50+ Golf Villas, Golf Cabins, Golf Hotels, Golf Resort Rentals, and other Private Golf Retreats in Shady Side |
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  2. Maryland
  3. Shady Side

Explore Shady Side Golf Retreats

About Shady Side Vacation Rentals

Explore over 50 golf accommodation rentals in Shady Side. 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 Shady Side.

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 Shady Side. 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 Shady Side offer approximately 1365.95 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 Shady Side typically ranges around US $520.

StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Shady Side. 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 Shady Side

Type Count
Vacation Homes 39
Cottages 5
Holiday Apartments 4
Cabin Rentals 2

Use these Quick Filters to Find a Vacation Rental in Shady Side

★ 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 Shady Side.

Weather in Shady Side, MD

View the weather forecast for Shady Side before booking your Shady Side 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

Activities Shady Side Guest Reviews Local Attractions

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


Shadyside Park
Captain Avery Museum
FedEx Field
U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Show Place Arena
Bowie State University
Chesapeake Beach Water Park
Anne Arundel Medical Center
Maryland State House
Navy-Marine Corps Memorial Stadium
Rod n Reel Charter Fishing
Annapolis Harbour Center
Kunta Kinte–Alex Haley Memorial
St. Michaels Winery
Prince George's Community College

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Captain Avery Museum 38 Properties
Shadyside Park 36 Properties

Frequently Asked Questions About Shady Side?

What are the best golf resorts, luxury villas, and vacation rentals in Shady Side?

Looking for a place to stay in Shady Side? 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:

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

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

How many StayAndPlay golf vacation rentals are available in Shady Side?

StayAndPlay, as of 2025, features over 50 unique golf villas, golf hotels, golf resorts, and more in Shady Side. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2025, StayAndPlay has curated over 50 stunning properties in Shady Side, sourced from trusted platforms. Plan your next golf trip now.

For 2025, StayAndPlay provides access to over 50 premier golf accommodations in Shady Side. Find your ideal golf-retreat and play your best game with StayAndPlay.

People Also Ask

Cabins in Shady Side and 45 rentals

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