Family-friendly holiday rentals in Benton Harbor

The Oriole feels like you’re sitting in a treehouse on the porch. Lovely! The interior is quaint and clean. Thoughtfully appointed space with a place to hang a few items of clothing and a suitcase rack, but otherwise don’t bring unnecessary luggage because, as described, the space is small. The location is walkable to all restaurants and shops. We enjoyed exploring a bit on the bikes which are great amenities along with the hot tub included in the stay. Would definitely recommend!

Cutest little house! Beautifully furnished, overall very peaceful and relaxing space.

My husband and I stayed 3 nights to celebrate our 25th anniversary. After going through many listings and reading guest comments, we decided to stay here. We wanted to be close to town, but we also wanted to enjoy relaxing in the outdoors. Her home is beautiful! Some guests mentioned that it was a bit outdated. We found it interesting. It was very well taken care of and very clean! We loved the floor to ceiling windows in the bedroom, the screened in porch, and all the windows facing the marsh and Kalamazoo River. It was so peaceful and EXACTLY what we needed. There were so many birds, squirrels, and even some muskrats playing in the river in the evening. We loved the fire ring next to the river. It felt very private even though there are neighbors on both sides, which you can't see too well in the photos. We stayed Mon.-Wed. and there was no one around. The only con is that the Hot Tub needs an upgrade. It didn't bother us as everything else was perfect.

We made a last minute booking and the host was very responsive. The house was great had everything we needed and we had an amazing time.

This is the second year I rented this place for my birthday weekend away with friends. The house has so many accommodations for sleeping and different sitting areas. However, the main event is the kitchen. My friends and I love to cook and that's why we came back a second year in a row. The kitchen is unbelievably well-stocked with anything you might need to cook. There are multiple sinks so someone can be cooking while someone else cleans. The layout is perfect for people to hang out with whoever is cooking. There are two ovens. It is a dream. The house feels comfortable and lived-in, and it feels like there has been a lot of thought and intention focused on the user-experience. Cannot say enough nice stuff about this house, cannot recommend enough. Will be coming back for my 29 birthday.

Very peaceful to stay put here--bring what you need and stay in these beautiful surroundings among birds and gardens and an art-filled home. Or spend time on nearby beaches and trails, wander the nearby small-town shops and nice variety of restaurants and look forward to a hot tub soak and campfire. Donna's home is welcoming and inspiring!

We had an absolutely amazing stay at this beautifully decorated and incredibly comfortable home. From the moment we arrived, we felt right at home — every detail was thoughtfully designed, creating a warm and inviting atmosphere. The space was spotless, stylish, and perfectly equipped for a relaxing getaway. One of the highlights of our experience was the exceptional management team. They were extremely kind, friendly, and responsive, making everything seamless from check-in to check-out. It’s rare to find such genuine hospitality!

What a beautiful cabin! My husband and I were looking to get away for a few days and enjoy a cozy, private place! This home checked all of our boxes! Very nicely kept, home was orderly, comfortable and had everything we needed. The hot tub was perfect as it snowed the day after our arrival and was peaceful and serene! We were able to start a fire in the fireplace and enjoyed relaxing on the comfy sofas! Huge soaker tub in upstairs bathroom and plenty of bedrooms and a fun basement area! The perfect setup! We will have to bring some friends back with us next time- tons of room for several guests to enjoy! We dined at several local restaurants (within a 10 minute drive) that were delicious and spent some time on Water St for shopping, food, and brews! A must-stay place!

We loved how close this cute little house was to the downtown area. It was clean and tidy, beds were firm, but ok. It has a nice big yard, with plenty of outdoor seating. Would recommend.

This place was super adorable. My friends and I needed a weekend away and this was the perfect place. Everything was super clean. There’s coffee, teas, all sorts of cookware to use, it was just super easy. It’s the name on the board when you walk in was a great touch. Hope to stay here again soon and highly recommend!!

We loved Rob’s house and would stay here again. The backyard and screen porch were wonderful. The house was clean and the beds were comfortable. It was a short walk to restaurants, shopping and the beach. Highly recommend!

There was plenty of space for our family and it was close to a lot of great/fun things to do during our trip to Michigan City, IN!

Really enjoyed our stay here. The place was even more beautiful that the pictures showed, and was in a quiet, peaceful area. Close distance to downtown Douglas and Saugatuck. Also is ~10 min to Virtue Cider and Fenn Valley Winery. It was the perfect spot for my partner and I, and our two dogs. Sara was an awesome host and very responsive. Would definitely stay here again!

We had a wonderful stay and will definitely be returning! The house was beautiful and extremely clean, the master bed was so comfy and the backyard was perfect for our pup to run around in. The location was also perfect and in a peaceful area, but also only about 10 minutes to New Buffalo and some amazing restaurants! I would definitely recommend and can’t wait to book our next trip back here!!

We had a great time with our family and dogs. The backyard was perfect and we had so much fun around the fire and hot tub. Would highly recommend and hope to stay again next year!

Always love staying at Happy Z’s! The house is very clean and it’s just a short walk to a neighborhood beach and a 5 minute drive to downtown. Great location. Cheryl is a wonderful host.

We had a great stay! The house was perfect. It was nice and clean with a great rooftop deck and screened in porch. The location could not have been better, walking distance to everything in town. Everything was easy as far as check in and check out with a book explaining everything in the house. Mark was great at responding to questions. I would highly recommend staying here.

Excellent location. Unit is small and bathroom/toilet is a tight fit. Very clean on arrival and furnishings are nice.

My girlfriends and I had a great stay! Ann’s place was peaceful and beautiful. We enjoyed relaxing outside, watching the animals and soaking in the hot tub. We will definitely be back!

Beautiful house with a stunning view, and walking distance from the beach.

Such a cute home. Right across the road from the Warren dunes. Easy to get back and forth with a bicycle. The cutest little ice cream shop right next door. Bed was comfortable and the bunk beds are roomy. Would definitely stay here again.

This is our 3rd year in a row to come for an extended Labor Day weekend and bring our kids and/or grandkids. We love the setting. The pool is perfect for the younger kids and the adults appreciate the beauty of all the surroundings, including at poolside. If we could change anything at all we would add another bedroom as we can't quite get all of our extended family here at one time. That said, we would like to return for a 4th year at Labor Day weekend time next year. The combination of beauty, privacy, amenities, condition (always in great shape!), and proximity to lovely South Haven can hardly be beat!

My family and I loved staying here! The pool was perfect and we used it every single day and the space was ideal for us - my 4 year old especially loved the games (first timer playing Sorry) and PAC Man along with the nature / fire pit (and pool of course). It was very close to downtown Saugatuck and the host was super responsive. Our dog was also very relaxed in this location as it was quiet and peaceful and he is getting older. Thanks for the great stay and we can’t wait to come back’

Tom and Charyl were amazing hosts ! We had open communication throughout our stay and even got a tour upon our arrival. The airbnb was everything as described and more ! The pool was incredible and the airbnb was only a 5 minute drive to the nearest beach. They even had a binder of recommendations available to us of local attractions/things to do. Our expectations were exceeded for this trip, and we can’t wait to come back !