Holiday houses in Eastman

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Top-rated holiday rentals in Eastman

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Top Guest favourite
A cozy sleeping area features a queen bed with a brown coverlet and contrasting pillows. A small dining table with two chairs is positioned nearby. Natural light enters through a window adorned with curtains, while exposed brick adds character to the room.
Apartment in McGregor
4.96 out of 5 average rating, 314 reviews

Cave Courtyard Guest Studio

The Cave Courtyard Guest Studio. A relaxing getaway located on the ground floor of an 1848 historic building just 1 block from the Mississippi River and unique shops and eateries. Sleeps 4 with a queen bed and daybed with pull out trundle, private entrance, private bath with shower, kitchenette with microwave and mini fridge, internet, cable tv and air-conditioning. There is also a private courtyard located below unique cliff side caves. Some food items are also supplied. Adults only-no pets.

Guest favourite
A quaint blue house is shown from the side, surrounded by lush green grass. A wooden fence partially outlines the property, with a few flowering plants positioned along the edge. Clear skies and sunlight illuminate the exterior, highlighting its welcoming presence.
Home in Prairie du Chien
4.98 out of 5 average rating, 156 reviews

Ohio Street Retreat- hot tub, massage chair, pool

After a fun day in The Driftless Area, come relax and unwind in Prairie du Chien. Beautifully decorated 2 bedroom home with a spacious kitchen, large island, dishwasher, washer/dryer & 5' walk in shower. We supply all cooking/baking items/utensils. High-speed internet with smart TVs in both bedrooms and living room. Outdoor pool (seasonal), hot tub and massage chair. We love dogs too, so we provide a dog run (there is a pet fee). For our fishermen- there is off street parking for your boats.

Top Guest favourite
A charming farmhouse is nestled among lush greenery, surrounded by tall trees. The two-story structure features a gabled roof and a covered front porch. Natural landscaping, including shrubs and grass, frames the house, creating a serene and private atmosphere amidst the forested hills.
Cabin in Gays Mills
4.98 out of 5 average rating, 363 reviews

Driftless Region Cabin/ Stream and Sauna

Settle into a quaint farmhouse nestled in a valley in the rolling, forested hills of the Driftless Region. Start your day with a cup of local coffee on the front porch. Go on a long walk or bike ride, then return to the cottage to cook, play board games, listen the record collection or visit Viroqua (25 minutes) for a farm-to-table 5-star dinner, or check out local music. Build a warm fire outdoors/ warm up by the gas stove indoors, or go down to the stream for a sauna by the cool water creek.

Top Guest favourite
A cozy cabin is perched on large boulders, surrounded by lush greenery. It features a spacious deck with railing and multiple seating areas, offering a serene view of the wooded area. The stone chimney adds character to the rustic design of the cabin.
Cabin in Avoca
5 out of 5 average rating, 221 reviews

Cool quiet country cabin on boulders and 120 acres

Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

Top Guest favourite
A serene view of the Mighty Mississippi River is captured during sunset. Soft hues of orange and purple fill the sky, while the landscape is framed by lush green trees and gentle mists rising from the water, creating a tranquil atmosphere.
Home in Lynxville
4.85 out of 5 average rating, 262 reviews

Highland Hideaway

A cozy, secluded two bedroom cabin located in the driftless region with incredible views of the Mighty Mississippi!!! If you’re looking for peace & quiet, beautiful sunsets, watching wildlife or barges cruise this is your place. Only 20 minutes from Wyalusing or pikes peak state park, The Effigy Mounds (Indian Burial Grounds)and Historic Villa Louis. This beautiful cabin centers you 30 miles from amazing hiking, fishing, hunting and nature for a weekend of disconnecting from busy life.

Superhost
A single-story farmhouse is set against a backdrop of greenery, showcasing a combination of stone and wooden exterior. The well-maintained lawn is complemented by surrounding trees, with a pathway leading towards the entrance. A spacious deck is visible to the side, enhancing the outdoor appeal.
Farm stay in Wauzeka
4.82 out of 5 average rating, 308 reviews

Larsen Farm Secluded Farmhouse with Hotub

Secluded farmhouse with glass hot tub room 600 acres of private trails to hike and explore the cave. Bring your UTV and ride the trails for $30 per driver and $10 per passenger or rent a UTV for $300. Close to trout fishing stream or Mississippi for fishing. Approx 15 miles from Prairie Du Chein, close to canoeing for the Kickapoo, Wisconsin river. Has a gas & charcoal grill, pool table, firepit, Smart TV. Private trails closed Oct 15th thru mid Feb There is Access to public UTV trails.

Top Guest favourite
The cabin's exterior is showcased against a backdrop of lush trees. A sloped metal roof complements the wooden siding. A welcoming entry is framed by a set of stairs leading to the front porch. Gravel surfaces surround the cabin, enhancing its secluded feel.
Cabin in Eastman
5 out of 5 average rating, 101 reviews

SereniTree Cabin-Modern Rustic Getaway

Modern Rustic Family Getaway- Our cabin is not a place to stay while on vacation...our cabin is the vacation! You can come and enjoy the surrounding areas if you want, but you can also just come and spend the entire time away from the outside world. It is a quiet, peaceful, relaxing place to just unwind. Located up on a bluff, between Prairie Du Chien and Ferryville, this cabin gets you about 5 minutes from the river but allows you the serenity of being tucked away in the trees.

Guest favourite
The two-story home is positioned beside a quiet road, featuring a light-colored exterior with a sloped roof. A spacious garage is integrated into the design, and an American flag is displayed on a nearby building. Lush greenery surrounds the property.
Home in Waterville
4.87 out of 5 average rating, 120 reviews

Paint Creek Place

Stay next to beautiful Paint Creek in the heart of Iowa's Driftless Region. Guests can choose from a queen bed or double futon upstairs in the main living area. We also have a queen air mattress available. Enjoy the scenic view of one of Iowa's best trout streams from the house or adjacent green space. Take a 5 minute drive to Yellow River State Forest, and enjoy close access to other public hunting and fishing areas, Effigy Mounds, Pike's Peak, and the Mississippi River.

Guest favourite
Cabin in Harpers Ferry
4.91 out of 5 average rating, 104 reviews

Timber Ridge Cabin getaway - HOT TUB-

The Timber Ridge Hideaway is the perfect NE Iowa family retreat, with 4 bedrooms/2 bathrooms on both levels with a Bunk Bed for kids downstairs and boasting over 2200 total Sq feet. Take in the beauty of the woods and all the wildlife from the covered deck and relax in the large outdoor Hot Tub Jacuzzi available year round or the swimming pool during the warmer summer months. Just minutes away from the Mississippi River and Yellow River Forest. Sleeps up to 14.

Superhost
A covered deck area features wooden railings and a serene view of a sunset lighting up the horizon. The space includes rocking chairs, adding to the tranquil ambiance. The golden hues of dusk create a peaceful atmosphere on this outdoor setting.
Farm stay in Eastman
4.86 out of 5 average rating, 100 reviews

Wrangler Outlaw Suite! Horses! Hydro-Massage Tub!

Enjoy morning coffee and sunsets on your covered deck. Cook your Cowboy Breakfast outside on the flat top griddle and grill. Come for a taste of Wisconsin's rolling green hills, bright blue skies, and fresh, crisp countryside air. Cody's Ranch is located on a ridgetop in beautiful Driftless Region of SW Wisconsin. Experience the rustic cowboy suite with a private entrance on the upper level on this lodge with a property manager on site.

Top Guest favourite
The exterior of a stone cottage is presented, featuring a front porch with a wooden overhang supported by triangular beams. Lush greenery surrounds the entrance, complemented by colorful flower boxes and well-maintained landscaping. The warm tones of the stone create a rustic and inviting appearance.
Cottage in Woodman
5 out of 5 average rating, 106 reviews

The Cottage at Streamwalk

Located off the beaten path in a beautiful pristine valley, this 1 bed, 1 ½ bath cottage offers high end furnishings with a vintage flair modeled after a true english stone cottage. The cottage offers miles of private walking trails on 100 private acres along the renowned Big Green trout stream. Our small highland cow herd roams the pastures, making it feel like you truly are in the Scottish Highlands.

Guest favourite
A secluded cabin is set amidst lush green grass and trees, featuring a brown wooden exterior and a stone chimney. The front yard showcases colorful flower beds and large windows that invite natural light into the welcoming interior.
Cabin in Steuben
4.97 out of 5 average rating, 127 reviews

3BR 2B Cabin Retreat in Beautiful Crawford County

The Cocorico Cabin is a three-bedroom, two-bath secluded cabin on over 9 acres of wooded land just 10 minutes from the Mississippi River. You'll have loads of yard space for games, or you can enjoy sitting on the deck watching birds or staring at the stars. The quarter-mile walking path through the woods leads to an outdoor bar and stage with a basketball hoop. A perfect getaway from your busy life.

Popular amenities for Eastman holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Crawford County
  5. Eastman