Holiday rentals 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, 52 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.

Top guest favourite
A round wooden dining table is centered in a well-lit space, surrounded by four wooden chairs. A simple vase with green foliage and decorative items sit on the table. Large windows provide views of the water, enhancing the light and airy feel of the room.
Guest house in Syracuse
5 out of 5 average rating, 44 reviews

Charming Wawasee Cottage

Have fun with the whole family at this quaint cottage on Lake Wawasee! With gorgeous lake views and a private dock for your boat, this cottage is perfect for 3-day weekends or longer getaways. Enjoy a campfire at night, morning coffee with a view and catch some sun on the water. Get your steps in walking through Oakwood Park and enjoy lunch and drinks at Oakwood Inn. You can also walk to Louie's Bar & Grill, The Frog Tavern or Pizza Hut. More dining and a grocery store are only a 5 minute drive.

Guest favourite
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
4.9 out of 5 average rating, 40 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.

Guest favourite
Cabin in North Webster
4.89 out of 5 average rating, 273 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.

Top guest favourite
A charming home exterior is shown with large glass windows offering views of the surrounding landscape. Outdoor seating areas are visible, including a dining table and lounge chairs situated on a wooden deck. Lush green grass surrounds the space, adding to the inviting atmosphere.
Home in Syracuse
5 out of 5 average rating, 32 reviews

Pickwick Perfection

Pickwick Channel front is a unique open channel with BEAUTIFUL lake scenery! It's a Family friendly home. Grocery, restaurants, shopping, and more less than a mile down the road in Syracuse.A perfect small home that sleeps up to 8 aduits and 2 children. 4 bedrooms, 2 kings, 2 queens and hallway bunks with 2 twins for children. A FULLY STOCKED kitchen with an overextended island allows for ample seating while being engaged with the living area that boasts an oversized sectional and rockers.

Top guest favourite
A cozy sleeping area features a plush queen bed, adorned with decorative pillows. Natural light streams through skylights, illuminating the space. A wooden dresser adds warmth, while a dreamcatcher hangs on the wall, complementing the tasteful decor and providing a relaxing atmosphere.
Flat in Warsaw
4.97 out of 5 average rating, 372 reviews

The Loft: 1880

Located near, Zimmer-Biomet, and Cinema. Perfect for business travelers & those visiting family & friends. We've hosted contract workers & parents visiting Grace College students. The Loft is a second-story self-contained annex attached via a private entrance. On-Site Parking. We are situated on 3 acres and love our 1909 farmhouse and The Barn 1880: Historic Venue. Open plan living/dining w/fully equipped kitchen w/coffee bar, separate private queen bedroom & private bathroom. See Reviews.

Top guest favourite
Cabin in Warsaw
4.97 out of 5 average rating, 156 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!

Superhost
Home in Nappanee
5 out of 5 average rating, 4 reviews

Indigo Hideaway | Romantic + Fire pit

BNB Breeze Presents: Indigo Hideaway Indigo Hideaway is a charming Indiana retreat in Nappanee, offering the comfort of a single-level 1-bedroom, 1-bath home. The home’s location makes it easy to explore the best of Nappanee and the surrounding area. Guests can enjoy local restaurants, shopping, and scenic drives, while nearby amenities and conveniences add to the appeal of this peaceful town setting. - Fire Pit - Large Yard - Pellet Grill ​​​​​​​- Jura Espresso Machine - Wifi - & More!

Guest favourite
A cozy living room is featured, showcasing a brick fireplace and a mounted television. A striped beige couch and a plush blue armchair provide comfortable seating. Natural light enters through a large window, illuminating the patterned carpet and a small table placed near the window.
Cottage in Syracuse
4.93 out of 5 average rating, 56 reviews

Dewart Lake lakefront, sunsets, swimming, fishing

Nice lakefront cottage on all-sports lake, faces west for beautiful sunsets across the lake. Screened-in porch faces lake. Can have campfires at lakefront. Pier to dock your boat. Perfect swimming for kids, sandy, very gradual depth. Great fishing lake. Close to Girl Scout camp and nice hike to Quaker Haven camp with beach and playground. Restaurants nearby in Syracuse and North Webster both 10 minutes away. Very peaceful. Notre Dame Stadium only 53 miles away. Make reservation soon.

Guest favourite
Cabin in Nappanee
5 out of 5 average rating, 5 reviews

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!

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, 443 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 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, 129 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.

Popular amenities for Milford holiday rentals