Vacation rentals in Orland

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Top-rated vacation rentals in Orland

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Top guest favorite

The exterior of a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.

Farm stay in Vandalia

5 out of 5 average rating, 216 reviews

One of a kind Grain Binn | Hot Tub | Creek View

*Escape the ordinary and experience rural country luxury *Whether sipping coffee at sunrise or star gazing the Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug and un

Top guest favorite

A light-filled living area showcases a comfortable curved sofa adorned with decorative pillows. Large windows reveal a verdant view of surrounding greenery, enhancing the tranquil atmosphere. A wooden table and floor plant complete the cozy, inviting space.

Tiny home in Fort Wayne

4.97 out of 5 average rating, 689 reviews

The Tiny Shed Glamping-Beautiful Country Escape

Welcome to the prettiest little tiny home in Fort Wayne! Nestled next to the woods, our guests enjoy a quiet, country getaway to escape all the busy of the city life! The stunning 9-foot windows in the bedroom give you the feel of sleeping in the woods, yet you have total privacy! We have recently renovated this sweet little shed, adding on a beautiful bedroom and a private bath just out side the door. SPECIAL NOTE: We were listed as the most unique Airbnb in Indiana by House Beautiful-2022!

Top guest favorite

A welcoming front porch features two rocking chairs positioned beside a small decorative table, adorned with bright pink flowers. Lush greenery is visible in nearby planters, while sunlit windows with green shutters complete the charming country setting.

Guest suite in Shipshewana

4.98 out of 5 average rating, 503 reviews

Picket Fence Farm Private Guest Retreat Suite

Stay in a 2nd story private suite in a modern farmhouse where we reside on a family farm in Amish country. Guests have the entire 2nd floor: 2 bedrooms, a private bath, and a sitting room. You can watch Amish buggies drive by while you rock on the front porch, access shared patio spaces or sit by a creek. We have cows, goats & chickens. We're in the heart of Shipshewana Amish/Mennonite community, minutes from downtown Shipshewana & all it has. An authentic, comfortable country getaway.

Guest favorite

A wooden dock extends along a calm canal, with reflections of trees lining the water's edge. The early morning light casts a soft glow on the serene surface, enhancing the tranquil setting. Boats can be seen docked nearby, adding to the peaceful atmosphere.

Home in Coldwater

4.81 out of 5 average rating, 188 reviews

Lake Escape Cottage (waterfront, jacuzzi, parking)

Discover the perfect family escape at this cozy lakefront cottage. Start your mornings on the back deck with a cup of coffee, overlooking the tranquil waters. End your days by the firepit, creating cherished memories by the lake. Inside, you'll find a stocked kitchen, two bedrooms, and a luxurious jacuzzi bathtub. Feel at home with the convenience of a washer and dryer. Restaurants and grocery stores are mere minutes away, making this the ideal home away from home for your lake getaway.

Top guest favorite

A comfortable living space features a sectional couch with yellow accent pillows, a wall-mounted TV, and a white entertainment unit. Large windows are dressed with sheer and orange curtains, allowing natural light to brighten the room. A patterned chair adds a touch of color.

Home in Angola

4.99 out of 5 average rating, 133 reviews

Fox Lake Road Bungalow (Near Trine University)

This two bed two bath home is very new and fresh with brand new high-end furniture. From the 65” TV to the gas fire pit on the patio overlooking the small creek and woods you won’t feel more relaxed. We are five short blocks from Trine University and a short drive to the center of town and one of our 101 lakes. Fox Lake Road Bungalow is equipped with several smart home features keeping your check-in fast and simple. We would love to host you. Thank you for your consideration.

Guest favorite

A charming tiny home is positioned alongside a spacious green lawn, featuring large windows that allow views of the tranquil lake and sunset. Trees line the property, and a serene atmosphere is enhanced by the gentle waves of the water in the background.

Tiny home in Shipshewana

4.93 out of 5 average rating, 148 reviews

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 4 w/ full-size bunks + sofa bed

Top guest favorite

The exterior of a lakefront double-wide house is shown, featuring a spacious sun porch with large windows that allow for ample natural light. A lush green lawn is visible in front, complemented by surrounding trees. A pathway leads to the entrance of the home.

Home in Coldwater

4.93 out of 5 average rating, 121 reviews

Jake's Lake Place w/pontoon rental

Jake's Place is on a private beautiful all sports lake (all DNR regulations apply) This is the perfect spot for your next family getaway. Spring feed lake, very clean and sandy bottom. This property has access to a second empty lot for additional yard. Multiple indoor and outdoor games, paddle boat, 4 kayaks and bond fire pit for relaxing after a great day on/in the lake. Jake's place faces the west for Gorgeous sunset viewing to end your day.

Top guest favorite

A comfortable living area features two soft sofas positioned around a light area rug. Natural light enters through a large window adorned with patterned curtains. A modern television sits on a wooden stand, and a lamp is placed beside a side table.

Apartment in Howe

4.95 out of 5 average rating, 238 reviews

The Upper Room

A newly remodeled full above-garage apartment with private entrance and access to a one car garage with a secure key pad. Only 15 minutes from Shipshewana Trading Place which is home to the midwest's largest flea market, beautiful Pumpkinvine Nature Trail amid Amish inspired shops and cuisine. Minutes from Indiana toll road exit 121 this quiet wooded setting is a great choice for an extended stay or ideal for a special getaway.

Top guest favorite

A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.

Cabin in Middlebury

4.99 out of 5 average rating, 353 reviews

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.

Top guest favorite

The exterior of the cottage features a combination of white siding and natural wood accents. Large floor-to-ceiling windows provide expansive views of the surrounding landscape. A manicured grassy area surrounds the structure, complemented by the presence of mature trees and a nearby black circular building.

Cottage in Fremont

4.97 out of 5 average rating, 181 reviews

The Cottage at The Mill District

Relax and unwind at our peaceful cottage at The Mill District. You will love the views out of the floor to ceiling windows. Everything inside and outside the cottage was recently remodeled including a brand new bathroom. You and your guests will love the well manicured property. Feel free to explore the grounds and bring your photographer (No sitting fee for guests). Peaceful location located next to clear lake.

Guest favorite

A hot tub is positioned on a wooden deck, overlooking a serene lake at dusk. String lights are draped above, casting a warm glow. Reflections of trees and a dock are visible on the calm water's surface, enhancing the tranquil atmosphere.

Home in Bronson

4.98 out of 5 average rating, 242 reviews

Water’s Edge-Hot Tub, Pet Friendly, No Fees

Tranquil lake living! The Water’s Edge is a great way to enjoy the lake. It is right on the water with kayaks, stand up paddle boards, and a canoe to venture out with. The hot tub accommodates 6 people. The sunroom has beautiful views as well as a couple of beds that can be used if the weather is nice. There is nothing better than falling asleep to lake sounds and a pleasant breeze! Please no college partyers.

Guest favorite

A wooden dining table is centered in the room, surrounded by four upholstered chairs. Natural light illuminates the space, highlighting a large artwork featuring a coastal scene on the wall. Decorative elements include a textured centerpiece and woven place settings.

Cottage in Fremont

4.87 out of 5 average rating, 120 reviews

Hilltop Bungalow on Jimmerson Lake

Welcome to Hilltop Bungalow at Jimmerson Lake! ✨ Relax, recharge, and reconnect at this cozy lake-view retreat. Enjoy lake-life surroundings, warm interiors, and a comfortable space to unwind or gather with loved ones. Just 1.3 miles from public lake access—perfect for pontoon and jet ski rentals.🚤 The space sleeps 6–9 comfortably with all the amenities you need for a peaceful getaway.