Cumberland Vacation Rentals & Homes - Maryland, United States | Airbnb

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Vacation rentals in Cumberland

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Top-rated vacation rentals in Cumberland

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Apartment in Cumberland

5.0 out of 5 average rating, 8 reviews

Mountain View Paradise

Welcome to Queen City! Wake up to a front row view of the sunrise over the mountains in my recently updated one bedroom one bath unit with an in-house washer and dryer, Keurig (got to have the coffee), TV's and each room and high-speed internet/Wi-Fi. Alexa equipped :) The city offers an array of activities, many within a 5-10 min walk, such as wineries, breweries, shops, museums, theatrical entertainment, a dispensary, and parks. Travelling nurse? The UPMC health systems is about 5 mins away.

Aug. 23 – 30

$154 CAD per night

Guest favourite

Apartment in Cumberland

4.95 out of 5 average rating, 109 reviews

The Dove's Nest w/no cleaning fees

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.

Dec. 11 – 18

$138 CAD per night

Guest favourite

Home in Cumberland

4.94 out of 5 average rating, 210 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.

Sep. 16 – 23

$155 CAD per night

Guest favourite

Loft in Cumberland

4.95 out of 5 average rating, 38 reviews

Historical loft, 2 Blocks from Trail & Downtown

When you enter your loft apartment you will have an interior space to secure your bikes. After a fun day on the C&O or GAP trail you will enjoy a shower, a cup of local Basecamp coffee, and restful sleep Conveniently located 2 blocks off a trail entrance. Downtown restaurants only a 5 minute drive Included in your room is a kitchen sink, microwave, fridge/freezer, toaster and 12 cup coffee pot with local Basecamp coffee in regular & decaf, & tea Keyless entry, entire place to yourself

Jul. 5 – 12

$111 CAD per night

Guest favourite

Apartment in Cumberland

4.84 out of 5 average rating, 295 reviews

WOW! Rustic-Modern Apt - PETS WELCOME!

Quaint and comfy one bedroom apartment located just one block from historic downtown cumberland. It is in a safe and quiet neighborhood. The Cumberland Theatre & Western Maryland Scenic Railroad, the C&O Canal and GAP Trail are just around the corner. We are pet friendly (one-time per pet fee applies, billed after booking) but we do a deep clean after each guest, you’d never know that pets have ever been hosted. AT THIS TIME, WE ARE UNABLE TO ACCOMMODATE EARLY CHECK-IN/OUT DUE TO COVID.

May 12 – 19

$127 CAD per night

Guest favourite

Apartment in Cumberland

4.99 out of 5 average rating, 324 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.

Apr. 26 – May 3

$148 CAD per night

Guest favourite

Cabin in Paw Paw

4.96 out of 5 average rating, 177 reviews

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 lots more room to spare, indoor toilet but BEST of all is showering outside!

Jun. 19 – 26

$151 CAD per night

Guest favourite

Home in Cumberland

4.83 out of 5 average rating, 144 reviews

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 jacuzzi tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

Jul. 18 – 25

$170 CAD per night

Guest favourite

Apartment in Frostburg

4.89 out of 5 average rating, 124 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.

Sep. 22 – 29

$121 CAD per night

Guest favourite

Home in Cumberland

4.9 out of 5 average rating, 461 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.

Jan. 14 – 21

$222 CAD per night

Cabin in Fort Ashby

4.86 out of 5 average rating, 101 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!

Dec. 28 – Jan. 4

$230 CAD per night

Guest favourite

Cottage in Cumberland

4.99 out of 5 average rating, 167 reviews

The Cottage on the Hill

Snuggled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in your private space, walk down to a unique retreat high above the city and 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.

May 9 – 16

$265 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for Cumberland vacation rentals

Free parking on premises

Air conditioning

Stay near Cumberland's top sights

Western Maryland Scenic Railroad19 locals recommend

Puccini Restaurant8 locals recommend

Crabby Pig6 locals recommend

El Jinete3 locals recommend

Cafe Mark11 locals recommend

Queen City Creamery, Cafe & Deli14 locals recommend

Other great vacation rentals in Cumberland

Guest favourite

Home in Cumberland

4.93 out of 5 average rating, 56 reviews

Great Location, Spacious, Comfy 2 bdrm home

Apr. 12 – 19

$189 CAD per night

Guest favourite

Home in Cumberland

5.0 out of 5 average rating, 10 reviews

Johnson Heights Getaway

Aug. 24 – 31

$218 CAD per night

Guest favourite

Home in Cumberland

4.86 out of 5 average rating, 29 reviews

Cozy Cottage

Oct. 12 – 19

$187 CAD per night

Guest favourite

Farm stay in Ellerslie

5.0 out of 5 average rating, 23 reviews

Historic Eden Ranch, built 1837

Mar. 6 – 13

$185 CAD per night

Guest favourite

Home in Cumberland

5.0 out of 5 average rating, 13 reviews

Charming Home Near Downtown

Jul. 31 – Aug. 7

$178 CAD per night

Guest favourite

Home in Cumberland

4.95 out of 5 average rating, 22 reviews

WiggerZen

Feb. 8 – 15

$223 CAD per night

Guest favourite

Home in Cumberland

5.0 out of 5 average rating, 65 reviews

NEW LISTING-"Cumberland Cottage"-charming,quaint

Jan. 31 – Feb. 7

$231 CAD per night

Guest favourite

Guesthouse in Fairhope

5.0 out of 5 average rating, 21 reviews

Mountain View Acres Getaway

Aug. 2 – 9

$149 CAD per night

Quick stats about vacation rentals in Cumberland

Total rentals
60 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
4K reviews
Nightly prices starting at
$55 CAD before taxes and fees

Destinations to explore