Vacation rentals in Deerfield

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Top-rated vacation rentals in Deerfield

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Guest favorite
A neatly arranged bedroom features a spacious bed with soft linens and accent pillows. Natural light fills the room through two large windows. A small bedside table with a lamp stands next to the bed, and a vintage-style ladder is positioned at the foot of the bed.
Home in Marshall
4.93 out of 5 average rating, 107 reviews

1898 Farmhouse on 75 acres - MJ's Farm

Nestled down a winding country road, relax and unwind on a traditional Wisconsin farm surrounded by a 2,296 acre Wildlife Area. Our farmhouse is licensed by Dane County & a short 20 minute drive to Madison! You will want a car so you can explore, the UW Campus, Allient Energy Center, WI State Capitol, Madison Farmers Market and much more. Relax, unwind, grill, play horse shoes or sit by the fire pit. Enjoy your privacy but know there is a farm manager close by and I am happy to help

Top guest favorite
Farm stay in Cambridge
4.99 out of 5 average rating, 114 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 favorite
Yurt in Cambridge
4.98 out of 5 average rating, 275 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

Guest favorite
An open living area showcases warm wooden flooring with a patterned area rug. A kitchen island is located in the foreground, while a comfortable seating arrangement is visible near large glass doors. A dining table with high-backed chairs is positioned adjacent to the seating area.
Home in Cambridge
4.92 out of 5 average rating, 119 reviews

Lake Ripley Getaway

This is the perfect place to unwind, located at the crest of a quiet circle, in a wooded lakeside neighborhood. Whatever you’re looking for, you can find it all in this beautiful and tranquil getaway. Vacationers can enjoy skiing, biking and exploring the gorgeous CamRock trail system. Lake Ripley, the sparkling gem of Cambridge, is loaded with fish for summer fun or ice-fishing. Shop our adorable downtown, with a thriving art scene. Our quaint little town is a slice of heaven in a busy world.

Guest favorite
A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.
Guest suite in Sun Prairie
4.89 out of 5 average rating, 447 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Top guest favorite
The image displays a serene waterfront view showcasing a private pier extending over calm waters. A stylish three-story house is framed by lush greenery, offering a welcoming outdoor space. The interior features a spacious living room with comfortable seating and a modern kitchen visible in an open layout.
Home in Edgerton
4.92 out of 5 average rating, 154 reviews

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill

Gather at the White House: a stylish lake house with private pier, 4Br/2.5bath/beds for 15 people, fire pit, gas grill, huge yard, 2 wooded acres. Lake Koshkonong is one of WI’s largest, famous for its boat-up restaurants/bars, fishing, and water sports all accessible from our private pier. Located along 39/90hwy - 90 mins to Chicago/30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living, dining & patio, playroom & much more!

Superhost
A screened porch features a glass-top table surrounded by four chairs, offering a view of the expansive green lawn and trees beyond. The wood flooring adds warmth to the space, while the surrounding screens provide a barrier from the outdoors.
Home in Deerfield
4.94 out of 5 average rating, 35 reviews

High Quality/Value 4+ Bed 3 Bath 20 min -Madison

Very nice clean and comfortable place. Search YouTube "217 Oak Savannah Walkthrough Deerfield Wisconsin" to see 8 minute video. Stay truly first class in this newly constructed high end Condo just 20 minutes east of Madison near the nicest bike/hike trail in Wisconsin where you can bike to beaches and a brewery! Pricing is per side - 2 available. No One Under 24 can book - ID Proof. Be honest with headcount - cameras on property. Identical 4 bedroom 3 bathroom condo airbnb.com/h/221oaksav

Top guest favorite
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, 409 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!

Guest favorite
A bright dining area is highlighted by a wooden table surrounded by chairs. A chandelier hangs above the table, while natural light enters through sliding glass doors leading to an outdoor space. A nearby console table displays decorative items, enhancing the open atmosphere.
Home in Cambridge
4.93 out of 5 average rating, 111 reviews

Quiet country retreat

Peaceful solitude or exciting sightseeing? You’ll have the best of both worlds at this quiet country home located just outside Madison on 10 magnificent acres. After, enjoying your morning coffee, take a stroll on the grounds and enjoy the sweeping views of the pastoral landscape. Then head into Wisconsin’s state capital (23 minutes by car) for an exciting day of sightseeing. Or visit the quaint town of Cambridge (8 minutes by car) to explore its unique pottery and antique shops.

Top guest favorite
Guest suite in Madison
4.99 out of 5 average rating, 253 reviews

Peaceful 2 BR/1 BA w/ patio, fireplace, pool table

• 1400 sq. ft. lower level suite • Private backyard with patio • Two TVs • Electric Fireplace • Pool table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • On-site parking in the driveway for one vehicle • Ample street parking • 16-min drive to the UW campus and downtown • 9-min drive to the airport • 6-min drive to shopping and restaurants • Extremely safe neighborhood • License No. LICHMD-2022-00079 • Zone Permit ZTRHP1-2022-00005

Top guest favorite
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, 181 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.

Guest favorite
Apartment in Madison
4.93 out of 5 average rating, 110 reviews

The Dylin Hotel | Studio

● Size: 372 SQFT ● Guests: 2 Guests ● Bed: 1 Queen Bed Experience a thoughtfully designed fully furnished Studio Apartment featuring a fully equipped kitchen, in-unit laundry, Wi-Fi, smart TV and a cozy sleeping area. The Dylin is a modern aparthotel in Madison’s Cap East neighborhood, offering apartment-style comfort with hotel consistency. Perfect for travelers who want more room to relax and live like a local —ideal for short or extended stays.

Popular amenities for Deerfield vacation rentals