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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Guest favorite

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 4 – 11

€ 96 per night

Guest favorite

Home in Cumberland

4.94 out of 5 average rating, 207 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.

Mar 25 – Apr 1

€ 108 per night

Guest favorite

Cabin in Frostburg

4.92 out of 5 average rating, 133 reviews

Big Savage Guest Cabin

Nestled on 10 acres near the summit of Big Savage Mountain is our home site which includes our guest cabin. Warm summer days and cool evenings make for a great vacation spot. In the country but just 1 mile from down town. Your retreat is just 3 minutes from dining, biking, hiking, swimming, and live music. Fall brings beautiful foliage and winter plenty of snow. There is something for fans of all seasons. We are only 5 minutes from Frostburg State University & 30 minutes from Deep Creek Lake.

Apr 26 – May 3

€ 117 per night

Guest favorite

Apartment in Cumberland

4.84 out of 5 average rating, 294 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.

Sep 22 – 29

€ 134 per night

Guest favorite

Apartment in Cumberland

4.99 out of 5 average rating, 320 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.

Sep 21 – 28

€ 103 per night

Guest favorite

Cabin in Paw Paw

4.96 out of 5 average rating, 174 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!

Jul 2 – 9

€ 105 per night

Guest favorite

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 7 – 14

€ 119 per night

Guest favorite

Home in Frostburg

4.93 out of 5 average rating, 205 reviews

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.

Nov 29 – Dec 6

€ 132 per night

Guest favorite

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.

Dec 18 – 25

€ 85 per night

Guest favorite

Home in Cumberland

4.9 out of 5 average rating, 457 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.

Mar 18 – 25

€ 145 per night

Superhost

Cabin in Fort Ashby

4.87 out of 5 average rating, 100 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!

Aug 6 – 13

€ 154 per night

Guest favorite

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.

Sep 10 – 17

€ 184 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cumberland vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 favorite

Guesthouse in Salisbury

4.95 out of 5 average rating, 440 reviews

The Homecoming Loft

Oct 8 – 15

€ 89 per night

Superhost

Apartment in Rockwood

4.9 out of 5 average rating, 432 reviews

Taking reservations *Newly Renovated* GORGEOUS!

Sep 20 – 27

€ 128 per night

Guest favorite

Guesthouse in Grantsville

4.92 out of 5 average rating, 117 reviews

“The Loft” Guest House w/wifi workspace, gym etc

Jan 17 – 24

€ 141 per night

Guest favorite

Home in Cumberland

4.93 out of 5 average rating, 56 reviews

Great Location, Spacious, Comfy 2 bdrm home

Jun 3 – 10

€ 114 per night

Guest favorite

Loft in Cumberland

4.94 out of 5 average rating, 36 reviews

Historical loft, 2 Blocks from Trail & Downtown

Oct 2 – 9

€ 77 per night

Guest favorite

Home in Cumberland

4.86 out of 5 average rating, 29 reviews

Cozy Cottage

Aug 29 – Sep 5

€ 130 per night

Guest favorite

Home in Cumberland

5.0 out of 5 average rating, 8 reviews

Spacious Parkside Oasis!

Apr 20 – 27

€ 124 per night

Guest favorite

Home in Cumberland

4.95 out of 5 average rating, 22 reviews

WiggerZen

Jan 29 – Feb 5

€ 155 per night

Show all

Other great vacation rentals in Cumberland

Guest favorite

Apartment in Oldtown

5.0 out of 5 average rating, 26 reviews

Sierra Farmstead - Guest House

Oct 31 – Nov 7

€ 130 per night

Superhost

Apartment in Cumberland

5.0 out of 5 average rating, 8 reviews

Mountain View Paradise

Jul 6 – 13

€ 107 per night

Guest favorite

Farm stay in Ellerslie

5.0 out of 5 average rating, 23 reviews

Historic Eden Ranch, built 1837

Dec 14 – 21

€ 132 per night

Guest favorite

Guesthouse in Fairhope

5.0 out of 5 average rating, 19 reviews

Mountain View Acres Getaway

Aug 6 – 13

€ 104 per night

Guest favorite

Home in Cumberland

4.91 out of 5 average rating, 44 reviews

Laverne’s Lodge

Sep 10 – 17

€ 133 per night

Guest favorite

Home in La Vale

4.98 out of 5 average rating, 48 reviews

Hila's House

Mar 9 – 16

€ 154 per night

Superhost

Home in Cumberland

4.9 out of 5 average rating, 10 reviews

The Art House

Nov 29 – Dec 6

€ 141 per night

Guest favorite

Cabin in Springfield

5.0 out of 5 average rating, 54 reviews

1832 Historic Washington Bottom Farm Log Cabin

Mar 28 – Apr 4

€ 169 per night

Show all

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
€ 38 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Cumberland?
Yes! Work meets play with ease at over 40 vacation rentals in Cumberland featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Cumberland?
Experience the best of Cumberland with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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.
Do apartment rentals in Cumberland have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Cumberland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cumberland have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Cumberland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Cumberland?
Cumberland has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Cumberland vacation rentals

Top-rated vacation rentals in Cumberland

Vacation rentals for every style

Houses

Cabins

Cottages

Popular amenities for Cumberland vacation rentals

Stay near Cumberland's top sights

Other great vacation rentals in Cumberland

Guesthouse in Salisbury

Apartment in Rockwood

Guesthouse in Grantsville

Home in Cumberland

Loft in Cumberland

Home in Cumberland

Home in Cumberland

Home in Cumberland

Other great vacation rentals in Cumberland

Apartment in Oldtown

Apartment in Cumberland

Farm stay in Ellerslie

Guesthouse in Fairhope

Home in Cumberland

Home in La Vale

Home in Cumberland

Cabin in Springfield

Quick stats about vacation rentals in Cumberland

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Cumberland?

How much does it cost to stay in house rentals in Cumberland?

Are there pet-friendly vacation rentals in Cumberland?

Do apartment rentals in Cumberland have wifi?

Do house rentals in Cumberland have self check-in?

Are there family-friendly house rentals in Cumberland?

Destinations to explore