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Cumberland Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Cumberland holiday rentals

Room
Abrams Creek Center

Cabin in Elk Garden

2.0 star property
7.4 out of 10, Good, (44)
"We DID NOT SEE THOS PHOTO BEFORE RENTING!! There was no water/air conditioning or refrigerator?!? This was not the photo of the cabin I renter either!! We were supposed to have a cabin with enough room for 8 to sleep"
United States
Samantha
The price is HK$395
HK$625 total
includes taxes & fees
10 Dec - 11 Dec
Abrams Creek Center
Fridge, microwave, coffee/tea maker, dining tables
Private cabin with two double beds (sleep 4)

Chalet in Flintstone

10.0 out of 10, Exceptional, (5)
"Only problem was coffee maker"
United States
Donna
The price is HK$802
HK$1,163 total
includes taxes & fees
10 Dec - 11 Dec
Private cabin with two double beds (sleep 4)
Interior
Mountainside Cabin 53-Hot Tub, Dog Friendly

Cabin in McHenry

10.0 out of 10, Exceptional, (3)
"Very nice clean private quite staff very helpfu near restaurants and shopping grounds are well kept "
United States
Thomas
The price is HK$2,117
HK$3,276 total
includes taxes & fees
1 Jan - 2 Jan 2026
Mountainside Cabin 53-Hot Tub, Dog Friendly
Outdoor spa tub
Grandview Cabin Suite 26-Hot Tub

Cabin in McHenry

10.0 out of 10, Exceptional, (1)
"Loved the view and how comfortable the beds were. Will definitely book again. Easy access and very clean"
United States
Scott B.
The price is HK$2,988
HK$4,973 total
includes taxes & fees
23 Dec - 24 Dec
Grandview Cabin Suite 26-Hot Tub
Property grounds
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Cabin in Oakland

2.0 star property
10.0 out of 10, Exceptional, (12)
"Nothing negative to say. Beautiful place and friendly owner. Owner is accessible and very accommodating. "
United States
Sean
The price is HK$1,673
HK$5,605 total
includes taxes & fees
10 Dec - 11 Dec
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Iron/ironing board, WiFi, bed sheets
Mountainside Cabin 51L

Cabin in McHenry

The price is HK$1,736
HK$2,797 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountainside Cabin 51L
Property grounds
Lakefront Lakeview Cabin 5-Hot Tub, Full Kitchen

Cabin in McHenry

10.0 out of 10, Exceptional, (2)
"Excellent "
United States
Kate D.
The price is HK$3,207
HK$5,298 total
includes taxes & fees
1 Jan - 2 Jan 2026
Lakefront Lakeview Cabin 5-Hot Tub, Full Kitchen
Fridge, microwave, oven, stovetop
Rustic Oasis for the Family - 6 min walk to Downtown

Holiday Home in Cumberland

2.0 star property
10.0 out of 10, Exceptional, (1)
"Property and location just as advertised. Owner was very good about communicating and letting you know he was available if any issues came up (which they did not). Would stay there again!"
United States
Bruce H.
The price is HK$2,205
HK$2,675 total
includes taxes & fees
10 Dec - 11 Dec
Rustic Oasis for the Family - 6 min walk to Downtown
Exterior
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Chalet in Oakland

10.0 out of 10, Exceptional, (4)
"The place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
The price is HK$1,008
HK$3,056 total
includes taxes & fees
21 Dec - 22 Dec
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Exterior
Luxury Chalet w/ views, hot tub, sauna, Tesla EV, starlink for the holidays!

Cabin in Swanton

10.0 out of 10, Exceptional, (4)
"Our stay at the Four Seasons Chalet in Swanton was absolutely perfect in every way! The location, amenities, furnishings, and thoughtful appointments made the home feel warm, welcoming, and fully stocked with everything we could have possibly needed. Communication was excellent, quick responses and helpful area recommendations were greatly appreciated and made our trip even smoother. We jet-skied, went to the beach at the lake, hiked Swallow Falls, and did the mountain coaster at Wisp! We would...
United States
Valentina B.
The price is HK$2,328
HK$5,413 total
includes taxes & fees
11 Dec - 12 Dec
Luxury Chalet w/ views, hot tub, sauna, Tesla EV, starlink for the holidays!
Fridge, microwave, oven, stovetop
Oldtown Guesthouse

Holiday Home in Oldtown

10.0 out of 10, Exceptional, (28)
"Absolutely loved this little guesthouse. It was Elian’s yet simple"
United States
Elizabeth
The price is HK$778
HK$1,402 total
includes taxes & fees
10 Dec - 11 Dec
Oldtown Guesthouse
Fridge, microwave, oven, dishwasher
Lakefront Cabin Suite 4-Hot Tub, Full Kitchen

Cabin in McHenry

9.4 out of 10, Exceptional, (3)
"This cabin had everything that we needed for our short stay. The location is great, just steps to see the lake. The hot tub was clean and mostly private. The check-in process was easy and the staff were very friendly. We will definitely stay there again."
United States
Anonymous traveller
The price is HK$2,482
HK$3,711 total
includes taxes & fees
21 Dec - 22 Dec
Lakefront Cabin Suite 4-Hot Tub, Full Kitchen
Dining
Private Home in Garrett County, surrounded by trees, fields and farmland.

Cottage in Grantsville

10.0 out of 10, Exceptional, (42)
"We had a very nice stay. Very comfortable and inviting a home away from home vibe. "
United States
Carol R.
The price is HK$1,237
HK$2,210 total
includes taxes & fees
10 Dec - 11 Dec
Private Home in Garrett County, surrounded by trees, fields and farmland.
Exterior
Pool, HotTub, FirePit, EVCharger, & Great Location

Cabin in Oakland

10.0 out of 10, Exceptional, (17)
"The property was great for our golf trip. We were close to a couple of the courses we played and close to everything else we needed. It was clean and very nice"
United States
Anonymous traveller
The price is HK$4,408
HK$8,742 total
includes taxes & fees
11 Dec - 12 Dec
Pool, HotTub, FirePit, EVCharger, & Great Location
TV, fireplace
Mountainside Loft Cabin 46L-Dog Friendly

Cabin in McHenry

Mountainside Loft Cabin 46L-Dog Friendly
Terrace/patio
Mountainside Cabin 48, Family Suite-Hot Tub, Dog Friendly

Cabin in McHenry

The price is HK$2,904
HK$4,926 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountainside Cabin 48, Family Suite-Hot Tub, Dog Friendly
Smart TV
Loft two story with first floor workout room, WIFI, complete cottage to yourself

Cottage in Grantsville

9.8 out of 10, Exceptional, (37)
"The clean and comfortable looking cabins "
United States
Torrance
The price is HK$945
HK$1,596 total
includes taxes & fees
15 Dec - 16 Dec
Loft two story with first floor workout room, WIFI, complete cottage to yourself
Fridge, microwave, oven, stovetop
Full home near C&O! Perfect for bikers or families!

Holiday Home in Cumberland

9.6 out of 10, Exceptional, (21)
"This stay was perfect for the beginning of our GAP Trail ride! "
United States
Marilyn S.
The price is HK$1,050
HK$1,831 total
includes taxes & fees
14 Dec - 15 Dec
Full home near C&O! Perfect for bikers or families!
TV, fireplace
Lakefront Cabin Suite 2-Hot Tub, Dog Friendly

Cabin in McHenry

The price is HK$2,482
HK$3,670 total
includes taxes & fees
14 Dec - 15 Dec
Lakefront Cabin Suite 2-Hot Tub, Dog Friendly
Beach
Will O' The Wisp: 107B One Bedroom/One Bath

Condo in Mountainside

10.0 out of 10, Exceptional, (2)
"Great place to visit. Hope to come back next year"
United States
Stacy S.
The price is HK$2,046
HK$2,638 total
includes taxes & fees
21 Dec - 22 Dec
Will O' The Wisp: 107B One Bedroom/One Bath
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

Hampton Inn Cumberland

Hampton Inn Cumberland

10/10 Excellent
"Staff is friendly and breakfast was great! Rooms are always clean as well. "
Laura 2-night trip
Posted 6 days ago
Hampton Inn Cumberland

Find out more about Cumberland

Search for holiday rentals in Cumberland on Expedia! You can easily find your home rentals, villas, holiday apartments in Cumberland using one of the methods below:

  • View our selection of featured holiday rentals in Cumberland
  • Use the map to find apartments and other holiday homes in the Cumberland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cumberland while they last

Look no further and take a look at our great range of rental properties in Cumberland!

Frequently asked questions

Can I find holiday rentals in Cumberland?

Yes, there are holiday rentals in Cumberland close to Western Maryland Scenic Railroad, or you can select a more 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 are some of the best holiday rentals that Cumberland has to offer?

NEW ON VRBO Mountain view Grand 6BR 3BA Large Home in LaVale, 15min to Rocky Gap: This highly rated holiday home rental in Cumberland offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other homes for rent in Cumberland include Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi and Full home near C&O! Perfect for bikers or families!.

How many holiday rentals will I find in Cumberland?

With 10 Expedia holiday rentals, you're guaranteed 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 Chesapeake and Ohio Canal, 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 holiday rental in Cumberland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for small groups.