929+ Private Villas and Holiday Rentals in Oakland |
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Oakland Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Oakland

Discover more than 929 vacation rentals available in Oakland. 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 Oakland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oakland, 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 Oakland. On average, places to stay near Oakland offer 1841.59 ft², with nightly prices averaging GB £350.

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

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Top Accommodation Types in Oakland

Type Count
Vacation Homes 694
Holiday Apartments 52
Cottages 10
Villas 2

Use these Quick Filters to Find a Holiday Rental in Oakland

★ 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 Oakland.

Weather in Oakland, MD

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

December - February
High 50°F       Low 20°F
March - May
High 69°F       Low 25°F
June - August
High 81°F       Low 56°F
September - November
High 73°F       Low 30°F

Top Attractions Around Oakland, MD

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


Deep Creek Lake
Swallow Falls State Park
Garrett Regional Medical Center
Deep Creek Lake State Park
Ohiopyle State Park
Blackwater Falls State Park
Wisp Resort
Canaan Valley Ski Resort
Dolly Sods Wilderness Area
Lady Luck Casino at Nemacolin
Coopers Rock State Forest
Timberline Four Season Resort
Blackwater Falls
Hovatter's Wildlife Zoo
Youghiogheny River Lake
New Germany State Park
Janet and Imre Szilagyi Center for the Visual and Performing Arts
Off-Road Driving Academy
Funland

Other Places to Stay in Oakland, MD


The View 1,734 Properties
Silver Ridge 1,453 Properties
Altamont 1,054 Properties
Thayerville 562 Properties
Mountain Lake Park 222 Properties
Garrett Regional Medical Center 146 Properties
Timbers on the Yough 104 Properties
Mountainside 75 Properties
Deer Park 66 Properties
Blakeslee 53 Properties
Deep Creek Lake 52 Properties
Paradise Point 31 Properties

Frequently Asked Questions About Oakland?

What are the top holiday rentals in Oakland?

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

How many holiday rentals have private pools in Oakland?

Discover a selection of holiday rentals with private pools near Oakland 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 Oakland are best for families?

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

How many Casai.uk holiday rentals are available in Oakland?

As of 2025, Casai boasts over 929 properties listed in the Oakland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oakland.

Nearby Neighborhood (6) 
Neighborhood Property Count
Mountainside Vacation Rentals in Cumberland, Maryland 75
Blakeslee Vacation Rentals in Cumberland, Maryland 53
Paradise Point Vacation Rentals in Cumberland, Maryland 31
Silver Ridge Vacation Rentals in Cumberland, Maryland 1453
The View Vacation Rentals in Cumberland, Maryland 1734
Timbers on the Yough Vacation Rentals in Cumberland, Maryland 104

People Also Ask

There are 929 Oakland, MD Holiday Rentals

Recently Booked Holiday Rentals in Oakland