Vacation rentals in Orland

Indiana Lake Escape

Fully renovated 4BR/3BA lakefront home perfect for families or group getaways. Enjoy private dock access for swimming, fishing, or tying up your boat. Relax outdoors with a grill, stunning lake views, EV charger, and boat trailer parking. Inside, you'll find a full kitchen, smart TV, washer/dryer, and a spacious game room with billiards, a dance floor, and premium sound system. Comfort, fun, and lakefront serenity all in one! Bonus: bring a carrot to feed the friendly donkey — a guest favorite!

Westward House

The "Westward House" on Dallas Lake offers stunning westward sunset views, modern/mid-century/Scandi design, and abundant natural light with water views from nearly every room. Located on the Indian Chain of Lakes, it provides full access to a two-story home with heated floors, a gas fireplace, four bedrooms, and a screened porch. Outdoor amenities include a dock, boat ramp, loungers, and a fire pit. Nearby activities include pontoon rentals, a sandbar and Shipshewana/Amish Country attractions.

Lake house with swimming and kayaks

*Lakeside Luxury Awaits: Your Tranquil Escape* Immerse yourself in the serenity of lakeside living at this stunning retreat, perfectly positioned just 10 minutes from the natural beauty of Pokehagen State Park. This 3-bedroom haven offers an unparalleled escape for families and friends seeking relaxation and adventure. Wake up to breathtaking lake views from almost every room. The sunroom beckons with its cozy ambiance, ideal for enjoying your morning coffee or losing yourself in a good book.

‘Tis our Cottage lake time awaiting & views

Whether you seek relaxation at the lake or adventure, this spot has it all. Just 2 miles from the Michigan border & Indiana Toll Road, this charming retreat is close to activities like a 45-min drive for sports enthusiasts cheering on the Notre Dame Fighting Irish or a round of golf at Cedar Lake Golf Course, 1 minute away. Explore Amish culture and shopping in Shipshewana, 15 minutes away. Groceries and essentials are 5 minutes away in Sturgis, MI & you have access to the public boat landing.

Lakefront! Girls getaway/Romantic Retreat/Booktok

Welcome to your peaceful escape! Delight in the charm of our cottagecore retreat, offering breathtaking lake views. Relax on the spacious screened porch, enjoying the outdoors without pesky bugs. The cozy bedroom, dining area, and living room all feature stunning lake vistas. Pamper yourself in the bathroom with a luxurious soaking tub and steam shower. The kitchen, fitted with new appliances, makes cooking a breeze. From the living room, step onto the deck and soak in the serene environment.

Cozy Lakefront Cottage on Huyck Lake

Relax with the whole family at this peaceful, cozy place! 3 bedrooms 1 bath. Living room has a comfortable couch that pulls out into a bed along with additional seating. Full bath, kitchen, and laundry room are fully stocked for your comfort and enjoyment. Huyck Lake is a quiet, no wake lake. This house is perfect for a small to medium sized family or a romantic getaway. Master bedroom and guest bedroom have mounted TV’s. Family friendly. No to the following: pets, smoking, parties.

Home on Jimmerson James lake chain

Relax with the whole family at this peaceful place to stay. Newly built home on the largest lake chain in Northern Indiana with fenced in back yard, spacious open side yard, grill, fire pit and hot tub (available when temperatures are above 45° ). Private neighborhood beach. Neighborhood park for the kids. 10 minutes from shopping, restaurants, golfing, multiple sightseeing adventures at Pokagon State Park and historic Angola, IN. Summer and wintertime fun! Pets welcome too!

Private Lake+Fire Pit+Sauna+Kayaks | Pine & Paddle

Welcome to Pine and Paddle — the perfect place to unplug, recharge, and reconnect with nature by the lake. Unwind at this cozy lakeside tiny home, perfect for couples, friends, or solo travelers seeking peace, nature, and a hint of adventure near downtown Shipshewana. 🔥 Campfire pad w/ firewood + lake views 🛶 Kayaks + fishing poles + private dock ♨️ Wooden barrel sauna for ultimate relaxation 🌳 Private lake, beach, & outdoor games 🛏️ Sleeps 5 w/ full-size bunks + couch

The Retreat at Cabin Creek Farms

Escape to our peaceful country cabin nestled down a quiet lane surrounded by rolling farmland and grazing cows. Enjoy spacious accommodations with a wrap-around patio perfect for morning coffee, cozy evenings by the indoor fireplace, and scenic hiking trails right at your doorstep. Your perfect rural getaway awaits! Small events for up to 30 people are allowed upon request with an extra fee, if interested in hosting an event please request before making the reservation!

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

The Dam Hideaway

Welcome to The Dam Hideaway! Nestled in Nevada Mills near the Jimmerson Lake Dam, our private loft is just one mile from the public boat launch with plenty of room for your boat and trailer. Enjoy a fully stocked coffee bar, 60-game arcade table, board games, private patio with an electric fireplace and charcoal grill, plus easy access to the Lake James Chain and Pokagon State Park. Start making memories!

The Steel Oasis-Container Home w/ Hot Tub!

Welcome to our modern shipping container home, tucked away in a 3 acre section of woods. This 40 foot high cube has been transformed into the perfect place to allow you to relax and escape reality. This Oasis includes everything from a porch swing daybed, hot tub, fire pit, and dual sided fireplace. The details are unmatched.