Holiday rentals in Trenton

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Top-rated holiday rentals in Trenton

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Guest favourite

Townhouse in Port Washington

4.92 out of 5 average rating, 117 reviews

Steps Away From the Lakefront and Downtown

Steps from picturesque downtown Port Washington and all the amenities available. Close to the action, but not too close. Restaurants, bars, shopping, the lakefront and marina, charter fishing, beaches, festivals, winery, brewery, beer garden, etc. are just a few of the things available to you in this quaint town which has been called the Cape Cod of the Midwest. Enjoy the entire lower level of this lovingly restored two-family home. Close driving distance to other historic areas like Cedarburg.

15–22 Oct

$128 SGD per night

Guest favourite

Barn in Cedarburg

4.96 out of 5 average rating, 151 reviews

Big Red Barn with a basketball court

A beautifully transformed dairybarn turned into a rustic Lodge with all the accommodations. Enjoy a full kitchen and bar filled with a gas fireplace, dart board and pool table. Head upstairs to the basketball court and onto a wraparound deck that over looks acres of wetlands with wildlife A birdwatchers paradise. If you need to detox we have a wood-burning sauna with all the wood and kindling for you to enjoy. We are located 2miles outside historic Cedarburg Wi and 25 minutes north of Milwaukee.

4–11 Dec

$303 SGD per night

Guest favourite

Flat in Port Washington

4.96 out of 5 average rating, 303 reviews

Grace Adventure House, walk to Port, Lake Michigan

I invite you to experience my spacious, peaceful and delightfully bright two bedroom Cream City Brick upper flat, only 4 blocks from the sparkling shores of Lake Michigan. You will find Grace Adventure House to be an escape from the pressures and busyness of your world where warmth and charm beckon you to enter into rest. Your place of retreat is furnished with Eastern European antiques from years of living overseas and is overflowing with character inside and out. We accept dogs only - sorry.

12–19 Mar

$194 SGD per night

Guest favourite

Flat in Port Washington

4.89 out of 5 average rating, 116 reviews

Lighthouse View -a real gem on Sweet Cake Hill

Enjoy the view of the Port Washington Lighthouse, Marina, and Lake Michigan from your private 1 queen bedroom (plus 2 futons in Living room) upper bungalow apartment. Our house was built in 1900 it has older architectural features. Please look at all the pictures. Private entrance, bathroom, and kitchen with range and refrigerator. Living room has plenty of seating and smart TV. Two block walk to the downtown with 17 restaurants and pubs within walking distance. Only 3 blocks to the marina!

15–22 Dec

$124 SGD per night

Guest favourite

Flat in Port Washington

4.95 out of 5 average rating, 240 reviews

Silvers Four-Six-Four *A home away from home*

An upper flat in walking distance from downtown Port Washington's restaurants, pubs, and summertime live music events. Walk and enjoy Lake Michigan's beaches, pier, and parks. A half block off of the interurban bike and running trail. Spacious apartment boasting a light, fresh, clean and airy feel. Plenty of room to help you feel at home. There is off road parking and a fenced in yard to park bikes or motorcycles. A garage is also available upon request when making your reservation.

26 Mar – 2 Apr

$162 SGD per night

Guest favourite

Cottage in Fond du Lac

4.97 out of 5 average rating, 234 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

22–29 Sep

$88 SGD per night

Guest favourite

Cabin in Fox Lake

4.95 out of 5 average rating, 122 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing by walking to the lake out your back door! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 fee/stay.

2–9 Mar

$146 SGD per night

Guest favourite

Flat in Port Washington

4.97 out of 5 average rating, 144 reviews

Inn on Billy Goat Hill

Come enjoy our upper 2-bedroom apartment in charming Port Washington filled with personal, welcoming touches. We live in a quiet neighborhood on Billy Goat Hill, which overlooks the downtown. The location is very walkable and close to fishing, swimming, boating, biking, shops, pubs, farmers' market, homemade ice cream , and historical sites of interest. We live downstairs and often will be here if you have any needs or concerns, but are very conscious of your desire for privacy.

10–17 Jan

$111 SGD per night

Guest favourite

Guest suite in Sussex

4.96 out of 5 average rating, 237 reviews

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

24–31 Mar

$138 SGD per night

Guest favourite

Home in Campbellsport

4.99 out of 5 average rating, 135 reviews

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

11–18 Aug

$174 SGD per night

Guest favourite

Guest suite in Sussex

4.99 out of 5 average rating, 124 reviews

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

18–25 Sep

$198 SGD per night

Guest favourite

Farm stay in US

4.98 out of 5 average rating, 181 reviews

Family friendly farmstay just outside Milwaukee

The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes all.

6–13 Jan

$150 SGD per night