983+ Vacation Rentals & Holiday Homes in Oakland |
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Oakland Accommodations - Hotels & Rentals

About Oakland Vacation Rentals

Discover More than 983 Incredible Getaway Rentals Available in Oakland. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Oakland.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Oakland, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Oakland. The Average Size of Places to Stay Near Oakland is 1751.58 ft², with Prices Averaging US $460 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Oakland. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Oakland

Type Count
Vacation Homes 735
Holiday Apartments 57
Cottages 10
Villas 2

Use these Quick Filters to Find a Vacation Rental in Oakland

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Oakland with Online Reservations.

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

Activities OaklandGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World OaklandGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Silver Ridge 1,613 Properties
The View 1,483 Properties
Altamont 938 Properties
Thayerville 530 Properties
Mountain Lake Park 184 Properties
Garrett Regional Medical Center 151 Properties
Timbers on the Yough 139 Properties
Swallow Falls State Park 85 Properties
Mountainside 63 Properties
Deep Creek Lake 43 Properties
Blakeslee 40 Properties
Paradise Point 27 Properties

Frequently Asked Questions About Oakland?

What are the top hotels, lake houses & vacation rentals in Oakland?

We provide an array of great vacation destinations in Oakland. If you are looking to stay in or around the Oakland area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Oakland:

How many Hotels & Vacation Rentals have private pools in Oakland?

We have 31 Hotels & Vacation Rentals featuring a private pool in and near Oakland. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Oakland is best for families?

Searching for a family-friendly getaway in Oakland? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Oakland?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 983 in the Oakland area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Oakland.

Nearby Neighborhood (6) 
Neighborhood Property Count
Mountainside Vacation Rentals in Cumberland, Maryland 63
Blakeslee Vacation Rentals in Cumberland, Maryland 40
Paradise Point Vacation Rentals in Cumberland, Maryland 27
Silver Ridge Vacation Rentals in Cumberland, Maryland 1613
The View Vacation Rentals in Cumberland, Maryland 1483
Timbers on the Yough Vacation Rentals in Cumberland, Maryland 139

People Also Ask

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