928+ Golf Villas, Golf Cabins, Golf Hotels, Golf Resort Rentals, and other Private Golf Retreats in Oakland |
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  3. Cumberland
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Explore Oakland Golf Retreats

About Oakland Vacation Rentals

Explore over 928 golf accommodation rentals in Oakland. From luxurious golf villas to cozy golf cabins, golf resorts, and exclusive golf hotels, each offers premium amenities designed for families, groups, and golf enthusiasts. Enjoy exceptional comfort and a one-of-a-kind golf experience with these incredible accommodations. Perfect for tranquil golf escapes, relaxing retreats, or golf-inspired getaways, these properties provide style and comfort in Oakland.

Looking for last-minute deals or the best offers on golf villas, golf cabins, golf resorts, and other golf retreats? StayAndPlay makes it easy to compare options in Oakland. Choose from spacious family-friendly stays, charming golf escapes, or luxurious golf retreats tailored for ultimate relaxation and play.

Find spacious family-friendly golf accommodations, golf cottage, or luxurious golf villas—all designed for maximum comfort and convenience during your visit.

On average, golf accommodation rentals in Oakland offer approximately 1840.88 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning golf course surroundings.

The average nightly rate for golf accommodation rentals in Oakland typically ranges around US $472.

StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Oakland. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in golf with us.

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Top Golf Accommodation Types in Oakland

Type Count
Vacation Homes 693
Cabin Rentals 65
Holiday Apartments 52
Ski Chalet Rentals 13
Cottages 10
Villas 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Oakland

★ Pro Tip: StayAndPlay simplifies your search for the best golf accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore golf villas, cozy golf cabins, golf hotels, and golf resorts. Filter by availability, pricing, cancellation options, and amenities to discover the ideal golf retreat 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

Activities Oakland Guest Reviews Local Attractions

StayAndPlay offers a diverse selection of the top golf villas, golf hotels, and other golf retreats around the world. Oakland Guest Reviews Find the Best Golf Experiences & Activities for Your Golf Trip


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 Nearby Cabin Rentals in these Cities & Neighborhoods


The View 1,734 Properties
Silver Ridge 1,453 Properties
Altamont 1,054 Properties
Thayerville 561 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 best golf resorts, luxury villas, and vacation rentals in Oakland?

Looking for a place to stay in Oakland? Explore these highly-rated golf vacation rentals for a one-of-a-kind golf retreat, where you can relax, unwind, and get ready to play your best game:

How many golf stays with private pools are available in Oakland?

Find exceptional golf retreats with private pools near Oakland on StayAndPlay. Relax in serene golf vacation rentals with exclusive pool access and picturesque golf course views. Whether it's a spacious golf villa or a secluded golf cabin, these properties offer the perfect blend of luxury and relaxation, so you can focus on your game.

What are the top-rated golf retreats in Oakland for family stays?

Searching for a family-friendly golf retreat in Oakland? Explore these top-rated options, each loved by families and groups who have stayed in Oakland:

How many StayAndPlay golf vacation rentals are available in Oakland?

StayAndPlay, as of 2025, features over 928 unique golf villas, golf hotels, golf resorts, and more in Oakland. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2025, StayAndPlay has curated over 928 stunning properties in Oakland, sourced from trusted platforms. Plan your next golf trip now.

For 2025, StayAndPlay provides access to over 928 premier golf accommodations in Oakland. Find your ideal golf-retreat and play your best game with StayAndPlay.

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

People Also Ask

There are 35 hotels in Oakland and 812 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Oakland