Vacation rentals in Trenton

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Top-rated vacation rentals in Trenton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A charming red farmhouse is set against a snowy landscape, surrounded by a white fence. Leafless trees create a serene backdrop, enhancing the rural setting. The house features a mix of traditional and modern architecture with snow covering the yard.
Guesthouse in Richfield
4.94 out of 5 average rating, 272 reviews

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

Top guest favorite
A rustic lodge stands with a red barn facade, complemented by a stone base and a silos on the side. Lush greenery surrounds the property, while a gravel pathway leads toward the entrance, showcasing a peaceful rural setting.
Barn in Cedarburg
4.97 out of 5 average rating, 198 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.

Guest favorite
The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Menomonee Falls
4.95 out of 5 average rating, 164 reviews

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Guest favorite
An inviting outdoor space showcases a wooden deck with two striped chairs positioned beside a large double door. A barbecue grill rests nearby, and a sign reading 'Hammer Hideaway' is mounted on the wall. Lush greenery and a clear sky provide a relaxed atmosphere.
Farm stay in Germantown
4.97 out of 5 average rating, 118 reviews

Lace & Woods Farm "Hammer Hideaway"

HEATED POOL MAY-SEPT FOR ADDITIONAL CHRG. Cozy designer custom built guest house nestled amongst a 10 acre hobby farm. come for a relaxing getaway. This home is an artistic gem! Boasting an open concept, with a queen bed on main level and twin mattress underneath , a full kitchen, cozy living area, wood burning fireplace. The loft has extra sleeping with a double bed and twin bed.Custom designed. Great location winter and summer, enjoy snowmobiling trails and skiing near by or beaches & hiking

Guest favorite
A welcoming home exterior is shown with a well-maintained lawn and colorful flowerbeds. The facade features a combination of stone and siding, with large windows that allow ample natural light, and a covered entrance adds to the appeal.
Apartment in Port Washington
4.96 out of 5 average rating, 149 reviews

Picturesque Port Washington-HomePort LLC

The apartment is the lower level of our home in picturesque Port Washington. Quiet neighborhood, close to parks and close to bike path. There is 1 parking space and a separate entrance in the back of the house. There is a double futon in living area, bedroom has a queen size bed and newly renovated bathroom with a large shower. We are located 2 miles west of downtown Port which has many quaint shops, restaurants and a marina offering many opportunities for outdoor recreation and relaxation.

Top guest favorite
A welcome booklet and guest book are displayed on a wooden table. The booklet features a clean design with the text 'Silvers Four Six Six Welcome' printed on the cover. The guest book is smaller and includes a similar design theme, both inviting guests to share their experiences.
Apartment in Port Washington
4.98 out of 5 average rating, 123 reviews

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

A lower 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. A perfect place to find comfort.

Top guest favorite
A historic cottage is set amidst lush greenery, featuring a mix of stone and siding on the exterior. A gravel driveway leads to the entrance, surrounded by well-maintained landscaping and mature trees that provide a tranquil atmosphere.
Home in Mequon
4.98 out of 5 average rating, 138 reviews

Historic cottage with fireplace. Pets Welcome!

Step back in time and immerse yourself in the charm of our historic 3-bedroom cottage, part of the renowned Jahn Farmstead, proudly listed on the National Register of Historic Places. Built in the mid-19th century, this Greek Revival-style farmhouse offers a unique blend of historical elegance and modern comfort, ensuring a relaxing and memorable stay. Located 2 miles from the Mequon Public Market and 5 miles from Cedarburg. Pets are welcome and we have acres of land for you to explore!

Top guest favorite
Cabin in Cascade
5 out of 5 average rating, 200 reviews

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

Top guest favorite
A quaint two-story building is set amidst a well-maintained green lawn, surrounded by mature trees. A gravel driveway leads to the side of the structure, with additional buildings visible in the background, contributing to a peaceful rural ambiance.
Guest suite in Germantown
4.92 out of 5 average rating, 154 reviews

1853 Farmhouse Apartment

Welcome to a two-bedroom apartment. The space includes a private bathroom, kitchen and living area. There is no kitchen/dining table. The apartment is on the second floor of the house and has an outside staircase leading up to it. The entrance/staircase is not shared by the hosts and there are no shared spaces in the home. The staircase may be steep for persons who have difficulty navigating stairs. Guests are welcome to use the patio area on the property.

Guest favorite
The exterior of Shalom House showcases a Frank Lloyd Wright style design, featuring a harmonious blend of stone and wood materials. Large windows allow for ample natural light, and a welcoming entryway is highlighted by decorative stonework.
Home in West Bend
4.89 out of 5 average rating, 104 reviews

Entire Use of Shalom House

Shalom House, a Frank Lloyd Wright style design, accommodates 1-12 guests with five bedrooms, 4 bathrooms, great room with fireplace, large kitchen, and labyrinth. NEW at Shalom House is WiFi, though the woods is a great place to connect with the world too. Wonderful drinking water and whole house water system. We have both!! *Shalom House is an experience-"a quiet place to be" *Enjoy the beauty of nature, friends, family, relaxation, celebration.

Top guest favorite
A rustic living area is highlighted by exposed log walls and hardwood floors. A stone fireplace is centered against one wall, while a comfortable plaid sofa faces a wooden coffee table. A dining table is set for meals, featuring simple floral decor.
Farm stay in West Bend
4.97 out of 5 average rating, 235 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.

Top guest favorite
A dining area is showcased, featuring a wooden table set with two plates. A vase with flowers sits at the center. Large windows frame the view of verdant trees, allowing natural light to fill the space.
Apartment in Campbellsport
4.97 out of 5 average rating, 104 reviews

GGG Spacious Log Cabin apartment on the IAT

With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated with new floors, paint, fixtures and more, it’s a perfect retreat from the city. Explore the adjoining 500 acres of state forest, with public lake and boat launch across the street for fishing and paddling. The adjacent trail leads right the Parnell Segment of the Ice Age trail and Mauthe Lake State Park.

Popular amenities for Trenton vacation rentals

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