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
Yurt in Cambridge
4.98 out of 5 average rating, 254 reviews

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Top Guest favourite
Farm stay in Cambridge
4.99 out of 5 average rating, 106 reviews

Stay With Horses Escape Near Madison

Get ready for a quiet and peaceful stay. Take your pick: - 1King+1Queen Bed & 1 bath for 4 people - 1King+2Queen Beds & 2 baths for 6. (+$125 per night, contact host for payment) This home is attached to a barn with 6 Icelandic horses! Wake up to Icelandic horses just outside your window. A scenic escape with quiet mornings, fuzzy horses, and a one-of-a-kind IamGlytja experience - only 25 minutes from Madison - No horse riding allowed, owners to supervise all horse visits - No smoking / parties

Top Guest favourite
An open living area showcases a brown leather sofa facing a modern entertainment unit with a television. Bright light flows from large sliding glass doors leading to the outdoors. The kitchen features a functional island and dining area, illuminated by decorative pendant lighting overhead.
Townhouse in Janesville
5 out of 5 average rating, 149 reviews

Spacious Executive 2BR Home Near Shopping & Dining

Professionally Managed by Kevin Bush, this rental is nestled in a safe and quiet neighborhood in a desired location that is convenient to Woodman’s Center, Janesville shopping and dining destinations. Enjoy the city’s hundreds of acres of tranquil parkland, miles of peaceful trails, and beautiful downtown riverwalk. Bonus: This location is an easy drive for day trips to Madison, Milwaukee, Chicago, and surrounding. Please check out our listing on Margate Drive for more dates. Kevin, Host

Top Guest favourite
An open-concept living area features a cozy sectional sofa, wooden coffee table, and three barstools positioned at a breakfast bar. A modern kitchen with stainless steel appliances and stylish cabinetry is visible in the background, complemented by warm wood flooring and soft overhead lighting.
Apartment in Whitewater
4.96 out of 5 average rating, 139 reviews

Pet-Friendly Industrial 2 Bedroom Near UWW Campus!

This newly renovated two bedroom unit is conveniently located near UWW, Starin Park, and the Kettle Moraine! We are pet friendly! We are within walking distance to sports fields and UWW. Explore all that Whitewater has to offer with our personalized guidebook! Hike the Kettle Moraine, enjoy many local dining options and events, or shop your heart out. We are local hosts and strive to provide a five star experience! If your group is larger than 4, we have two other units in the same building.

Top Guest favourite
The two-story house features a grey exterior with a gabled roof and decorative shingles. A welcoming front porch is adorned with seasonal decorations, including small pumpkins. A well-maintained lawn and a stone pathway lead to the entrance, surrounded by lush greenery and trees.
Home in Lake Mills
5 out of 5 average rating, 34 reviews

The Yellow Door Guest House-Lower

Welcome to this turn of the century 2 story home where West Coast cool meets Midwest mod and is the hippest place in town. Two separate apartments available. Located in a convenient, friendly, residential neighborhood, curated with midcentury decor and curiosities, spacious rooms, and an old world charm with a big backyard and firepit. Your favorite space will undoubtedly be “the cabin” as you sip your coffee and tea, and plan your day. You just might want to live here! Adults only!

Top Guest favourite
The exterior of the getaway features a charming log cabin style with multiple windows allowing natural light to fill the space. A landscaped yard displays a variety of plants and flowers, while nearby trees provide greenery. A barn-like structure can be seen in the background.
Home in Lake Mills
4.97 out of 5 average rating, 34 reviews

The Shack on Sandy Beach Road

A charming, cozy getaway centrally located in the quaint City of Lake Mills. The Shack on Sandy Beach Road features 3 bedrooms (king, queen and two twin beds), 2 full baths, and all the amenities to make your getaway complete. It is a 3 minute walk to crystal clear Rock Lake and Sandy Beach. Pickle Ball, playground, bowling alley, and ice cream shop are practically in the front yard. Enjoy a cup of coffee in the spacious backyard overlooking the Glacial Drumlin Bike/Walking Trail.

Top Guest favourite
A cozy living area features a white-bricked fireplace with an arch-shaped mirror above it. A round table with two chairs stands adjacent to the fireplace, while a light blue chair is positioned nearby. Soft natural light enters through the window, enhancing the serene atmosphere.
Guesthouse in Sun Prairie
4.98 out of 5 average rating, 400 reviews

Charming Milkhouse Cottage, minutes from Madison!

Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

Top Guest favourite
The Orchard House is illuminated against a twilight sky, showcasing its wooden exterior. Large glass doors reveal a cozy interior with soft glowing lights. A tranquil setting is framed by surrounding trees and open grassland.
Home in Stoughton
4.98 out of 5 average rating, 52 reviews

The Orchard House

In a complex world that makes so many demands your time and attention, the Orchard House is a simple, Nordic-inspired refuge where you can be restored, reconnected, and refreshed. Midweek special: $1000 for 5 nights, Sunday evening through Friday morning. The Orchard House is a private retreat set on 30 acres in the Wisconsin countryside, just 20 minutes from Madison. A wood -fired hot tub set in a secluded forest clearing is available year round for outdoor soaking.

Top Guest favourite
Cottage in Johnson Creek
4.98 out of 5 average rating, 41 reviews

A-Frame Escape | Riverfront, Fire Pit, Kayaks!

Escape to this cozy A-Frame on the Rock River with 100 ft of private frontage. Sip coffee at the bistro table, relax around the gas fire table, or wood fire pit. Inside, enjoy a loft bedroom, full kitchen, and modern comforts. Complimentary kayaks/canoe, pedal boat (upon request) invite you to explore the river. At the end of your day you can enjoy a seat in the sauna. Perfect for a peaceful retreat, yet close to Madison, Milwaukee, wineries, hiking, and much, much more!

Top Guest favourite
The image depicts a charming three-building arrangement situated on a cul-de-sac. The structures feature varying architectural styles with a mix of siding colors. Lush greenery is visible in the surrounding landscape, and an American flag is displayed on one of the buildings under a blue sky with scattered clouds.
Guest suite in Deerfield
4.96 out of 5 average rating, 173 reviews

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Top Guest favourite
A cozy living room features a plush carpet and seating arrangement with reclining chairs, each equipped with cup holders. A television is displayed prominently, while a small table adds a decorative touch. Natural light enters through the window, enhancing the room's comfortable ambiance.
Apartment in Fort Atkinson
4.96 out of 5 average rating, 116 reviews

The Riverview Retreat, unique spacious upper.

Enjoy the upper level of this charming home nestled at the banks of the Rock River. Newly remodeled spacious 2 bedroom suite with eat in kitchen and separate living room. Private porch and laundry room. Clawfoot tub in the bathroom with a shower attachment. This suite offers plenty of natural light with views overlooking the river. Within walking distance to downtown and everything Fort Atkinson has to offer.

Guest favourite
A spacious living room is presented with a large sectional sofa and a wooden coffee table. Natural light fills the area through multiple windows, while built-in shelves display various decorative items. A flat-screen TV is mounted on the wall above a modern fireplace.
Home in Lake Mills
4.94 out of 5 average rating, 141 reviews

Rock Lake Retreat - Lake Mills Wisconsin

Welcome to Rock Lake Guest House, a serene lakeside retreat on the shores of Rock Lake, just minutes from charming, legendary Lake Mills. This light-filled, updated home offers a private wooded escape with treetop and lake views from every room. The cozy living room features built-ins and opens to a wraparound deck overlooking the water—perfect for relaxing in this peaceful, all-season getaway.

Popular amenities for Milford holiday rentals

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  4. Jefferson County
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