Holiday houses in Milford

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Top-rated holiday rentals in Milford

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Top Guest favourite
A yurt is depicted, nestled among lush greenery. A wooden deck equipped with two chairs and an umbrella provides seating. The entrance features double doors framed by angled wooden roofing, with a wood-burning stove visible on the side. The surrounding forest offers a sense of seclusion.
Yurt in Cambridge
4.98 out of 5 average rating, 237 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
The cozy sitting area features a mix of patterned sofas and an armchair, with warm ambient lighting from two table lamps. Rich green walls create a comfortable environment, while a view into the dining area is visible through an open doorway, adding to the home's vintage charm.
Home in Watertown
4.93 out of 5 average rating, 189 reviews

Beautiful Victorian in Historic District

My Victorian home, "Belle Maison" (beautiful house), is waiting just for you. Newly restored, with 2 bedrooms, 2 baths - one with its original claw foot tub!- and a queen size sofa bed in the TV room. It is located in historic, downtown Watertown. Just a block from Main Street - with lots of shops and restaurants within walking distance - and the beautiful Rock River. The location is perfect - whether you're visiting Jefferson County or looking for a home base between Madison and Milwaukee.

Top Guest favourite
An open-concept living space features warm wood paneling and large glass sliding doors offering views of the river. A seating area is arranged with plush cushions, and a wooden table with bar stools is positioned nearby, inviting relaxation while enjoying the serene waterfront scenery.
Cabin in Edgerton
5 out of 5 average rating, 163 reviews

Waterfront modern cabin w/ kayaks

VERY romantic getaway for 2! Enjoy your own private dock, welcome to tie off your own boat or rent locally. Complimentary use of 2 kayaks. Beautiful modern riverfront cabin near Lake Koshkonong's eateries and entertainment. Soak in the gorgeous Wisconsin summer with water activities at your fingertips. The rest of the year take in the pristine wonderland views in our enclosed balcony. Only 30 minutes from Madison's world class culinary experiences, performance arts, sports & festivals.

Top Guest favourite
A private deck features a round table surrounded by four chairs with cushions, offering views of the lake. The area is adorned with trees and distant seating by the water, while the sky is filled with clouds, creating a serene outdoor atmosphere.
Cabin in Fort Atkinson
4.91 out of 5 average rating, 160 reviews

Cozy Lake Cottage With The Best View & Pontoon!

Location, Location, Location! Incredible views! Retreat to this cozy Lake Koshkonong cottage with vaulted ceiling and southern exposure. Enjoy spectacular sunsets and views of the 10,000 acre lake from the north shore. Fish, hunt, boat, ski, swim, snowmobile, or simply soak up the sun and take in the view from this quiet retreat on a dead-end street. Fresh paint, bedding, and furniture make this little gem very comfortable. Great Walleye ice fishing right in front of this property!

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, 386 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 tranquil scene captures a vibrant sunset over the lake, reflecting hues of orange and gold on the water's surface. Silhouetted against the colorful sky, two ducks glide peacefully by the shoreline, framed by a quiet lake house and rocky beach area.
Home in Milton
4.99 out of 5 average rating, 128 reviews

Buoys UP! Lake Life & Sunsets

Looking to unwind & enjoy Lake Life-where weekends begin any day of the week-any season you choose? Here at Buoys UP! you will be able to do just that. Enjoy private access to our newly remodeled 2 bedroom lake house at Lake Koshkonong, WI. Overlook the private road this little gem is located on and enjoy the wonderful lake views and the beautiful sunsets. Stroll down the road for apx. a 2 minute walk to take advantage of your personal lake access Buoys UP! offers just for you.

Superhost
Cabin in Edgerton
4.84 out of 5 average rating, 293 reviews

The Overlook on Lake Koshkonong - Custom Log Cabin

Custom Log cabin on Lake Koshkonong. Great yard for campfires & lawn games; over-sized deck to enjoy sunsets and breathtaking lake views. Lake access at public boat launch just down the road for swimming, fishing, or kayaking. Full bath with large suite featuring a king size bed & two single beds can accommodate up to 5 guests. Full bath with stand up shower in lower level and washer/dryer on site also. Kayak rentals included. Lawn games, poker table, board games & more available!

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, 30 reviews

The Yellow Door Guest House-Lower

You will love being here! Welcome to this turn of the century 2 story home where West Coast cool meets Midwest mod and is the hippest place in town. 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 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, 165 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 charming cottage is located near the water's edge, framed by lush green grass and a few trees. Outdoor equipment, including kayaks and a table setup for dining, adds convenience for guests. The exterior is painted in a soft blue, enhancing its inviting appearance.
Cottage in Hustisford
4.96 out of 5 average rating, 130 reviews

Charming and Cozy Cottage on Lake Sinissippi!

Pine Shore Retreat is a charming cottage so close to the lake that you feel like you are in a houseboat! The east side location means you have fabulous sunset views, as well as swimmable, hard bottom frontage off the platform pier. It is a small space, just one bedroom, but very cozy. Comfort is the focus, with new, high-end furnishings. The stainless steel refrigerator, granite countertops and a gas range in the kitchen offer a higher end experience.

Guest favourite
A charming two-story family home is seen through vibrant autumn foliage, showcasing yellow and orange leaves. A white wooden fence borders the property, with fallen leaves scattered across the lawn. The house features an upper balcony and large windows welcoming natural light.
Home in Oconomowoc
4.82 out of 5 average rating, 171 reviews

Quiet Lake Country Retreat

Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Olympia Resort, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison. *** Coming fall 2024 the back patio will be completely renovated.

Top Guest favourite
The kitchen features white cabinetry with sleek hardware and a large sink positioned under a window. A tile backsplash adds a modern touch. Ample counter space is available for meal preparation, and kitchen essentials are organized in drawers.
Home in Sun Prairie
4.97 out of 5 average rating, 138 reviews

Nothing Else Like It!

There is absolutely nothing else like it available, and you’ll agree as soon as you step foot inside! This beautifully designed home makes your stay comfortable with it's high end furnishings, bedding, towels, mattresses and dishes. Kick back and relax in this calm, stylish space. Fully fenced backyard great for dogs, entertaining and room for kids to play. Private work space available too! All bedrooms have room darkening shades!

Popular amenities for Milford holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Jefferson County
  5. Milford