2994+ Private Villas and Holiday Rentals in Cumberland |
  1. USA
  2. Maryland
  3. Cumberland

Cumberland Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Cumberland

Discover more than 2994 vacation rentals available in Cumberland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Cumberland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Cumberland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Cumberland. On average, places to stay near Cumberland offer 2029.46 ft², with nightly prices averaging US $499.

With Casai, finding and comparing holiday rentals in Cumberland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Cumberland

Type Count
Vacation Homes 2402
Holiday Apartments 135
Cottages 40
Villas 8

Use these Quick Filters to Find a Holiday Rental in Cumberland

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Cumberland.

Weather in Cumberland, MD

View the weather forecast for Cumberland before booking your Cumberland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Cumberland, MD

Casai offers a large selection of top attractions around Cumberland . Research things to do on your vacation before you visit Cumberland.


Deep Creek Lake
Deep Creek Lake State Park
Wisp Resort
Rocky Gap State Park
Rocky Gap Casino and Golf Course
Frostburg State University
Noah's Ark
Downtown Cumberland Historic District
Rocky Gap Golf Resort
Western Maryland Railroad Station
Swallow Falls State Park
New Germany State Park
LaVale Library
Allegeny College of Maryland
Frostburg Library
Funland
F. Brooke Whiting House and Museum
Palace Theater
La Vale Tollgate House
Dan's Mountain State Park

Other Places to Stay in Cumberland, MD


Garrett County 2,602 Properties
McHenry 1,165 Properties
Oakland 940 Properties
Thayerville 671 Properties
Swanton 451 Properties
Mountain Lake Park 216 Properties
Allegany County 90 Properties
Waterfront Greens 81 Properties
Mountainside 76 Properties
Deep Creek Lake 54 Properties
North Glade Hills 54 Properties
Blakeslee 53 Properties

Frequently Asked Questions About Cumberland?

What are the top holiday rentals in Cumberland?

With numerous options available in Cumberland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Cumberland:

How many holiday rentals have private pools in Cumberland?

Discover a selection of holiday rentals with private pools near Cumberland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Cumberland are best for families?

If you're searching for a family-friendly holiday home in Cumberland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Cumberland:

How many Casai.com holiday rentals are available in Cumberland?

As of 2025, Casai boasts over 2994 properties listed in the Cumberland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Cumberland.

Nearby Neighborhood (12) 
Neighborhood Property Count
Waterfront Greens Vacation Rentals in Cumberland, Maryland 81
Mountainside Vacation Rentals in Cumberland, Maryland 76
North Glade Hills Vacation Rentals in Cumberland, Maryland 54
Blakeslee Vacation Rentals in Cumberland, Maryland 53
Sky Valley Vacation Rentals in Cumberland, Maryland 34
Paradise Point Vacation Rentals in Cumberland, Maryland 33
Sunplace Vacation Rentals in Cumberland, Maryland 1952
Silver Ridge Vacation Rentals in Cumberland, Maryland 1453
The View Vacation Rentals in Cumberland, Maryland 1734
Penelacres Vacation Rentals in Cumberland, Maryland 2159
Turkey Neck Vacation Rentals in Cumberland, Maryland 1023
Timbers on the Yough Vacation Rentals in Cumberland, Maryland 104

People Also Ask

There are 2994 Cumberland, MD Holiday Rentals

Recently Booked Holiday Rentals in Cumberland