Vacation rentals in Rolling Prairie

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Top-rated vacation rentals in Rolling Prairie

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost

Condo in St. Joseph

4.86 out of 5 average rating, 7 reviews

Surf Loft – Vacay Dwntn nr Beach, Park, Amenities

AngelaRating, 5 stars3 months ago
Can’t say enough good about the place and host! Had a beautiful weekend in St Joseph. The location is perfect. Walked everywhere! Highly recommend!! Thanks Juniper Holiday & Home!!!
Superhost

Cottage in Lakeside

4.79 out of 5 average rating, 48 reviews

Fun Duplex 200Yds 2 Lake Michigan-Pool/HotTub&More

MichaelRating, 5 stars3 months ago
This made for an excellent airBnB for my family staying for a wedding in the area. Frank was responsive and communicated well with FAQs. Thank you!
Guest favorite

Cottage in New Buffalo

4.96 out of 5 average rating, 183 reviews

Voted #1 Family Getaway In SW MI for 2019-2024

NicoleRating, 5 stars5 months ago
Great property for two families with small kids! The listing has everything you need, including pack and plays & a highchair. Dana was super responsive and laid out easy instructions + local recommendations. S’mores on our last night was a big hit!
Guest favorite

Cottage in Union Pier

4.98 out of 5 average rating, 212 reviews

"The Pines" in Union Pier: Year-round getaway

KiraRating, 5 stars1 month ago
We had an amazing time at John’s home! It was so incredibly cozy and comfortable, and in a great location. It was so dreamy sitting by the fire every day. There was plenty of space for our family and family friends, and we were pleasantly surprised by how kid friendly it was. W would love to come back another time!
Superhost

Apartment in New Buffalo

4.9 out of 5 average rating, 21 reviews

Charming 2BR/2BA Cottage with Full Kitchen & Patio

MaryJoRating, 5 stars4 months ago
My husband and I and our mini-golden doodle rented cottage 14. It was super clean and exactly as described in the listing. We enjoyed our coffee on the front patio in the morning. We also spent some time at the pool (it was clean). The Neighborhood is located in an extremely quiet area and within walking distance to the beach. We walked the short distance to the beach and enjoyed the sunset a few nights. The dining recommendations provided by Jonathan were GREAT too! We tried David's Deli, Rio's and Redamak's. We also discovered a tasty pizza place, Villa Nova, in New Buffalo. It's next to Barney's. We would definitely recommend The Neighborhood to friends and family.
Guest favorite

Home in Sawyer

4.96 out of 5 average rating, 78 reviews

Here and Now

ErikaRating, 5 stars5 months ago
My 3 friends and I had a great stay at Brandon and Lisa’s place. The home was clean and comfortable, and was exactly as advertised in the photos. The home is close to the Warren dunes state park, wineries, and an easy drive to New Buffalo as well. 10/10 recommend!
Guest favorite

Home in Three Oaks

4.82 out of 5 average rating, 96 reviews

Three Oaks Creek House Perfect

BenRating, 5 stars2 months ago
I will call it "Mary Poppins", practically perfect in every way. If you are looking for a quite scenic vacation spot, this is it. Their are obviously things that could have been better, but we got exactly what we wanted, no notes, no issues, no problems.
Guest favorite

Home in Michigan City

5 out of 5 average rating, 11 reviews

Villa Vesta-Lake Retreat

FoziaRating, 5 stars4 months ago
Vesta was super welcoming and VERY accommodating. The hot tub was fun, the adult and the kiddos enjoyed it very much! The place was super clean and organized and was equipped with everything we needed! Thanks Vesta!
Guest favorite

Home in Lakeside

5 out of 5 average rating, 57 reviews

Beautiful New Retreat in Lakeside - Walk to Beach

AnnetteRating, 5 stars2 months ago
Absolutely perfect! Great spot to retreat from it all. Beautiful home and location. Super nice hosts!
Guest favorite

Home in Michigan City

4.89 out of 5 average rating, 113 reviews

Roomy and Private Getaway for Families & Friends

KarynRating, 5 stars1 month ago
Very spacious and just as described. Perfect location for visiting family and would be great in the summer!
Guest favorite

Apartment in Michigan City

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

MariaRating, 5 stars5 months ago
We've stayed here before. It's always really clean and nice. The towels are super soft, and the pillows and linens are awesome. You're right across from the outlet mall, and a farmers market type store across the other way. There's a cute little ice cream shop on the corner. You're close to the beach and the zoo. It's just a nice place to rest and reset. I highly recommend it.
Guest favorite

Cabin in Benton Harbor

4.99 out of 5 average rating, 267 reviews

Charming Cabin-Private Beach & Golf

EmilyRating, 5 stars3 months ago
I brought my four kids age 2-16 for some special time at the lake, dunes, and St Joseph. We really enjoyed the home, it was very comfortable, clean and tastefully decorated… comfy beds, well stocked but not cluttered kitchen, and my little ones absolutely loved the children’s bedroom. The private beach is an easy walk and it’s beautiful. Kristi had great recommendations and is the most gracious and hospitable host.

Popular amenities for Rolling Prairie vacation rentals

Other great vacation rentals in Rolling Prairie

Guest favorite

Home in Michigan City

4.86 out of 5 average rating, 28 reviews

"Beachy Bliss: Sun, Slots, Sips & Shops!"

JennaRating, 5 stars5 months ago
My friends and I had a wonderful stay! The house is super cute and is close to the beach, shops, restaurants , the grocery store, and more! We were out of a few things but they responded immediately and dropped it off asap! We would definitely come back! Thank you!
Guest favorite

Home in Michigan City

4.95 out of 5 average rating, 62 reviews

Home near the lake with an inground pool

DavidRating, 5 stars2 months ago
This is a great place. Very spacious and comfortable and close to downtown and attractions. We enjoyed our stay very much.
Guest favorite

Cottage in Vandalia

4.9 out of 5 average rating, 21 reviews

Private Vandalia Beach Front Cottage

AmyRating, 5 stars5 months ago
This was such a nice weekend with our family. The cottage was stocked with everything you need! The lake is super quiet and pretty private! The place was clean and remodeled in the inside. Our first time booking an AIRBNB so we were nervous but we are so glad we did!
Guest favorite

Vacation home in Baroda

4.94 out of 5 average rating, 16 reviews

Location location

AmyRating, 5 stars5 months ago
This was our second time staying in Pawel's place as a group of 8 friends and this home provides a very comfy stay with plenty of separation of space. We enjoyed the porch and pool table and the large dining space, as well as the close proximity to wineries, breweries, and Granor Farm.
Guest favorite

Home in Chesterton

4.92 out of 5 average rating, 50 reviews

4 Season House

KateRating, 5 stars2 months ago
Great location for our visits to family in the area. Very accommodating our sudden change of plans and willing to work with us. Easy and quick communication. Delightful stay. Would highly recommend and hope to return again. Thanks Cheryl!
Superhost

Home in Miller

4.9 out of 5 average rating, 108 reviews

Sunset beach house

JoshuaRating, 5 stars5 months ago
At first I thought all the 5 star ratings were fake but I completely understand now !😂 our stay was great ! She communicated well, she was able to make accommodations for us, and everything went smoothly. The location is great!
Superhost

Home in Benton Harbor

4.75 out of 5 average rating, 12 reviews

Family Getaway

CyrilRating, 5 stars5 months ago
Fantastic stay for a nice quiet weekend in at Joseph. Great location and atmosphere located away from town activity but close enough to beaches and fun ! Fire pit and ambience was really enjoyable. And dog friendly !
Guest favorite

Cottage in Union Pier

4.96 out of 5 average rating, 192 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

AmeliaRating, 5 stars2 months ago
Second time staying in this home and it was even better than the last. Great neighborhood and layout and they’ve made some really nice cosmetic updates to the house as well. Can’t wait to come back in the summer!

Destinations to explore