Holiday houses in Orland Township

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Miller Beach Cozy Cottage with indoor fireplace

Have fun with the whole family at this stylish place. Have fun with your friends. Have a quite time if you need to escape from a crowd. Just simple as it is. Just enjoy being here, in a modern costal farmhouse loaded with almost everything you need for perfect and relaxing getaway. Please be a guest of our lovley restaurants, brewery, be a visitor of our small downtown, explore the beaches, dunes, and hiking trails of Lake Michigan and surrounding areas! Only 45min from Chicago!

Cheerful, charming, super comfy 2BR 2Bath Condo

This cozy, lovely, & stylish getaway is the perfect go to spot for your visits to the many exquisite dunes & beaches of Indiana. Ten minutes from the National Park & its also amazing trails & preserves. Located in a quiet suburb of Valparaiso, just moments from the beloved university & the thriving downtown social hub flourishing with fun, food, & festivities. The South Shore train station is also close by for jaunts to Chicago & the plethora of Lake Michigan shoreline amenities.

Miller Beach FairyForest Retreat

Escape to a whimsical retreat nestled atop the Indiana Dunes. Walk to the beach, only 3 blocks. Our mid-century modern 3-bedroom/1bth apartment boasts a magical fairy forest theme, enchanting guests from the moment they arrive. Perched on a sand dune within the bio-swale ecosystem, each room offers treetop views. The true gem is our sprawling 400sqft screened porch, an elevated haven that immerses you in the tranquility of the woodland, evoking the sense you’re in a treehouse.

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Miller Beach Family Getaway!

Escape to the tranquil shores of Miller Beach with our charming Airbnb getaway. Nestled along the picturesque Indiana Dunes National Parks, our cozy retreat offers quiet views, modern amenities, and easy access to the beach with only a 4 block walk from the house. Whether you're seeking a romantic weekend for two or a fun-filled family vacation, our meticulously curated space provides the perfect home base for your family adventure!

Brightstone Lake Cabin 1

Escape to our enchanting lakeside cabin nestled on a sprawling 65-acre property, boasting a private 18-acre lake. Immerse yourself in the serenity as you swim in pristine waters, explore scenic hiking trails, and unwind in the comfort of our cozy cabin. Fishing enthusiasts will delight in the abundant catches. Experience the perfect blend of tranquility and adventure. Book now, for an unforgettable getaway!

On Walden Lake

Bring the whole family to this great place with lots of room to enjoy time with loved ones! Comforts abound from the double waterfall shower in the master bath to the beautifully updated kitchen. Windows let natural light pour into this space, and the lake views are breathtaking. A finished basement with a second kitchen and full bathroom provides plenty of room for family gatherings or co-working retreat.