A river flowing through a town with a bridge and a large building with a sign.

Cumberland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cumberland vacation rentals

A garden with a variety of flowers and plants, a wooden structure, and a white fence.

1. Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
Cumberland
9.8 out of 10, Exceptional, (51 reviews)
"The house was very clean and the view from the deck was spectacular."
United States
Toni R.
The price is CA $170
CA $273 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi
A kitchen with wooden cabinets, a refrigerator, a sink, and a glass-top island with a stool.

2. Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!

Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
Cumberland
10.0 out of 10, Exceptional, (11 reviews)
"Easy walk into town and the train station."
United States
Kathy M.
The price is CA $219
CA $281 total
includes taxes & fees
Sep 29 - Sep 30
Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!
A covered patio with a table and chairs, a hanging basket, and a satellite dish.

3. Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /

Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
Cumberland
10.0 out of 10, Exceptional, (63 reviews)
"Host was very polite and helpful!"
United States
Quintin
The price is CA $170
CA $247 total
includes taxes & fees
Sep 29 - Sep 30
Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /
A pond with cattails and a white boat.

4. BIG D's POND & North Branch of the Potomac river Camping.

BIG D's POND & North Branch of the Potomac river Camping.
Cumberland
10.0 out of 10, Exceptional, (4 reviews)
"Big D'S Pond is beautiful and the owner, is very kind and helpful. We had an amazing time!"
United States
Mary G.
The price is CA $113
CA $188 total
includes taxes & fees
Sep 28 - Sep 29
BIG D's POND & North Branch of the Potomac river Camping.
A living room with a brown leather sofa, a blue couch with patterned pillows, a coffee table, and a wooden floor.

5. Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!

Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
Cumberland
9.8 out of 10, Exceptional, (17 reviews)
"Lovely place! "
United States
Courtney N.
The price is CA $212
CA $273 total
includes taxes & fees
Sep 28 - Sep 29
Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!
A staircase with carpeted steps, a white door, and a wall-mounted bulletin board.

6. The Suite On Smallwood

The Suite On Smallwood
Cumberland
9.8 out of 10, Exceptional, (9 reviews)
"Perfect accommodation for our party. Great coffee bar and television selection. Very clean."
United States
Thomas
The price is CA $198
CA $273 total
includes taxes & fees
Oct 19 - Oct 20
The Suite On Smallwood
A bedroom with a bed, desk, chair, and a television.

7. Newly renovated 1905 house, within walking distance to all downtown attractions!

Newly renovated 1905 house, within walking distance to all downtown attractions!
Cumberland
The price is CA $229
CA $385 total
includes taxes & fees
Oct 19 - Oct 20
Newly renovated 1905 house, within walking distance to all downtown attractions!
A modern kitchen with stainless steel appliances, white cabinetry, and a window with a view of the outdoors.

8. Oldtown Guesthouse

Oldtown Guesthouse
Oldtown
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property and house. Very clean and comfortable."
United States
Don B.
The price is CA $181
CA $303 total
includes taxes & fees
Sep 28 - Sep 29
Oldtown Guesthouse
A rustic log cabin with a green roof, a porch with outdoor seating, and a sign indicating an office entrance.

9. Private cabin with two full beds. ADA accessible.

Private cabin with two full beds. ADA accessible.
Flintstone
10.0 out of 10, Exceptional, (7 reviews)
"This cabin has all the necessities, is in a great location and is clean and well maintained. Absolutely perfect for a couple and close to lots of outdoor activities! Will absolutely stay here in the future."
United States
Leah I.
The price is CA $158
CA $224 total
includes taxes & fees
Sep 30 - Oct 1
Private cabin with two full beds. ADA accessible.
A kitchen with white tiled backsplash, wooden shelves holding glassware, and a coffee maker on the counter.

10. Secluded, romantic cabin with hot tub on 12 acres of woodland.

Secluded, romantic cabin with hot tub on 12 acres of woodland.
Cumberland
10.0 out of 10, Exceptional, (121 reviews)
"Everything we expected and more. Visited relatively early in the Spring so we're coming back in June to make better use of outdoor dining, etc. The cabin was super cozy and we made full use of the hot tub and fireplace. We really enjoyed our stay."
United States
Steven H.
The price is CA $262
CA $457 total
includes taxes & fees
Sep 30 - Oct 1
Secluded, romantic cabin with hot tub on 12 acres of woodland.
A two-story building with a green exterior, a black front door, and a small balcony with a metal railing.

11. 5 minute walk to downtown. Cozy family sized home with everything you need.

5 minute walk to downtown. Cozy family sized home with everything you need.
Frostburg
9.4 out of 10, Exceptional, (33 reviews)
"Lovely place, had all we needed for a comfortable stay. Thanks!"
United States
Molly M.
The price is CA $163
CA $325 total
includes taxes & fees
Oct 4 - Oct 5
5 minute walk to downtown. Cozy family sized home with everything you need.
A small cabin with a porch, surrounded by a forest.

12. Abrams Creek Center

Abrams Creek Center
2.0 star property
Elk Garden
7.6 out of 10, Good, (48 reviews)
"Did not stay no bath house just a porta john"
United States
Bill
The price is CA $93
CA $137 total
includes taxes & fees
Sep 28 - Sep 29
Abrams Creek Center
A cozy room with a wooden floor, a white bed, a sofa, and a small table.

13. Loft two story with first floor workout room, WIFI, complete cottage to yourself

Loft two story with first floor workout room, WIFI, complete cottage to yourself
Grantsville
9.8 out of 10, Exceptional, (43 reviews)
"Everything was lovely! The loft was stocked with everything we needed, it was spotlessly clean, and very comfortable."
United States
Leanna B.
The price is CA $172
CA $290 total
includes taxes & fees
Sep 28 - Sep 29
Loft two story with first floor workout room, WIFI, complete cottage to yourself
A modern kitchen with a white island, black chairs, and a view of the outdoors.

14. Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.

Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
Grantsville
10.0 out of 10, Exceptional, (6 reviews)
"Great place to stay!! Very clean and extremely close to local attractions. "
United States
Mitchum
The price is CA $262
CA $312 total
includes taxes & fees
Sep 28 - Sep 29
Spacious riverfront cottage with full kitchen, cozy charm, and Casselman views.
A deck with a white railing, a table, and a view of a forested landscape.

15. Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale

Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
La Vale
8.8 out of 10, Excellent, (3 reviews)
"This was a really lovely place to stay on a quick trip to Cumberland. It’s in a quiet neighborhood with a great Mountain View off the back deck. The property was clean and the owner was communicative. Convenient to town and the scenic railroad. The only complaint I have was the thermostat was auto set to a temp that was too high for the summer, and I had to wake up twice to make it cooler. Other than that it really is exactly as advertised and I would stay again."
United States
Kasey G.
The price is CA $255
CA $307 total
includes taxes & fees
Sep 28 - Sep 29
Gorgeous, fully renovated 3-bedroom house with AC in tranquil La Vale
A wooden interior with a spiral staircase, a kitchen area, and a dining space.

16. Private Home in Garrett County, surrounded by trees, fields and farmland.

Private Home in Garrett County, surrounded by trees, fields and farmland.
Grantsville
10.0 out of 10, Exceptional, (59 reviews)
"Awesome house. And great location "
United States
Richard M.
The price is CA $190
CA $355 total
includes taxes & fees
Oct 4 - Oct 5
Private Home in Garrett County, surrounded by trees, fields and farmland.
A kitchen with white cabinets, a granite countertop, and a wooden ceiling.

17. All about the view

All about the view
McHenry
9.8 out of 10, Exceptional, (17 reviews)
"The location is awesome."
United States
Dale S.
The price is CA $202
CA $552 total
includes taxes & fees
Sep 28 - Sep 29
All about the view
A lodge with a green roof, wooden exterior, and a star emblem. It features a covered porch with chairs and a table, surrounded by a gravel driveway and a forested hillside.

18. Private cabin with two double beds (sleep 4)

Private cabin with two double beds (sleep 4)
Flintstone
10.0 out of 10, Exceptional, (7 reviews)
"Weve stayed here before, enroute to visit family in Maryland. The cabins are very amply large, with modern ammenities. The beds were comfy, eating area was clean and spacious, with even a well thought out large front porch, with a rocking chair to enjoy the serenity of the distant mountains. We'll be back!"
Canada
Karl
The price is CA $158
CA $224 total
includes taxes & fees
Sep 28 - Sep 29
Private cabin with two double beds (sleep 4)
A bedroom with wooden paneling, a dresser with drawers, a mirror, and a television on a stand.

19. Glendale Getaway: Nostalgic not Fancy

Glendale Getaway: Nostalgic not Fancy
Swanton
The price is CA $153
CA $348 total
includes taxes & fees
Sep 29 - Sep 30
Glendale Getaway: Nostalgic not Fancy
A wooden cabin with a porch, a star on the roof, and a green door.

20. Private cabin with two double beds (sleeps 4)

Private cabin with two double beds (sleeps 4)
Flintstone
9.6 out of 10, Exceptional, (4 reviews)
"Cute, clean cabins conveniently located to highway and nearby Cumberland. Nice stay!"
United States
Amy R.
The price is CA $158
CA $224 total
includes taxes & fees
Sep 28 - Sep 29
Private cabin with two double beds (sleeps 4)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cumberland Hotel Reviews

Best Western Braddock Inn

Best Western Braddock Inn

8/10 Good
"The bed was fine; the room was a bit old—the furniture, specifically—but it was okay. They really need to replace the shower curtain; there was also some mold, so it needs a deep cleaning and a new curtain. thank !"
Johanna 1-night trip
Posted 7 hours ago
Best Western Braddock Inn

Find out more about Cumberland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cumberland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Cumberland?

Yes, there are vacation rentals in Cumberland close to Western Maryland Scenic Railroad, or you can go with a secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the mountain landscape and riverfront in Cumberland. Make sure you have time to check out the casinos and churches during your trip.

What's the top vacation rental in Cumberland?

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi: Visitors like this Cumberland vacation home rental. It is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave. Some other homes for rent in Cumberland include The Dacha. Cumberland vacation and Make memories: Mountain view Grand 6BR 3BA LaVale Home, 15 min to Rocky Gap.

How many vacation rentals will I find in Cumberland?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Cumberland stay.

What’s there to see and do in Cumberland?

Enjoy the outdoors at Lake Habeeb Beaches and Lake Habeeb, or simply take in cultural attractions like Windsor Hall and Allegany Museum. Downtown Cumberland Historic District and Western Maryland Scenic Railroad are other places to visit while you're in town.

What’s a vacation rental in Cumberland like?

Vacation rentals are private properties you can book for several days or longer in Cumberland. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for small groups.