Explore Oakland Golf Retreats
About Oakland Vacation Rentals
Explore over 1207 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 1847.12 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 $526.
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.
Top Golf Accommodation Types in Oakland
| Type | Count |
|---|---|
| Vacation Homes | 931 |
| Cabin Rentals | 73 |
| Holiday Apartments | 60 |
| Ski Chalet Rentals | 17 |
| Cottages | 10 |
| Villas | 3 |
| 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.
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
Find Nearby Cabin Rentals in these Cities & Neighborhoods
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:
- Sunny Escape 2 - A new era for a well loved lake front home
- 5 STAR OWNER Managed, Lake Xcess, dock, Pool, Pickle-ball, Home Theater, firepit
- Level lakefront, family-friendly, hot tub, low fees, private dock
- Timroc II, FIVE STAR REVIEWS! 15 MINUTES FROM WISP! HOT TUB! PRIVATE 2 ACRES!
- AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table
- Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip
- Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
- HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee
- Beautiful Lakeside Cottage on Quiet Street with Private Dock, Kayaks & Fire Pit
- The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
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.
- New: Lakefront Luxury Home with Private Indoor Heated Pool!
- Celebration at Deep Creek
- Chic Lake Stay w/Pool, Dock & Fireplaces
- Smore Fun
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:
- Radiant Floors, Sauna & Forest Views
- Celebration at Deep Creek
- The Whiskey Barrel Lodge by Taylor Made Deep Creek
How many StayAndPlay golf vacation rentals are available in Oakland?
StayAndPlay, as of 2026, features over 1207 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 2026, StayAndPlay has curated over 1207 stunning properties in Oakland, sourced from trusted platforms. Plan your next golf trip now.
For 2026, StayAndPlay provides access to over 1207 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 | 78 |
| Blakeslee Golf Rental Cottages and Golf Getaways in Cumberland, Maryland | 54 |
| Paradise Point Golf Rental Cottages and Golf Getaways in Cumberland, Maryland | 37 |
| Silver Ridge Golf Rental Cottages and Golf Getaways in Cumberland, Maryland | 1960 |
| The View Golf Rental Cottages and Golf Getaways in Cumberland, Maryland | 1785 |
| Timbers on the Yough Golf Rental Cottages and Golf Getaways in Cumberland, Maryland | 139 |
