Photo by Kristy Burton

Search Rolling Prairie Cottages

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Cottages in Rolling Prairie

The Hideaway House - Private, Peaceful, Cozy
Beach

The Hideaway House - Private, Peaceful, Cozy

10.0 out of 10, Exceptional, (9)
"Communication with management made our minds at ease when booking our stay. House was very clean, peaceful settings. The Beach was absolutely beautiful. Our family with definitely stay again. "
The Hideaway House - Private, Peaceful, Cozy
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Fridge, microwave, oven, stovetop

Brand New Cottage Walkable to All Downtown Michigan City & Beach!

10.0 out of 10, Exceptional, (5)
"We really enjoyed our stay. The home was very comfortable and close to downtown. We were minutes away from the mall, casino and breweries. The owner was very responsive to all our needs. We would definitely stay here again. "
$324 nightly
The price is $362
Aug 18 - Aug 19
Total includes taxes and fees
Brand New Cottage Walkable to All Downtown Michigan City & Beach!
Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries
Outdoor dining

Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries

10.0 out of 10, Exceptional, (27)
"Wonderful cottage, perfect for our friends weekend. Great hospitality. "
Blue Haven Cottage - New Buffalo Beach, near Wineries & Breweries
Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration
Smart TV, fireplace, DVD player

Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration

9.6 out of 10, Exceptional, (93)
"The house is bright and sunny, warm and inviting. Even after it snowed and was cold outside. We enjoyed all the sunlight. The thoughtful details and amenities for everything we needed. We’re looking forward to coming again in the summer. "
Grand Beach Getaway – Hot Tub, Fire Pit & walk to the Lake | Weekend Restoration
Treehouse Bungalow- Quaint and Cozy Getaway!
Beach nearby

Treehouse Bungalow- Quaint and Cozy Getaway!

8.8 out of 10, Excellent, (49)
"Unsafe parking, uncomfortable couch and beds. We didn’t stay the night due to the poor conditions."
$393 nightly
The price is $440
Aug 11 - Aug 12
Total includes taxes and fees
Treehouse Bungalow- Quaint and Cozy Getaway!
Surf Cottage - Hot Tub - 3 bedroom 2.5 bath in Harbert - near Warren Dunes Beach
Fridge, microwave, oven, stovetop

Surf Cottage - Hot Tub - 3 bedroom 2.5 bath in Harbert - near Warren Dunes Beach

9.8 out of 10, Exceptional, (7)
"Had a great stay at the property the house was very clean and appears as listed. The owners were vey nice and responsive to any outreach we made."
Surf Cottage - Hot Tub - 3 bedroom 2.5 bath in Harbert - near Warren Dunes Beach
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, (42)
"House was immaculately clean, well appointed & extremely comfortable. By far, our best rental at Beachwalk Resort!"
$507 nightly
The price is $568
Sep 3 - Sep 4
Total includes taxes and fees
Sweet Inn Coach House near beautiful beach on Lake Michigan in Beachwalk
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Property grounds

Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5

9.8 out of 10, Exceptional, (190)
"This was a great little get away for our 21st Anniversary. Very clean and neat. Everything we needed!"
Adorable Cottage New Buffalo, Mi. Near Grand Beach.1 Bedroom, Sleeps 5
Crestview Cottage - Hot Tub - 3 Bedroom 2 Bath - 3 Minutes to Beach
Interior

Crestview Cottage - Hot Tub - 3 Bedroom 2 Bath - 3 Minutes to Beach

10.0 out of 10, Exceptional, (5)
"Fabulous! Beautiful home and great location!We will stay again "
$554 nightly
The price is $578
Aug 14 - Aug 15
Total includes taxes and fees
Crestview Cottage - Hot Tub - 3 Bedroom 2 Bath - 3 Minutes to Beach
Historic property is a comfortable, peaceful, and safe place to stay.
Property grounds

Historic property is a comfortable, peaceful, and safe place to stay.

10.0 out of 10, Exceptional, (76)
"Was a great little cottage provide us us with everything we needed for our short stay for the Notre Dame game"
Historic property is a comfortable, peaceful, and safe place to stay.
UNION PIER HOME WITH PRIVATE HEATED POOL!
A heated pool

UNION PIER HOME WITH PRIVATE HEATED POOL!

9.0 out of 10, Wonderful, (16)
"Clean, convienent to New Buffalo and Indian Oaks. Great location and nice property"
UNION PIER HOME WITH PRIVATE HEATED POOL!
Private Beach Steps to the Beach.
Terrace/patio

Private Beach Steps to the Beach.

10.0 out of 10, Exceptional, (91)
"Such a cute house and John was a great host!"
$1,097 nightly
The price is $1,097
Aug 31 - Sep 1
Total includes taxes and fees
Private Beach Steps to the Beach.
Cozy Michigan City Cottage #1
Interior

Cozy Michigan City Cottage #1

9.6 out of 10, Exceptional, (21)
"We really enjoyed our stay. The cottage is very nice, very clean, recently upgraded. Susan and Tom were very responsive and provided helpful information We are planning to come back"
Cozy Michigan City Cottage #1
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom
Interior

Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom

8.6 out of 10, Excellent, (17)
"The house is clean, comfortable and relaxing. The pool was clean and so very lovely in the last days of summer."
Charming cottage with fast WiFi, fire pit, above-ground pool, & huge sunroom
Beautiful Private Cottage, Sleeps 6, Walk to Beach
Property grounds

Beautiful Private Cottage, Sleeps 6, Walk to Beach

10.0 out of 10, Exceptional, (22)
"The house had everything we needed and is in a great location for the beach, shops, and other activities! The yard is beautiful and our teenagers spent a lot of time out there in the evenings. We would definitely stay again. "
Beautiful Private Cottage, Sleeps 6, Walk to Beach
2-3 nt min Steps to McKinley Beach walk to all in Union Pier Fire Pit
Beach

2-3 nt min Steps to McKinley Beach walk to all in Union Pier Fire Pit

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay! The cottage was cute and comfortable. It was so nice and convenient to be so close to the beach!!"
2-3 nt min Steps to McKinley Beach walk to all in Union Pier Fire Pit
Glamping Getaway
Property grounds

Glamping Getaway

9.2 out of 10, Wonderful, (14)
"Peaceful place, very accommodating! Thank you for everything!"
Glamping Getaway
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Fridge, microwave, oven, stovetop

Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach

10.0 out of 10, Exceptional, (41)
"Adorable cottage and perfect for a girls weekend. Comfortable furnishings and really well kept! Would love to book again!"
Modern Cottage "M" Luxury home w/hot tub, community pool-walk to town & beach
Quiet remodeled cottage near downtown Sawyer - private deck, gas grill, firepit
Exterior

Quiet remodeled cottage near downtown Sawyer - private deck, gas grill, firepit

9.8 out of 10, Exceptional, (8)
"We enjoyed our time with family at the tower hill cottage: quick walk to the beach, room for game playing. We loved the back yard!"
Quiet remodeled cottage near downtown Sawyer - private deck, gas grill, firepit
Cottage w/Firepit & Fireplace. Walk to Beach | Hidden Gem in Union Pier
Beach nearby, beach towels

Cottage w/Firepit & Fireplace. Walk to Beach | Hidden Gem in Union Pier

9.8 out of 10, Exceptional, (36)
"Perfect location for a guys weekend. Golf, Micro Breweries, bourbon, bonfires and NCAA football. Will stay here again. "
Cottage w/Firepit & Fireplace. Walk to Beach | Hidden Gem in Union Pier
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Rolling Prairie Hotel Reviews

Wingate by Wyndham South Bend/Notre Dame

Wingate by Wyndham South Bend/Notre Dame

10/10 Excellent
"I and my family loved this property, it was really nice on the inside, the outside was okay. Everything was clean in our rooms, and the breakfast in the morning was great also. We will be back !!"
AnnTina 1-night trip
Posted 23 hours ago
Wingate by Wyndham South Bend/Notre Dame