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Rolling Prairie Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Rolling Prairie

The Neighborhood Hotel - Grand Beach
3 bedrooms, premium bedding, memory-foam beds, blackout curtains
The Neighborhood Hotel - Grand Beach
4.0 star property
9.6 out of 10, Exceptional, (62)
"Absolutely perfect, we loved every bit of our stay!"
The Neighborhood Hotel - Grand Beach
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Exterior
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
9.6 out of 10, Exceptional, (117)
"I stayed here with a large group of friends. It's a beautiful property, it fit our group perfectly. Fun location with plenty of great things to do nearby. "
Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
Outdoor spa tub
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
9.4 out of 10, Exceptional, (103)
"Our family spent the holiday at this incredible house and everything was perfect. We would definitely stay here again and highly recommend it. "
Juniper Presents: Lakefront Getaway and Outdoor Living Redefined
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Pool
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
9.6 out of 10, Exceptional, (236)
"We enjoyed our stay. Everything was picturesque and would definitely recommend staying here."
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
Outdoor dining
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
10.0 out of 10, Exceptional, (78)
"Overall wonderful experience. Mary was so communicative and helpful. The house was beautiful and the perfect place for a long weekend with friends. Great outdoor area for gathering! Can’t recommend this place enough, we will definitely be back! "
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
TV, fireplace, books, stereo
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
8.6 out of 10, Excellent, (87)
"Great house, beautiful view, very clean"
View of the lake from 2 decks in this 6BR Lake Shore Dr home, steps to the beach
Sunset Dunes Vacation Villas
Private kitchenette
Sunset Dunes Vacation Villas
3.0 star property
9.6 out of 10, Exceptional, (11)
"This is an attractive, comfortable, well-maintained, and conveniently located rental. We enjoyed our stay and would stay here again."
Sunset Dunes Vacation Villas
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
A heated pool
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
10.0 out of 10, Exceptional, (202)
"great stay"
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Property grounds
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
9.4 out of 10, Exceptional, (121)
"It was an amazing place! Super clean and cozy."
The price is HK$972
HK$1,873 total
includes taxes & fees
20 Oct - 21 Oct
BEACHFRONT/HOT TUB/STEAM ROOM/MASSAGE CHAIR/PINBALL/BIKES/KAYAKS/PADDLEBOARDS.
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn
Outdoor spa tub
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn
2.0 star property
10.0 out of 10, Exceptional, (27)
"House was perfect for our multi family family vacation! Amenities were wonderful and its clear that Tim is passionate about hosting a wonderful saty for all his guests! "
Newly renovated, 7700 Sq. Ft, 8BR, 7BTH, Heated Pool, Hot Tub, Arcade Game Barn
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Outdoor pool, a heated pool
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
9.2 out of 10, Wonderful, (68)
"We have stayed at this property 7x and it was another great experience. Peaceful and quiet setting and with the hot weather, the pool was used extensively. Walking distance to everything and the neighborhood is perfect for walking our dog. "
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!
Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK
Outdoor spa tub
Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK
9.6 out of 10, Exceptional, (45)
"Liked the location, hot tub was great.Walked to the zoo."
The price is HK$771
HK$2,556 total
includes taxes & fees
22 Oct - 23 Oct
Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
Interior
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
9.8 out of 10, Exceptional, (148)
"Amazing house for a large group of friends!"
Lifetime Memories*Big Beach Front House*Fire Place/Pit*Free WiFi*Paddle Boards
Sweet Stay By-The-Lake in Michigan City with AC, WiFi
Fridge, microwave, oven, stovetop
Sweet Stay By-The-Lake in Michigan City with AC, WiFi
2.0 star property
9.6 out of 10, Exceptional, (25)
"Cute cottage, close to the beach. It was clean and the owners were very friendly and helpful!"
Sweet Stay By-The-Lake in Michigan City with AC, WiFi
Red Zen | HotTub-all yr | Firepit | Grill | DogsOK
Beach
Red Zen | HotTub-all yr | Firepit | Grill | DogsOK
9.6 out of 10, Exceptional, (34)
"We had an amazing time! Enjoyed every part of the house "
Red Zen | HotTub-all yr | Firepit | Grill | DogsOK
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
On the beach, sun-loungers
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
9.6 out of 10, Exceptional, (327)
"Wonderful fun property. Beautiful views and close to everything. "
BEACHFRONT /HOTTUB/STEAM ROOM/GAME ROOM/JACUZZI/PETS/MASSAGE CHAIR/KAYAKS/BIKES
Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.
Beach nearby
Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.
9.4 out of 10, Exceptional, (12)
"Very nice very convenient would stay again."
Beach house with Private Heated Pool, Jacuzzi, Firepit. Steps to beach and park.
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views
Beach
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views
9.6 out of 10, Exceptional, (73)
"Good location to the beach. Property was small and dated but clean and provided what we needed for a short weekend. "
The price is HK$3,417
HK$3,966 total
includes taxes & fees
3 Nov - 4 Nov
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
Terrace/patio
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
10.0 out of 10, Exceptional, (181)
"Great house for our family! It was clean and spacious and very convenient to everything fun in New Buffalo!"
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Outdoor pool
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
9.6 out of 10, Exceptional, (48)
"The house was great and had everything you would need. The community was amazing, so much for the kids to do. "
The price is HK$1,393
HK$3,277 total
includes taxes & fees
20 Oct - 21 Oct
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Rolling Prairie Hotel Reviews

Doubletree Hotel South Bend

Doubletree Hotel South Bend

10/10 Excellent
"Hotel staff were great! Very friendly and helpful. The only thing I wasn’t pleased with was $18 breakfast buffet that was not worth the price. It’s the same food you get at hotels offering free breakfast. The hotel was clean, my overall experience was great! I would definitely stay there again "
Tara 3-night trip
Posted 1 day ago
Doubletree Hotel South Bend

Find out more about Rolling Prairie

Search for holiday rentals in Rolling Prairie on Expedia! You can easily find your home rentals, villas, holiday apartments in Rolling Prairie using one of the methods below:

  • View our selection of featured holiday rentals in Rolling Prairie
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  • Enter your travel dates to view the best deals on holiday rentals in Rolling Prairie while they last

Look no further and take a look at our great range of rental properties in Rolling Prairie!

Frequently asked questions

Are there holiday rentals in Rolling Prairie?

Yes, there are holiday rentals close to the most popular sights in Rolling Prairie, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rolling Prairie has to offer?

Big Family House 5 Minutes from Lake Michigan/Blue Chip Casino/Brewery/Wineries!: This holiday home rental outside of Rolling Prairie is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Rolling Prairie?

Saugany Lake and Silver Lake are a couple of lovely local spots to get outside and enjoy nature. While here, Rolling Prairie Branch and Hunt Lake are other places worth a visit.

What’s a holiday rental in Rolling Prairie like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rolling Prairie. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family gatherings.