168+ Golf Villas, Golf Cabins, Golf Hotels, Golf Resort Rentals, and other Private Golf Retreats in Chesapeake |
  1. USA
  2. Virginia
  3. Norfolk - Virginia Beach
  4. Chesapeake

Explore Chesapeake Golf Retreats

About Chesapeake Vacation Rentals

Explore over 168 golf accommodation rentals in Chesapeake. 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 Chesapeake.

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 Chesapeake. 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 Chesapeake offer approximately 448.85 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 Chesapeake typically ranges around US $190.

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

Type Count
Vacation Homes 59
Holiday Apartments 20
Cottages 2
Others 1
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Chesapeake

★ 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 Chesapeake.

Weather in Chesapeake, VA

View the weather forecast for Chesapeake before booking your Chesapeake Vacation Rentals to confirm your best time to go.

December - February
High 62°F       Low 35°F
March - May
High 76°F       Low 41°F
June - August
High 90°F       Low 69°F
September - November
High 80°F       Low 44°F

Activities Chesapeake Guest Reviews Local Attractions

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


Greenbrier Mall
Chesapeake Square Mall
Great Dismal Swamp National Wildlife Refuge
Chesapeake Conference Center
Chesapeake Veterans' Memorial
Chesapeake City Park
Chesapeake City Hall
Chesapeake Arboretum
Chesapeake Golf Club
Chesapeake Central Library
Jillian's Billiards
Portlock Galleries at SoNo
Oak Grove Lake Park
Float First
Cahoon Plantation Golf Course
Adventure Kayak Tours Day Tours
Lake Drummond
Chesapeake Regional Medical Center
Virginia Beach Boardwalk
Naval Station Norfolk

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Great Bridge East 535 Properties
Cahoon Plantation Golf Course 170 Properties
Chesapeake City County 166 Properties
Deep Creek South 165 Properties
Portlock Galleries at SoNo 154 Properties
Chesapeake Veterans' Memorial 154 Properties
Great Bridge 137 Properties
Greenbrier West 82 Properties
South Norfolk 79 Properties
Jolliff 45 Properties
Greenbrier East 38 Properties
Western Branch North 29 Properties

Frequently Asked Questions About Chesapeake?

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

Looking for a place to stay in Chesapeake? 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 Chesapeake?

Find exceptional golf retreats with private pools near Chesapeake 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 Chesapeake for family stays?

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

How many StayAndPlay golf vacation rentals are available in Chesapeake?

StayAndPlay, as of 2025, features over 168 unique golf villas, golf hotels, golf resorts, and more in Chesapeake. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.

By 2025, StayAndPlay has curated over 168 stunning properties in Chesapeake, sourced from trusted platforms. Plan your next golf trip now.

For 2025, StayAndPlay provides access to over 168 premier golf accommodations in Chesapeake. Find your ideal golf-retreat and play your best game with StayAndPlay.

Nearby Neighborhood (7) 
Neighborhood Property Count
Greenbrier East Golf Rental Cottages and Golf Getaways in Chesapeake, Virginia 38
Western Branch North Golf Rental Cottages and Golf Getaways in Chesapeake, Virginia 29
Greenbrier West Golf Rental Cottages and Golf Getaways in Chesapeake, Virginia 82
Great Bridge Golf Rental Cottages and Golf Getaways in Chesapeake, Virginia 137
Deep Creek South Golf Rental Cottages and Golf Getaways in Chesapeake, Virginia 165
Churchland Golf Rental Cottages and Golf Getaways in Chesapeake, Virginia 73
Great Bridge East Golf Rental Cottages and Golf Getaways in Chesapeake, Virginia 535

People Also Ask

There are 74 hotels in Chesapeake and 79 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Chesapeake