Entire condo

🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan!

Photo gallery for 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan!

An aerial view of a property with a swimming pool surrounded by trees, a clear view of the sea, and a well-maintained lawn. - 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! (South Haven)
A spacious living room with a fireplace, a television, and a dining area with wooden chairs. - 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! (South Haven)
A white, curved two-story house with a covered patio, a small garden, and a lawn. - 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! (South Haven)
A tennis court complex surrounded by dense trees. - 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! (South Haven)
A coastal property with a paved walkway along the beach, a stone wall, and a house with a view of the sea. - 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! (South Haven)
🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! provides amenities, such as a playground and laundry facilities. Stay connected with free in-room WiFi.

Reviews

9.4 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 6804 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Add dates for prices

About this property

🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan!

  • Gateway 50 is a luxurious two-bedroom, two-bathroom villa offering spacious accommodations, thoughtful amenities, and a comfortable setting for a relaxing stay at Sleepy Hollow Beach Resort. Designed to sleep up to six guests, this inviting villa provides plenty of room for families or friends to gather and enjoy their Lake Michigan getaway.

    The open-concept living, dining, and kitchen area creates a bright and welcoming central gathering space, perfect for relaxing after a day at the beach or enjoying time together. A gas fireplace adds warmth and ambiance to the living area, while a queen-size sleeper sofa provides additional sleeping accommodations without sacrificing the villa’s comfortable and spacious feel.

    The primary bedroom features a luxurious king-size bed and private bathroom, creating a peaceful retreat at the end of the day. The second bedroom offers both a full-size bed and a twin-size bed, providing flexible sleeping arrangements for children or additional guests. A second full bathroom adds convenience and privacy for everyone staying in the villa.

    Gateway 50 is equipped with central air conditioning for added comfort throughout the warmer summer months. A washer and dryer are conveniently located in the basement, which is accessed through an exterior entrance on the east side of the building.

    Guests also enjoy access to Sleepy Hollow Beach Resort’s exceptional amenities, including 1,000 feet of private Lake Michigan beach, an Olympic-sized heated swimming pool, tennis and pickleball courts, beautifully maintained grounds, and countless opportunities for recreation and relaxation. Whether spending the day along the shoreline, enjoying the resort’s many activities, or simply unwinding together, Gateway 50 offers a wonderful combination of luxury, comfort, and classic Sleepy Hollow charm.

    Gateway 50 rents on Fridays.

Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Shower
  • Towels provided

Living spaces

  • Fireplace

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Charcoal grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Location highlights

  • On a lake

Things to do

  • Bicycles
  • Heated pool
  • Tennis
  • Basketball nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Bicycles
  • Unit size: 804 square feet

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Policies

Check-in

Check-in time starts at 4:30 PM
Contactless check-in and check-out are available

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

Events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events are allowed on site
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Located on the beach, this condo is in Downtown, a neighbourhood in South Haven. The area's natural beauty can be seen at Lake Michigan and Pilgrim Haven Natural Area, while Michigan Maritime Museum and Liberty Hyde Bailey Museum & Gardens are cultural highlights. South Haven Center for the Arts and The Fun Park are also worth visiting. Take the opportunity to explore the area for water adventures such as swimming. Visit our South Haven travel guide
View more Condo rentals in South Haven
Map
South Haven, MI

What's nearby

  • A lighthouse at sunset with people on a pier.
    North Beach
    11 min walk - 0.6 miles
  • A pier with a lighthouse, a kite surfer, and a clear sky.
    South Beach
    13 min walk - 0.7 miles
  • South Haven Center for the Arts
    2 min walk - 0.1 miles
  • Warner Vineyards
    3 min walk - 0.2 miles
  • Southside Municipal Marina
    3 min walk - 0.2 miles

Getting around

  • Bangor Station
    20 min drive
  • Kalamazoo, MI (AZO-Kalamazoo-Battle Creek Intl.)
    61 min drive

Restaurants

  • South Beach Cafe
    10 min walk
  • Culver's
    2 min drive
  • McDonald's
    2 min drive
  • Burger King
    14 min walk
  • Clementine's
    1 min walk

Frequently asked questions

Is 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! pet-friendly?

No, pets are not allowed at this property.

How much is parking at 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan!?

On-site parking is available at the property.

What time is check-in at 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan!?

Check-in begins at 4:30 PM.

What time is check-out at 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan!?

Checkout is at 11:00 AM.

Where is 🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! located?

Located in Downtown, this condo building is within 1 mi (2 km) of South Haven Center for the Arts and Lake Michigan. Southside Municipal Marina and Warner Vineyards are also within 5 minutes.

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Reviews

🏖️Sleepy Hollow Beach Resort, Gateway 50 – Family Fun on Lake Michigan! Reviews

9.4

Exceptional

9.4

Cleanliness

10

Location

8.0

Property conditions & facilities
Rating 10 - Excellent. 21 out of 27 reviews
Rating 8 - Good. 3 out of 27 reviews
Rating 6 - Okay. 2 out of 27 reviews
Rating 4 - Poor. 1 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

Reviews

Verified review

6/10 Okay

Liked: Cleanliness, property conditions & facilities, communication
Gatway 50 could be a nicer experience. NEG: Master bathroom needs deep cleaning, especially shower (black dirt, mold ?!), sticky and dirty handles in both bathrooms and kitchen, dirty doors. Some furniture are worn out and/or dirty and stained. Dirty washcloth on the sink in the master bath! I got the message that there is no fireplace, but there's a fireplace in the unit and it was on! All rugs were slippery. Hard and very uncomfortable pillows. Positive: Big unit (2 bedrooms and 2 bathrooms), enough space for four people, a lot of plates and glasses, clean sheets. Nice private beach and nice place for families with children. A lot of space for outside recreation and playing sports.
Stayed 3 nights in Aug 2025
From a partner site

10/10 Excellent

50 is nifty

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a great time at Sleepy Hollow. While we don’t have little kids or teens anymore, this is a perfect spot for families to come together. We enjoyed the pool, the adult activities, the beach, pickleball and the friendly staff.
From a partner site

10/10 Excellent

Another magical stay in Sleepy Hollow

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Sleepy Hollow is a place where our family can relax and enjoy so many activities from the pool to the beach, basketball, arts and crafts, tennis lessons, badminton, bike riding, etc... My kids feel such a sense of independence as they are able to run free on the beautiful and safe gated grounds. Unit 50 is a special one.
From a partner site

10/10 Excellent

Gateway 50

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Perfect cottage in a beautiful resort.
From a partner site

10/10 Excellent

Great Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very nice stay, everything was as it stated and clean.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Resort!

We had a wonderful stay at Sleepy Hollow. The unit was very clean and comfortable. Our kids age 5 and 3 loved the private beach, heated pool, the basketball courts, and riding their bikes around the property. The daily kids activities at the office were a plus, too! We hope we come back again next year.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent, thank you!
Stayed 3 nights in Jun 2025
From a partner site

8/10 Good

Beautiful Resort, Perfect for Kids

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had an overall very good stay in Gateway 50. The resort property is beautiful, and our daughters loved the pool and beach (though the pool can be cold). Management was always responsive and professional. The main area for improvement would be cleaning of the cottage. Floors are not mopped, and we ended up cleaning the floors and under rugs ourselves. Despite this, we'll likely return next year.
From a partner site

8/10 Good

End of summer get away

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The unit was very nice. I would like to have a full/queen-size bed in the second bedroom rather than two twins. We came mostly to use the "heated" pool. The heater was not working, and in fact, a new one was being installed. The pool was very cold, which limited our time in the water. Our friends never went in the pool because it was too cold. It was very disappointing.
From a partner site

10/10 Excellent

Chamber Music Three Day Weekend

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a WONDERFUL EXPERIENCE!! Gateway 50 is a great place to stay. Everything is very clean and organized. Everything in the kitchen was extra clean and very nice. The beds were very comfortable and furnished with high-end bedding. The bathrooms were sparkling clean, the towels were soft and luxurious. The whole place was bright and light with beautiful views of the woods. It seemed quiet and private, even though other condos were nearby. Our group would love to stay there twice a year for Chamber Music forever!! Thank you so much, owners, for making such a nice place available to us, we appreciate it very much.
From a partner site

4/10 Poor

Aug 10-17

Rating Details: The property manager was more than helpful. The vacation rental was somewhat dirty. I was happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: I rented 2 units Gateway 50 and 37A. 50 was ok but we were very unhappy with 37A.Reasons:-only 1 key when we arrived(got more on Monday)-noticed ants on floor(went to store and bought traps and by Wed. was in control)-bed cover on 1 twin bed was dirty (tracked down housekeeping and asked them to change it-shower door was off its track (got mentance to repair on Monday- foul oder in kitchen near sink, finally figured out that it was under lip of sink and had to live with it-unit is very noisy from people in 37A-
From a partner site

10/10 Excellent

Great getaway spot!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We stayed at Sleepy Hollow for the week of our wedding/honeymoon last month, and it was a perfect getaway spot! The customer service was over the top - very quick to respond to any questions we had, extremely flexible and understanding to any changes we needed! There are great amenities and community activities, and the property was kept very nice. The private beach was quiet, nicely maintained and they even provided some lounge chairs. This spot is conveniently located just north of town. We will absolutely be back!
From a partner site

10/10 Excellent

Perfect vacation rental!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved staying at Gateway 50. It was clean and well stocked. Enjoyed sitting on the back deck. No need to bring a book - they had a great selection of the latest titles. I only wish that the date we could come in 2023 was available.
From a partner site

10/10 Excellent

Enjoyed our stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We spent a couple of days this Fall, and really enjoyed our stay.The condo was very comfortable and had everything we needed. We loved sitting on the back patio in the early evening, the curved Art Deco vibe of the patio was very cool. And then when it cooled off we had the nice gas fireplace inside. We plan to come back!
Stayed 2 nights in Sep 2021
From a partner site

8/10 Good

Loved the property, but wished it was cleaner.

Rating Details: The property manager was very helpful. The vacation rental was somewhat dirty. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We liked the property, however, it was not clean. When we opened up the pull out sofa, it had dirty linens on it. In addition, the coffee pot had a moldy filter in it and the floor had not been swept.
From a partner site

10/10 Excellent

Michigan trip

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Family trip to Lake Michigan. Great place to stay with family. Everything was perfect. Hope to be back next year!!
From a partner site

6/10 Okay

August 11 2018 Review of Cabin

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: Our experience was mixed: some good, some bad. The pull-out sofa bed was rusty, spotting the sheets. Maintenance corrected the problem the first day. The cabin was roomy, well furnished and otherwise clean.
Archival

10/10 Excellent

Wonderful family vacation!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My family of 5 had a wonderful time at sleepy hollow in unit 50. The beach was a bit small due to the swelling of the lake, but my kids did not mind one bit!
Archival

10/10 Excellent

Happy Time

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great vacation. The grounds and trees and flowers were beautiful. It is an ideal place for children. It is very relaxing time for the parents. The patio of this unit was great. We gathered there often to plan our day. Over all we had a great vacation.
Archival

10/10 Excellent

Sleepy Hollow Vacation

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great place for multi-family trip!
Archival

10/10 Excellent

Reliving Memories @ Sleepy Hollow

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was more than happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We spent a week at Sleepy Hollow with our children and grandchildren because it is the place where we spent summer vacations when our children were growing up and we all love it. The only problem was a refrigerator that was not working properly and it took almost the entire week to fix. Fortunately we had two units so we were able to keep the food next door, but it was inconvenient. However, the owners of the unit did offer a generous rebate on our rental.
Archival

10/10 Excellent

Can't wait to return!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had such a great time and enjoyed the pool, beach and took advantage of the kids activities! Can't wait to return to Sleepy Hollow!
Archival

10/10 Excellent

Relaxing Family Vacation Getaway

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had been coming to sleepy hollow for years. After skipping it last year to address our kids' request for 'something different' we heard something different from the kids ... 'We miss sleepy hollow!' So back we were this year and everyone enjoyed themselves!
Archival

10/10 Excellent

Swick Review

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great. The only misgiving we had is that we think it was too expensive. For a 2 bedroom it was pretty much
Archival

10/10 Excellent

South Haven

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: great