Explore Chestertown Golf Retreats
About Chestertown Vacation Rentals
Explore over 69 golf accommodation rentals in Chestertown. 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 Chestertown.
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 Chestertown. 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 Chestertown offer approximately 898.43 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 Chestertown typically ranges around US $550.
StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Chestertown. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in golf with us.
Top Golf Accommodation Types in Chestertown
| Type | Count |
|---|---|
| Vacation Homes | 48 |
| Holiday Apartments | 8 |
| Cottages | 3 |
| Cabin Rentals | 2 |
| Others | 2 |
| B&B | 1 |
Use these Quick Filters to Find a Vacation Rental in Chestertown
★ 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 Chestertown.
Weather in Chestertown, MD
View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.
Activities Chestertown Guest Reviews Local Attractions
StayAndPlay offers a diverse selection of the top golf villas, golf hotels, and other golf retreats around the world. Chestertown Guest Reviews Find the Best Golf Experiences & Activities for Your Golf Trip
Find Nearby Cabin Rentals in these Cities & Neighborhoods
Frequently Asked Questions About Chestertown?
What are the best golf resorts, luxury villas, and vacation rentals in Chestertown?
Looking for a place to stay in Chestertown? 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:
- Eagles Point Landing
- Historic Downtown Garden Oasis with Private Patio
- Breathtaking waterfront home on the Chester River
- Historic Manor House on Beautiful Eastern Shore Estate
- Harbor View Haven | Waterfront w/Hot Tub + Dock!
- Beautiful, spacious waterfront home, an easy walk to historic Chestertown
- First Floor Studio Apartment in Historic Chestertown
- Comfort Inn & Suites Chestertown
- The Lodge at Great Oak Landing
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
What are the top-rated golf retreats in Chestertown for family stays?
Searching for a family-friendly golf retreat in Chestertown? Explore these top-rated options, each loved by families and groups who have stayed in Chestertown:
- Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Walk to Historic Chestertown Dog-Friendly Retreat
- Circa 1900 Home in the Heart of Historic Downtown Chestertown
How many StayAndPlay golf vacation rentals are available in Chestertown?
StayAndPlay, as of 2026, features over 69 unique golf villas, golf hotels, golf resorts, and more in Chestertown. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.
By 2026, StayAndPlay has curated over 69 stunning properties in Chestertown, sourced from trusted platforms. Plan your next golf trip now.
For 2026, StayAndPlay provides access to over 69 premier golf accommodations in Chestertown. Find your ideal golf-retreat and play your best game with StayAndPlay.
