Explore Sleepy Hollow Golf Retreats
Apartment
- Chicago
- ·
- West Dundee
- 1.50 mi to center
10.0Exceptional
(26 Reviews)
1 Bedroom
1 Bath
2 Guests
425 ft²
Parking
Kitchen
Air Conditioner
Internet
US $243/Night
7 Nights - US $1,699
Apartment
- Chicago
- ·
- West Dundee
- 1.48 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
570.49 ft²
- Parking
View- Air Conditioner
- Internet
US $237/Night
7 Nights - US $1,659
Hotel
- Chicago
- ·
- West Dundee
- 1.90 mi to center
8.6Fabulous
(1042 Reviews)
1 Bath
Breakfast- Parking
Pool
Balcony/Terrace
US $104/Night
7 Nights - US $726
Apartment
- Chicago
- ·
- West Dundee
- 1.48 mi to center
10.0Exceptional
(22 Reviews)
1 Bedroom
1 Bath
2 Guests
575 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $266/Night
7 Nights - US $1,861
Apartment
- Chicago
- ·
- West Dundee
- 1.50 mi to center
9.8Exceptional
(22 Reviews)
1 Bedroom
1 Bath
2 Guests
419.79 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $200/Night
7 Nights - US $1,397
Apartment
- Chicago
- ·
- West Dundee
- 1.50 mi to center
10.0Exceptional
(20 Reviews)
1 Bedroom
1 Bath
2 Guests
425 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $238/Night
7 Nights - US $1,669
Apartment
- Chicago
- ·
- West Dundee
- 1.48 mi to center
10.0Exceptional
(19 Reviews)
1 Bedroom
1 Bath
2 Guests
575 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $266/Night
7 Nights - US $1,861
Apartment
- Chicago
- ·
- West Dundee
- 1.47 mi to center
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
575 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,839
Apartment
- Chicago
- ·
- West Dundee
- 1.50 mi to center
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
425 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $243/Night
7 Nights - US $1,699
Luxury Places to Stay in Sleepy Hollow
Over 62+ Luxury Places to Stay in or Near Sleepy Hollow
House
- Chicago
- ·
- West Dundee
- 0.57 mi to center
3 Bedrooms
2 Baths
8 Guests
1280.91 ft²
- Parking
- Internet
Child Friendly
Laundry
US $347/Night
7 Nights - US $2,428
Hotel
- Chicago
- ·
- West Dundee
- 1.51 mi to center
10.0Exceptional
(21 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $314/Night
7 Nights - US $2,195
New
Apartment
- Chicago
- ·
- West Dundee
- 1.45 mi to center
3 Bedrooms
1 Bath
4 Guests
355.21 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $275/Night
7 Nights - US $1,927
Apartment
- Chicago
- ·
- West Dundee
- 1.47 mi to center
9.8Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
575 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $263/Night
7 Nights - US $1,839
Apartment
- Chicago
- ·
- West Dundee
- 1.47 mi to center
9.4Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
570.49 ft²
- Parking
- View
- Air Conditioner
- Internet
US $256/Night
7 Nights - US $1,790
Apartment
- Chicago
- ·
- West Dundee
- 1.47 mi to center
9.8Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
570.49 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $256/Night
7 Nights - US $1,790
New
Apartment
- Chicago
- ·
- West Dundee
- 1.45 mi to center
2 Bedrooms
1 Bath
4 Guests
355.21 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $247/Night
7 Nights - US $1,727
Apartment
- Chicago
- ·
- West Dundee
- 1.50 mi to center
9.8Exceptional
(20 Reviews)
1 Bedroom
1 Bath
2 Guests
425 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $231/Night
7 Nights - US $1,620
Apartment
- Chicago
- ·
- West Dundee
- 1.51 mi to center
9.7Exceptional
(20 Reviews)
4 Bedrooms
1 Bath
2 Guests
376.74 ft²
- Parking
- Air Conditioner
- Internet
Security/Safety
US $230/Night
7 Nights - US $1,610
Top-Rated Villas with a Pool in Sleepy Hollow
Over 41+ Top-Rated Private Villas with a Pool in or Near Sleepy Hollow
Hotel
- Chicago
- ·
- West Dundee
- 1.90 mi to center
8.5Fabulous
(578 Reviews)
1 Bath
Private Pool
Oceanfront- Parking
- Pool
US $101/Night
7 Nights - US $705
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
10.0Exceptional
(1 Review)
3 Baths
12 Guests
1065 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $436/Night
7 Nights - US $3,050
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
10.0Exceptional
(1 Review)
2 Baths
8 Guests
710 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $293/Night
7 Nights - US $2,054
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
8.0Excellent
(1 Review)
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $138/Night
7 Nights - US $964
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
8.0Excellent
(1 Review)
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $134/Night
7 Nights - US $940
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
2.0Average
(1 Review)
2 Baths
8 Guests
710 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $314/Night
7 Nights - US $2,195
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
2.0Average
(1 Review)
1 Bath
4 Guests
355 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $146/Night
7 Nights - US $1,019
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
4 Bedrooms
4 Baths
16 Guests
1420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $652/Night
7 Nights - US $4,563
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
4 Bedrooms
4 Baths
16 Guests
1420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $646/Night
7 Nights - US $4,523
Pet-Friendly Villas in Sleepy Hollow
Over 11+ Pet-Friendly Private Villas in or Near Sleepy Hollow
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
3 Guests
420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $326/Night
7 Nights - US $2,281
Apartment
- Chicago
- ·
- West Dundee
- 1.48 mi to center
9.8Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
570.49 ft²
- Parking
- View
- Air Conditioner
- Internet
US $218/Night
7 Nights - US $1,529
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
2 Bedrooms
2 Baths
8 Guests
710 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $323/Night
7 Nights - US $2,258
Hotel
- Chicago
- ·
- West Dundee
- 1.95 mi to center
5.7Average
(226 Reviews)
2 Baths
355.21 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $199/Night
7 Nights - US $1,393
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
3 Guests
420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $302/Night
7 Nights - US $2,116
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
4 Guests
355 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $161/Night
7 Nights - US $1,129
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $149/Night
7 Nights - US $1,043
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $148/Night
7 Nights - US $1,035
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
3 Bedrooms
3 Baths
12 Guests
1065 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $439/Night
7 Nights - US $3,074
Large Private Villas in Sleepy Hollow
Over 9+ Large Villas in or Near Sleepy Hollow for Groups and Families
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
4 Bedrooms
4 Baths
16 Guests
1420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $633/Night
7 Nights - US $4,430
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
4 Bedrooms
4 Baths
16 Guests
1420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $626/Night
7 Nights - US $4,383
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
4 Bedrooms
4 Baths
16 Guests
1420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $587/Night
7 Nights - US $4,108
House
- Chicago
- ·
- West Dundee
- 0.76 mi to center
4 Bedrooms
2 Baths
90 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $521/Night
7 Nights - US $3,644
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
3 Bedrooms
3 Baths
12 Guests
1065 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $488/Night
7 Nights - US $3,418
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
3 Bedrooms
3 Baths
12 Guests
1065 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $484/Night
7 Nights - US $3,387
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
3 Bedrooms
3 Baths
12 Guests
1065 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $474/Night
7 Nights - US $3,316
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
3 Bedrooms
3 Baths
12 Guests
1065 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $470/Night
7 Nights - US $3,292
Other
- Chicago
- ·
- Sleepy Hollow
- 1.14 mi to center
5.0Average
(3 Reviews)
6 Bedrooms
6 Baths
16 Guests
5500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $782/Night
7 Nights - US $5,474
Wheelchair Accessible Holiday Homes in Sleepy Hollow
Over 18+ Wheelchair Accessible Villas and Holiday Homes in or Near Sleepy Hollow
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
2 Bedrooms
2 Baths
8 Guests
710 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $326/Night
7 Nights - US $2,281
Hotel
- Chicago
- ·
- West Dundee
- 1.91 mi to center
6.6Good
(672 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $77/Night
7 Nights - US $541
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
2 Bedrooms
2 Baths
8 Guests
710 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $316/Night
7 Nights - US $2,211
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
4 Guests
355 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $162/Night
7 Nights - US $1,137
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $153/Night
7 Nights - US $1,074
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $150/Night
7 Nights - US $1,051
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $146/Night
7 Nights - US $1,019
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $143/Night
7 Nights - US $1,004
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
2 Baths
8 Guests
710 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $290/Night
7 Nights - US $2,031
Sleepy Hollow Villas, Airbnb and Holiday Homes Under $200
Over 12+ Sleepy Hollow Private Villas, Airbnb and Holiday Homes Under $200
Apartment
- Chicago
- ·
- West Dundee
- 1.69 mi to center
1 Bedroom
1 Bath
2 Guests
764 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $118/Night
7 Nights - US $825
New
Apartment
- Chicago
- ·
- West Dundee
- 1.69 mi to center
2 Bedrooms
2 Baths
4 Guests
1281 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $140/Night
7 Nights - US $982
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bath
4 Guests
355 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $158/Night
7 Nights - US $1,105
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bath
4 Guests
355 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $157/Night
7 Nights - US $1,097
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $149/Night
7 Nights - US $1,043
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bath
4 Guests
355 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $146/Night
7 Nights - US $1,020
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $144/Night
7 Nights - US $1,011
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $135/Night
7 Nights - US $948
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bath
2 Guests
334 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $133/Night
7 Nights - US $933
Instantly Bookable Villa Rentals in Sleepy Hollow
Over 4+ Instantly Bookable Private Villas in or Near Sleepy Hollow
Resort
- Chicago
- ·
- West Dundee
- 1.91 mi to center
4 Baths
16 Guests
1420 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $581/Night
7 Nights - US $4,069
Apartment
- Chicago
- ·
- West Dundee
- 2.06 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
2066 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $125/Night
7 Nights - US $876
Apartment
- Chicago
- ·
- West Dundee
- 1.93 mi to center
1 Bedroom
1 Bath
3 Guests
2066 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,332
House
- Chicago
- ·
- West Dundee
- 1.91 mi to center
1 Bedroom
1 Bath
3 Guests
420 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $289/Night
7 Nights - US $2,025
Book a Last Minute Place to Stay in Sleepy Hollow
About Sleepy Hollow Vacation Rentals
Explore over 71 golf accommodation rentals in Sleepy Hollow. 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 Sleepy Hollow.
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 Sleepy Hollow. 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 Sleepy Hollow offer approximately 706.12 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 Sleepy Hollow typically ranges around US $277.
StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in Sleepy Hollow. 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 Sleepy Hollow
| Type | Count |
|---|---|
| Vacation Homes | 26 |
| Holiday Apartments | 24 |
| Others | 1 |
Use these Quick Filters to Find a Vacation Rental in Sleepy Hollow
★ 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 Sleepy Hollow.
Weather in Sleepy Hollow, IL
View the weather forecast for Sleepy Hollow before booking your Sleepy Hollow 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 Sleepy Hollow Guest Reviews Local Attractions
StayAndPlay offers a diverse selection of the top golf villas, golf hotels, and other golf retreats around the world. Sleepy Hollow Guest Reviews Find the Best Golf Experiences & Activities for Your Golf Trip
Frequently Asked Questions About Sleepy Hollow?
What are the best golf resorts, luxury villas, and vacation rentals in Sleepy Hollow?
Looking for a place to stay in Sleepy Hollow? 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:
- Best Western Plus Elgin - Chicago
- 124 Lofts #3 - Downtown Dundee - Walk to Dining
- Kildahl House - Boutique Farmhouse Suite #3
- Sinclair Suites
- 124 Lofts #2 - Downtown Dundee - Walk to Dining
- Kildahl House - Boutique Farmhouse Suite #4
- Kildahl House - Boutique Farmhouse Suite #2
- 124 Lofts #1 - Downtown Dundee - Walk to Dining
- Kildahl House - Boutique Farmhouse Suite #3
- 124 Lofts - Downtown Dundee - Walk to Dining
What are the top-rated golf retreats in Sleepy Hollow for family stays?
Searching for a family-friendly golf retreat in Sleepy Hollow? Explore these top-rated options, each loved by families and groups who have stayed in Sleepy Hollow:
How many StayAndPlay golf vacation rentals are available in Sleepy Hollow?
StayAndPlay, as of 2026, features over 71 unique golf villas, golf hotels, golf resorts, and more in Sleepy Hollow. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.
By 2026, StayAndPlay has curated over 71 stunning properties in Sleepy Hollow, sourced from trusted platforms. Plan your next golf trip now.
For 2026, StayAndPlay provides access to over 71 premier golf accommodations in Sleepy Hollow. Find your ideal golf-retreat and play your best game with StayAndPlay.
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