rating, 51 reviews

Small, cheerful house!

Rental unit in Cumberland

4.97 out of 5 average rating, 68 reviews

BlueSideUp! Comfy, light filled, eclectic, retreat

Home in Cumberland

5 out of 5 average rating, 86 reviews

NEW LISTING-"Cumberland Cottage"-charming,quaint

Home in Cumberland

4.98 out of 5 average rating, 62 reviews

The Dacha. Rebirth sauna experience

Condo in Cumberland

4.92 out of 5 average rating, 79 reviews

Private apartment in residential Cumberland, MD

Home in La Vale

4.97 out of 5 average rating, 76 reviews

Hila's House

Quick stats about vacation rentals in Cumberland

Total rentals
80 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Cumberland?
Yes! Work meets play with ease at over 50 vacation rentals in Cumberland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Cumberland?
Four-legged friends are welcome in Cumberland. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Cumberland?
Experience the best of Cumberland with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Cumberland have wifi?
Absolutely! We offer over 40 house rentals with wifi in Cumberland. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore