Holiday rentals in Dorchester

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Top-rated holiday rentals in Dorchester

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Top guest favourite
A modern tiny house is set within a lush green yard, featuring wooden siding and a metal roof. Large windows provide views of surrounding trees and landscaping. Decorative stones and plants enhance the outdoor space, while a wooden deck offers an entryway to the home.
Tiny home in Black River Falls
4.97 out of 5 average rating, 482 reviews

Tiny on the River

According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Top guest favourite
A spacious living area features a comfortable gray sofa adorned with decorative pillows. Two armchairs are positioned nearby, and a coffee table rests in front. Light colored flooring complements the neutral walls and a ceiling fan adds a practical touch.
Bungalow in Thorp
4.99 out of 5 average rating, 98 reviews

Yellowstone Trail Bungalow

Our home is located on the Yellowstone Trail and is a newly remodeled 4 bedroom, 2 bath space that features hints to the 1950’s with updated touches to make sure you are comfortable! You will find luxury linens atop quality memory foam mattresses to warm cozy details throughout. We have thought of everything! Whether you are traveling to see family, buying world famous cheese, shopping our many local businesses or just passing through, our home is perfect for families, couples or groups up to 8.

Top guest favourite
The home is framed by lush greenery and a variety of trees, surrounded by vibrant flower beds. Natural light filters through the leaves, casting gentle shadows on the yard. The house, two stories tall, is partially visible through the foliage, adding to the tranquil rural setting.
Home in Sheldon
5 out of 5 average rating, 19 reviews

Country paradise

Brand new home. Amish built kitchen cabinets and stairs, balcony overlooking the living room. Take it easy at this unique and tranquil getaway located in a rural setting surrounded by crop fields and wildlife. Marked UTV town roads and trails Marked snowmobile trails. Many hunting and fishing opportunities are prominent throughout the area. located close to the Chequamegon National Forest and Miller dam Flambeau river. Flambeau River state park. The Jump River and Lake Holcomb, seasonal fun

Top guest favourite
A log cabin is nestled among tall pine trees, featuring a covered porch and large windows. A fire pit and a picnic table with benches are located in the grassy area in front of the cabin. A charcoal grill is positioned nearby.
Cabin in Greenwood
4.97 out of 5 average rating, 34 reviews

Grandma's Cabin, wooded hideaway

This is the cabin in the woods that you've always dreamed of. This quiet and secluded split log cabin is surrounded by towering pine trees to keep out the noises of the world. Free yourself of electronic distractions and enjoy nature. You will see lots of wildlife as you sit in peace on the covered porch or the back deck watching the sun set. There is a game room, puzzles, board games, and more. Other locations are a place to stay when you go to your destination, this cabin IS your destination.

Top guest favourite
The cabin is set among lush greenery, featuring a sturdy wooden exterior and a welcoming front deck adorned with railings. A staircase leads to an inviting entrance, while a neatly stacked firewood pile is visible underneath. The large yard provides a spacious area for outdoor activities.
Cabin in Medford
4.98 out of 5 average rating, 127 reviews

Cozy two bedroom log cabin on a peaceful lake

Relax with the whole family or some friends at this peaceful place to stay. Kayak, fish, and swim in the lakes. Sit around the fire, play yard games, rest in the hammock, or watch a movie. There are plenty of ways to keep the kids active inside and outside. This cabin includes a game table, sandbox, board/card games, art supplies, kayaks, row boat, and fishing poles. Make many memories together skipping rocks, catching fireflies, eating smores, taking in the beautiful views, and sharing laughs.

Top guest favourite
A calm lake view is captured from the dock, featuring clear blue water reflecting the bright sky. Lush trees line the opposite shore, creating a serene backdrop for outdoor activities.
Home in Merrill
4.99 out of 5 average rating, 219 reviews

Big Bear’s Den - On Lake Alexander

This spacious home is located on beautiful Lake Alexander just west of Merrill, Wisconsin. Enjoy the tranquil view year-round as you plan the many activities that this location offers. You bring the boat, and we'll supply the dock. Throw in your ski's or wakeboard, and don't forget your fishing poles! Three pound small mouth bass are not uncommon and the monster's of fresh water fish, the musky, are plentiful. Add in walleyes, crappies, northern pike and this location is a fisherman's dream!

Top guest favourite
A quaint house features a green roof and white siding, set amidst a grassy area. Large windows allow for natural light, and nearby trees add to the tranquil setting. A pathway leads from the road to the front steps of the home.
Home in Gilman
5 out of 5 average rating, 35 reviews

Sportsman's Getaway

Sportsman's Getaway is centrally located between several great fishing and hunting spots! There are lots of activities for the non-sports person as well. Bring the whole family! This property is located in Donald, WI. It now has a population of 0 and is no longer on the map. There are trains that go by at all hours, otherwise it is quite peaceful. There is 1 acre of land, a patio set and a fire pit to enjoy outside. The house is cozy but has all that you'll ever need. We hope you see you soon!

Top guest favourite
Tiny home in Medford
5 out of 5 average rating, 19 reviews

Luxury Lakefront Tiny Home with WiFi & Kayaks

Escape to a romantic lakefront tiny home (est. 2025) on peaceful Sackett Lake, perfect for couples, quiet getaways, remote work, and unplugged weekends. Wake to lake views from the queen bed, sip coffee by the water, paddle the calm non-motorized lake, and relax by the fire pit under the stars. Inside, enjoy Starlink Wi‑Fi, a full kitchen, heated bathroom floors, self check-in, and the comforts you need. Outside, enjoy kayaks, a private dock, fire pit, and peaceful lakefront surroundings.

Guest favourite
A charming A-frame cabin is surrounded by lush greenery, with a stone pathway leading to the entrance. The exterior features a pleasant mix of light-colored siding and decorative foliage. Sunlight filters through the trees, creating a tranquil outdoor setting.
Cottage in Medford
4.84 out of 5 average rating, 340 reviews

Cozy A-frame on Clear Lake

Relax and enjoy the slower pace of lake life. Catch pan fish from the dock or kayak the chain of lakes! Water not your thing? Use our Cozy A-frame as the base camp for your summer UTV trip or winter snowmobile fun, we sit right on the trail systems. This cozy A-frame built in 2005 features a fireplace, tile floor, full bath and loft area that sleeps 5. Located on Clear Lake near Medford in north central Wisconsin, just down the road from the High View supper club.

Top guest favourite
A serene bedroom is featured with a large bed dressed in a white coverlet and plush pillows. A dark accent wall enhances the modern decor. Natural light enters through a nearby window, while a round mirror and stylish light fixture add to the room's aesthetic.
Home in Marshfield
5 out of 5 average rating, 152 reviews

HGTV STYLE Traveling Professionals

Redesigned HGTV style two bedroom home. Home is located just a few blocks off main street, with easy access to our quaint downtown area. Our downtown area has a movie theater, coffee shops, restaurants, bakery, beauty spots, personal health, and shopping. Home is nice and clean. NON SMOKING HOME **** PARKING: per Marshfield Police Department: Nov 1-Apr 30 no overnight street parking. 2:30 am-6:00 am.

Top guest favourite
The exterior of the log cabin features a spacious wooden balcony with a railing. A swing hangs near the entrance door, while large windows adorn the upper area, inviting natural light. The structure is surrounded by wooded scenery, emphasizing its secluded location.
Cabin in Neillsville
4.96 out of 5 average rating, 185 reviews

Secluded Cabin near the East Fork!

Cozy log cabin on 40 private wooded acres with a south facing wall of windows to enjoy looking at the outdoors. Its off the beaten path, but five miles from the recreational hub of Hatfield, WI and the Black River Forest. We offer a private cabin for up to 4 guests. South Enjoy the outdoors: hiking, canoe/kayaking, ATVing, XC and downhill skiing, hunting, fishing, mountain biking etc.

Top guest favourite
An inviting interior features wooden walls that highlight natural textures. A comfortable seating area includes a recliner and side table. A spiral staircase leads to the loft. Large windows offer a view of the surrounding woods, and a patterned rug adds color to the warm tones.
Cabin in Athens
5 out of 5 average rating, 115 reviews

Grass Creek Getaway: Private, romantic, cozy cabin

Words that past guests have used to describe their stay at Grass Creek Getaway and why I think they chose these words. PRIVATE: located a 1/4 mile off a country road. AMAZING CRAFTSMANSHIP: interior is tediously handcrafted from top to bottom. TRANQUIL: located in wooded area your amongst nature. If you want to get away from the hustle and bustle of everyday life this is the place for you.

Popular amenities for Dorchester holiday rentals