Vacation rentals in Eastman

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Top-rated vacation rentals in Eastman

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Top guest favorite

The A-frame cabin is nestled among lush greenery, showcasing a wooden exterior and an inviting deck. A winding driveway leads up to the entrance, framed by trees. Flower boxes adorn the front windows, enhancing the cabin's natural surroundings.

Cabin in Eastman

4.97 out of 5 average rating, 139 reviews

TranquiliTree Cabin- Secluded and Relaxing

Are you looking for a cozy, and quiet get-away spot to rest & relax? Our little Tree house Cabin is the perfect spot! Located between Prairie Du Chien, WI and Ferryville, WI- this little A-frame cabin gets you within 5 min. from the river, but allows you to be tucked in a quiet wooded area. It is 900 sq. ft of pure relaxation & nature! Enjoy your morning coffee in the outdoor room or relax nightly by the fire pit. Disconnect 2 Reconnect. TranquiliTree Cabin is a great place to escape and unwind.

Top guest favorite

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, 345 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.

Guest favorite

A spacious living area showcases high vaulted ceilings with exposed wooden beams. Large windows allow natural light to fill the space, highlighting the comfortable seating area and dining table set for a meal. A staircase leads to an upper loft area, enhancing the openness of the layout.

Cottage in Eastman

4.97 out of 5 average rating, 156 reviews

Hypoint Loft-Rural SW Wisconsin Mississippi River

Newly Constructed, (2018) Family Owned Loft House in a quiet, relaxing, 2 acre country setting overlooking the Mississippi River! 2500 sq. ft. Just 4 miles from Gatherings on the Ridge, 20 minutes from Historic Downtown Prairie Du Chien and a short jaunt to the river. Sleeps 8-10, master bedroom with a queen, 2 queens & queen sofa sleeper in loft, queen in basement , 2 baths, master bath has jetted tub, full kitchen (pots, pans, dishes, toaster, keurig, coffee pot, coffee, waffle iron, etc.)

Superhost

A screened-in porch features a round dining table surrounded by four chairs, positioned against expansive glass windows that showcase sweeping river views. The ceiling fan adds a functional touch, while the tranquil water can be seen in the background.

Cottage in Harpers Ferry

4.84 out of 5 average rating, 191 reviews

Harpers Slough Cottage w/ Hot tub

Stunning inside and out with amazing river views! 80 feet of riverfront with private covered dock. Updated 3 bedroom and 2 bath home with views from balcony or the screened in porch with access from the master bedroom. Covered balcony and concrete beneath the entire property for lounging or activities. 30 mins from Lansing, Prairie Du Chien, Marquette, and Waukon. Also including the parks Pikes Peak, Spook Cave, and Yellow River Forest. Awesome for boating, fishing, and duck/goose hunting.

Guest favorite

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, 149 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 so all you need are your food, drinks and ingredients. Full 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).

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, 297 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 $25 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.

Guest favorite

A tranquil pond reflects a vibrant sky filled with fluffy clouds, bordered by lush greenery. A small, light-colored building is nestled at the water's edge, enhancing the serene setting.

Tiny home in Monona

4.94 out of 5 average rating, 203 reviews

Creekside-water and nature lovers paradise

Is this Heaven? Maybe. Are you looking for a fun getaway for yourself, family, or friends? Well, look no further. Our place is ready for you to make lifelong memories. Create and tell stories while sitting under the stars next to the crackling campfire. Do your morning yoga by the babbling stream. Hike the trails. Soak up the sun on the sandy beach while listening to the waterfall. Laugh and splash your kiddos in our pond. Beach chairs, sand toys, floaties, kayaks, and more.

Top guest favorite

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

4.88 out of 5 average rating, 116 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 favorite

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

4.84 out of 5 average rating, 244 reviews

Highland Hideaway

A cozy, secluded two bedroom cabin located in the driftless region with incredible views of the Mighty Mississippi!!! If your looking for peace, quiet, and beautiful sunsets this is your place. Only 20 minutes from Wyalusing state park, The Effigy Mounds (sacred Indian Burial Grounds) Pikes Peak 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.

Guest favorite

A historic home is showcased, featuring a large front porch with white railings and steps leading to the entrance. The exterior has light gray siding, multiple windows, and a unique gable roof. A lawn with green grass and small planters adds to the charm.

Home in McGregor

4.92 out of 5 average rating, 128 reviews

Modern & Spacious Mississippi River Retreat

Our home is a historic treasure with modern charm that is perfect for large families and groups of friends who are traveling to the Driftless Region of Northeast Iowa. We are half a mile from the Mississippi River nestled between the beautiful bluffs that frame historic McGregor. Just steps from bustling Main Street, you will find a wonderful selection of local food, beer & wine, home goods, antiques and live music and entertainment.

Superhost

A rustic log cabin is showcased, featuring a sloped roof with a gabled dormer. The exterior is accented by natural wood logs and a stone foundation. A grassy area surrounds the cabin, with trees visible in the background, creating a serene, natural setting.

Cabin in Harpers Ferry

4.79 out of 5 average rating, 146 reviews

Andy Mountain Cabin #3

Whether you are….. Camping, Gathering with family or friends, Hunting the Yellow River State Forest, Fishing and Boating on the Mississippi River or Snowmobiling ……Andy Mountain Cabins is the perfect Home Base for intimate or large groups. Andy Mountain Cabins, LLC is the prime log cabin choice for lodging or motels in Northeast Iowa, Allamakee County, Harpers Ferry Ia, Prairie du Chien WI or McGregor Iowa.

Top guest favorite

An overhead view displays a spacious living area with a light wood dining table surrounded by four chairs. A comfortable gray sofa, accented with cushions, faces a wood stove. Natural light floods the room, highlighting the warm wood beams and various indoor plants.

Guesthouse in Viroqua

4.98 out of 5 average rating, 191 reviews

stylish guesthouse minutes from viroqua

Experience for yourself everything the Driftless has to offer during your stay in this stylish, timber-framed, eco-friendly guesthouse on our 8-acre rural retreat. Completed in 2021, you'll love this bright, clean, private, and peaceful space. Fish nearby trout streams, go for a bike ride, explore great state and county parks, or shop and dine in Viroqua (7 miles away) and Westby (3 miles).