Holiday houses in Milford

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Top-rated holiday rentals in Milford

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

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Top Guest favourite

Home in Syracuse

4.98 out of 5 average rating, 47 reviews

Lake Wawasee, Outdoor TV, Surround Sound, Bikes

☀️55” Outdoor TV w/ Covered Patio ☀️3 Bedrooms, 1 King, 1 Queen, Bunk Room ☀️Sleeps 12 People ☀️Flatscreen TVs w/ YouTube TV ☀️Surround Sound System in Living Room ☀️Record Player/Bluetooth Speaker ☀️ Fire Table ☀️Fully Stocked Kitchen ☀️ Fireplace ☀️Beach Cruiser Bicycles ☀️High Speed WiFi ☀️Washer & Dryer 🌊 Located down the street from Indiana’s largest natural lake, Lake Wawasee, you will find everything you could possibly enjoy while you stay in Syracuse, IN at the Wawasee FROG house.

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Superhost

An inviting porch features a spacious area with wooden beams supporting the roof. A blue swing hanging from the ceiling is complemented by comfortable seating arrangements and planters filled with greenery. The serene view of the lake is visible in the background.

Home in Syracuse

4.87 out of 5 average rating, 31 reviews

Dewart Lakefront Cottage

Escape to our charming Lake Cottage, nestled on the peaceful Dewart Lake in Syracuse, IN. Whether you're seeking a relaxing weekend or an adventurous getaway, this cozy retreat offers stunning lake views, beautiful sunrises and sunsets, private access on an all sport lake and all the comforts you need for a memorable stay anytime of the year. Enjoy the lake with kayaks, fishing from the pier and space for a boat, BBQ grill, smart TVs and campfire pit are just a few amenities we have to offer.

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Guest favourite

Cabin in North Webster

4.89 out of 5 average rating, 270 reviews

Dock of Bay Cabin- Private Dock on Lake Webster

"Last Cast" is close to town, creating the perfect space to have access to peace & quiet while being close to town & water. This cabin is on a private property that guests will have all to themselves while they are here. You will have access to an eat in kitchen, living room, private bathroom, and a loft which has two beds. This cabin comes w/channel dock space on the S. side of Lake Webster. There is space for your boat & water toys to bring along w/ you or rent items @ a marina while here.

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Top Guest favourite

A comfortable living area features a large sectional sofa and a cozy bean bag chair, with light streaming through two windows. A coffee table sits at the center, and a fireplace adds warmth. A desk with a chair is positioned in one corner, while a ceiling fan circulates air.

Cottage in Warsaw

4.98 out of 5 average rating, 153 reviews

The Channel House @ Hoffman Lake

2 bedroom 2 bathroom cottage that is located on Hoffman Lake Channel. The Channel House is great for fishing right out of the back door. Conveniently located a drive from Warsaw, IN and several smaller towns. Bring nothing to this fully furnished cottage except your clothes and plan for fun. On site drive way parking, laundry, garage with pool table, darts, & air hockey. Several activities inside and out. Fire pit, outdoor seating and lounge chairs. We live nearby & can assist your stay!

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Guest favourite

Cabin in Warsaw

4.97 out of 5 average rating, 150 reviews

Romantic A-frame · HeartJacuzzi · Firepit · Kayaks

Peaceful channel-front A-frame cabin on Barbee Chain of 7 lakes! This cozy retreat features a charming, rustic interior, fully stocked kitchen, and heart-shaped jacuzzi. You'll love stargazing or drinking morning coffee on your spacious deck with gas firepit and gas grill. Unwind by the cozy fireplace, kayak and fish on the Barbee Chain of 7 lakes, and make s’mores by the waterside firepit! Minutes from boat launch. Book now for unforgettable memories in this intimate, picturesque getaway!

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Top Guest favourite

Home in Goshen

4.97 out of 5 average rating, 118 reviews

Hidden Log Cabin | Hot Tub | Ping Pong | Family |

Escape to The Trillium Lane Cabin - Your Home Away from Home! Experience the perfect place for you and your loved ones to escape the hustle and bustle of everyday life in this 3 bed/2 bath authentic log cabin in the heart of woods! Unwind in tranquility as you soak in the peaceful setting, whether it be on the front porch, secluded hot tub, or by the fire (wood provided). Secluded feel, but conveniently located near Goshen, Middlebury, Shipshewana (20 min), and Nappanee (30 min).

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Guest favourite

A charming lakeside cottage features a light-colored exterior with multiple windows. A private pier extends into the water, while a grassy area offers space for outdoor seating, visible near the entrance. The backdrop includes lush trees, enhancing the natural setting of Waubee Lake.

Home in Milford

5 out of 5 average rating, 15 reviews

Crown Cottage on Waubee Lake

Escape to Crown Cottage, a charming lakefront retreat in Milford, Indiana. Nestled on Waubee Lake, this cozy three-bedroom cottage is perfect for families, couples, or small groups. Enjoy an open floor plan ideal for relaxing, a fully equipped kitchen for easy meals, and a lakeside patio with stunning views. Fish or kayak from your private pier, and enjoy the nearby public beach and playground. Crown Cottage offers the perfect blend of comfort and fun for your next getaway.

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Top Guest favourite

A comfortable sitting area features a gray sofa with an accompanying ottoman, situated beside two side tables with lamps. Natural light enters through the window, highlighting neutral-colored walls and plush carpeting, creating a relaxed environment for guests.

Home in Nappanee

4.99 out of 5 average rating, 122 reviews

Country Cottage

Located in the peaceful countryside of Nappanee, enjoy this charming house which is less than 3 miles to the nearest town with grocery store, restaurants, and shops. The front porch is a lovely place to unwind and relax, weather it's after a day of work or play or then to sip your morning coffee, with the occasional passing of a horse and buggy on this country road. There is No smoking in the house or on the property. No pets allowed.

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Top Guest favourite

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, 436 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.

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Top Guest favourite

A modern farmhouse exterior is showcased, featuring a white façade with stone accents and a grey metal roof. The front porch is adorned with comfortable seating and surrounded by landscaped gardens. A garage is visible on the left, enhancing the welcoming appearance of the property.

Apartment in Nappanee

4.97 out of 5 average rating, 214 reviews

Nappanee Loft

Welcome to the Nappanee Loft, a modern farmhouse, above-garage apartment located in the historic town of Nappanee, Indiana. Inside, you'll find touches of Nappanee with a restored, vintage Coppes Nappanee kitchen. The host also provide Keurig coffee and supplies. We hope they'll help you feel the warmth of small town hospitality in the heart of Amish Country.

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Top Guest favourite

The heated in-ground pool features a diving board and a slide, surrounded by a spacious deck with lounge chairs and a shaded patio area. The inviting turquoise water reflects the clear sky, creating a relaxing outdoor space for leisure and enjoyment.

Home in Milford

4.98 out of 5 average rating, 122 reviews

Summer of Fun - Luxury Home, Pool, Hot Tub, Arcade

Ultimate Milford getaway: beautifully renovated 1940s home with sparkling heated pool, large hot tub, and huge heated/AC game room. Perfect for families, couples, or work trips. Features fast Wi-Fi, king & queen beds, and ample parking. Enjoy small-town charm, nearby coffee shops, and dining. Comfortably fits multiple guests seeking relaxation and fun.

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Guest favourite

A modern shipping container home is set amidst a wooded landscape. The structure features large glass windows and a welcoming entryway. A daybed swing is visible on the porch, surrounded by lush green grass and tall trees, creating an inviting outdoor space.

Shipping container in Columbia City

4.94 out of 5 average rating, 221 reviews

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.

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